WO2007040280A1 - 環状アミン化合物および有害生物防除剤 - Google Patents
環状アミン化合物および有害生物防除剤 Download PDFInfo
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- WO2007040280A1 WO2007040280A1 PCT/JP2006/320126 JP2006320126W WO2007040280A1 WO 2007040280 A1 WO2007040280 A1 WO 2007040280A1 JP 2006320126 W JP2006320126 W JP 2006320126W WO 2007040280 A1 WO2007040280 A1 WO 2007040280A1
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- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/22—Bridged ring systems
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- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
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- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
- A01N43/42—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings condensed with carbocyclic rings
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- 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
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- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
- A01N43/76—1,3-Oxazoles; Hydrogenated 1,3-oxazoles
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- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
- A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
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- A—HUMAN NECESSITIES
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- 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
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
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- A—HUMAN NECESSITIES
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- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/82—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with three ring hetero atoms
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- A—HUMAN NECESSITIES
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- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
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- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/54—Sulfur atoms
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- C07D211/00—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings
- C07D211/04—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D211/06—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no double bonds between ring members or between ring members and non-ring members
- C07D211/36—Heterocyclic compounds containing hydrogenated pyridine rings, not condensed with other rings with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having no 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D211/56—Nitrogen atoms
- C07D211/58—Nitrogen atoms attached in position 4
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- C07D221/02—Heterocyclic compounds containing six-membered rings having one nitrogen atom as the only ring hetero atom, not provided for by groups C07D211/00 - C07D219/00 condensed with carbocyclic rings or ring systems
- C07D221/22—Bridged ring systems
- C07D221/24—Camphidines
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- C07D237/00—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings
- C07D237/02—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings
- C07D237/06—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D237/08—Heterocyclic compounds containing 1,2-diazine or hydrogenated 1,2-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
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- C07D241/02—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings
- C07D241/10—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D241/14—Heterocyclic compounds containing 1,4-diazine or hydrogenated 1,4-diazine rings not condensed with other rings having three 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
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- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
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- C07D417/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings
- C07D417/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for by group C07D415/00 containing two hetero rings directly linked by a ring-member-to-ring-member bond
Definitions
- the present invention relates to a novel cyclic amine compound and the like and a pest control agent containing the cyclic amine compound and the like as an active ingredient.
- a compound represented by the formula is known. (See Patent Document 1). However, the structure is limited to the 4-aminoviridine derivative and the 4-hydroxypyridine derivative, and other structures have been specifically disclosed.
- Patent Document 1 Special Table Hei 09-502446
- An object of the present invention is to provide a novel skeleton pest control agent that can be advantageously synthesized industrially, has excellent biological activity, and has a safety problem.
- Y 1 and Y 2 each independently represent a nitrogen atom or a carbon atom, and * represents a bonding position).
- X represents an oxygen atom, a sulfur atom, a sulfinyl group, a sulfonyl group, or a nitrogen atom that is unsubstituted or substituted.
- R may be bonded to form a ring but may not be bonded to form a ring.
- R represents a hydroxyl group, a halogen atom, an unsubstituted or substituted amino group, a nitro group, or an organic group.
- ⁇ represents 0 or an integer of 1 to 9, and when ⁇ is 2 or more, Rs are the same or different.
- Cy 2 represents an unsubstituted or substituted cyclic hydrocarbon group or an unsubstituted or substituted heterocyclic ring.
- a phenyl group having a Cy 1 is an unsubstituted or substituted group
- Cy 2 is pyridyl - 2
- pyridyl Cy 2 is substituted by least when one Shiano group - 2-I le radical Represents.
- a salt thereof or an N-oxide thereof as an active ingredient is
- the second of the present invention is the formula (2)
- Cy 3 represents any one of the formulas (b) to (! I),
- R 6 represents a haloalkyl group or a haloalkoxy group.
- R 7 represents an unsubstituted or substituted alkoxy group, an unsubstituted or substituted alkoxycarbo group, an unsubstituted or substituted alkoxyalkyl group, or a group represented by the formula (i):
- R 15 and R 16 are each independently a hydrogen atom, an unsubstituted or substituted hydrocarbon group, an unsubstituted or substituted heterocyclic group, an unsubstituted or substituted amino group; , A hydrocarbonoxy group, or a hydrocarbonthio group, R 15 and R 16 may combine to form a ring, in which case they both represent a functional group that can form a ring together.
- Z 1 represents an oxygen atom or an unsubstituted or substituted nitrogen atom. Represents a functional group.
- R 8 to R 14 are each independently a hydroxyl group, thiol group, halogen atom, nitro group, formyl group, cyano group, haloalkyl group, haloalkoxy group, haloalkenyl group, unsubstituted or substituted with G 1 Alkyl group, unsubstituted or substituted with G 1 , alkyl carbo group, alkoxy carbo yl group, alkyl group, alkoxy group, alkynyloxy group, unsubstituted or with G 1 It represents a substituted aryl group or a functional group represented by formula (i).
- G 1 represents a hydroxyl group, a halogen atom, an unsubstituted or substituted amino group, a nitro group, or an organic group.
- k, 1, n, and o each independently represent 0 or an integer from 1 to 4, and k, 1, n, and o.
