WO2013111885A1 - Dérivé d'oxyde de benzyloxypyrimidine, pesticide à usage agricole ou horticole contenant le dérivé d'oxyde de benzyloxypyrimidine et applications associées - Google Patents

Dérivé d'oxyde de benzyloxypyrimidine, pesticide à usage agricole ou horticole contenant le dérivé d'oxyde de benzyloxypyrimidine et applications associées Download PDF

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WO2013111885A1
WO2013111885A1 PCT/JP2013/051665 JP2013051665W WO2013111885A1 WO 2013111885 A1 WO2013111885 A1 WO 2013111885A1 JP 2013051665 W JP2013051665 W JP 2013051665W WO 2013111885 A1 WO2013111885 A1 WO 2013111885A1
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group
halo
alkyl
same
alkoxy
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PCT/JP2013/051665
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Japanese (ja)
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英孝 佐藤
良太 笠原
博人 原山
元文 中野
浩介 深津
佳代 犬飼
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日本農薬株式会社
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    • A—HUMAN NECESSITIES
    • A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
    • A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
    • A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
    • A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
    • A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61P—SPECIFIC THERAPEUTIC ACTIVITY OF CHEMICAL COMPOUNDS OR MEDICINAL PREPARATIONS
    • A61P33/00—Antiparasitic agents
    • A61P33/14—Ectoparasiticides, e.g. scabicides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
    • C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
    • C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
    • C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
    • C07D239/32—One oxygen, sulfur or nitrogen atom
    • C07D239/34—One oxygen atom

Definitions

  • the present invention relates to an agricultural and horticultural insecticide containing a novel benzyloxypyrimidine oxide derivative or a salt thereof as an active ingredient and a method of using the same.
  • Patent Document 1 Although it is disclosed that the pyrimidine derivative described in Patent Document 1 is useful as an insecticide, the structure is different from that of the pyrimidine derivative of the present invention. Although it is disclosed that the pyrimidine derivative described in Patent Document 2 is useful as an insecticide, a compound having a substituent disclosed in the present invention in the substituent at the 4-position of pyrimidine is not described. Furthermore, Patent Documents 1 and 2 do not disclose the compound of the present invention in which the nitrogen atom of the pyrimidine ring is oxidized.
  • the present inventors have found that the benzyloxypyrimidine oxide derivative represented by the general formula (I) of the present invention is a novel compound not described in the literature, It was found useful as an agricultural and horticultural insecticide and completed the present invention.
  • R 1 is (a1) hydrogen atom; (a2) a (C 1 -C 6 ) alkyl group; (a3) (C 3 -C 7 ) cycloalkyl group (the cycloalkyl group may be condensed with a benzene ring); (a4) (C 2 -C 6 ) alkenyl group; (a5) (C 2 -C 6 ) alkynyl group; (a6) a halo (C 1 -C 6 ) alkyl group; (a7) a halo (C 3 -C 6 ) cycloalkyl group; (a8) a halo (C 2 -C 6 ) alkenyl group; (a9) a halo (C 2 -C 6 ) alkynyl group; (a10) a (C 1 -C 6 ) alkoxy (C 1 -C 6 ) alkyl group; (a11) a (C 3 -C 6 ) cycloalky
  • (a22) an aryl (C 1 -C 6 ) alkyl group; (a23) may be the same or different, (a) halogen atom, (b) cyano group, (c) nitro group, (d) formyl group, (e) (C 1 -C 6 ) alkyl group, (f) Halo (C 1 -C 6 ) alkyl group, (g) (C 1 -C 6 ) alkoxy group, (h) halo (C 1 -C 6 ) alkoxy group, (i) (C 3 -C 6 ) cycloalkyl (C 1 -C 6 ) alkoxy group, (j) (C 1 -C 6 ) alkylthio group, (k) halo (C 1 -C 6 ) alkylthio group, (l) (C 1 -C 6 ) alkylsulfinyl group (M) halo (C 1 -C 6 ) alkylsulf
  • (a34) an arylcarbonyl group; (a35) may be the same or different, (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) a formyl group, (e) a (C 1 -C 6 ) alkyl group, (f) Halo (C 1 -C 6 ) alkyl group, (g) (C 1 -C 6 ) alkoxy group, (h) halo (C 1 -C 6 ) alkoxy group, (i) (C 3 -C 6 ) cycloalkyl (C 1 -C 6 ) alkoxy group, (j) (C 1 -C 6 ) alkylthio group, (k) halo (C 1 -C 6 ) alkylthio group, (l) (C 1 -C 6 ) alkylsulfinyl group (M) halo (C 1 -C 6 ) alkylsul
  • (a40) an arylsulfonyl (C 1 -C 6 ) alkyl group; (a41) may be the same or different, (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) a formyl group, (e) a (C 1 -C 6 ) alkyl group, (f) Halo (C 1 -C 6 ) alkyl group, (g) (C 1 -C 6 ) alkoxy group, (h) halo (C 1 -C 6 ) alkoxy group, (i) (C 3 -C 6 ) cycloalkyl (C 1 -C 6 ) alkoxy group, (j) (C 1 -C 6 ) alkylthio group, (k) halo (C 1 -C 6 ) alkylthio group, (l) (C 1 -C 6 ) alkylsulfinyl group (M) hal
  • (a52) a heterocyclic group; (a53) may be the same or different, (a) halogen atom, (b) cyano group, (c) nitro group, (d) formyl group, (e) (C 1 -C 6 ) alkyl group, (f) Halo (C 1 -C 6 ) alkyl group, (g) (C 1 -C 6 ) alkoxy group, (h) halo (C 1 -C 6 ) alkoxy group, (i) (C 3 -C 6 ) cycloalkyl (C 1 -C 6 ) alkoxy group, (j) (C 1 -C 6 ) alkylthio group, (k) halo (C 1 -C 6 ) alkylthio group, (l) (C 1 -C 6 ) alkylsulfinyl group (M) halo (C 1 -C 6 ) alkylsulfinyl group, (n) (C 1
  • a heterocyclic group having 1 to 5 substituents selected from oxo group on the ring; (a54) a heterocyclic (C 1 -C 6 ) alkyl group; (a55) may be the same or different, (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) a formyl group, (e) a (C 1 -C 6 ) alkyl group, (f) Halo (C 1 -C 6 ) alkyl group, (g) (C 1 -C 6 ) alkoxy group, (h) halo (C 1 -C 6 ) alkoxy group, (i) (C 3 -C 6 ) cycloalkyl (C 1 -C 6 ) alkoxy group, (j) (C 1 -C 6 ) alkylthio group, (k) halo (C 1 -C 6 ) alkylthio group, (
  • R 2 and R 3 may be the same or different, (b1) a hydrogen atom; (b2) a (C 1 -C 6 ) alkyl group; (b3) (C 3 -C 6 ) cycloalkyl group; (b4) (C 2 -C 6 ) alkenyl group; (b5) (C 2 -C 6 ) alkynyl group; (b6) a halo (C 1 -C 6 ) alkyl group; (b7) a halo (C 3 -C 6 ) cycloalkyl group; (b8) a halo (C 2 -C 6 ) alkenyl group; (b9) a halo (C 2 -C 6 ) alkynyl group; (b10) a (C 3 -C 6 ) cycloalkyl (C 1 -C 6 ) alkyl group; (b11) (b1) a hydrogen atom; (b2) a (C 1 -C 6 ) alky
  • X may be the same or different, (c1) hydrogen atom; (c2) a halogen atom; (c3) hydroxyl group; (c4) a cyano group; (c5) a nitro group; (c6) N (R 4 ) (R 5 ) group (wherein R 4 and R 5 are as defined above); (c7) N (R 4 ) CO (R 5 ) group (wherein R 4 and R 5 are the same as above); (c8) N (R 4 ) SO 2 (R 5 ) group (wherein R 4 and R 5 are the same as above); (c9) N (R 4 ) CO 2 (R 5 ) group (wherein R 4 and R 5 are the same as above); (c10) CO (R 4 ) group (wherein R 4 is as defined above); (c11) CO 2 (R 4 ) group (wherein R 4 is the same as above); (c12) CON (R 4 ) (R 5 ) group (wherein R 4 and R 5 are the same as above); (c13) C (R
  • (c76) aryl group; (c77) may be the same or different, (a) halogen atom, (b) cyano group, (c) nitro group, (d) (C 1 -C 6 ) alkyl group, (e) halo (C 1 -C 6 ) alkyl group, (f) (C 1 -C 6 ) alkoxy group, (g) halo (C 1 -C 6 ) alkoxy group, (h) (C 2 -C 6 ) alkenyloxy group, (i) halo (C 2 -C 6 ) alkenyloxy group, (j) (C 2 -C 6 ) alkynyloxy group, (k) halo (C 2 -C 6 ) alkynyloxy group, (l) (C 3 -C 6 ) Cycloalkoxy group, (m) halo (C 3 -C 6 ) cycloalkoxy group, (n) (C 3 -C 6
  • (c80) aryloxy group; (c81) may be the same or different, (a) halogen atom, (b) cyano group, (c) nitro group, (d) (C 1 -C 6 ) alkyl group, (e) halo (C 1 -C 6 ) alkyl group, (f) (C 1 -C 6 ) alkoxy group, (g) halo (C 1 -C 6 ) alkoxy group, (h) (C 2 -C 6 ) alkenyloxy group, (i) halo (C 2 -C 6 ) alkenyloxy group, (j) (C 2 -C 6 ) alkynyloxy group, (k) halo (C 2 -C 6 ) alkynyloxy group, (l) (C 3 -C 6 ) Cycloalkoxy group, (m) halo (C 3 -C 6 ) cycloalkoxy group, (n) (C 3 -C
