WO2010018686A1 - 含窒素ヘテロ環誘導体および農園芸用殺菌剤 - Google Patents
含窒素ヘテロ環誘導体および農園芸用殺菌剤 Download PDFInfo
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- WO2010018686A1 WO2010018686A1 PCT/JP2009/003845 JP2009003845W WO2010018686A1 WO 2010018686 A1 WO2010018686 A1 WO 2010018686A1 JP 2009003845 W JP2009003845 W JP 2009003845W WO 2010018686 A1 WO2010018686 A1 WO 2010018686A1
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- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229960005322 streptomycin Drugs 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 125000001273 sulfonato group Chemical group [O-]S(*)(=O)=O 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- JXHJNEJVUNHLKO-UHFFFAOYSA-N sulprofos Chemical compound CCCSP(=S)(OCC)OC1=CC=C(SC)C=C1 JXHJNEJVUNHLKO-UHFFFAOYSA-N 0.000 description 1
- 238000001308 synthesis method Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- ZZYSLNWGKKDOML-UHFFFAOYSA-N tebufenpyrad Chemical compound CCC1=NN(C)C(C(=O)NCC=2C=CC(=CC=2)C(C)(C)C)=C1Cl ZZYSLNWGKKDOML-UHFFFAOYSA-N 0.000 description 1
- DOMXUEMWDBAQBQ-WEVVVXLNSA-N terbinafine Chemical compound C1=CC=C2C(CN(C\C=C\C#CC(C)(C)C)C)=CC=CC2=C1 DOMXUEMWDBAQBQ-WEVVVXLNSA-N 0.000 description 1
- 229960002722 terbinafine Drugs 0.000 description 1
- IWVCMVBTMGNXQD-UHFFFAOYSA-N terramycin dehydrate Natural products C1=CC=C2C(O)(C)C3C(O)C4C(N(C)C)C(O)=C(C(N)=O)C(=O)C4(O)C(O)=C3C(=O)C2=C1O IWVCMVBTMGNXQD-UHFFFAOYSA-N 0.000 description 1
- ISIJQEHRDSCQIU-UHFFFAOYSA-N tert-butyl 2,7-diazaspiro[4.5]decane-7-carboxylate Chemical compound C1N(C(=O)OC(C)(C)C)CCCC11CNCC1 ISIJQEHRDSCQIU-UHFFFAOYSA-N 0.000 description 1
- 235000019364 tetracycline Nutrition 0.000 description 1
- 150000003522 tetracyclines Chemical class 0.000 description 1
- 229940040944 tetracyclines Drugs 0.000 description 1
- 125000004192 tetrahydrofuran-2-yl group Chemical group [H]C1([H])OC([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 125000005329 tetralinyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- 229960005199 tetramethrin Drugs 0.000 description 1
- 125000004523 tetrazol-1-yl group Chemical group N1(N=NN=C1)* 0.000 description 1
- 239000004308 thiabendazole Substances 0.000 description 1
- WJCNZQLZVWNLKY-UHFFFAOYSA-N thiabendazole Chemical compound S1C=NC(C=2NC3=CC=CC=C3N=2)=C1 WJCNZQLZVWNLKY-UHFFFAOYSA-N 0.000 description 1
- 235000010296 thiabendazole Nutrition 0.000 description 1
- 229960004546 thiabendazole Drugs 0.000 description 1
- 125000004305 thiazinyl group Chemical group S1NC(=CC=C1)* 0.000 description 1
- 125000000437 thiazol-2-yl group Chemical group [H]C1=C([H])N=C(*)S1 0.000 description 1
- 125000004495 thiazol-4-yl group Chemical group S1C=NC(=C1)* 0.000 description 1
- 150000003558 thiocarbamic acid derivatives Chemical class 0.000 description 1
- DNVLJEWNNDHELH-UHFFFAOYSA-N thiocyclam Chemical compound CN(C)C1CSSSC1 DNVLJEWNNDHELH-UHFFFAOYSA-N 0.000 description 1
- BAKXBZPQTXCKRR-UHFFFAOYSA-N thiodicarb Chemical compound CSC(C)=NOC(=O)NSNC(=O)ON=C(C)SC BAKXBZPQTXCKRR-UHFFFAOYSA-N 0.000 description 1
- QGHREAKMXXNCOA-UHFFFAOYSA-N thiophanate-methyl Chemical group COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC QGHREAKMXXNCOA-UHFFFAOYSA-N 0.000 description 1
- 229960002447 thiram Drugs 0.000 description 1
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-M toluene-4-sulfonate Chemical compound CC1=CC=C(S([O-])(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-M 0.000 description 1
- HYVWIQDYBVKITD-UHFFFAOYSA-N tolylfluanid Chemical compound CN(C)S(=O)(=O)N(SC(F)(Cl)Cl)C1=CC=C(C)C=C1 HYVWIQDYBVKITD-UHFFFAOYSA-N 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 125000004306 triazinyl group Chemical group 0.000 description 1
- IQGKIPDJXCAMSM-UHFFFAOYSA-N triazoxide Chemical compound N=1C2=CC=C(Cl)C=C2[N+]([O-])=NC=1N1C=CN=C1 IQGKIPDJXCAMSM-UHFFFAOYSA-N 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- UBOXGVDOUJQMTN-UHFFFAOYSA-N trichloroethylene Natural products ClCC(Cl)Cl UBOXGVDOUJQMTN-UHFFFAOYSA-N 0.000 description 1
- 125000004784 trichloromethoxy group Chemical group ClC(O*)(Cl)Cl 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- DQJCHOQLCLEDLL-UHFFFAOYSA-N tricyclazole Chemical compound CC1=CC=CC2=C1N1C=NN=C1S2 DQJCHOQLCLEDLL-UHFFFAOYSA-N 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- ITMCEJHCFYSIIV-UHFFFAOYSA-N triflic acid Chemical compound OS(=O)(=O)C(F)(F)F ITMCEJHCFYSIIV-UHFFFAOYSA-N 0.000 description 1
- ONCZDRURRATYFI-TVJDWZFNSA-N trifloxystrobin Chemical compound CO\N=C(\C(=O)OC)C1=CC=CC=C1CO\N=C(/C)C1=CC=CC(C(F)(F)F)=C1 ONCZDRURRATYFI-TVJDWZFNSA-N 0.000 description 1
- HSMVPDGQOIQYSR-KGENOOAVSA-N triflumizole Chemical compound C1=CN=CN1C(/COCCC)=N/C1=CC=C(Cl)C=C1C(F)(F)F HSMVPDGQOIQYSR-KGENOOAVSA-N 0.000 description 1
- XAIPTRIXGHTTNT-UHFFFAOYSA-N triflumuron Chemical compound C1=CC(OC(F)(F)F)=CC=C1NC(=O)NC(=O)C1=CC=CC=C1Cl XAIPTRIXGHTTNT-UHFFFAOYSA-N 0.000 description 1
- 125000004044 trifluoroacetyl group Chemical group FC(C(=O)*)(F)F 0.000 description 1
- 125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- RVKCCVTVZORVGD-UHFFFAOYSA-N trinexapac-ethyl Chemical group O=C1CC(C(=O)OCC)CC(=O)C1=C(O)C1CC1 RVKCCVTVZORVGD-UHFFFAOYSA-N 0.000 description 1
- 239000004061 uncoupling agent Substances 0.000 description 1
- 125000000297 undecanoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- JARYYMUOCXVXNK-IMTORBKUSA-N validamycin Chemical compound N([C@H]1C[C@@H]([C@H]([C@H](O)[C@H]1O)O[C@H]1[C@@H]([C@@H](O)[C@H](O)[C@@H](CO)O1)O)CO)[C@H]1C=C(CO)[C@H](O)[C@H](O)[C@H]1O JARYYMUOCXVXNK-IMTORBKUSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- DUBNHZYBDBBJHD-UHFFFAOYSA-L ziram Chemical compound [Zn+2].CN(C)C([S-])=S.CN(C)C([S-])=S DUBNHZYBDBBJHD-UHFFFAOYSA-L 0.000 description 1