- R 8 s , R 9 s , R 11 s , and R 12 s are the same or different.
- n 0 or an integer of 1 to 5, and when m is 2 or more, R 1Qs are the same or different.
- p and q each independently represent 0 or any integer of 1 to 3, and when p and q are 2 or more, R 13 and R 14 are the same or different.
- X represents an oxygen atom, a sulfur atom, a sulfinyl group, a sulfonyl group, or a nitrogen atom that is unsubstituted or substituted.
- R 1 and R 2 , R 1 and R 4 , R 2 and R 3 , or R 3 and R 4 may be joined together to form a saturated ring, and may be joined together to form a saturated ring R 1 , R 1 , R 2 , R 2 , R 3 , R 3 , R 4 , R 4 , R 5 are respectively
- it represents a hydrogen atom, a hydroxyl group, a halogen atom, an unsubstituted or substituted amino group, a nitro group, or an organic group.
- Cy is a functional group represented by formula (c), (g), or (h), it is unsubstituted or substituted with G 2 (pyridine 2-yl substituted with one or more cyan groups) Group, pyridine 3-yl group, pyridazine 3-yl group, pyrajur group, thiazole-2-yl group, pyrimidine 2-yl group, 1,3,4-thiadiazole-2-yl group, or phenol Group)
- Cy 3 is a functional group represented by the formula (b), (e) or (f), it is unsubstituted or substituted by G 2 (pyridine-2-substituted with one or more cyan groups).
- Cy is a functional group represented by the formula (d), it is unsubstituted or substituted with G 2 (a pyridine-2-yl group substituted with one or more cyano groups, a birazinyl group, or 1, 3,4-Chiasia Zole 2—yl group).
- G 2 is a hydroxyl group, halogen atom, cyano group, nitro group, formyl group, unsubstituted or substituted with G 3 (alkyl group, alkoxy group), haloalkyl group, haloalkoxy group, alkylthiocarbol group, alkylsulfo group.
- -Lamino group haloalkylsulfo-lamino group, bis (alkylsulfol) amino group, bis (noxylalkylsulfol) amino group, alkoxycarbonyl group, unsubstituted or substituted with G 1 aryl group, (Containing at least one heteroatom selected from oxygen atom, nitrogen atom and sulfur atomic energy) 5- to 6-membered heterocyclic group, or formula (1) to (1)
- R 17 and R 18 are each independently a hydrogen atom, an unsubstituted or substituted hydrocarbon group, an unsubstituted or substituted heterocyclic group, an unsubstituted or substituted amino group;
- R 19 and R 22 each independently represent a hydrogen atom, an unsubstituted or substituted hydrocarbon group, an unsubstituted or substituted heterocyclic group.
- R 20 represents a hydrogen atom, an unsubstituted or substituted hydrocarbon group
- R 21 represents a hydrogen atom, an unsubstituted or substituted hydrocarbon group.
- R 17 and R 18 , R 19 and R 2 °, R 21 and R 22 may be combined to form a ring.
- G 3 represents a hydroxyl group, a cyano group, an alkoxy group, an alkoxyalkoxy group, or a trialkylsilyloxy group. Or a salt thereof or an N monoxide thereof.
- a highly safe pest control agent having excellent biological activity, particularly in insecticidal and acaricidal activity, and a cyclic amine compound having a novel structure, or The salt or its N-acid can be provided.
- a pest control agent comprising a cyclic amine compound represented by the formula (1), a salt thereof or an N-acid compound as an active ingredient.
- the pest control agent of the present invention is characterized in that it contains a cyclic amine compound represented by the formula (1), or a salt or N-acid salt thereof as an active ingredient.
- Cy 1 is an unsubstituted or substituted heterocyclic 5-membered cyclic group or a functional group represented by the formula (a) having an unsubstituted or substituted group.
- the hetero 5-membered ring group is not particularly limited as long as it is a 5-membered ring having one or more hetero atoms in the ring, and may be saturated or unsaturated.
- Specific examples include pyrrolidine 2-yl group, pyrrolidine-3-yl group, furan-2-yl group, furan-3-yl group, thiophene-2-yl group, thiophene 3-yl group, Group, pyrrole 3-yl group, oxazole-2-yl group, oxazole-4-yl group, oxazole-5-yl group, thiazole-2-yl group, thiazole-4-yl group, thiazole-5-yl group, Isoxazole-3-yl group, Isoxazole-4-yl group, Isoxazole-5-yl group, Isothiazole-3-yl group, Isothiazole-4-yl group, Isothiazole-5-yl group
- Formula (a) is unsubstituted or substituted (a phenyl group, a pyridine-2-yl group, a pyridin-3-yl group, or a pyridazine-3-yl group), which is unsubstituted or substituted.
- a phenyl group having a group is preferred.