  • (c84) arylthio group; (c85) may be the same or different, (a) halogen atom, (b) cyano group, (c) nitro group, (d) (C 1 -C 6 ) alkyl group, (e) halo (C 1 -C 6 ) alkyl group, (f) (C 1 -C 6 ) alkoxy group, (g) halo (C 1 -C 6 ) alkoxy group, (h) (C 2 -C 6 ) alkenyloxy group, (i) halo (C 2 -C 6 ) alkenyloxy group, (j) (C 2 -C 6 ) alkynyloxy group, (k) halo (C 2 -C 6 ) alkynyloxy group, (l) (C 3 -C 6 ) Cycloalkoxy group, (m) halo (C 3 -C 6 ) cycloalkoxy group, (n) (C 3 -
  • (c114) heterocyclic oxy group; (c115) may be the same or different, (a) a halogen atom, (b) cyano group, (c) nitro group, (d) formyl group, (e) (C 1 -C 6 ) alkyl group, (f) Halo (C 1 -C 6 ) alkyl group, (g) (C 1 -C 6 ) alkoxy group, (h) halo (C 1 -C 6 ) alkoxy group, (i) (C 3 -C 6 ) cycloalkyl (C 1 -C 6 ) alkoxy group, (j) (C 1 -C 6 ) alkylthio group, (k) halo (C 1 -C 6 ) alkylthio group, (l) (C 1 -C 6 ) alkylsulfinyl group (M) halo (C 1 -C 6 ) alkylsulfinyl group, (n) (
  • (c120) a heterocyclic sulfonyl group; (c121) may be the same or different, (a) halogen atom, (b) cyano group, (c) nitro group, (d) formyl group, (e) (C 1 -C 6 ) alkyl group, (f) Halo (C 1 -C 6 ) alkyl group, (g) (C 1 -C 6 ) alkoxy group, (h) halo (C 1 -C 6 ) alkoxy group, (i) (C 3 -C 6 ) cycloalkyl (C 1 -C 6 ) alkoxy group, (j) (C 1 -C 6 ) alkylthio group, (k) halo (C 1 -C 6 ) alkylthio group, (l) (C 1 -C 6 ) alkylsulfinyl group (M) halo (C 1 -C 6 ) alkylsulfinyl group
  • (c128) a heterocycle (C 1 -C 6 ) alkyl group; (c129) may be the same or different, (a) halogen atom, (b) cyano group, (c) nitro group, (d) formyl group, (e) (C 1 -C 6 ) alkyl group, (f) Halo (C 1 -C 6 ) alkyl group, (g) (C 1 -C 6 ) alkoxy group, (h) halo (C 1 -C 6 ) alkoxy group, (i) (C 3 -C 6 ) cycloalkyl (C 1 -C 6 ) alkoxy group, (j) (C 1 -C 6 ) alkylthio group, (k) halo (C 1 -C 6 ) alkylthio group, (l) (C 1 -C 6 ) alkylsulfinyl group (M) halo (C 1 -C 6 ) alkylsulf
  • R 1 is (a1) hydrogen atom; (a2) a (C 1 -C 6 ) alkyl group; (a3) (C 3 -C 7) cycloalkyl group (said cycloalkyl may be condensed with a benzene ring); (a4) (C 2 -C 6 ) alkenyl group; (a5) (C 2 -C 6 ) alkynyl group; (a6) a halo (C 1 -C 6 ) alkyl group; (a8) a halo (C 2 -C 6 ) alkenyl group; (a10) a (C 1 -C 6 ) alkoxy (C 1 -C 6 ) alkyl group; (a11) a (C 3 -C 6 ) cycloalkyl (C 1 -C 6 ) alkyl group; (a12) a (C 1 -C 6 )
  • [1] the same) aryl having 1 to 5 substituents on the ring selected from (C 1 -C 6) alkyl group; (a24) a cyano (C 1 -C 6 ) alkyl group; (a30) an aryl group; (a31) may be the same or different, (a) halogen atom, (b) cyano group, (c) nitro group, (d) formyl group, (e) (C 1 -C 6 ) alkyl group, (f) Halo (C 1 -C 6 ) alkyl group, (g) (C 1 -C 6 ) alkoxy group, (h) halo (C 1 -C 6 ) alkoxy group, (i) (C 3 -C 6 ) cycloalkyl (C 1 -C 6 ) alkoxy group, (j) (C 1 -C 6 ) alkylthio group, (k) halo (C 1 -C 6 ) alkylthi
  • (a32) an arylsulfonyl group; (a33) may be the same or different, (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) a formyl group, (e) (C 1 -C 6 ) alkyl group, (f) Halo (C 1 -C 6 ) alkyl group, (g) (C 1 -C 6 ) alkoxy group, (h) halo (C 1 -C 6 ) alkoxy group, (i) (C 3 -C 6 ) cycloalkyl (C 1 -C 6 ) alkoxy group, (j) (C 1 -C 6 ) alkylthio group, (k) halo (C 1 -C 6 ) alkylthio group, (l) (C 1 -C 6 ) alkylsulfinyl group (M) halo (C 1 -C 6 ) alkyls
  • a heterocyclic group having 1 to 5 substituents selected from oxo group on the ring; (a54) a heterocyclic (C 1 -C 6 ) alkyl group; (a55) may be the same or different, (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) a formyl group, (e) a (C 1 -C 6 ) alkyl group, (f) Halo (C 1 -C 6 ) alkyl group, (g) (C 1 -C 6 ) alkoxy group, (h) halo (C 1 -C 6 ) alkoxy group, (i) (C 3 -C 6 ) cycloalkyl (C 1 -C 6 ) alkoxy group, (j) (C 1 -C 6 ) alkylthio group, (k) halo (C 1 -C 6 ) alkylthio group, (
  • A is —O—, —S—, —SO—, or —SO 2 —;
  • R 2 and R 3 may be the same or different, (b1) a hydrogen atom; (b2) a (C 1 -C 6 ) alkyl group; (b3) (C 3 -C 6 ) cycloalkyl group; (b6) a halo (C 1 -C 6 ) alkyl group; (b11) (C 1 -C 6 ) alkoxy (C 1 -C 6 ) alkyl groups; (b12) a (C 1 -C 6 ) alkylthio (C 1 -C 6 ) alkyl group; or (b13) a (C 1 -C 6 ) alkoxycarbonyl group,
  • X may be the same or different, (c1) hydrogen atom; (c2) a halogen atom; (c5) a nitro group; (c14) (C 1 -C 12 ) alkyl group; (c17) (C 3 -C 12 ) cycloalkyl group; (c18) a halo (C 1 -C 12 ) alkyl group; (c21) a halo (C 3 -C 12 ) cycloalkyl group; (c22) Tri (C 1 -C 12 ) alkylsilyl group (the alkyl groups may be the same or different); (c27) (C 1 -C 12 ) alkoxy group; (c30) (C 3 -C 12) cycloalkyl group (said cycloalkyl may be condensed with a benzene ring.); (c31) a halo (C 1 -C 12 ) alkoxy group; (c38) a halo (C
  • (c112) a heterocyclic group; (c113) may be the same or different, (a) halogen atom, (b) cyano group, (c) nitro group, (d) formyl group, (e) (C 1 -C 6 ) alkyl group, (f) Halo (C 1 -C 6 ) alkyl group, (g) (C 1 -C 6 ) alkoxy group, (h) halo (C 1 -C 6 ) alkoxy group, (i) (C 3 -C 6 ) cycloalkyl (C 1 -C 6 ) alkoxy group, (j) (C 1 -C 6 ) alkylthio group, (k) halo (C 1 -C 6 ) alkylthio group, (l) (C 1 -C 6 ) alkylsulfinyl group (M) halo (C 1 -C 6 ) alkylsulfinyl group, (n) (C 1
  • a heterocyclic oxy group having 1 to 5 substituents selected from an oxo group on the ring; (c130) a heterocyclic oxy (C 1 -C 6 ) alkyl group; or (c131) may be the same or different, (a) a halogen atom, (b) cyano group, (c) nitro group, (d) formyl group, (e) (C 1 -C 6 ) alkyl group, (f) Halo (C 1 -C 6 ) alkyl group, (g) (C 1 -C 6 ) alkoxy group, (h) halo (C 1 -C 6 ) alkoxy group, (i) (C 3 -C 6 ) cycloalkyl (C 1 -C 6 ) alkoxy group, (j) (C 1 -C 6 ) alkylthio group, (k) halo (C 1 -C 6 ) alkylthio group, (l) (C 1
  • X together with adjacent R 2 or R 3 , can form a (c132) bicyclo ring, which may be the same or different, (a) a halogen atom, (b) (C 1 -C 6 ) alkyl group, (c) halo (C 1 -C 6 ) alkyl group, (d) (C 1 -C 6 ) alkoxy group, (e) halo (C 1 -C 6 ) alkoxy group, (f ) (C 1 -C 6 ) alkylthio group, (g) halo (C 1 -C 6 ) alkylthio group, (h) (C 1 -C 6 ) alkylsulfinyl group, (i) halo (C 1 -C 6 ) May have one or more substituents selected from an alkylsulfinyl group, (j) (C 1 -C 6 ) alkylsulfonyl group, and (k) halo (C 1
  • R 1 is (a2) a (C 1 -C 6 ) alkyl group; (a6) a halo (C 1 -C 6 ) alkyl group; (a30) an aryl group; or (a31) may be the same or different, (a) halogen atom, (b) cyano group, (c) nitro group, (d) formyl group, (e) (C 1 -C 6 ) alkyl group, (f) Halo (C 1 -C 6 ) alkyl group, (g) (C 1 -C 6 ) alkoxy group, (h) halo (C 1 -C 6 ) alkoxy group, (i) (C 3 -C 6 ) cycloalkyl (C 1 -C 6 ) alkoxy group, (j) (C 1 -C 6 ) alkylthio group, (k) halo (C 1 -C
  • the benzyloxypyrimidine oxide derivative or its salt of the present invention has an excellent effect as an agricultural and horticultural insecticide. On the other hand, it is also effective against pets such as dogs and cats or pests parasitic on livestock such as cattle and sheep.
  • halo means “halogen atom”, which represents a chlorine atom, bromine atom, iodine atom or fluorine atom
  • C 1 -C 6 ) alkyl group means, for example, methyl group, ethyl group, normal propyl group, isopropyl group, normal butyl group, isobutyl group, secondary butyl group, tertiary butyl group, normal pentyl group, isopentyl group, tertiary Direct pentyl group, neopentyl group, 1,2-dimethylpropyl group, 1-ethylpropyl group, 1-methylbutyl group, 2-methylbutyl group, normal hexyl group, isohexyl group, 1,1,2-trimethylpropyl group, etc.
  • (C 2 -C 6) Al “Nyl group” means, for example, vinyl group, allyl group, isopropenyl group, 1-butenyl group, 2-butenyl group, 2-methyl-2-propenyl group, 1-methyl-2-propenyl group, 1,1-dimethyl group.