- FJBGIXKIXPUXBY-UHFFFAOYSA-N {2-[3-(4-chlorophenyl)propyl]-2,4,4-trimethyl-1,3-oxazolidin-3-yl}(imidazol-1-yl)methanone Chemical compound C1=CN=CN1C(=O)N1C(C)(C)COC1(C)CCCC1=CC=C(Cl)C=C1 FJBGIXKIXPUXBY-UHFFFAOYSA-N 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- 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
- A01N43/72—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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D417/00—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
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
- C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D495/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D498/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D498/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and oxygen atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
- C07D498/04—Ortho-condensed systems
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
- C07F5/02—Boron compounds
- C07F5/025—Boronic and borinic acid compounds
Definitions
- the present invention relates to a novel nitrogen-containing heterocyclic compound and a salt thereof, and an agricultural and horticultural fungicide containing at least one of these compounds as an active ingredient.
- control agents are used against crop diseases, but their control efficacy is insufficient, their use is limited by the emergence of drug-resistant pathogens, or From the viewpoints of causing phytotoxicity and pollution to plants, or toxicity to human and livestock fish and impact on the environment, there are many things that are not necessarily satisfactory control agents. Accordingly, there is a strong demand for the emergence of such a drug that can be safely used with few defects.
- Patent Documents 1 and 2 listed below disclose quinoline derivatives having a chemical structure similar to the compound of the present invention, and agricultural and horticultural fungicides containing the same as active ingredients. However, the compounds of the present invention are not described.
- An object of the present invention is to provide a novel nitrogen-containing heterocyclic compound and a salt thereof, and an agricultural and horticultural fungicide that contains at least one of these compounds as an active ingredient and can be used safely and safely.
- the present invention further provides a boronic acid derivative, which is an intermediate for producing the above compound, and a method for producing the same.
- the present invention provides a nitrogen-containing heterocyclic compound represented by the following formula (I) (hereinafter sometimes referred to as “the present compound”) or a salt thereof.
- R 1 and R 2 each independently represents a hydrogen atom, a C1-20 alkyl group which may have a substituent, a C2-20 alkenyl group which may have a substituent, or a substituent; C2-20 alkynyl group which may have, C3-20 cycloalkyl group which may have substituent, C4-20 cycloalkenyl group which may have substituent, C8 which may have substituent -20 cycloalkynyl group, optionally substituted C6-10 aryl group, optionally substituted heterocyclic group, optionally substituted C1-20 acyl group, substituted A (1-imino) C1-20 alkyl group, a hydroxyl group which may have a substituent, an amino group which may have a substituent, a mercapto group which may have a substituent, a substituent; A sulfonyl group, a halogeno group, a cyano group, or a nitro group.
- R 1 and R 2 may be combined to form a 5- to 8-membered ring which may have a substituent.
- R 3 to R 6 each independently have a hydrogen atom, a C1-20 alkyl group which may have a substituent, a C2-20 alkenyl group which may have a substituent, or a substituent.
- C2-20 alkynyl group C3-20 cycloalkyl group which may have a substituent
- C4-20 cycloalkenyl group which may have a substituent C8-20 cycloalkynyl which may have a substituent Group
- a C6-10 aryl group which may have a substituent a heterocyclic group which may have a substituent
- a C1-20 acyl group which may have a substituent
- (1-imino) C1-20 alkyl group, a hydroxyl group which may have a substituent, an amino group which may have a substituent, a mercapto group which may have a substituent, a sulfonyl group which has a substituent, A halogeno group or a cyano group is shown.
- a plurality of groups selected from R 3 to R 6 may be selected together to form a 3- to 8-membered ring which may have a substituent.
- R 3 and R 4 , or R 5 and R 6 may be combined to form an oxo group, a thioxo group, or an imino group which may have a substituent.
- AB is A is a carbon atom
- B is a nitrogen atom
- Formula: C N
- R 7 is a hydrogen atom, an optionally substituted C1-20 alkyl group, an optionally substituted C2-20 alkenyl group, an optionally substituted C2-20 alkynyl group, a substituted C1-20 acyl group which may have a group, hydroxyl group which may have a substituent, amino group which may have a substituent, mercapto group which may have a substituent, halogeno group, or cyano Indicates a group.
- R 8 represents a hydrogen atom, an optionally substituted C1-20 alkyl group, an optionally substituted C2-20 alkenyl group, an optionally substituted C2-20 alkynyl group, or A C1-20 acyl group which may have a substituent is shown.