- substituent for Cy 1 include: hydroxyl group; thiol group; halogen atom such as fluorine atom, chlorine atom, bromine atom and iodine atom; cyan group; nitro group; formyl group; amino group, methyl amino group, benzylamino group , ⁇ - Rinomoto, Jimechiruamino group, Jechiruamino group, Hue - unsubstituted or substituted amino groups such as Le Echiruamino group; a methyl group, Echiru radical, n-propyl group, an isopropyl radical, n-butyl group, s-butyl group, an isobutyl group, t alkyl group such as butyl group, n-pentyl group, n- hexyl group (c alkyl group is preferred);
- Alkenyl groups such as aryl groups and 2-methoxyethenyl groups
- alkyl groups such as etulyl groups, 1-propynyl groups, 2-phenylethyl groups and propargyl groups
- methoxy groups, ethoxy groups, propoxy groups isopropoxy groups Group, n -butoxy group, s butoxy group, isobutoxy group, t-butoxy group, etc. (C alkoxy group is preferred)
- Alkenyloxy groups such as ethynoxy groups and propargyloxy groups
- Alryloxy groups such as phenoxy groups and benzyloxy groups
- Heteroaryloxy groups such as 2-pyridyloxy groups
- Chloromethyl groups and fluoromethyl groups Group bromomethyl group, dichloromethyl group, difluoromethyl group, dibromomethyl group, trichloromethyl group, trifluoromethyl group, bromodifluoromethyl group, 1, 1, 1 trifluoroethyl group, 1 chloroethyl group
- Haloalkyl groups such as 2-chloroethyl, 1 bromoethyl, 2-bromoethyl, pentafluoroethyl (C haloalkyl is preferred! /,);
- Fluoromethoxy group chloromethoxy group, bromomethoxy group, difluoromethoxy group, dichloromethoxy group, dibromomethoxy group, trifluoromethoxy group, trichloromethoxy group, tribromomethoxy group, 1, 1, 1 trifluoroethoxy group, Haloalkoxy groups such as pentafluoroethoxy group and heptafluoroisopropoxy group (C haloalkoxy group is preferred);
- Tilthiocarbol group ethylthiocarbol group, propylthiocarbol group, iso Alkylthio group such as propylthiocarbonyl group, n-butylthiocarbonyl group, isobutylthiocarbonyl group, sbutylthicarbol group, t-butylthiocarbonyl group (C alkylthiocarbol group is preferred! /,); Methylsulfo-lumino group
- Alkylsulfo-lamino groups such as ethylsulfo-lamino group, n-propylsulfo-lamino group, isopropylsulfo-lamino group, n-butylsulfo-lamino group, t-butylsulfo-lamino group (C alkylsulfo-lamino group is preferred! /,); Phenolsulfo
- -Arylsulfo-Luamino group such as -Luamino group (C-Arylsulfo-Luamino group is preferred)
- Alkyl carbolumino groups such as carbolumino group, n-propyl carbolumino group, isopropyl carbolumino group (C alkyl carbolumino group is preferred);
- Alkoxycarbolamino groups such as toxicarbolamino group, ethoxycarbolamino group, n-propoxycarboamino group, isopropoxycarbolamino group (C
- fluoromethylsulfo-lumino group chloromethylsulfo-lamino group, bromomethylsulfo-lamino group, difluoromethylsulfo-lamino group, dichloromethylsulfo-lamino group, difluro group
- Haloalkylsulfo-amino groups such as trifluoroethylsulfo-amino group, trifluoromethylsulfo-lumino group, 1, 1, 1 trifluoroethylsulfo-lumino group, pentafluoroethylsulfo-lumino group (C haloalkyl) Sulfo-Lamino group is preferred); bis (methylsulfo) amino group, bis
- alkylsulfol such as (n-propylsulfol) amino group, bis (isopropylsulfol) amino group, bis (n-butylsulfol) amino group, bis (t-butylsulfol) amino group Amino group (bis (C alkylsulfo) amino group is preferred); bis (full
- Fluoromethylsulfo) amino group bis (chloromethylsulfol) amino group, bis (bromomethylsulfol) amino group, bis (difluoromethylsulfol) amino group, bis (dichroylmethylsulfol) amino Group, bis (difluoroethylsulfol) amino group, bis (trifluoromethylsulfol) amino group, bis (1,1,1-trifluoroethylsulfol) amino group, bis ( Bis (noxyl alkylsulfo) such as pentafluoroethylsulfol) amino group -L) amino group (preferably bis (C haloalkylsulfo) amino group); hydrazino group
- Unsubstituted or substituted hydrazino groups such as ⁇ '-phenylhydrazino group, ⁇ '-methoxycarbo-hydrazino group; methoxycarbonyl group, ethoxycarbonyl group, propoxycarbonyl group, isopropoxycarbol group, ⁇ butoxycarbo- Group, alkoxyl group such as t-butoxycarbonyl group (C alkoxycarbonyl group is preferred);
- Aralkyl groups such as benzyl and phenethyl groups (c aralkyl groups are preferred); furan
- Cyclic group 2-tetrahydrafullylmethyl group, 3-piperazylmethyl group, N-methyl-3 pyrrolidyl Saturated heterocyclic alkyl groups such as methyl group and morpholinomethyl group; N unsubstituted such as N dimethylaminoiminomethyl group, 1-N-phenyl-minoethyl group, N hydroxyiminomethyl group, N-methoxyiminomethyl group or the like N-substituted minoalkyl group; N 'methyl hydrazino carbo ol group, N'-phenol hydrazino carbo ol group, hydrazino carbo ol group, etc.