  • -2-propenyl group, 2-methyl-1-propenyl group, pentenyl group, 1-hexenyl group and the like are straight-chain or branched alkenyl groups having 2 to 6 carbon atoms, such as “(C 2 -C 6 ) Alkynyl ”means, for example, ethynyl, 1-propynyl, 2-propynyl, 1-methyl-2-propynyl, 1,1-dimethyl-2-propynyl, 1-butynyl, 2-butynyl Straight chain or branched chain alkynyl having 2 to 6 carbon atoms such as a group, 3-butynyl group, 3-methyl-1-propynyl group, 2-methyl-3-propynyl group, pentynyl group, 1-hexynyl group, etc. Show group
  • (C 1 -C 12 ) alkyl group means, for example, methyl group, ethyl group, normal propyl group, isopropyl group, normal butyl group, isobutyl group, secondary butyl group, tertiary butyl group, normal pentyl group, isopentyl group Tertiary pentyl group, neopentyl group, 2,3-dimethylpropyl group, 1-ethylpropyl group, 1-methylbutyl group, normal hexyl group, isohexyl group, 1,1,2-trimethylpropyl group, heptyl group, octyl A linear or branched alkyl group having 1 to 12 carbon atoms such as a group, nonyl group, decyl group, undecyl group, dodecyl group, etc., and “(C 2 -C 12 ) alkenyl group” means, for example, Vinyl, allyl, isopropen
  • a chain-like alkenyl group having 2 to 12 carbon atoms and “(C 2 -C 12 ) alkynyl group” means, for example, ethynyl group, 1-propynyl group, 2-propynyl group, 1-butynyl group, 2 -Butynyl group, 3-butynyl group, 3-methyl-1-propynyl group, 2-methyl-3-propynyl group, pentynyl group, 1-hexynyl group, heptynyl group, octynyl group, nonynyl group, decynyl group, undecynyl group, A linear or branched alkynyl group having 2 to 12 carbon atoms such as a dodecynyl group is shown.
  • the "(C 3 -C 6) cycloalkyl group” include cyclopropyl group, a cyclobutyl group, a cyclopentyl group, an alkyl group having a carbon number of 3 to 6 ring such as a cyclohexyl group, "(C 3 - C 7 ) cycloalkyl group (the cycloalkyl group may be condensed with a benzene ring) ”means, for example, 3 to 7 carbon atoms such as cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl and the like.
  • a cyclic alkyl group or a group in which the cyclic alkyl group is condensed with a benzene ring (for example, indan-1-yl group, 1,2,3,4-tetrahydronaphthalen-1-yl group, etc.) the C 1 -C 6) alkoxy group "include a methoxy group, an ethoxy group, normal propoxy group, isopropoxy group, normal butoxy group, Candary butoxy group, tertiary butoxy group, normal pentyloxy group, isopentyloxy group, tertiary pentyloxy group, neopentyloxy group, 2,3-dimethylpropyloxy group, 1-ethylpropyloxy group, 1-methyl butyloxy group, n-hexyl group, isohexyl group, 1,1,2 a linear or branched C 1 -C 6 alkoxy group such as trimethyl propyl group, "(C 2 -C 6) as
  • (C 3 -C 12 ) cycloalkyl means, for example, cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, cycloundecyl, cyclo A cyclic alkyl group having 3 to 12 carbon atoms such as a dodecyl group, and the “(C 1 -C 12 ) alkoxy group” includes, for example, a methoxy group, an ethoxy group, a normal propoxy group, an isopropoxy group, a normal group; Butoxy group, secondary butoxy group, tertiary butoxy group, normal pentyloxy group, isopentyloxy group, tertiary pentyloxy group, neopentyloxy group, 2,3-dimethylpropyloxy group, 1-ethylpropyloxy group,
  • An alkoxy group having 1 to 12 carbon atoms, and examples of the “(C 2 -C 12 ) alkenyloxy group” include propenyloxy group, butenyloxy group, pentenyloxy group, hexenyloxy group, heptenyloxy group, octenyl
  • a linear or branched alkenyloxy group having 2 to 12 carbon atoms such as an oxy group, a nonenyloxy group, a decenyloxy group, an undecenyloxy group, a dodecenyloxy group, etc., is represented by “(C 2 -C 12 ) alkynyloxy”.
  • Examples of the “group” include propynyloxy group, butynyloxy group, pentynyl A linear or branched alkynyloxy group having 2 to 12 carbon atoms such as an oxy group, a hexynyloxy group, a heptynyloxy group, an octynyloxy group, a nonynyloxy group, a decynyloxy group, an undecynyloxy group, or a dodecynyloxy group.
  • Examples of the “(C 1 -C 6 ) alkylthio group” include a methylthio group, an ethylthio group, a normal propylthio group, an isopropylthio group, a normal butylthio group, a secondary butylthio group, a tertiary butylthio group, and a normal pentylthio group.
  • the “(C 1 -C 6 ) alkylsulfinyl group” includes, for example, Methylsulfinyl group, ethylsulfinyl group, normal propylsulfinyl group, isopropyl Rufinyl group, normal butylsulfinyl group, secondary butylsulfinyl group, tertiary butylsulfinyl group, normal pentylsulfinyl group,
  • alkyl sulfinyl group and the "(C 1 -C 6) alkylsulfonyl group"
  • Examples of the “(C 1 -C 12 ) alkylthio group” include methylthio group, ethylthio group, normal propylthio group, isopropylthio group, normal butylthio group, secondary butylthio group, tertiary butylthio group, and normal pentylthio group.
  • Examples of the “(C 2 -C 12 ) alkenylthio group” include, for example, propenylthio group, butenylthio group, pentenylthio group, hexenylthio group, heptenylthio group, octenylthio group, nonenylthio group, decenylthio group, undecenylthio group, dodecenylthio group, etc.
  • a straight or branched alkenylthio group having 2 to 12 carbon atoms, and examples of the “(C 2 -C 12 ) alkynylthio group” include a propynylthio group, a butynylthio group, a pentynylthio group, and a hexynylthio group.
  • a straight chain or branched chain alkynylthio group having 2 to 12 carbon atoms such as a group, heptynylthio group, octynylthio group, nonynylthio group, decynylthio group, undecynylthio group, dodecynylthio group;
  • Examples of the “(C 2 -C 12 ) alkenylsulfinyl group” include propenylsulfinyl group, butenylsulfinyl group, pentenylsulfinyl group, hexenylsulfinyl group, heptenylsulfinyl group, octenylsulfinyl group, nonenylsulfinyl group, A linear or branched alkenylsulfinyl group having 2 to 12 carbon atoms such as a senylsulfinyl group, an undecenylsulfinyl group, a dodecenylsulfinyl group, etc., is represented by “(C 2 -C 12 ) alkynylsulfinyl”.
  • Examples of the ⁇ group '' include propynylsulfinyl group, butynylsulfinyl group, pentynylsulfinyl group, hexynylsulfinyl group, heptynylsulfinyl group, octynylsulfinyl group, nonynylsulfinyl group, decynylsulfinyl group, Sheet showing the Nils sulfinyl group, dodecylcarbamoyl Nils sulfinyl group linear or branched C 2 -C 12 alkynylsulfinyl group and the like.
  • Examples of the “(C 2 -C 12 ) alkenylsulfonyl group” include propenylsulfonyl group, butenylsulfonyl group, pentenylsulfonyl group, hexenylsulfonyl group, heptenylsulfonyl group, octenylsulfonyl group, nonenylsulfonyl group, Senirusuruhoniru group, undecenyl sulfonyl group, a linear or branched C 2 -C 12 alkenyl-sulfonyl group such as dodecenyl sulfonyl group, "(C 2 -C 12) alkynyl-sulfonyl Examples of the group include a propynylsulfonyl group, a butynylsulfonyl group, a pentynylsulfonyl
  • (C 3 -C 6 ) cycloalkoxy group means a cyclic alkoxy group having 3 to 6 carbon atoms such as cyclopropoxy group, cyclobutoxy group, cyclopentyloxy group, cyclohexyloxy group, etc.
  • C 3 -C 12 ) cycloalkyloxy group (the cycloalkyl may be condensed with a benzene ring)” means, for example, cyclopropoxy group, cyclobutoxy group, cyclopentyloxy group, cyclohexyloxy group, cycloheptyloxy group
  • a cyclic alkoxy group having 3 to 12 carbon atoms such as cyclooctyloxy group, cyclononyloxy group, cyclodecyloxy group, cycloundecyloxy group, cyclododecyloxy group or the like, or the cyclic alkoxy group is condensed with a benzene ring Groups such as indan-1-yloxy, 1,2,3,4-the
  • a “(C 3 -C 12 ) cycloalkylthio group” means, for example, a cyclopropylthio group, a cyclobutylthio group
  • cyclooctyl thio group a cycloalkyl Noni thio group, a cycloalkyl decyl thio group, cycloundecyl thio group, cyclododecyl thio group cyclic alkylthio group having a carbon atom number of 3 to 12, such as, "(C 3 - “C 12 ) cycloalkyl sulfinyl group” means, for example, cyclopropylsulfinyl group, cyclobutylsulfinyl group, cyclopentylsulfinyl group, cyclohexylsulfinyl group, cycloheptylsulfinyl group, cyclooctylsulfinyl group, cyclononylsulfinyl group, cyclodecylsulfinyl group A cyclic alkyl
  • Halo (C 1 -C 6 ) alkyl group “halo (C 2 -C 6 ) alkenyl group”, “halo (C 2 -C 6 ) alkynyl group”, “halo (C 3 -C 6 )”, respectively “Cycloalkyl group”, “halo (C 3 -C 6 ) cycloalkoxy group”, “halo (C 3 -C 12 ) cycloalkyloxy group (which may be condensed with a benzene ring)”, “ “Halo (C 1 -C 6 ) alkoxy”, “halo (C 2 -C 6 ) alkenyloxy”, “halo (C 2 -C 6 ) alkynyloxy”, “halo (C 1 -C 6 ) alkylthio” Group ”,“ halo (C 1 -C 6 ) alkylsulfinyl group ”,“ halo (C 1 -C 6 ) alkylsulfin
  • Tri (C 1 -C 6 ) alkylsilyl group and “tri (C 1 -C 12 ) alkylsilyl group” include, for example, trimethylsilyl group, triethylsilyl group, tertiary butyldimethylsilyl group, ethyldimethylsilyl group Represents a straight or branched trialkylsilyl group having 1 to 6 or 1 to 12 carbon atoms, such as isopropyldimethylsilyl group, n-propyldimethylsilyl group, and the like. In this case, the three alkyl groups may be the same or different.
  • Examples of the di (C 1 -C 12 ) alkylhalo (C 1 -C 6 ) alkylsilyl group include a chloromethyldimethylsilyl group. In this case, the two alkyl groups may be the same or different.
  • Examples of the di (C 1 -C 12 ) alkyl (C 1 -C 6 ) alkylthio (C 1 -C 6 ) alkylsilyl group include a methylthiomethyldimethylsilyl group. In this case, the two alkyl groups may be the same or different.
  • Examples of the di (C 1 -C 12 ) alkylhydrosilyl group include a diisopropylsilyl group.