- Y represents an oxygen atom, a sulfur atom, or a sulfinyl group.
- X and X ′ are each independently a C1-20 alkyl group which may have a substituent, a C2-20 alkenyl group which may have a substituent, or a C2-20 which may have a substituent.
- a compound of the following formula (IV) or a salt thereof, in which R 1 and R 2 are combined to form a ring, is preferable.
- the present invention further provides a method for producing a production intermediate used for producing the nitrogen-containing heterocyclic compound represented by the formula (IV) and the formula (IX). That is, a C1-6 alkylmagnesium halide and a C1-6 alkyllithium are reacted, and then the formula (V) (In the formula, each X ′′ independently represents a C1-20 alkyl group which may have a substituent, a C2-20 alkenyl group which may have a substituent, or a C2 which may have a substituent.
- the present invention further provides a boronic acid derivative represented by the following formula (VIII), which is a production intermediate used in the production of the nitrogen-containing heterocyclic compound represented by the formula (IV) and the formula (IX).
- X 2 represents a fluorine atom or a chlorine atom.
- R 13 each independently represents a hydrogen atom or a C1-20 alkyl group. R 13 together is a 5- to 8-membered group. A ring may be formed.
- the present invention further provides a boronic acid derivative represented by the following formula (X), which is a production intermediate used in the production of the nitrogen-containing heterocyclic compound represented by the formula (IV) and the formula (IX).
- X 3 represents a hydrogen atom, a fluorine atom or a chlorine atom.
- R 14 each independently represents a C1-20 alkyl group. R 14 together represents a 5- to 8-membered ring.
- M represents an alkali metal.
- the compound of following formula (X ') is preferable among the compounds represented by Formula (X).
- X 3 and M have the same meaning as described above.
- R 15 represents a C1-20 alkyl group.
- the present invention further provides an agricultural and horticultural fungicide containing, as an active ingredient, at least one of a compound represented by the above formula (I), formula (IV) or formula (IX) or a salt thereof.
- the nitrogen-containing heterocyclic compound and its salt of the present invention are novel compounds, and are useful as active ingredients of agricultural and horticultural fungicides that can be used safely and reliably.
- the agricultural and horticultural fungicide of the present invention is an agent that has an excellent control effect, does not cause phytotoxicity to plants, and has little toxicity to human livestock and environmental impact.
- the boronic acid derivative of the present invention is useful as an intermediate for the nitrogen-containing heterocyclic compound of the present invention.
- the present invention relates to a nitrogen-containing heterocyclic compound represented by the formula (I) or a salt thereof.
- the compound of the present invention or a salt thereof includes hydrates, various solvates and crystal polymorphs. Furthermore, this invention compound includes the stereoisomer based on an asymmetric carbon atom, a double bond, etc., and mixtures thereof.
- C1-20 alkyl group” of the “optionally substituted C1-20 alkyl group” for R 1 to R 8 , X and X ′ is a linear or branched C 1-20 carbon atom. An alkyl group is meant.
- C2-20 alkenyl group” of the “optionally substituted C2-20 alkenyl group” for R 1 to R 8 , X and X ′ is a carbon-carbon double at any one or more of the alkyl groups. It means a straight or branched alkenyl group having 2 to 20 carbon atoms having a bond.
- C2 2-ethy
- the “C2-20 alkynyl group” of the “optionally substituted C2-20 alkynyl group” for R 1 to R 8 , X and X ′ is a carbon-carbon triple bond at any one or more positions of the alkyl group Means a straight-chain or branched alkynyl group having 2 to 20 carbon atoms and having For example, ethynyl group, 1-propynyl group, propargyl group, 1-butynyl group, 2-butynyl group, 3-butynyl group, 1-pentynyl group, 2-pentynyl group, 3-pentynyl group, 4-pentynyl group, 1- Hexynyl group, dodecinyl group, butadecynyl group, heptadecinyl group, 1-methyl-2-propynyl group, 2-methyl-3-butynyl group, 1-methyl-2-butynyl group, 2-methyl-3-pentyn
- C3-20 cycloalkyl group” of the “optionally substituted C3-20 cycloalkyl group” for R 1 to R 6 , X and X ′ is an alkyl group having 3-20 carbon atoms having a cyclic moiety. Means. Examples thereof include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, and a norbornyl group. Of these, C3-6 cycloalkyl groups are preferred.
- C4-20 cycloalkenyl group of “optionally substituted C4-20 cycloalkenyl group” for R 1 to R 6 , X and X ′ is an alkenyl group having 4 to 20 carbon atoms having a cyclic moiety. Means. Examples include 1-cyclobutenyl group, 1-cyclopentenyl group, 3-cyclopentenyl group, 1-cyclohexenyl group, 3-cyclohexenyl group, 3-cycloheptenyl group, 4-cyclooctenyl group and the like. Of these, C4-8 cycloalkenyl groups are preferred.
- C8-20 cycloalkynyl group of “optionally substituted C8-20 cycloalkynyl group” for R 1 to R 6 , X and X ′ is an alkynyl group having 8-20 carbon atoms having a cyclic moiety.
- C6-10 aryl group of “optionally substituted C6-10 aryl group” for R 1 to R 6 , X and X ′ is a monocyclic or polycyclic aryl group having 6 to 10 carbon atoms Means.
- a polycyclic aryl group a partially saturated group is included in addition to the fully unsaturated group. Examples thereof include a phenyl group, a naphthyl group, an azulenyl group, an indenyl group, an indanyl group, and a tetralinyl group. Of these, a phenyl group is preferred.
- heterocyclic group of the “heterocyclic group which may have a substituent” of R 1 to R 6 , X and X ′ is a nitrogen atom, an oxygen atom and a sulfur atom in addition to the carbon atom as the atoms constituting the ring
- a 3- to 7-membered aromatic heterocycle, a saturated heterocycle, an unsaturated heterocycle, or a 9- to 10-membered condensed heterocycle obtained by condensing these heterocycles and a benzene ring. means.