- N unsubstituted or N substituted hydrazino carbo ol group N-substituted or N-substituted aminocarbonyl group such as dimethylaminocarbonyl group, N-phenyl N-methylaminocarbonyl group; hydrazino group, N'-acetyl hydrazino group, N 'methylhydra group N-unsubstituted or N-substituted hydrazino groups such as dino group, N 'phenhydrazino group, N'-methoxycarbohydrazino group, N'-2-propylidenehydrazino group; methylthio Alkylthio groups such as ethylthio group and t_butylthio group; alkylthio groups such as bierthio group and allylthio group; alkylthio groups such as ethynylthio group and propargylthio group; furthio group, 4-chloro
- hydrocarbon group examples include alkyl groups such as methyl group, ethyl group, isopropyl group, ⁇ -propyl group, ⁇ -hexyl group, and ⁇ -octyl group, bur group, and aryl group.
- Alkyl groups such as alkyl groups such as alkyl groups, 1 propellate groups, 2 ferrule groups, ethur groups, and open pargil groups, phenol groups, 1 naphthyl groups, 9 anthracel groups, etc.
- An aromatic hydrocarbon group etc. can be illustrated.
- heterocyclic group examples include a furan 2-yl group, a furan 3-yl group, a thiophene 2-yl group, a thiophene 3-yl group, a pyrrole 2-yl group, and a pyrrole-luo 3— Group, oxazole 2-yl group, oxa Sol-4-yl group, oxazole-5-yl group, thiazole-2-yl group, thiazo 4-yl group, thiazole-5-yl group, isoxazol-3-yl group, isoxazo-lu 4-yl Group, isoxazole-5-yl group, isothiazole-3-yl group, isothiazole-4-yl group, isothiazole-5-yl group, imidazole-2-yl group, imidazole-4-yl group, imidazole-5-yl group , Pyrazol-3-yl group, pyrazole-4-yl group,
- Unsaturated hetero 6-membered ring alkyl group Tetrahydrofuran-2-yl group, Tetrahydran-4-yl group, Piperidine-3-yl group, Pyrrolidine-2-yl group, Morpholino group, Piperidino group, N —Saturated heterocyclic groups such as methylbiperazyl group; Examples thereof include saturated heterocyclic alkyl groups such as 2-tetrahydrafuranylmethyl group, 3-piperazylmethyl group, N-methyl 3-pyrrolidylmethyl group, morpholinomethyl group and the like.
- hydrocarbonoxy group and the hydrocarbonthio group include a methoxy group, an ethoxy group, an isopropoxy group, a phenoxy group, a benzyloxy group, a 2-pyridyloxy group, a methylthio group, an ethylthio group, a phenylthio group, Examples thereof include a benzylthio group and a 2-pyridylthio group.
- substituent of the functional group contained in R 6 and R 7 are the same as the specific examples exemplified as the substituent of Cy 1 .
- Specific examples of the functional group represented by the formula (i) include functional groups represented by the following formula.
- Y 1 and Y 2 each independently represent a nitrogen atom or a carbon atom.
- X represents an oxygen atom; a sulfur atom; an unsubstituted or a nitrogen atom having a substituent similar to the specific example of the substituent of Cy 1 ; a sulfier group; a sulfole group; and an oxygen atom is particularly preferred.
- Rs may be joined together to form a saturated ring, particularly the piperidine ring is preferably bonded at the 2nd and 6th positions and the 3rd and 5th positions to form a saturated ring. It is preferable that the number of atoms of the bridging site forming the ring is 2 or 3.
- the element constituting the bridge portion of the saturated ring is not particularly limited as long as it is within a chemically acceptable range, and specifically, a carbon atom, an oxygen atom, a sulfur atom, a nitrogen atom, or a key atom Etc., and can be configured by combining two or more of them within the chemically acceptable range.
- each atom can have a hydrogen atom or a substituent within a chemically acceptable range, and within a chemically acceptable range, a double bond is formed with an oxygen atom, a sulfur atom, or a nitrogen atom.
- a carbonyl group a thiocarbonyl group, an imino group, or the like.
- R does not form a saturated ring, each independently represents a hydrogen atom, a halogen atom, an unsubstituted or substituted amino group, a nitro group, a hydroxyl group, or an organic group.
- the organic group include a cyan group; a formyl group; an alkyl group, an alkoxycarbo group, an alkoxy group, a haloalkyl group, a haloalkoxy group, an alkylthiocarbol group, an alkyl sulfo-lamino group, and a haloalkyl sulfo-lumino group.
- an alkyl group; an alkoxycarbo group; an alkoxy group is preferred C alkyl group; a C alkoxycarbo group; a C alkoxy group
- n 0 or an integer of 1 to 9, and when n is 2 or more, Rs are the same or different.
- Cy 2 represents an unsubstituted or substituted cyclic hydrocarbon group or an unsubstituted or substituted heterocyclic ring.
- aromatic hydrocarbon groups such as phenyl, naphthyl-1-yl, naphthyl-2-yl, etc .
- Cy 1 is an unsubstituted or substituted phenol group, and Cy 2 has a substituent.
- Cy 2 represents a pyridyl-2-yl group substituted with at least one cyano group.