  • the two alkyl groups may be the same or different.
  • Examples of the di (C 1 -C 12 ) alkylhydroxysilyl group include a dimethylhydroxysilyl group.
  • the two alkyl groups may be the same or different.
  • Examples of the di (C 1 -C 12 ) alkylphenylsilyl group include a dimethyl (phenyl) silyl group.
  • the two alkyl groups may be the same or different.
  • Examples of the di (C 1 -C 12 ) alkylbenzylsilyl group include a dimethyl (benzyl) silyl group. In this case, the two alkyl groups may be the same or different.
  • aryl group refers to an aromatic hydrocarbon group having 6 to 10 carbon atoms such as a phenyl group, 1-naphthyl group, 2-naphthyl group and the like.
  • expressions such as “(C 1 -C 12 )”, “(C 2 -C 12 )”, and “(C 3 -C 12 )” indicate the range of the number of carbon atoms of various substituents. Further, the above definition can be given for a group to which the above substituent is linked. For example, in the case of a “(C 1 -C 6 ) alkoxy (C 1 -C 6 ) alkyl group”, a straight chain or branched chain It indicates that an alkoxy group having 1 to 6 carbon atoms is bonded to a linear or branched alkyl group having 1 to 6 carbon atoms.
  • a group formed by linking two X groups examples include: Examples include a propylene group, a butylene group, a pentylene group, a hexylene group, a 1,1,4,4-tetramethylbutylene group, and the “halo (C 1 -C 6 ) alkylenedioxy group” includes difluoromethylenedioxy group. An oxy group, a tetrafluoroethylene dioxy group, etc. are mentioned.
  • X is, as a bicyclo ring formed together with R 2 or R 3 adjacent, 1,2,3,4-tetrahydronaphthalene, indene, indane, 1,2,3,4-tetrahydro-1, Bicyclo rings such as 4-methanonaphthalene and 1,2,3,4-tetrahydro-1,4-ethanonaphthalene are exemplified.
  • the condensed ring formed by combining two Xs include condensed rings such as 2,3-dihydrobenzofuran and 2,3-dihydrobenzothiophene, and two adjacent Xs on the aromatic ring are combined.
  • the bicyclo ring formed becomes, 1,2,3,4-tetrahydronaphthalene, indene, indane, 1,2,3,4-tetrahydro-1,4-methanonaphthalen-1,2,3,4 -Bicyclo rings such as tetrahydro-1,4-ethanonaphthalene.
  • Heterocyclic group and “heterocycle” are 5- or 6-membered monocyclic aromatics containing 1 to 4 heteroatoms selected from oxygen, sulfur and nitrogen atoms in addition to carbon atoms as ring-constituting atoms.
  • ⁇ aromatic heterocyclic group '' for example, furanyl, thienyl, pyridyl, pyrimidinyl, pyridazinyl, pyrazinyl, pyrrolyl, imidazolyl, pyrazolyl, thiazolyl, isothiazolyl, oxazolyl, isoxazolyl, oxadiazolyl, thiadiazolyl, triazolyl, tetrazolyl, triazinyl and the like Cyclic aromatic heterocyclic groups; quinolyl, isoquinolyl, quinazolyl, quinoxalyl, benzofuranyl, benzothienyl, benzoxazolyl, benzisoxazolyl, benzothiazolyl, benzimidazolyl, benzotriazolyl, indolyl, indazolyl, pyrrolopyrazinyl, imidazopyr Aromatic condensed heterocyclic groups;
  • non-aromatic heterocyclic group examples include oxiranyl, thiylyl, aziridinyl, oxetanyl, thietanyl, azetidinyl, pyrrolidinyl, piperidinyl, morpholinyl, thiomorpholinyl, piperazinyl, hexamethyleneiminyl, oxazolidinyl, thiazolidinyl, azolidinyl, azolidinyl, azolidinyl, azolidinyl, Imidazolinyl, dioxolyl, dioxolanyl, dihydrooxadiazolyl, 2-oxo-1,3-oxazolidin-5-yl, pyranyl, tetrahydropyranyl, thiopyranyl, tetrahydrothiopyranyl, 1-oxidetetrahydrothiopyranyl, 1,1- Dioxidetetrahydrothio
  • heterocyclic group preferably, isoquinolinyl, tetrazolyl, quinolinyl, furanyl, tetrahydrofuranyl, isoxazolyl, pyrimidinyl, pyrazinyl, pyridyl, pyrazolyl, benzimidazolyl, 2,3-dioxaisoindolyl, tetrahydrofuranyl, oxiranyl, Thienyl, pyridazinyl and the like can be mentioned.
  • salts of the benzyloxypyrimidine oxide derivative represented by the general formula (I) of the present invention include inorganic acid salts such as hydrochloride, sulfate, nitrate and phosphate, acetate, fumarate, maleate, Illustrate organic acid salts such as oxalate, methanesulfonate, benzenesulfonate, paratoluenesulfonate, and salts with inorganic or organic bases such as sodium ion, potassium ion, calcium ion, and trimethylammonium. Can do.
  • inorganic acid salts such as hydrochloride, sulfate, nitrate and phosphate, acetate, fumarate, maleate
  • Illustrate organic acid salts such as oxalate, methanesulfonate, benzenesulfonate, paratoluenesulfonate
  • salts with inorganic or organic bases such as sodium ion,
  • the benzyloxypyrimidine oxide derivative represented by the general formula (I) of the present invention and a salt thereof may have one or more asymmetric centers in the structural formula, and two or more optical isomers and In some cases, diastereomers may exist, and the present invention includes all the optical isomers and a mixture in which they are contained in an arbitrary ratio. Further, the benzyloxypyrimidine oxide derivative represented by the general formula (I) of the present invention and a salt thereof may have two kinds of geometric isomers derived from a carbon-carbon double bond in the structural formula. However, the present invention includes all the geometric isomers and mixtures containing them in any proportion.
  • R 1 (a1) hydrogen atom; (a2) a (C 1 -C 6 ) alkyl group; (a3) (C 3 -C 7) cycloalkyl group (said cycloalkyl may be condensed with a benzene ring); (a4) (C 2 -C 6 ) alkenyl group; (a5) (C 2 -C 6 ) alkynyl group; (a6) a halo (C 1 -C 6 ) alkyl group; (a8) a halo (C 2 -C 6 ) alkenyl group; (a10) a (C 1 -C 6 ) alkoxy (C 1 -C 6 ) alkyl group; (a11) a (C 3 -C 6 ) cycloalkyl (C 1 -C 6 ) alkyl group; (a12) a (C 1 -C 6 ) alkylthio (C 1 -C 6 ) alkyl group;
  • [1] the same) aryl having 1 to 5 substituents on the ring selected from (C 1 -C 6) alkyl group; (a24) a cyano (C 1 -C 6 ) alkyl group; (a30) an aryl group; (a31) may be the same or different, (a) halogen atom, (b) cyano group, (c) nitro group, (d) formyl group, (e) (C 1 -C 6 ) alkyl group, (f) Halo (C 1 -C 6 ) alkyl group, (g) (C 1 -C 6 ) alkoxy group, (h) halo (C 1 -C 6 ) alkoxy group, (i) (C 3 -C 6 ) cycloalkyl (C 1 -C 6 ) alkoxy group, (j) (C 1 -C 6 ) alkylthio group, (k) halo (C 1 -C 6 ) alkylthi
  • (a32) an arylsulfonyl group; (a33) may be the same or different, (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) a formyl group, (e) (C 1 -C 6 ) alkyl group, (f) Halo (C 1 -C 6 ) alkyl group, (g) (C 1 -C 6 ) alkoxy group, (h) halo (C 1 -C 6 ) alkoxy group, (i) (C 3 -C 6 ) cycloalkyl (C 1 -C 6 ) alkoxy group, (j) (C 1 -C 6 ) alkylthio group, (k) halo (C 1 -C 6 ) alkylthio group, (l) (C 1 -C 6 ) alkylsulfinyl group (M) halo (C 1 -C 6 ) alkyls
  • a heterocyclic group having 1 to 5 substituents selected from oxo group on the ring; (a54) a heterocyclic (C 1 -C 6 ) alkyl group; (a55) may be the same or different, (a) a halogen atom, (b) a cyano group, (c) a nitro group, (d) a formyl group, (e) a (C 1 -C 6 ) alkyl group, (f) Halo (C 1 -C 6 ) alkyl group, (g) (C 1 -C 6 ) alkoxy group, (h) halo (C 1 -C 6 ) alkoxy group, (i) (C 3 -C 6 ) cycloalkyl (C 1 -C 6 ) alkoxy group, (j) (C 1 -C 6 ) alkylthio group, (k) halo (C 1 -C 6 ) alkylthio group, (
  • A is preferably —O—, —S—, —SO—, or —SO 2 —, more preferably —O— or —S—, and still more preferably —O—.
  • R 2 and R 3 may be the same or different, (b1) a hydrogen atom; (b2) a (C 1 -C 6 ) alkyl group; (b3) (C 3 -C 6 ) cycloalkyl group; (b6) a halo (C 1 -C 6 ) alkyl group; (b11) (C 1 -C 6 ) alkoxy (C 1 -C 6 ) alkyl groups; (b12) a (C 1 -C 6 ) alkylthio (C 1 -C 6 ) alkyl group; or (b13) (C 1 -C 6 ) alkoxycarbonyl group is preferred, (b1) A hydrogen atom is more preferable.
  • X may be the same or different, (c1) hydrogen atom; (c2) a halogen atom; (c5) a nitro group; (c14) (C 1 -C 12 ) alkyl group; (c17) (C 3 -C 12 ) cycloalkyl group; (c18) a halo (C 1 -C 12 ) alkyl group; (c21) a halo (C 3 -C 12 ) cycloalkyl group; (c22) Tri (C 1 -C 12 ) alkylsilyl group (the alkyl groups may be the same or different); (c27) (C 1 -C 12 ) alkoxy group; (c30) (C 3 -C 12) cycloalkyl group (said cycloalkyl may be condensed with a benzene ring.); (c31) a halo (C 1 -C 12 ) alkoxy group; (c38) a halo (C
  • (c112) a heterocyclic group; (c113) may be the same or different, (a) halogen atom, (b) cyano group, (c) nitro group, (d) formyl group, (e) (C 1 -C 6 ) alkyl group, (f) Halo (C 1 -C 6 ) alkyl group, (g) (C 1 -C 6 ) alkoxy group, (h) halo (C 1 -C 6 ) alkoxy group, (i) (C 3 -C 6 ) cycloalkyl (C 1 -C 6 ) alkoxy group, (j) (C 1 -C 6 ) alkylthio group, (k) halo (C 1 -C 6 ) alkylthio group, (l) (C 1 -C 6 ) alkylsulfinyl group (M) halo (C 1 -C 6 ) alkylsulfinyl group, (n) (C 1
  • a heterocyclic oxy group having 1 to 5 substituents selected from an oxo group on the ring; (c130) a heterocyclic oxy (C 1 -C 6 ) alkyl group; or (c131) may be the same or different, (a) a halogen atom, (b) cyano group, (c) nitro group, (d) formyl group, (e) (C 1 -C 6 ) alkyl group, (f) Halo (C 1 -C 6 ) alkyl group, (g) (C 1 -C 6 ) alkoxy group, (h) halo (C 1 -C 6 ) alkoxy group, (i) (C 3 -C 6 ) cycloalkyl (C 1 -C 6 ) alkoxy group, (j) (C 1 -C 6 ) alkylthio group, (k) halo (C 1 -C 6 ) alkylthio group, (l) (C 1
  • a halo (C 1 -C 12 ) alkoxy group is more preferred.