- C1-20 acyl group” of “optionally substituted C1-20 acyl group” for R 1 to R 8 , X and X ′ is a hydrogen atom, a linear or branched C1-19 alkyl group A linear or branched C2-19 alkenyl group, a linear or branched C2-19 alkynyl group, a monocyclic or polycyclic C6-19 aryl group, or a carbon atom as an atom constituting the ring
- a 5- to 7-membered heterocyclic group containing 1 to 4 heteroatoms selected from a nitrogen atom, an oxygen atom and a sulfur atom is bonded to a carbonyl group.
- (1-Imino) C1-20 alkyl group” of “optionally substituted (1-imino) C1-20 alkyl group” of R 1 to R 6 , X and X ′ is linear or branched This means a group in which the C1-19 alkyl group of the chain is bonded to an iminomethyl group.
- iminomethyl group for example, iminomethyl group, (1-imino) ethyl group, (1-imino) propyl group, (1-imino) butyl group, (1-imino) pentyl group, (1-imino) hexyl group, (1-imino)
- Examples include heptyl group, (1-imino) octylimino group, (1-imino) isobutyl group, (1-imino) isopentyl group, (1-imino) neopentyl group and the like.
- (1-imino) C1-6 alkyl groups are preferred.
- halogeno group examples include a fluorine atom, a chlorine atom, a bromine atom and an iodine atom.
- R 1 and R 2 may be combined to form a 5- to 8-membered ring which may have a substituent.
- the 5- to 8-membered ring include an aromatic hydrocarbon ring, an aromatic heterocycle, an aliphatic hydrocarbon ring, and an unsaturated heterocycle, and an aromatic hydrocarbon ring is preferable.
- the aromatic hydrocarbon ring includes a benzene ring
- the aromatic heterocycle includes a furan ring, a thiophene ring, a pyrrole ring, a pyridine ring, a pyrazine ring, a pyrimidine ring, a pyridazine ring, and an imidazole.
- the aliphatic hydrocarbon ring include a cycloalkene ring, and examples thereof include a cyclopentene ring, a cyclohexene ring, a cycloheptene ring, and a cyclooctene ring.
- the unsaturated heterocycle include a dihydro-2H-pyran ring, a dihydro-2H-thiopyran ring, and a tetrahydropyridine ring.
- a benzene ring is preferred. That is, in the compound of the present invention, the pyridine ring and the benzene ring in the formula (I) are preferably condensed to form a quinoline ring.
- R 3 to R 6 may be selected as a plurality and together form a 3- to 8-membered ring which may have a substituent.
- the 3- to 8-membered ring include an aliphatic hydrocarbon ring, an aromatic hydrocarbon ring, an aromatic heterocycle, and an unsaturated heterocycle.
- the aliphatic hydrocarbon ring includes a cycloalkane ring, and examples thereof include a cyclopropane ring, a cyclopentane ring, a cyclohexane ring, a cycloheptane ring, and a cyclooctane ring.
- Examples of the aromatic hydrocarbon ring include a benzene ring
- examples of the aromatic heterocycle include a furan ring, a thiophene ring, a pyrrole ring, a pyridine ring, a pyrazine ring, a pyrimidine ring, a pyridazine ring, an imidazole ring, a pyrazole ring
- Examples include a thiazole ring, an oxazole ring, and an isoxazole ring
- Examples of the unsaturated heterocycle include a dihydro-2H-pyran ring, a dihydro-2H-thiopyran ring, and a tetrahydropyridine ring.
- R 3 to R 6 can be variously selected, but a C1-6 alkyl group is preferable.
- the compound of the present invention can be variously selected as X and X ′, but a halogeno group is preferred.
- AB is A is a carbon atom
- B is a nitrogen atom
- Formula: C N
- R 7 is a hydrogen atom, an optionally substituted C1-20 alkyl group, an optionally substituted C2-20 alkenyl group, an optionally substituted C2-20 alkynyl group, a substituted C1-20 acyl group which may have a group, hydroxyl group which may have a substituent, amino group which may have a substituent, mercapto group which may have a substituent, halogeno group, or cyano Indicates a group.
- R 8 represents a hydrogen atom, an optionally substituted C1-20 alkyl group, an optionally substituted C2-20 alkenyl group, an optionally substituted C2-20 alkynyl group, or A C1-20 acyl group which may have a substituent is shown.
- Y represents an oxygen atom, a sulfur atom, or a sulfinyl group. Preferably, it is an oxygen atom.
- the salt of the compound of the present invention is not particularly limited as long as it is an agriculturally and horologically acceptable salt.
- salts of inorganic acids such as hydrochloric acid and sulfuric acid; salts of organic acids such as acetic acid and lactic acid; salts of alkali metals such as lithium, sodium and potassium; salts of alkaline earth metals such as calcium and magnesium; iron and copper
- salts of organic metals such as ammonia, triethylamine, tributylamine, pyridine, hydrazine, and the like.
- “having a substituent” or “may have a substituent” means that any hydrogen atom in each of the above “groups” is substituted with the “substituent”. Or it may be substituted.
- the “substituent” include the above-mentioned “groups”, but the “substituent” may be a “substituent” further substituted with “another group”.
- another group include the above-mentioned “groups”. Examples in which each of the above “groups” is substituted with any of the above “groups” are shown below.
- Examples of the “ ⁇ 20 alkyl group” include a cyclopropylmethyl group, a 2-cyclopropylethyl group, a cyclopentylmethyl group, a 2-cyclohexylethyl group, a 2-cyclooctylethyl group, and the like. Of these, C4-10 cycloalkyl C1-6 alkyl groups are preferred.
- C1-20 alkyl group optionally having substituent (s) in “C1-20 alkyl group optionally having substituent (s)” for R 1 to R 8 , X and X 'is substituted with "C1 Examples of the “ ⁇ 20 alkyl group” include a cyclopentenylmethyl group, a 3-cyclopentenylmethyl group, a 3-cyclohexenylmethyl group, a 2- (3-cyclohexenyl) ethyl group, and the like. Of these, C4-8 cycloalkenyl C1-6 alkyl groups are preferred.
- Examples of the “ ⁇ 20 alkyl group” include a 5-cyclooctynylmethyl group. Of these, C9-13 cycloalkynyl C1-6 alkyl groups are preferred.