- Cy 1 is an unsubstituted or substituted phenyl group
- Cy does not include an unsubstituted pyridyl-2-yl group.
- a pyridyl-2-yl group substituted with one cyan group may have a substituent other than a cyan group.
- Cy 3 represents the above formulas (b) to ( 1) Indicates a functional group represented by one of the above.
- R 6 include the same as those exemplified as a part of specific examples of the substituent of Cy 1 .
- R 8 to R 14 may be the same as some of those specifically exemplified as the substituent for Cy 1 .
- G 1 which can be a part of the substituents of R 8 to R 14 , specifically, the same examples as those partly exemplified as the substituent of Cy 1 can be exemplified. Can do.
- X is a nitrogen atom having a substituent
- specific examples of the substituent of the nitrogen atom include the same substituents as the specific examples of the substituent of Cy 1 .
- R 1 and R 2 , R 1 and R 4 , R 2 and R 3 , or R 3 and R 4 are joined together to form a saturated ring
- R 1 and R 4 And R 2 , or R 3 and R 4 are preferably joined together to form a saturated ring.
- the number of atoms of the bridging site forming the saturated ring is preferably 2 or 3.
- the elements constituting the crosslinking site of the saturated ring are within a chemically acceptable range. There are no particular limitations, and specific examples include carbon atoms, oxygen atoms, sulfur atoms, nitrogen atoms, or key atoms, and two of these are within the chemically acceptable range. These can be combined.
- each atom can have a hydrogen atom or a substituent within a chemically acceptable range, and through a double bond with an oxygen atom, a sulfur atom, or a nitrogen atom within the chemically acceptable range.
- a carbonyl group a thiocarbonyl group, an imino group, or the like.
- R 1 , R 1 , R 2 , R 2 , R 3 , R 3 , R 4 , R 4 , and R 5 that are not joined together to form a saturated ring are
- the organic group represents a general functional group containing a carbon atom, and specific examples thereof include a cyan group; a formyl group; an alkyl group; an alkoxycarbo group; an alkoxy group; a haloalkyl group; a haloalkoxy group; Alkylsulfuramine group; haloalkylsulfo-lumino group; bis (alkylsulfo-amino) group; bis (nocylalkylsulfo-amino) amino group; alkoxycarboro group; aryl group; it can.
- the organic group is preferably an alkyl group; an alkoxycarbo group; an alkoxy group; a C alkyl group; a C alkoxycarbo group; a C alk
- Specific examples of a part of G 2 in Cy 4 can be the same as some of the specific examples exemplified as the substituent of Cy 1 .
- specific examples of the hydrocarbon group commonly contained in R ′′ to R 22 include a methyl group, an ethyl group, an isopropyl group, an n-propyl group, Alkynyl such as n-hexyl group, alkyl group such as n-octyl group, vinyl group, aryl group, 1 propylene group, 2-alkyl group, alkenyl group, ethur group, propargyl group, etc.
- aromatic hydrocarbon groups such as a group, a phenyl group, a 1 naphthyl group, and an 9 anthracel group, etc.
- Specific examples of the cyclic group include furan-2-yl group, furan-3-yl group, thiophene 2-yl group, thiophene-3-yl group, pyrrole-2-yl group, pyrrole-lue 3— Yl group, oxazole-2-yl group, oxazole-4-yl group, oxazole-5-yl group, thiazole -2-I group, Chiazoru 4 Iru group, Chiazoru 5 I group, Isoxazole-3-yl group, isoxazole-4-yl group, isoxazole-5-yl group, isothiazole-3-yl group, isothiazole-4-yl group,
- hydrocarbon oxy group and the hydrocarbon thio group commonly contained in R 17 and R 18 include methoxy group, ethoxy group, isopropoxy group, phenoxy group, benzyloxy group, 2-pyridyloxy group, methylthio group. Group, ethylthio group, phenolthio group, benzylthio group, 2-pyridylthio group and the like.
- substituent of the functional group contained in R 17 to R 22 are the same as the specific examples exemplified as the substituent of Cy 1 .
- Z and Y each independently represent an oxygen atom or an unsubstituted nitrogen or a nitrogen atom having a substituent, and the substituent on the nitrogen atom is the same as the specific example exemplified as the substituent of Cy 1
- Specific examples of the alkyl group in G 2 and G 3 as a substituent of the alkoxy group include hydroxy Group: a cyan group; an alkoxy group similar to the specific example of the substituent of Cy 1 (C alkoxy group is preferred)
- Alkoxyalkoxy groups such as methoxymethoxy, ethoxymethoxy and propoxyethoxy groups (C alkoxy C alkoxy groups are preferred); trimethylsilyloxy groups
- N-acids of the compounds represented by formulas (1) and (2) include nitrogen atoms in the cyclic amine part of the compounds represented by formulas (1) and (2) and nitrogen on the nitrogen-containing heterocycle Examples include compounds in which atoms are oxidized.
- salts of the compounds represented by the formulas (1) and (2) include salts of inorganic acids such as hydrochloride, nitrate, sulfate and phosphate; acetate, lactate, propionate, benzoate And salts of organic acids such as acid salts.
- Compound (2) is, for example, a compound represented by formula (3) (hereinafter referred to as “compound”
- X ′ represents a leaving group such as a halogen atom, and R, represents a protecting group.