  • l and n one is preferably 1 and the other is 0.
  • l is more preferably 1, and n is more preferably 0.
  • m 1, 2 or 3 is preferable, and 1 is more preferable.
  • R 1 , R 2 , R 3 , A, X, l, m, and n are the same as described above, and Y represents a leaving group such as a chlorine atom, a bromine atom, and an iodine atom.
  • the benzyl represented by the general formula (I-1) By reacting the pyrimidine compound represented by the general formula (III) and the compound represented by the general formula (II) in the presence of a base in an inert solvent, the benzyl represented by the general formula (I-1) By producing an oxypyrimidine derivative and then oxidizing it, the benzyloxypyrimidine oxide derivative represented by the general formula (I) of the present invention can be produced.
  • the compound represented by the general formula (III) can be produced according to the method described in Journal of the Chemical Society (1960), 4590. or JP-A-49-92080. Moreover, what is necessary is just to use the product sold as the raw material compound represented by general formula (II). Or it can manufacture according to the method as described in well-known literature (For example, 4th edition Experimental Chemistry Course 24 The Chemical Society of Japan edition) or these.
  • the benzyl represented by the general formula (I-1) is obtained by reacting the pyrimidine compound represented by the general formula (III) with the compound represented by the general formula (II) in the presence of a base in an inert solvent.
  • Oxypyrimidine derivatives can be produced.
  • the base that can be used in this reaction include sodium hydroxide, potassium hydroxide, sodium carbonate, potassium carbonate, cesium carbonate, sodium hydrogen carbonate, potassium hydrogen carbonate and other inorganic bases, sodium hydride, potassium hydride and the like.
  • Examples include alkoxides such as alkali metal hydrides, sodium methoxide, sodium ethoxide, potassium tertiary butoxide and the like.
  • the amount of the base used is usually in the range of about 1 to 5 moles compared to the compound represented by the general formula (II).
  • the inert solvent that can be used in this reaction is not particularly limited as long as it does not significantly inhibit this reaction. Examples thereof include alcohols such as methanol, ethanol, propanol, butanol, and 2-propanol; chains such as diethyl ether, tetrahydrofuran, and dioxane.
  • aromatic hydrocarbons such as benzene, toluene and xylene
  • halogenated hydrocarbons such as methylene chloride, chloroform and carbon tetrachloride
  • halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene
  • acetonitrile Nitriles such as ethyl acetate
  • esters such as ethyl acetate
  • polar solvents such as N, N-dimethylformamide, N, N-dimethylacetamide, dimethyl sulfoxide, 1,3-dimethyl-2-imidazolinone, etc.
  • the reaction temperature in this reaction may usually be in the range of about 0 ° C. to the boiling point of the solvent used, and the reaction time is not constant depending on the reaction scale, reaction temperature, etc., but may be appropriately selected within the range of several minutes to 48 hours. .
  • the compound represented by the general formula (II) is usually used in an amount of about 1 to 5 times the molar amount of the pyrimidine compound represented by the general formula (III). Further, this reaction may be performed in an atmosphere of an inert gas such as nitrogen gas or argon gas.
  • the target product may be isolated from the reaction system containing the target product by a conventional method, and the target product can be produced by purification by recrystallization, column chromatography or the like, if necessary. Moreover, after completion
  • the benzyloxypyrimidine oxide derivative represented by the general formula (I) can be produced.
  • the oxidizing agent used in this reaction includes manganese compounds such as manganese dioxide; chromic acids such as sodium chromate; lead compounds such as lead tetraacetate; mercury compounds such as mercury oxide; osmium tetroxide, ruthenium tetroxide, selenium dioxide.
  • Oxidizing agents such as: metal halogenating agents such as iron chloride and copper iodide, halogens such as iodine and bromine; palladiums such as palladium on carbon; quinone-based oxidizing agents such as DDQ; hydrogen peroxide solution, perbenzoic acid, and peroxides such as m-chloroperbenzoic acid. Among these hydrogen peroxide, perbenzoic acid, m- chloroperbenzoic acid is preferred.
  • These oxidizing agents can be appropriately selected in the range of 0.8 to 10 times mol with respect to the benzyloxypyrimidine derivatives represented by the general formula (I-1), preferably 1 to 2 times mol. The range of is preferable.
  • the inert solvent that can be used in this reaction is not particularly limited as long as it does not significantly inhibit this reaction.
  • chain or cyclic ethers such as diethyl ether, tetrahydrofuran, and dioxane
  • aromatic carbonization such as benzene, toluene, and xylene.
  • Halogenated hydrocarbons such as methylene chloride, chloroform and carbon tetrachloride; Halogenated aromatic hydrocarbons such as chlorobenzene and dichlorobenzene; Nitriles such as acetonitrile; Esters such as ethyl acetate; Formic acid and acetic acid Organic solvents such as N, N-dimethylformamide, N, N-dimethylacetamide, 1,3-dimethyl-2-imidazolinone, water and the like, and these inert solvents may be used alone or A mixture of more than one species can be used.
  • the reaction temperature in this reaction may be suitably selected in the range of the reflux temperature of the inert solvent used -30 ° C..
  • the reaction time varies depending upon the reaction scale, reaction temperature, etc. by changing, may be appropriately selected in the range of constant not but a few minutes to 48 hours.
  • the target product may be isolated from the reaction system containing the target product by a conventional method, and the target product can be produced by purification by recrystallization, column chromatography or the like, if necessary.
  • the agricultural and horticultural insecticide containing the benzyloxypyrimidine oxide derivative represented by the general formula (I) of the present invention or a salt thereof as an active ingredient is a variety of agricultural and forestry that harms paddy rice, fruit trees, vegetables, other crops and florets, It is suitable for pest control such as horticulture, stored grain pests, hygiene pests or nematodes.
  • Examples of the pests or nematodes include the following. Lepidoptera (Lepidoptera) pests such as Parasa consocia, Redwood (Anomis mesogona), Papilio xuthus, Matsumuraeses azukivora, Ostrinia scapulalis, African exotic empti (Spod) (Hyphantria cunea), Awanoiga (Ostrinia furnacalis), Ayayoto (Pseudaletia separata), iga (Tinea translucens), rush saint moth (Bactra furfurana), Ichinomosei (Parnara guttata), Inaitei inferens), Brachmia triannulella, Monema flavescens, Iraqusinu Waiba (Trichoplusia ni), Pleuroptya ruralis, Cystidia couaggaria, Lampides boeticus, Males flamingo (
  • Hemiptera pests, for example, Nezara antennata, red beetle (Stenotus rubrovittatus), red beetle (Graphosoma rubrolineatum), red beetle (Trigonotylus coelestialium), Aeschynteles maculatus), red beetle (Creontiades pallidifer), red beetle bug (Dysdercus cingulatus), red beetle (Chrysomphalus ficus), red beetle (Aonidiella aurantii), red crab beetle (Graptops) Scale insects (Icerya purchasi), Japanese beetle (Piezodorus hybneri), Japanese beetle (Lagynotomus elongatus), Japanese white-winged beetle (Thaia subrufa), Japanese black beetle (Scotinophara luridaito
  • Coleoptera (Coleoptera) pests include, for example, Xystrocera globosa, Aobaarie-hane-kakushi (Paederus fuscipes), Ahanamuri (Eucetonia roelofsi), Azuki beetle (Callosobruchus chinensis), Arimodosium (Hypera postica), rice weevil (Echinocnemus squameus), rice beetle (Oulema oryzae), rice beetle (Oulema oryzae), rice beetle (Donacia provosti), rice weevil (Lissorhoptruss (Epilachna varivestis), bean weevil (Acanthoscelides obtectus), western corn rootworm (Diabrotica virgifera virgifera), beetle weevil (Involvulus cupreus), cucumber beetle (Aulacophora fe
  • Culex pipiens pallens red flies fly (Pegomya hyoscyami), red spider fly (Liriomyza huidobrensis), house fly (Musca domestica), rice flies Flies Fruit flies (Rhacochlaena japonica), fruit flies (Muscina stabulans), fruit flies such as fruit flies (Megaselia spiracularis), giant butterflies (Clogmia albipunctata), mushroom moth (Tipula aino), hormone moth (Pipula) rhynchus), Anopheles sinensis, Japanese flies (Hylemya brassicae), Soybean fly (Asphondylia sp.), Panax fly (Delia platura), Onion fly (Delia antiqua) RRen ), Ceratitis capitata, Bradysia agrestis, sugar beetle fly (P
  • Hymenoptera Pristomyrmex ⁇ ponnes
  • Arbatidae Moneorumium pharaohnis
  • Pheidole noda Athalia rosae
  • Cristoforma Kuriphilus
  • Hornets black bee (Athalia infumata ata infumata), horned bee (Arge pagana), Japanese bee (Athalia japonica), cricket (Acromyrmex spp.), Fire ant (Solenopsis spp.), Apple honey bee (Arlen beli) (Ochetellus glaber) and the like.
  • insects of the order Diptera Hortocoryphus lineosus
  • Kera Gryllotalpa sp.
  • Coago Oxya hyla intricata
  • Cobainago Oxya yezoensis
  • Tosama locust Locusta migrago
  • Oneya Homorocoryphus jezoensis
  • emma cricket Teogryllus emma
  • Thrips examples of thrips of the order Thrips (Selenothrips rubrocinctus), thrips (Stenchaetothrips biformis), Thrips thrips (Haplothrips , Lithrips floridensis, Thrips simplex, Thrips nigropilosus, Helothripes Leeuwenia pasanii), Shiimaruda thrips (Litotetothrips pasaniae), Citrus srips (Scirtothrips citri), Saddle thrips (Haplothrips chinensis), Soybean thrips (Mycterothrips glycines), Da Thrips setosus, Thripsrtsaw Thrips hawaiiensis, Haplothrips kurdjumovi, Thrips coloratus , Lilyripa vaneeckei, and the like.