- the “C1-20 alkyl group” substituted by the “halogeno group” in the “optionally substituted C1-20 alkyl group” for R 1 to R 8 , X and X ′ is, for example, fluoromethyl Group, chloromethyl group, bromomethyl group, difluoromethyl group, dichloromethyl group, dibromomethyl group, trifluoromethyl group, trichloromethyl group, tribromomethyl group, 2,2,2-trifluoroethyl group, 2,2, 2-trichloroethyl group, pentafluoroethyl group, 4-fluorobutyl group, 4-chlorobutyl group, 3,3,3-trifluoropropyl group, 2,2,2-trifluoro-1-trifluoromethylethyl group, Perfluorohexyl group, perchlorohexyl group, perfluorooctyl group, perchlorooctyl group, 2,4,6-trichlorohe
- C1-20 alkyl group optionally having substituent (s)” in R 1 to R 8 , X and X ′ “C1 ⁇ Examples of the “20 alkyl group” include benzyl group, phenethyl group, 3-phenylpropyl group, 1-naphthylmethyl group, 2-naphthylmethyl group and the like. Of these, C6-10 aryl C1-6 alkyl groups are preferred.
- C1-20 alkyl substituted by “heterocyclic group optionally having substituent” in “optionally substituted C1-20 alkyl group” of R 1 to R 8 , X and X ′
- Examples of the group include 2-pyridylmethyl group, 3-pyridylmethyl group, 4-pyridylmethyl group, 2- (2-pyridyl) ethyl group, 2- (3-pyridyl) ethyl group, 2- (4- Pyridyl) ethyl group, 3- (2-pyridyl) propyl group, 3- (3-pyridyl) propyl group, 3- (4-pyridyl) propyl group, 2-pyrazinylmethyl group, 3-pyrazinylmethyl group, 2- (2- Pyrazinyl) ethyl group, 2- (3-pyrazinyl) ethyl group, 3- (2-pyrazinyl) propyl group, 3- (3-pyrazinyl) propyl group, 2-pyr
- the “C1-20 alkyl group” substituted by the “hydroxyl group” includes, for example, a hydroxymethyl group , Hydroxyethyl group, hydroxypropyl group and the like. Of these, hydroxy C1-6 alkyl groups are preferred.
- the C1-20 alkyl group substituted by the hydroxyl group which may have a substituent that is, among the “hydroxy C1-20 alkyl group which may have a substituent”, the “having a substituent”
- Examples of the “hydroxy C1-20 alkyl group” substituted by “optional C1-20 alkyl group” include, for example, methoxymethyl group, ethoxymethyl group, methoxyethyl group, ethoxyethyl group, methoxy n-propyl group, ethoxymethyl Group, ethoxyethyl group, n-propoxymethyl group, i-propoxyethyl group, s-butoxymethyl group, t-butoxyethyl group, 2,2-dimethoxyethyl group and the like.
- C1-6 alkoxy C1-6 alkyl groups are preferred.
- the “hydroxy C1-20 alkyl group” substituted by “optionally substituted C1-20 acyl group” includes: Examples include formyloxymethyl group, acetoxymethyl group, 2-acetoxyethyl group, propionyloxymethyl group, propionyloxyethyl group and the like. Of these, C2-7 acyloxy C1-6 alkyl groups are preferred.
- C3-20 cycloalkyl group optionally having substituent (s) of R 1 to R 6 , X and X ′
- Examples of the “ ⁇ 20 cycloalkyl group” include 2,3,3-trimethylcyclobutyl group, 4,4,6,6-tetramethylcyclohexyl group, 1,3-dibutylcyclohexyl group and the like. Of these, C4-10 cycloalkyl groups in which 1 to 3 C1-6 alkyls are substituted are preferred.
- C4 substituted with an optionally substituted C1-20 alkyl group examples include a 2-methyl-3-cyclohexenyl group and a 3,4-dimethyl-3-cyclohexenyl group. Of these, a C5-9 cycloalkenyl group in which 1 to 3 C1-6 alkyl is substituted is preferable.
- C8-20 cycloalkynyl group optionally having substituent (s) of R 1 to R 6 , X and X ′
- C8 substituted with a C1-20 alkyl group optionally having substituent (s) examples include a 2,3-diethyl-4-cyclodecynyl group. Of these, a C9-12 cycloalkynyl group in which 1 to 3 C1-6 alkyl is substituted is preferable.
- the “C2-20 alkenyl group” substituted by the “halogeno group” includes, for example, 3- Chloro-2-propenyl group, 4-chloro-2-butenyl group, 4,4-dichloro-3-butenyl group, 4,4-difluoro-3-butenyl group, 3,3-dichloro-2-propenyl group, 2 , 3-dichloro-2-propenyl group, 3,3-difluoro-2-propenyl group, 2,4,6-trichloro-2-hexenyl group and the like.
- C2-6 alkenyl groups substituted with 1 to 3 halogen atoms are preferred.
- the “C2-20 alkynyl group” substituted by the “halogeno group” includes, for example, 3- Chloro-1-propynyl group, 3-chloro-1-butynyl group, 3-bromo-1-butynyl group, 3-bromo-2-propynyl group, 3-iodo-2-propynyl group, 3-bromo-1-hexynyl Group, 4,4,6,6-tetrafluoro-1-dodecynyl group, 5,5-dichloro-2-methyl-3-pentynyl group, 4-chloro-1,1-dimethyl-2-butynyl group, etc. .
- C2-6 alkynyl groups substituted with 1 to 3 halogen atoms are preferred.
- the “hydroxyl group optionally having substituent (s)” of R 1 to R 7 , X and X ′ the “hydroxyl group” substituted by “the C1-20 alkyl group optionally having substituent (s)”, ie, “ Examples of the “C1-20 alkoxy group optionally having a substituent” include a methoxy group, an ethoxy group, an n-propoxy group, an n-butoxy group, an n-pentyloxy group, an n-hexyloxy group, a decyloxy group, Dodecyloxy group, lauryloxy group, i-propoxy group, i-butoxy group, s-butoxy group, t-butoxy group, 1-ethylpropoxy group, isohexyloxy group, 4-methylpentoxy group, 3-methylpentene Toxyl group, 2-methylpentoxy group, 1-methylpentoxy group, 3,3-dimethylbutoxy group, 2,2-dimethylbutoxy group, 1,
- alkoxy group substituted by “optionally C3-20 cycloalkyl group” or “optionally substituted C6-10 aryl group” include, for example, cyclopropylmethyloxy group, 2-cyclopentylethyl An oxy group, a benzyloxy group, etc. are mentioned. Of these, C1-7 alkoxy groups are preferred.