- Compound (3) which is a production intermediate, can be produced by a general reaction as follows.
- the X 1 and X 2 each independently represent a hydroxyl group or a mercapto group, and X 3 represents a leaving group such as a halogen atom.
- Compound (2) can also be produced by the general method shown below.
- X 4 represents a leaving group such as a halogen atom
- X 5 represents a hydroxyl group or a mercapto group.
- the starting compound (10) can be produced by a general reaction as shown in the following reaction formula (IV).
- X 6 represents a leaving group such as a halogen atom.
- compound (16) The compound represented by the formula (16) (hereinafter referred to as “compound (16)”) can be produced by a general method as shown in the following reaction formula (V).
- the R ′ represents a substituent on a nitrogen atom such as a hydrogen atom, a trifluoroacetyl group, or a trifluoromethylsulfonyl group.
- X 7 represents a halogen atom; a leaving group such as a sulfonyloxy group.
- Compound (16) which is the compound of the present invention can also be produced by a general coupling reaction as shown in the following reaction formula (VII).
- a pest control agent comprising a cyclic amine compound represented by formula (1) or formula (2), or a salt thereof or an N-oxide thereof as an active ingredient.
- the compounds of the present invention (Compounds (1) and (2), their salts or N-acid compounds) have excellent killing, larvicidal, larvicidal and ovicidal action and are It can be used to control pests, sanitary pests, storage shell pests, clothing pests, house pests, etc. Typical examples include the following.
- Lepidopterous pests for example, Spodoptera, Scutum, Tamanayaga, Aomushi, Tamanaginu Sugano, Konaga, Shiyanokokakumonamaki, Chihamaki, Momosintaiiga, Nashihimeshingi, Mikanhamogiga, Chiyanhosoga, Kinmonhosoga Corn borer, white-faced butterfly, genus Helicotis, genus Helicobelpa, genus Agrotis, iga, codling moth, stag beetle, and the like, Hemiptera pests, for example, peach aphid, stag aphid, cedar aphid, wheat Kubira beetle, hoso-helical beetle, horn-tailed beetle, arachnid scale, beetle beetle, on-white bug, tobacco whitefly, silver leaf whitefly, pear Lice, no tingidae, Tobii
- Coleopterous pests e.g., Kisomomi beetle, cucumber worm, Colorado potato beetle, rice weevil, beetle, azuki beetle, bean bug, beetle, diabrotica, tobacco beetle, beetle worm, beetle, beetle ⁇ Tamizomushi, etc.
- Diptera pests for example, houseflies, blue flies, centribuses, uriminosukue, citrus fruit flies, terrestrial flies, rice fly wings, Drosophila melanogaster flies, sand flies, cochlear mosquitoes, net power, power
- Azamuma pests for example, Southern thrips, Cyanophyllum thrips, etc.
- Hymenoptera pests for example, Himeari, Kirosuzubachi, power brahwachi, etc.
- Straight-eyed pests for example, Tonosama grasshopper, Crested cockroach, Crested cockroach, Black-eye cockroach, etc.
- Termite pests such as termites, termites,
- Lepidoptera e.g., human fleas, cat fleas, lice, pests, e.g., human lice, ticks, e.g., Nami Hadaji, Nisenami Hadaji, Kanza Hadaji, Citrus mite, Apple Hada-, Mika Sabida-, Apple Sabida, Tiyano Korida, Brevipalpus genus, Meteor Tranicus genus, Robinne tick, Kenagakonadani mite, Scarlet mite, tick ticks, winged tick, etc.
- Plant parasitic nematodes for example, Satsumaemonebu Sentiyu, Nesare Sentiyu, Dizushi Sentiyu, Rice Singale Sentiyu, Matsunoza Sentiyu and the like.
- Pests that are preferably applied are lepidopterous insects, semilepidopterous insects, mites, azamuma insects, and coleopteran insects, and particularly preferably mites.
- the compound of the present invention is an agent having an insecticidal and acaricidal effect that is excellent not only for susceptible strains, but also for insects resistant to organophosphates, carbamates, and pyrethroids, and mites that are resistant to acaricides.
- the compound of the present invention is a highly safe drug with low toxicity to fish and warm-blooded animals with less phytotoxicity.
- the compound of the present invention can also be used as an antifouling agent for preventing aquatic organisms from adhering to underwater contact objects such as ship bottoms and fish nets.
- some of the compounds of the present invention exhibit bactericidal activity, herbicidal activity, and planting action. Some intermediate compounds of the compounds of the present invention exhibit insecticidal and acaricidal activity. It goes without saying that the compounds of the present invention are sufficiently effective alone, but other pesticides, fungicides, insecticides / acaricides, herbicides, plant regulators, synergists, fertilizers, soil conditioners, It can also be mixed or used in combination with one or more animal feeds.
- active ingredients such as bactericides, insecticides, acaricides, plant growth regulators and the like that can be used in combination with or in combination with the compounds of the present invention are shown below.