  • mite moths (Leptotrombidium akamushi), Ashinowa spider mite (Tetranychus ludeni), American dock ticks (Dermacentor variabilis), Ichinami spider mite (Tetranychus truncatus), house dust mite (Ornithonyssus bacoti), mite Tetranychus viennensis), ticks (Tetranychus kanzawai), ticks (Rhipicephalus sanguineus) and other ticks (Cheyletus acc malaccensis), stag beetle tick (Tyrophagus putrescent moth) Tick (Dermacentor taiwanicus), Chinese cabbage mite (Acaphylla theavagrans), Chinese dust mite (Polyphagotarsonemus latus), Tomato mite (Aculops lycopersici), Trichoid mite (Ornithonyssus sylvairum), Nami spider mite (
  • Amite termites (Reticulitermes miyatakei), American termites (Incisitermes minor), Termites (Coptotermes formosanus), Termites (Hodotermopsis japonica), Common termites (Reticulitermes termm ants) , Glyptotermes , Nakajima termite (Glyptotermes nakajimai), Nitobe termite (Pericapritermes nitobei), Yamato termite (Reticulitermes speratus) and the like.
  • cockroach Periplaneta fuliginosa
  • German cockroach Blattella germanica
  • Great cockroach Blatta orientalis
  • Greater cockroach Periplaneta brunnea
  • Greater cockroach Blattella lituriplanet (Periplaneta americana) and the like.
  • fleas examples include human fleas (Pulex irritans), cat fleas (Ctenocephalides felis), and fleas (Ceratophyllus gallinae).
  • Nematodes for example, strawberry nematode (Nothotylenchus acris), rice scallop nematode (Aphelenchoides besseyi), red-footed nematode (Pratylenchus penetrans), red-knot nematode (Meloidogyne hapla), sweet potato nematode (Meloidogyne rostochiensis), Javaloid nematode (Meloidogyne javanica), soybean cyst nematode (Heterodera glycines), southern nematode nematode (Pratylenchus coffeae), and pterolenchus nematode (Pratylenchus neglectus)
  • mollusks examples include Pomacea canaliculata, Achatina fulica, slug (Meghimatium bilineatum), Lehmannina valentiana, Limax flavus, and Acusta despecta Is mentioned.
  • the agricultural and horticultural insecticide of the present invention has a strong insecticidal effect against tomato kibaga (Tuta absoluta) as other pests.
  • animal parasite ticks Boophilus microplus
  • black tick ticks Raicephalus sanguineus
  • yellow tick ticks Haemaphysalis longicornis
  • yellow ticks Haemaphysalis flava
  • tsurigane tick ticks Haemaphysata tick
  • Tick Haemaphysalis concinna
  • tick Haemaphysalis japonica
  • tuna Haemaphysalis kitaokai
  • tick Haemaphysalis ias
  • tick Ixodes ovatus
  • tick desmite Ticks Dermanyssus, ticks such as Amblyomma testudinarium, Haemaphysalis megaspinosa, Dermacentor reticulatus, and Dermacentor taiwanesis gallinae
  • avian mite Ornithonyssus sylviarum
  • fleas to be controlled include, for example, ectoparasite worms belonging to the order Flea (Siphonaptera), more specifically fleas belonging to the family Flea (Pulicidae), Cleaphyllus (Ceratephyllus), etc. .
  • Fleas belonging to the family flea family include, for example, dog fleas (Ctenocephalides canis), cat fleas (Ctenocephalides felis), human fleas (Pulex irritans), elephant fleas (Echidnophaga gallinacea), keops mouse fleas (Xenopsylla cheopis), Leptopsylla segnis), European mouse minnow (Nosopsyllus fasciatus), and Yamato mouse minnow (Monopsyllus anisus).
  • ectoparasites to be controlled include, for example, cattle lice (Haematopinus eurysternus), horse lice (Haematopinus asini), sheep lice (Dalmalinia ovis), cattle lice (Linognathus vituli), pig lice (Haematopinus ⁇ suius ⁇ pubis), And lice like head lice (Pediculus capitis), and lice like dog lice (Trichodectes canis), blood-sucking dipteries such as Tabibus trigonus, Culicoides schultzei, and Simulium ornatum Examples include pests.
  • endoparasites include nematodes such as pneumoniae, benthic, nodular worms, gastric parasites, roundworms, and filamentous worms, manson cleft worms, broad-headed crest worms, berries Tapeworms such as tapeworms, multi-headed tapeworms, single-banded tapeworms, and multi-banded tapeworms, flukes such as Schistosoma japonicum, and liver fluke, and coccidium, malaria parasites, intestinal granulocysts, toxoplasma And protozoa such as Cryptosporidium.
  • nematodes such as pneumoniae, benthic, nodular worms, gastric parasites, roundworms, and filamentous worms, manson cleft worms, broad-headed crest worms, berries Tapeworms such as tapeworms, multi-headed tapeworms, single-banded tapeworms, and multi-banded tapeworms,
  • the agricultural and horticultural insecticide containing the benzyloxypyrimidine oxide derivative represented by the general formula (I) of the present invention or a salt thereof as an active ingredient damages paddy field crops, field crops, fruit trees, vegetables, other crops, and flowers. It has a remarkable control effect on the pests that give the seedlings, so that it matches the time when the occurrence of the pests is predicted, before the occurrence of the pests or at the time when the occurrence is confirmed,
  • the desired effects of the agricultural and horticultural insecticides of the present invention can be achieved by treating other crops, seeds such as flower buds, paddy field water, stalks and leaves, or cultivation carriers such as soil.
  • Useful plants to which the agricultural and horticultural insecticide of the present invention can be used are not particularly limited, and examples thereof include cereals (eg, rice, barley, wheat, rye, oats, corn, etc.), beans (soybean, Red beans, broad beans, green beans, green beans, peanuts, etc.), fruit trees and fruits (apples, citrus fruits, pears, peaches, peaches, plums, cherry peaches, walnuts, chestnuts, almonds, bananas, etc.), leaves and fruit vegetables (cabbage, Tomato, spinach, broccoli, lettuce, onion, green onion (satsuki, parrot), green pepper, eggplant, strawberry, pepper, ladle, leek, etc., root vegetables (carrot, potato, sweet potato, sweet potato, daiko, kabu, lotus root, gobo) , Garlic, raccoon, etc.), crops for processing (crab, hemp, beet, hop, sugar cane, sugar beet, olive, rubber, coffee, tobacco, tea, etc
  • the “plant” includes HPPD inhibitors such as isoxaflutol, ALS inhibitors such as imazetapyr and thifensulfuron methyl, EPSP synthase inhibitors such as glyphosate, glutamine synthase inhibitors such as glufosinate, cetoxydim and the like. Also included are plants that have been rendered resistant by classical breeding methods or genetic recombination techniques to herbicides such as acetyl CoA carboxylase inhibitors, bromoxynil, dicamba, 2,4-D.
  • Plants to which tolerance to an acetyl CoA carboxylase inhibitor has been imparted are Procedures of the National Academy of Sciences of the United States of America (Proc. Natl. Acad. Sci). USA) 87, 7175-7179 (1990).
  • a mutant acetyl CoA carboxylase resistant to an acetyl CoA carboxylase inhibitor has been reported in Weed Science 53, 728-746 (2005).
  • Introducing a plant resistant to an acetyl-CoA carboxylase inhibitor by introducing a mutation associated with imparting resistance to a plant or introducing a mutation associated with imparting resistance into a plant acetyl-CoA carboxylase, and further, chimeric plastic technology (Gura T. et al. 1999.
  • toxins expressed in transgenic plants insecticidal proteins derived from Bacillus cereus and Bacillus popirie; ⁇ - such as Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1 or Cry9C derived from Bacillus thuringiensis Endotoxins, insecticidal proteins such as VIP1, VIP2, VIP3 or VIP3A; nematicidal insecticidal proteins; toxins produced by animals such as scorpion toxins, spider toxins, bee toxins or insect-specific neurotoxins; filamentous fungal toxins; plant lectins; Agglutinin; protease inhibitors such as trypsin inhibitor, serine protease inhibitor, patatin, cystatin, papain inhibitor; lysine, corn-RIP, abrin, ruffin, saporin, bryodin, etc.
  • ⁇ - such as Cry1Ab, Cry1Ac, Cry1F,
  • Bosome inactivating protein RIP
  • steroid metabolic enzymes such as 3-hydroxysteroid oxidase, ecdysteroid-UDP-glucosyltransferase, cholesterol oxidase; ecdysone inhibitor; HMG-CoA reductase; sodium channel, calcium channel inhibitor, etc. Ion channel inhibitor; juvenile hormone esterase; diuretic hormone receptor; stilbene synthase; bibenzyl synthase; chitinase; glucanase and the like.
  • toxins expressed in such genetically modified plants Cry1Ab, Cry1Ac, Cry1F, Cry1Fa2, Cry2Ab, Cry3A, Cry3Bb1, Cry9C, Cry34Ab or Cry35Ab and other ⁇ -endotoxin proteins, VIP1, VIP2, VIP3A, etc.
  • insecticidal protein hybrid toxins partially defective toxins, and modified toxins.
  • Hybrid toxins are produced by new combinations of different domains of these proteins using recombinant techniques.
  • Cry1Ab lacking a part Cry1Ab lacking a part of the amino acid sequence is known.
  • the modified toxin one or more amino acids of the natural toxin are substituted.
  • Examples of these toxins and recombinant plants capable of synthesizing these toxins are EP-A-0 374 753, WO 93/07278, WO 95/34656, EP-A-0 427 529, EP-A-451 878. , WO 03/052073, etc.
  • Toxins contained in these recombinant plants particularly confer resistance to Coleoptera, Hemiptera pests, Diptera pests, Lepidoptera pests and nematodes.
  • the agricultural and horticultural insecticides of the present invention can be used in combination or systematized with these techniques.
  • the insecticide for agricultural and horticultural use according to the present invention is used to control various insect pests as they are, or appropriately diluted with water or the like, or suspended in an amount effective for controlling insects or nematodes.
  • pests and nematodes occurring in fruit trees, cereals, vegetables, etc., in addition to spraying on the foliage, seed immersion in seeds, seed dressing, calper treatment Etc.