- Examples of the “group” in which the “alkoxy group” is substituted with the “halogeno group” include, for example, chloromethoxy group, dichloromethoxy group, trichloromethoxy group, trifluoromethoxy group, 1-fluoroethoxy group, 1,1 -Difluoroethoxy group, 2,2,2-trifluoroethoxy group, pentafluoroethoxy group and the like.
- a C1-6 alkoxy group substituted with 1 to 3 halogen atoms hereinafter sometimes referred to as “C1-6 haloalkoxy group” is preferable.
- the “hydroxyl group having a substituent” of R 1 to R 7 , X and X ′ the “hydroxyl group” substituted by the “optionally substituted C2-20 alkynyl group”, that is, “C2-20 alkynyl”
- the “oxy group” include ethynyloxy group, propynyloxy group, propargyloxy group, 1-butynyloxy group, 2-butynyloxy group, 3-butynyloxy group, 1-pentynyloxy group, 2-pentynyloxy group, 3 -Pentynyloxy group, 4-pentynyloxy group, 1-hexynyloxy group, dodecynyloxy group, butadecynyloxy group, heptadecynyloxy group, 1-methyl-2-propynyloxy group, 2-methyl-3-butynyloxy group Group, 1-methyl-2-butynyloxy group, 2-methyl-3-pent
- the “hydroxyl group having a substituent” of R 1 to R 7 , X and X ′ the “hydroxyl group” substituted by the “optionally substituted C3-20 cycloalkyl group”, ie, “C3-20
- the “cycloalkoxy group” include a cyclopropyloxy group, a cyclobutyloxy group, a cyclopentyloxy group, a cyclohexyloxy group, a cycloheptyloxy group, and a cyclooctyloxy group, and may further have a “substituent”.
- Examples of the cycloalkoxy group substituted by “C1-20 alkyl group” include, for example, 2-methylcyclopropyloxy group, 2-ethylcyclopropyloxy group, 2,3,3-trimethylcyclobutyloxy group, 2- Methylcyclopentyloxy group, 2-ethylcyclohexyloxy group, 2-ethylcyclooctyloxy group , 4,4,6,6-tetramethyl-cyclohexyl group, 1,3-butylcyclohexyl group, and the like. Of these, C3-6 cycloalkoxy groups are preferred.
- the “hydroxyl group having a substituent” of R 1 to R 7 , X and X ′ the “hydroxyl group” substituted by the “optionally substituted C6-10 aryl group”, ie, “having a substituent”
- the “optionally C6-10 aryloxy group” include phenyloxy group, naphthyloxy group, azulenyloxy group, indenyloxy group, indanyloxy group, tetralinyloxy group and the like. Of these, C6-10 aryloxy groups are preferred.
- the “hydroxyl group having a substituent” of R 1 to R 7 , X and X ′ the “hydroxyl group” substituted by the “optionally substituted C1-20 acyl group”, ie, “having a substituent”
- the “optionally C1-20 acyloxy group” include an acetyloxy group, a propionyloxy group, an n-propylcarbonyloxy group, an i-propylcarbonyloxy group, an n-butylcarbonyloxy group, and an i-butylcarbonyloxy group.
- the “C1-20 acyl group” substituted by the “halogen group” in the “optionally substituted C1-20 acyl group” for R 1 to R 8 , X and X ′ is, for example, monofluoro Acetyl group, monochloroacetyl group, monobromoacetyl group, difluoroacetyl group, dichloroacetyl group, dibromoacetyl group, trifluoroacetyl group, trichloroacetyl group, tribromoacetyl group, 3,3,3-trifluoropropionyl group, 3 , 3,3-trichloropropionyl group, 2,2,3,3,3-pentafluoropropionyl group and the like.
- C1-6 acyl groups substituted with 1 to 3 halogen atoms are preferred.
- R 1 to R 8 X and X ′ “C1-20 acyl group optionally having substituent (s)”, “C2-20 alkenyl group optionally having substituent (s)” and “having substituent (s)” "C1-20 acyl group” substituted by "optionally substituted C2-20 alkynyl group", “optionally substituted C6-10 aryl group” or “optionally substituted heterocyclic group” Examples thereof include 3-allyl-phenylcarbonyl group, 3-ethynyl-phenylcarbonyl group, benzylcarbonyl group, phenethylcarbonyl group, 2-pyridylmethylcarbonyl group and the like.
- examples of the “carboxyl group” substituted by the “optionally substituted C1-20 alkyl group” include a methoxycarbonyl group, an ethoxycarbonyl group, and n-propoxy group.
- Carbonyl group i-propoxycarbonyl group, n-butoxycarbonyl group, i-butoxycarbonyl group, t-butoxycarbonyl group, n-pentyloxycarbonyl group, n-hexyloxycarbonyl group, decyloxycarbonyl group, dodecyloxycarbonyl group 2-ethyldecyloxycarbonyl group, lauryloxycarbonyl group and the like.
- examples of the “alkyl-substituted carboxyl group” substituted by “an optionally substituted C3-20 cycloalkyl group” or “an optionally substituted C6-10 aryl group” include cycloalkyl Examples include propylmethyloxycarbonyl group, 2-cyclopentylethyloxycarbonyl group, benzyloxycarbonyl group and the like. Of these, C1-7 alkoxycarbonyl groups are preferred.
- the hydrogen atom on the nitrogen atom of the iminomethyl group is substituted with “hydroxyl group”.
- the “group” means “an optionally substituted (1-hydroxyimino) C1-20 alkyl group”. Examples thereof include a hydroxyiminomethyl group, (1-hydroxyimino) ethyl group, (1-hydroxyimino) propyl group, (1-hydroxyimino) butyl group and the like. Of these, (1-hydroxyimino) C1-6 alkyl groups are preferred.
- the hydrogen atom on the hydroxyl group is substituted with the “optionally substituted C1-20 alkyl group”.