- Fungicide Quybutane, phorpet, thiuram, ziram, dineb, mannebu, mancozeb, propineb, polycarbamate, chlorothinine, quintozene, captaphor, diplodione, prosiminone, fluorimide, meprol, flutral, pencyclon, oxycarboxy , Fosetyl aluminum, propamocurve, triadimethone, triadimenol, propiconazonole, diclobutrazoneore, bitenoretanonore, hexaconazonole, microbutaninole, flusilazole, etaconazole, flutrimazole, flutriafen, penconazonore, diniconasole , Cyproconazoze, Huena Limonole, Trifnore Misonore, Prokuguchi Raz, Imazalinole, Pephrazoate, Tridemonolev,
- Microbial pesticides such as BT and insect pathogenic viruses.
- Plant growth regulator Plant growth regulator:
- Gibberellins eg, gibberellin A3, gibberellin A4, gibberellin A7 IAA, NAA and the like.
- the pest control agent of the present invention contains one or more of the compounds of the present invention as an active ingredient.
- the compound of the present invention without adding other components can be used as a pest control agent as it is, but it can also be used after being formulated. That is, at least one of the compounds of the present invention is mixed with a solid carrier, liquid carrier or gaseous carrier, or at least one of the compounds of the present invention is impregnated in a base material such as a porous ceramic board nonwoven fabric, and if necessary.
- a pesticide it can be formulated into a form that can be used by general pesticides by adding surfactants and other adjuvants.
- Agrochemical preparations include wettable powders, granules, powders, emulsions, aqueous solvents, suspensions, wettable granules, floats, aerosols, fumes, heat transpirations, smoke, poison baits, and microcapsules. Can be mentioned.
- Additives and carriers include solid powders such as soybean grains and wheat flour, mineral powders such as diatomaceous earth, apatite, gypsum, talc, bentonite, neurophyllite and clay, and benzoic acid. Organic and inorganic compounds such as soda, urea and mirabilite can be used.
- petroleum fractions such as kerosene, xylene and solvent naphtha, cyclohexane, cyclohexanone, dimethylformamide, dimethyl sulfoxide, alcohol, acetone, methyl isobutyl ketone, mineral oil, vegetable oil, Water or the like can be used as a solvent.
- gaseous carrier used in the propellant butane gas, LPG, dimethyl ether and carbon dioxide can be used as the gaseous carrier used in the propellant.
- bait ingredients such as cereal flour, vegetable oil, sugar and crystalline cellulose, antioxidants such as dibutylhydroxytoluene and nordihydroguaretic acid, preservatives such as dehydroacetic acid, Pest-attracting fragrances such as anti-fouling agents for children and pets such as pepper powder, cheese fragrances, and onion fragrances can be used.
- a surfactant can be added if necessary in order to obtain a uniform and stable form in these preparations.
- the surfactant is not particularly limited, and examples thereof include alkyl ethers attached with polyoxyethylene and higher fats attached with polyoxyethylene.
- Nonionic surfactants such as fatty acid esters, sorbitan higher fatty acid esters added with polyoxyethylene, tristyryl phenyl ethers added with polyoxyethylene, sulfates of alkylphenol ethers attached with polyoxyethylene, Examples include alkyl naphthalene sulfonate, polycarboxylate, lignite sulfonate, formaldehyde condensate of alkyl naphthalene sulfonate, and a copolymer of isobutylene maleic anhydride.
- the amount of the active ingredient in the preparation is 0.01 to 90% by weight, particularly preferably 0.05 to 85% by weight.
- Dilants, emulsions, suspensions, flowables, aqueous solvents, and granule wettable powders are diluted with water to a prescribed concentration, and then used as dissolved solutions, suspensions, or emulsions. Used in a spraying method.
- the compound of the present invention when used as a pest control agent for prevention of epidemics, emulsions, wettable powders, flowables, etc. are diluted with water to a predetermined concentration before application, oils, aerosols, fumes, poison baits. Apply it as it is about anti-tick sheets.
- the preparation of the compound of the present invention is usually used.
- administration is performed by tablets, capsules, immersion liquid, feed mixing, suppositories, injection (intramuscular, subcutaneous, intravenous, intraperitoneal, etc.).
- an oily or aqueous solution is administered by spraying, pour-on, dropping-on, etc.
- the compound of the present invention is usually used at a ratio of 0.01-lOOOOmg per lkg of the host animal.
- the reaction mixture was cooled to room temperature, poured into water and extracted with ethyl acetate. The organic layer was washed with water, dried over anhydrous magnesium sulfate, filtered, and concentrated under reduced pressure.
- the concentrate was purified by silica gel column chromatography (eluent: mixed solvent consisting of n-hexane and ethyl acetate) to obtain the title compound (B) (0.82 g).
- the concentrate was purified by silica gel column chromatography (eluent: mixed solvent of n-hexane and ethyl acetate), and the trans fraction (H) (0.35 g) was used as the second fraction as the first fraction.
- the cis-form (H) (0.21 g)
- reaction mixture was cooled to room temperature, poured into water, and extracted with ethyl acetate. The organic layer was washed with brine and dried over anhydrous magnesium sulfate. The solvent was distilled off under reduced pressure to obtain 3.5 g of compound (M) as crystals.
- R 1 and R 2 are also shown in a simplified manner when two or more substituents are present, vis indicates a viscous oil, and amor is amorphous.
- CPr is a cyclopropyl group and cHex is cyclohexyl.