  • the agricultural and horticultural insecticide of the present invention may be used as it is, or appropriately diluted with water or the like, or an amount effective for controlling pests in a place where the occurrence of the pests is predicted.
  • the agricultural and horticultural insecticide of the present invention may be used as it is, or appropriately diluted with water or the like, or an amount effective for controlling pests in a place where the occurrence of the pests is predicted.
  • they can also be used for application to house building materials, smoke, baits, and the like.
  • Seed treatment methods include, for example, a method in which a liquid or solid preparation is diluted or undiluted and the seed is immersed in a liquid state to infiltrate the drug, a solid preparation or liquid preparation is mixed with the seed, Examples thereof include a method of treating and adhering to the surface of the seed, a method of coating the seed by mixing with an adhesive carrier such as resin and polymer, and a method of spraying around the seed simultaneously with planting.
  • the “seed” for performing the seed treatment means a plant body at an early stage of cultivation used for plant propagation. For example, in addition to seeds, bulbs, tubers, seed buds, stock buds, baskets, bulbs, or cuttings Mention may be made of plants for vegetative propagation.
  • the “soil” or “cultivation carrier” of the plant when carrying out the method of use of the present invention refers to a support for cultivating crops, particularly a support for growing roots, and the material is not particularly limited. However, any material that can grow plants may be used, and so-called soil, seedling mats, water, etc. may be used. It may be a molecular substance, rock wool, glass wool, wood chip, bark or the like.
  • a spraying method to crop foliage or stored grain pests, house pests, hygiene pests, forest pests, etc. dilute liquid preparations such as emulsions and flowables or solid preparations such as wettable powders or granular wettable powders with water as appropriate.
  • Examples of application methods to soil include, for example, a method in which a liquid preparation is diluted or not diluted with water and applied to a plant stock or a seedling nursery, etc.
  • a method of spraying to a nursery, etc. a method of spraying powder, wettable powder, granule wettable powder, granule, etc. before sowing or transplanting and mixing with the whole soil, a planting hole, making before planting or planting a plant body
  • Examples include a method of spraying powder, wettable powder, wettable powder, granule, etc. on the strip.
  • the dosage form may vary depending on the time of application such as application at seeding, application at greening period, application at transplanting, etc. Apply by mold. It can also be applied by mixing with soil, and it can be mixed with soil and powder, granulated wettable powder or granules, for example, mixed with ground soil, mixed with soil covering, mixed with the entire soil. Simply, the soil and various preparations may be applied alternately in layers.
  • solid preparations such as jumbo agents, packs, granules, granule wettable powders, and liquid preparations such as flowables and emulsions are usually sprayed on flooded paddy fields.
  • an appropriate preparation can be sprayed and injected into the soil as it is or mixed with fertilizer.
  • a chemical solution such as emulsion or flowable as a source of water flowing into a paddy field such as a water mouth or an irrigation device, it can be applied in a labor-saving manner along with the supply of water.
  • a field crop In a field crop, it can be processed to a seed or a cultivation carrier close to a plant body from sowing to raising seedling.
  • treatment on a plant source of a plant being cultivated is suitable. It is possible to perform spraying treatment using a granule or irrigation treatment in a liquid of a drug diluted or not diluted in water. It is also a preferable treatment to mix the granules with the cultivation carrier before sowing and then sow.
  • the irrigation treatment of the liquid drug or the spraying treatment of the granule to the seedling nursery is preferable.
  • the agricultural and horticultural insecticide of the present invention is generally used in a form convenient for use according to a conventional method for agricultural chemical preparations.
  • the benzyloxypyrimidine oxide derivative represented by the general formula (I) of the present invention or a salt thereof is dissolved in an appropriate inert carrier or, if necessary, together with an auxiliary agent in an appropriate ratio. , Separated, suspended, mixed, impregnated, adsorbed or adhered, and formulated into appropriate dosage forms such as suspensions, emulsions, solutions, wettable powders, wettable granules, granules, powders, tablets, packs, etc. And use it.
  • the composition of the present invention can contain, in addition to the active ingredient, additive components usually used in agricultural chemical formulations or animal parasite control agents as required.
  • additive components include a carrier such as a solid carrier and a liquid carrier, a surfactant, a dispersant, a wetting agent, a binder, a tackifier, a thickener, a colorant, a spreading agent, a spreading agent, and an antifreezing agent. , Anti-caking agents, disintegrants, decomposition inhibitors and the like. In addition, you may use a preservative, a plant piece, etc. for an additional component as needed. These additive components may be used alone or in combination of two or more.
  • the solid carrier examples include natural minerals such as quartz, clay, kaolinite, pyrophyllite, sericite, talc, bentonite, acid clay, attapulgite, zeolite, diatomaceous earth, and inorganic salts such as calcium carbonate, ammonium sulfate, sodium sulfate, and potassium chloride.
  • liquid carrier examples include monohydric alcohols such as methanol, ethanol, propanol, isopropanol, and butanol, and polyhydric alcohols such as ethylene glycol, diethylene glycol, propylene glycol, hexylene glycol, polyethylene glycol, polypropylene glycol, and glycerin.
  • monohydric alcohols such as methanol, ethanol, propanol, isopropanol, and butanol
  • polyhydric alcohols such as ethylene glycol, diethylene glycol, propylene glycol, hexylene glycol, polyethylene glycol, polypropylene glycol, and glycerin.
  • Alcohols such as propylene glycol ether, ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone, cyclohexanone, ethyl ether, dioxane, ethylene glycol monoethyl ether, dipropyl ether, tetrahydrofuran, etc.
  • ketones such as acetone, methyl ethyl ketone, methyl isobutyl ketone, diisobutyl ketone, cyclohexanone, ethyl ether, dioxane, ethylene glycol monoethyl ether, dipropyl ether, tetrahydrofuran, etc.
  • Ethers normal paraffins, naphthenes, isoparaffins, kerosene, mineral oils and other aliphatic hydrocarbons
  • Aromatic hydrocarbons such as benzene, toluene, xylene, solvent naphtha, alkylnaphthalene, halogenated hydrocarbons such as dichloromethane, chloroform, carbon tetrachloride, ethyl acetate, diisopropyl phthalate, dibutyl phthalate, dioctyl phthalate, dimethyl adipate, etc.
  • Esters lactones such as ⁇ -butyrolactone, amides such as dimethylformamide, diethylformamide, dimethylacetamide, N-alkylpyrrolidinone, nitriles such as acetonitrile, sulfur compounds such as dimethylsulfoxide, soybean oil, rapeseed oil, Examples thereof include vegetable oils such as cottonseed oil and castor oil, and water. These may be used alone or in combination of two or more.
  • surfactants used as dispersants and wetting agents include sorbitan fatty acid esters, polyoxyethylene sorbitan fatty acid esters, sucrose fatty acid esters, polyoxyethylene fatty acid esters, polyoxyethylene resin acid esters, polyoxyethylene fatty acid diesters, Polyoxyethylene alkyl ether, polyoxyethylene alkyl aryl ether, polyoxyethylene alkyl phenyl ether, polyoxyethylene dialkyl phenyl ether, polyoxyethylene alkyl phenyl ether formalin condensate, polyoxyethylene polyoxypropylene block copolymer, polystyrene polyoxyethylene Block polymer, alkyl polyoxyethylene polypropylene block copolymer ether, polyoxye Lenalkylamine, polyoxyethylene fatty acid amide, polyoxyethylene fatty acid bisphenyl ether, polyalkylene benzyl phenyl ether, polyoxyalkylene styryl phenyl ether, acetylene dio
  • binders and tackifiers include carboxymethyl cellulose and salts thereof, dextrin, water-soluble starch, xanthan gum, guar gum, sucrose, polyvinyl pyrrolidone, gum arabic, polyvinyl alcohol, polyvinyl acetate, sodium polyacrylate, and an average molecular weight of 6000 to 20000.
  • Polyethylene glycol polyethylene oxide having an average molecular weight of 100,000 to 5,000,000, phospholipid (for example, cephalin, lecithin, etc.) cellulose powder, dextrin, modified starch, polyaminocarboxylic acid chelate compound, cross-linked polyvinylpyrrolidone, maleic acid and styrenes Polymers, (meth) acrylic acid copolymers, half-esters of polycarboxylic alcohol polymers and dicarboxylic acid anhydrides, water soluble salts of polystyrene sulfonic acid, para Fin, terpene, polyamide resins, polyacrylate, polyoxyethylene, wax, polyvinyl alkyl ethers, alkylphenol-formalin condensates, synthetic resin emulsions, and the like.
  • phospholipid for example, cephalin, lecithin, etc.
  • cellulose powder dextrin
  • polyaminocarboxylic acid chelate compound cross-linked polyviny
  • thickener examples include xanthan gum, guar gum, diyutane gum, carboxymethylcellulose, polyvinylpyrrolidone, carboxyvinyl polymer, acrylic polymer, starch derivative, water-soluble polymer such as polysaccharide, high-purity bentonite, fumed silica (fumed Inorganic fine powders such as silica and white carbon.
  • the colorant examples include inorganic pigments such as iron oxide, titanium oxide and Prussian blue, organic dyes such as alizarin dyes, azo dyes and metal phthalocyanine dyes.
  • antifreezing agent examples include polyhydric alcohols such as ethylene glycol, diethylene glycol, propylene glycol, and glycerin.
  • Adjuvants for preventing caking and promoting disintegration include, for example, polysaccharides such as starch, alginic acid, mannose, galactose, polyvinylpyrrolidone, fumed silica (fumed silica), ester gum, petroleum resin, sodium tripolyphosphate, Sodium hexametaphosphate, metal stearate, cellulose powder, dextrin, methacrylate copolymer, polyvinylpyrrolidone, polyaminocarboxylic acid chelate compound, sulfonated styrene / isobutylene / maleic anhydride copolymer, starch / polyacrylonitrile graft copolymer A polymer etc. are mentioned.
  • the decomposition inhibitor examples include desiccants such as zeolite, quicklime and magnesium oxide, antioxidants such as phenolic compounds, amine compounds, sulfur compounds and phosphoric acid compounds, and ultraviolet absorbers such as salicylic acid compounds and benzophenone compounds. It is done.
  • desiccants such as zeolite, quicklime and magnesium oxide
  • antioxidants such as phenolic compounds, amine compounds, sulfur compounds and phosphoric acid compounds
  • ultraviolet absorbers such as salicylic acid compounds and benzophenone compounds. It is done.
  • preservative examples include potassium sorbate, 1,2-benzothiazolin-3-one, and the like.