- the “group” include methoxyiminomethyl group, (1-ethoxyimino) methyl group, (1-ethoxyimino) ethyl group, and the like. Of these, (1- (C1-6 alkoxy) imino) C1-6 alkyl groups are preferred.
- the “amino group optionally having substituent (s)” of R 1 to R 7 , X and X ′ examples thereof include a methylamino group, an ethylamino group, a dimethylamino group, and a diethylamino group. Of these, a mono C1-6 alkylamino group or a di C1-6 alkylamino group is preferable.
- Examples of the “group” in which two hydrogen atoms on the amino group are substituted with the same carbon atom of the “optionally substituted C1-20 alkyl group” include, for example, a methylideneamino group and an ethylideneamino group Etc. Of these, mono C1-6 alkylideneamino groups are preferred.
- monoarylamino groups such as phenylamino group and 4-methylphenylamino group (preferably mono-C6-10 arylamino group); diarylamino groups such as di1-naphthylamino group (preferably Are di-C6-10 arylamino groups); acylamino groups such as acetylamino groups and benzoylamino groups (preferably C1-6 acylamino groups).
- examples of the “carbamoyl group” substituted by the “optionally substituted C1-20 alkyl group” include, for example, a methylcarbamoyl group, an ethylcarbamoyl group, a dimethylcarbamoyl group And diethylcarbamoyl group.
- a mono C1-6 alkylcarbamoyl group or a diC1-6 alkylcarbamoyl group is preferable.
- carbamoyl group for example, carbamoyl group; monoarylcarbamoyl group such as phenylcarbamoyl group and 4-methylphenylcarbamoyl group (preferably mono C6-10 arylcarbamoyl group); acyl such as acetylcarbamoyl group and benzoylcarbamoyl group And a rucarbamoyl group (preferably a C1-6 acylcarbamoyl group).
- “mercapto group” substituted by “C1-20 alkyl group optionally having substituent (s)” examples thereof include a methylthio group and an ethylthio group. Of these, C1-6 alkylthio groups are preferred.
- an arylthio group such as a phenylthio group or a 4-methylphenylthio group (preferably a C6-10 arylthio group), an acylthio group such as an acetylthio group or a benzoylthio group (preferably a C1-6 acylthio group) )
- an arylthio group such as a phenylthio group or a 4-methylphenylthio group (preferably a C6-10 arylthio group)
- an acylthio group such as an acetylthio group or a benzoylthio group (preferably a C1-6 acylthio group)
- the like examples thereof include a methylthio group and an
- the “sulfonyl group” substituted by the “optionally substituted C1-20 alkyl group” includes, for example, methyl Sulfonyl group, ethylsulfonyl group, n-propylsulfonyl group, isopropylsulfonyl group, n-butylsulfonyl group, isobutylsulfonyl group, sec-butylsulfonyl group, tert-butylsulfonyl group, n-pentylsulfonyl group, isopentylsulfonyl group, Neopentylsulfonyl group, 1-ethylpropylsulfonyl group, n-hexylsulfonyl group, isohexylsulfonyl group and
- C1-6 alkylsulfonyl groups are preferred.
- a haloalkylsulfonyl group such as a trifluoromethylsulfonyl group (preferably a C1-6 haloalkylsulfonyl group); an arylsulfonyl group such as a phenylsulfonyl group, a 4-methylphenylsulfonyl group (preferably C6- 10 arylsulfonyl group); sulfo group; alkoxysulfonyl group such as methoxysulfonyl group and ethoxysulfonyl group (preferably C1-6 alkoxysulfonyl group); sulfamoyl group; N-methylsulfamoyl group, N-ethylsulfamoyl group , Sulfamoyl groups such as N, N-dimethylsulfamoyl group
- Examples of the “imino group” substituted by “optionally substituted hydroxyl group” such as methylimino group, benzylimino group, and the like include hydroxyimino group, ethoxyimino group, and the like.
- the “substituent” of “having a substituent” or “may have a substituent” includes, for example, —Si (Me) 3 , -SiPh 3 , -Si (cPr) 3 , -Si (Me) 2 (t-Bu) (t-Bu represents a tertiary butyl group; the same shall apply hereinafter) -Si (R 20 ) (R 21 ) Or a group represented by (R 22 ).
- R 21 , R 22 and R 23 are each independently a C1-6 alkyl group or a phenyl group. Examples of the C1-6 alkyl group are the same as those exemplified for R 1 to R 8 , X and X ′.
- B1-64 and B1-67 are HCl salts
- B1-65 and B1-66 are TFA salts (trifluoroacetate).
- the compound represented by the formula (1) is a boronic acid derivative represented by the formula (2) and an imidoyl halide derivative represented by the formula (3), for example, the non-patent document 1 or the non-patent document 2 described above. It can be prepared by Suzuki coupling using the palladium complex described in 1. In some cases, the imidoyl halide derivative represented by the formula (3) may be coupled after introducing the halogen atom of X 4 to an alkyl sulfonate group or a haloalkyl sulfonate group.
- boronic acid derivative represented by the formula (2) instead of the boronic acid derivative represented by the formula (2), a boronic acid derivative represented by the following formula (2 ′) may be used.
- R 1 to R 2 , X ′, and m represent the same meaning as described above.
- R ′ 14 represents a C1 to 20 alkyl group.
- M represents an alkali metal such as lithium, sodium, and potassium.
- R 3 to R 6 , X, Y, and n represent the same meaning as described above.
- X 4 represents a halogen atom.
- the compound represented by the formula (3) can be prepared by a method in which the cyclic amide represented by the formula (4) is reacted in the presence of an acid halide such as phosgene, oxalyl chloride, and thionyl chloride. . Further, a mixed system of triphenylphosphine and carbon tetrachloride can be similarly obtained.
- the compound represented by the formula (4) can be prepared by the Beckmann rearrangement after the cyclic acetophenone derivative represented by the formula (5) is induced by a Schmitt reaction or into an oxime.
- a Schmitt reaction for example, as described in Non-Patent Document 3 or Non-Patent Document 4, a ketone is dissolved in sodium azide and a strong acid such as concentrated hydrochloric acid, sulfuric acid, trifluoroacetic acid, or methanesulfonic acid.
- a strong acid such as concentrated hydrochloric acid, sulfuric acid, trifluoroacetic acid, or methanesulfonic acid.