- nPr is a normal propyl group
- iPr is an isopropyl group
- n Bu is a noremanolebutinore group
- iBu is an isobutinole group
- tBu is a tertiary butinore group
- cPen is cyclopentyl.
- O TMS indicates trimethylsilyl group
- THF indicates tetrahydrofuranyl group
- R 1, R 2b, R 3a, R 3b, R 4a, R 4b and R 5 represent a hydrogen atom.
- R1b, R2b, R3a, R3b, R4a, R4b, and R5 represent a hydrogen atom.
- Rlb, R2b, R3a, R3b, R4a, R4b, and R5 represent hydrogen atoms.
- Ri a , R 1, R 4 , R 4 a and R 5 represent a hydrogen atom.
- cis and trans represent the positional relationship between and ( ⁇ , R 2 a , R 3 a , R 4 a or R 5 ).
- R ' a C (S) OMe, 2-48 5-CN NH 2-C (0) 0CH 2 0Me-4-CF 3
- R 3 a NHS0 2 Me, 2-53 5-0cHex N e 2-C (0) 0tBu-4-CF 3
- R 3 N (S0 2 Me) 2 , -60 5-OCF3 NC0 2 Me 2- OBn- 4- CF 3
- Rl a, R, R, R ⁇ Pi R 5 represents a hydrogen atom.
- Cis ⁇ Pi trans represents X and the (Ri a, R 2 a, R 3 a, R 4 a , or R 5) positional relationship.
- R ' a C (S) OMe, 3-48 5-CN NH 6-C (0) 0CH 2 0He-4-CF 3 3-49 5-N0 2 NH 6-C (0) 0CH 2 tBu-4 -CF 3
- R 3 a NHS0 2 Me, 3-53 5-0cHex NMe 3-C (0) 0 e-4-CF 3
- R 3 a N (S0 2 e) 2 , -60 5-OCF3 NC0 2 Me 3-OBn- 4- CF 3
- R, K 3 a , R and R 5 represent a hydrogen atom.
- cis and trans represent the positional relationship between and ( ⁇ , R 2 a , R a a , R 4 a or R 5 ).
- R 2 a, R 3 a, R 4 a and R 5 represent a hydrogen atom.
- cis and trans represent X and the (Ri a, R 2 a, R 3 a, R 4 a , or R 5) positional relationship.
- Rl a R 2 a R 3 a R 4 a and R 5 represents a hydrogen atom.
- Cis and trans represent positional relationship between X and (Ri a R 2 a, ⁇ R 4 a , or R 5).
- composition of the present invention will be shown.
- additives and addition ratios can be varied in a wide range, which should not be limited to these examples.
- the parts in the preparation examples are parts by weight.
- the above was mixed uniformly and finely pulverized to obtain a powder with 10% active ingredient.
- Test Examples show that the compounds of the present invention are useful as active ingredients for acaricides and insecticides.
- the drug solution was diluted with water to a compound concentration of 125 ppm according to the formulation of the emulsion shown in Example 2 of the drug.
- Test Example 3 Efficacy test against skin
- a 1% solution was prepared using dimethyl sulfoxide (containing 0.5% tween 20), and this was treated dropwise with an amount equivalent to 10 g of the compound on the feed surface.
- the insecticidal rate was examined after 2 days at 25 ° C. The test was performed in duplicate.
- a highly safe pest control agent having excellent biological activity particularly in insecticidal and acaricidal activity, and further, a cyclic amine compound having a novel structure, or a salt thereof, or The N-acid can be provided.
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Abstract
Description
Claims
Priority Applications (8)
Application Number | Priority Date | Filing Date | Title |
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US12/083,127 US8338607B2 (en) | 2005-10-06 | 2006-10-06 | Cyclic amine compounds and agents for pest control |
JP2007538803A JP4871289B2 (ja) | 2005-10-06 | 2006-10-06 | 環状アミン化合物および有害生物防除剤 |
BRPI0616839-6A BRPI0616839A2 (pt) | 2005-10-06 | 2006-10-06 | agentes para controle de praga, e, compostos de amina cìclicos |
DK06811453.7T DK1947098T3 (da) | 2005-10-06 | 2006-10-06 | Cykliske aminforbindelser og skadedyrskontrolmiddel |
ES06811453T ES2375639T3 (es) | 2005-10-06 | 2006-10-06 | Compuestos de aminas c�?clicas y agente para el control de plagas. |
EP06811453A EP1947098B1 (en) | 2005-10-06 | 2006-10-06 | Cyclic amine compounds and pest control agent |
PL06811453T PL1947098T3 (pl) | 2005-10-06 | 2006-10-06 | Cykliczne związki aminowe i środek do zwalczania szkodników |
SI200631244T SI1947098T1 (sl) | 2005-10-06 | 2006-10-06 | Ciklične aminske spojine in sredstvo za zatiranje škodljivcev |
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JP2005297803 | 2005-10-12 | ||
JP2006016877 | 2006-01-25 | ||
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PCT/JP2006/320126 WO2007040280A1 (ja) | 2005-10-06 | 2006-10-06 | 環状アミン化合物および有害生物防除剤 |
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PT (1) | PT1947098E (ja) |
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