  • functional aids such as metabolic degradation inhibitors such as piperonyl butoxide, antifreezing agents such as propylene glycol, antioxidants such as BHT, UV absorbers and other supplements as necessary Agents can also be used.
  • the blending ratio of the active ingredient compound can be adjusted as necessary, and may be appropriately selected from the range of 0.01 to 90 parts by weight in 100 parts by weight of the agricultural and horticultural insecticide of the present invention.
  • 0.01 to 50 parts by weight 0.01 to 50% by weight based on the total weight of the agricultural and horticultural insecticide
  • the amount of the agricultural and horticultural insecticide of the present invention depends on various factors such as purpose, target pests, crop growth status, pest occurrence tendency, weather, environmental conditions, dosage form, application method, application location, application time, etc.
  • the active ingredient compound may be suitably selected from the range of 0.001 g to 10 kg per 10 ares, preferably 0.01 g to 1 kg depending on the purpose.
  • the pesticides of the present invention can be further controlled against other pests, insecticides for agro-horticultural use, acaricides, It can be used by mixing with nematodes, fungicides, biological pesticides, etc., and it can also be used by mixing with herbicides, plant growth regulators, fertilizers, etc. depending on the situation of use. .
  • XMC 3,5-xylyl methylcarbamate
  • Bacillus thuringienses aizawai Bacillus thuringienses israelensis, Bacillus thuringienses japonensis, Bacillus thuringienses kurstaki, Bacillus thuringienses tenebrionis, Bacillus thuringienses produced crystalline protein toxin, BPMC, Bt toxin C chlorfenson), DCIP (dichlorodiisopropyl ether), DD (1, 3-dichloropropene), DDT, NAC, O-4-dimethylsulfamoylphenyl O, O-diethyl phosphorothioate (DSP), O-ethyl O-4-nitrophenyl phenylphosphonothioate (EPN), tripropy
  • Examples of agricultural and horticultural fungicides used for similar purposes include aureofungin, azaconazole, azithiram, acipetacs, acibenzolar, acibenzolar-S-methyl. ), Azoxystrobin, anilazine, amisulbrom, ampropylfos, ametoctradin, allyl alcohol, aldimorph, amobam, isothianyl (Isotianil), isovaledione, isopyrazam, isoprothiolane, ipconazole, iprodione, iprovalicarb, iprobenfos, imazalil Iminoctadine, iminoctadine-albesilate, iminoctadine-triacetate, imibenconazole, uniconazole, uniconazole-P, eclomeole, echlomez Edifenphos, etaconazole, ethaboxam, e
  • Inorganic fungicides sodium hypochlorote, cupric hydroxide, wettable sulfur, calcium polysulfide, potassium hydrogen carbonate ), Sodium hydrogen carbonate, inorganic sulfur, copper sulfate anhydride, nickel dimethyldithiocarbamate, copper compounds such as 8-hydroxyquinoline copper (oxine copper) Examples thereof include zinc sulfate, copper sulfate pentahydrate and the like.
  • herbicides for example, 1-naphthylacetamide, 2,4-PA, 2,3,6-TBA, 2,4,5-T, 2,4,5-TB, 2,4-D, 2, 4-DB, 2,4-DEB, 2,4-DEP, 3,4-DA, 3,4-DB, 3,4-DP, 4-CPA, 4-CPB, 4-CPP, MCP, MCPA, MCPA thioethyl, MCPB, ioxynil, aclonifen, azafenidin, acifluorfen, aziprotryne, azimsulfuron, aslam, acetochlor, Atrazine, atraton, anisuron, anilofos, abiglycine, abscisic acid, amicarbazone, amidosulfuron, amitrole, amino Cyclopyrachlor (aminocyclopyrachlor), aminopyralid (aminopyralid), Amibu Amibuzin, amiprophos-methyl,
  • biological pesticides include nuclear polyhedrosis virus (NPV), granulosis virus (GV), cytoplasmic polyhedrosis virus (CPV), insect pox virus (Entomopoxivirus, EPV) ) And other virus preparations, Monocrosporium phymatophagum, Steinernema carpocapsae, Steinernema kushidai, Pasturia ⁇ pene insecticides, and Pasturia pene insecticides Microbial pesticides used as agents, bactericides such as Trichoderma lignorum, Agrobacterium radiobactor, non-pathogenic Erwinia carotovora, Bacillus subtilis Microbial pesticide to be used in, by using mixed such as biological pesticides utilized as herbicides, such as Xanthomonas campestris (Xanthomonas campestris), the same effect can be expected.
  • NPV nuclear polyhedrosis virus
  • GV granulosis virus
  • CPV
  • examples of biological pesticides include Encarsia formosa, Aphidius colemani, Aphidoletes aphidimyza, Diglyphus isaea, Dacnusahysrica persimilis), natural enemies such as Amblyseius cucumeris, Orius sauteri, microbial pesticides such as Beauveria brongniartii, (Z) -10-tetradecenyl acetate, (E, Z) ) -4,10-tetradecadinyl acetate, (Z) -8-dodecenyl acetate, (Z) -11-tetradecenyl acetate, (Z) -13-icosen-10-one, 14-methyl-1 - May also be used in combination with pheromone agents such as octadecene It is a function.
  • pheromone agents such as octadecene It is a function.
  • Formulation Example 1 Compound of the present invention 10 parts Xylene 70 parts N-methylpyrrolidone 10 parts Mixture of polyoxyethylene nonylphenyl ether and calcium alkylbenzenesulfonate 10 parts The above components are uniformly mixed and dissolved to prepare an emulsion.
  • Formulation Example 2 Compound of the present invention 3 parts Clay powder 82 parts Diatomaceous earth powder 15 parts The above is mixed and ground uniformly to form a powder.
  • Formulation Example 3 Compound of the present invention 5 parts Mixed powder of bentonite and clay 90 parts lignin sulfonate 5 parts The above is uniformly mixed, kneaded with an appropriate amount of water, granulated and dried to give granules.
  • Formulation Example 4 Compound of the present invention 20 parts Kaolin, synthetic highly dispersed silicic acid 75 parts Polyoxyethylene nonylphenyl ether and calcium alkylbenzene sulfonate 5 parts The above is uniformly mixed and ground to obtain a wettable powder.
  • Control value test for peach aphid ( Myzus persicae ) Chinese cabbage was planted in a plastic pot having a diameter of 8 cm and a height of 8 cm to breed a peach aphid, and the number of parasites in each pot was investigated.
  • the benzyloxypyrimidine oxide derivative represented by the general formula (I) of the present invention or a salt thereof is dispersed in water and diluted to a chemical solution of 500 ppm. The chemical solution is sprayed on the stems and leaves of potted Chinese cabbage and air-dried.
  • the number of parasites of the peach aphid parasitizing each Chinese cabbage was stored on the 6th day after spraying the chemical, and the control value was calculated from the following formula, and the determination was made according to the following criteria.
  • Ta Number of parasites before spraying in the treated zone
  • Ca Number of parasites before spraying in the untreated zone
  • C Criteria for determining the number of parasites after spraying in the untreated zone.
  • Test Example 2 Insecticidal test against green planthopper (Nilaparvata lugens)
  • the benzyloxypyrimidine oxide derivative represented by the general formula (I) of the present invention or a salt thereof is dispersed in water and diluted to a chemical solution of 500 ppm, and rice seedlings (variety: Nipponbare) )
  • rice seedlings variety: Nipponbare
  • Test Example 3 Mite killing test for Haemaphysalis longicornis Sponge cotton is spread on the bottom of a glass bottle with a diameter of 3cm x height of 4.5cm, and the benzyloxypyrimidine oxide derivative represented by the general formula (I) of the present invention or its salt is dispersed in water 2 ml of the chemical solution diluted to 200 ppm was added dropwise. After inoculating 5 each of the tick tick, cover with a mesh, 4 days after inoculation, the number of live and dead insects was investigated, the corrected death rate was calculated from the following formula, and the determination was made according to the criteria of Test Example 1 .
  • the compounds Nos. 1-19 and 1-71 showed an acaricidal effect of D against Phytophthora tick.
  • the benzyloxypyrimidine oxide derivative or its salt of the present invention has an excellent effect as an agricultural and horticultural insecticide. On the other hand, it is also effective against pets such as dogs and cats or pests parasitic on livestock such as cattle and sheep.

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Abstract

La présente invention concerne un dérivé d'oxyde de benzyloxypyrimidine représenté par la formule générale (I) ou son sel ; un pesticide à usage agricole ou horticole, qui contient le composé comme principe actif ; et une utilisation agricole ou horticole du pesticide. (Dans la formule, R1 représente un groupe alkyle, un groupe cycloalkyle, un groupe alcényle, un groupe alcynyle, un groupe halogénoalkyle, un groupe halogénoalcényle, un groupe halogénoalcynyle, un groupe alcoxyalkyle ou similaire ; R2 ou R3 représente un atome d'hydrogène, un groupe alkyle ou similaire ; X représente un groupe alkyle, un groupe cycloalkyle, un groupe alcényle, un groupe alcynyle, un groupe halogénoalkyle, un groupe halogénoalcényle, un groupe halogénoalcynyle, un groupe trialkylsilyle ou similaire ; A représente un atome d'oxygène ou similaire ; l représente 0 ou 1 ; m représente un nombre entier allant de 0 à 5 ; et n représente 0 ou 1. A cet égard, l et n ne valent pas 0 en même temps.)
PCT/JP2013/051665 2012-01-26 2013-01-25 Dérivé d'oxyde de benzyloxypyrimidine, pesticide à usage agricole ou horticole contenant le dérivé d'oxyde de benzyloxypyrimidine et applications associées WO2013111885A1 (fr)

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WO2010064688A1 (fr) * 2008-12-03 2010-06-10 日本農薬株式会社 Dérivés pyrimidines, insecticides pour cultures maraîchères comportant de tels dérivés et leur procédé d’utilisation
WO2012086768A1 (fr) * 2010-12-24 2012-06-28 日本農薬株式会社 Dérivé de benzyloxypyrimidine, insecticide agricole/horticole comprenant le dérivé et son procédé d'utilisation

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WO2016104516A1 (fr) * 2014-12-22 2016-06-30 日本農薬株式会社 Composition d'agent de lutte contre les organismes nuisibles pour des applications agricoles et horticoles, et procédé d'utilisation de ladite composition
CN106998689A (zh) * 2014-12-22 2017-08-01 日本农药株式会社 用于农业和园艺应用的有害生物防除剂组合物和应用该组合物的方法
JPWO2016104516A1 (ja) * 2014-12-22 2017-09-28 日本農薬株式会社 農園芸用有害生物防除剤組成物及びその使用方法

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