- a solvent such as acetonitrile, chloroform or methylene chloride.
- the oxime of the carbonyl compound is reacted with polyphosphoric acid or its trimethylsilyl ester, or Lewis acid, such as aluminum triiodide or iron (III) chloride impregnated montmorillonite and in the absence of solvent or like acetonitrile
- the reaction is carried out in a solvent at an elevated temperature. It can also be prepared by forming the oxime mesylate or tosylate and then treating with a base such as aqueous sodium hydroxide solution or treating with a Lewis acid such as diethylaluminum chloride.
- Oxime formation is accomplished in a known manner by adding a base such as pyridine, sodium acetate or aqueous sodium hydroxide solution in a solvent such as ethanol by reaction with hydroxylamine hydrochloride and adding a solvent.
- a base such as pyridine, sodium acetate or aqueous sodium hydroxide solution in a solvent such as ethanol
- a solvent such as ethanol
- the compound represented by the formula (1 ′) is obtained by converting the compound represented by the formula (1) into, for example, (i) a catalytic reduction catalyst such as palladium-carbon, platinum oxide, and Raney nickel, and catalytic hydrogen using hydrogen. It can be prepared by an addition method, ii) a reduction method using a metal hydride compound such as lithium aluminum hydride or sodium borohydride.
- the present invention further relates to a method for producing a production intermediate used for producing the compound of the present invention. That is, a C1-6 alkylmagnesium halide and a C1-6 alkyllithium are reacted, and then the formula (V)
- each X ′′ independently represents a C1-20 alkyl group which may have a substituent, a C2-20 alkenyl group which may have a substituent, or a C2 which may have a substituent.
- a mercapto group, a fluorine atom, a chlorine atom, or a nitro group which may be contained is shown.
- q represents an integer of 0 to 6.
- X 1 represents a bromine atom or an iodine atom.
- B OR 12
- each R 12 independently represents a C1-6 alkyl group.
- Is reacted with a compound represented by formula (VII) (hereinafter referred to as “trialkoxyborane reagent”).
- This boronic acid derivative can be used as a production intermediate of the compound of the present invention.
- C1-6 alkylmagnesium halide used in the present invention is, for example, methylmagnesium chloride, ethylmagnesium chloride, n-propylmagnesium chloride, n-butylmagnesium chloride, s-butylmagnesium chloride, t-butylmagnesium chloride, n- Examples thereof include butyl magnesium bromide and n-butyl magnesium iodide. N-butylmagnesium chloride is preferable. These can be used alone or in combination of two or more.
- C1-6 alkyl lithium examples include methyl lithium, ethyl lithium, n-propyl lithium, n-butyl lithium, s-butyl lithium, t-butyl lithium and the like. Preferred is n-butyllithium. These can be used alone or in combination of two or more.
- the amount of C1-6 alkylmagnesium halide used is 0.25 to 2 moles, preferably 0.3 to 1.0 moles per mole of the compound represented by the formula (V).
- the amount of C1-6 alkyllithium used is 2.0 to 2.5 times moles per mole of C1-6 alkylmagnesium halide.
- the “C1-6 alkyl group” of R 12 in the formula (VI) means a linear or branched alkyl group having 1 to 6 carbon atoms.
- neopentyl group 2-methylbutyl group, 2,2-dimethylpropyl group, isohexyl group and the like.
- Preferred are a methyl group and an i-propyl group.
- the amount of trialkoxyborane reagent represented by formula (VI) is 1.0 to 2.5 times mol, preferably 1.0 to 1.times. Mol per 1 mol of compound represented by formula (V). 2 moles. These can be used alone or in combination of two or more.
- an alkylmagnesium halide and 2-fold mole of alkyllithium form an art-type complex in the reaction system, and this art-type complex contributes to the progress of the reaction. Therefore, in this reaction, it is preferable to form an art-type complex in the reaction system in advance, then react the compound represented by the formula (V), and then react the trialkoxyborane reagent.
- the solvent used in this reaction is not particularly limited as long as the reaction is not inhibited, but hydrocarbon solvents such as hexane, cyclohexane, benzene, toluene, and ether solvents such as diethyl ether and THF can be used. These can be used alone or in combination of two or more.
- the amount of the solvent to be used is not particularly limited, and is usually expressed as [compound represented by formula (V) (parts by weight)]: [solvent (parts by volume)], usually 1: 3 to 1: 100, preferably 1: 4 to 1:40.
- the treatment temperature can be suitably carried out between ⁇ 78 ° C. and room temperature, but is preferably ⁇ 10 ° C. to 0 ° C.
- R 12 ′ each independently represents a C1-20 alkyl group. R 12 ′ together is a 5- to 8-membered ring. May be formed.
- a boronic acid ester derivative represented by the formula can also be used as an intermediate for producing the compound of the present invention.
- the boronic acid ester derivative represented by the formula (VII ′) can be produced by esterifying the boronic acid derivative represented by the formula (VII).
- the esterification method the methods described in Non-Patent Document 5, Non-Patent Document 6, and the like can be used.
- the desired product can be efficiently isolated by subjecting it to conventional post-treatment operations in organic synthetic chemistry and, if necessary, conventionally known separation and purification means.
- the structure of the target product can be identified and confirmed by measuring 1 H-NMR spectrum, IR spectrum, mass spectrum, elemental analysis, or the like.
- the present invention also relates to a production intermediate of the compound of the present invention. That is, the formula (VIII) (In the formula, X 2 represents a fluorine atom or a chlorine atom. R 13 each independently represents a hydrogen atom or a C1-20 alkyl group. R 13 together represents a 5- to 8-membered group. A ring may be formed.) It is related with the boronic acid derivative represented by these. This boronic acid derivative is particularly useful as an intermediate for producing the compound of the present invention.
- Examples of the “C1-20 alkyl group” for R 13 in formula (VIII) include the same “group” as the C1-20 alkyl group exemplified for X.
- a C1-6 alkyl group is preferable, and examples thereof include a methyl group and an i-propyl group.
- the boronic acid derivative represented by the formula (VIII) can be produced according to the production method described above.
- boronic acid derivative represented by the formula (VIII) include compounds shown in the following table [Table 18].
- Me represents methyl and i-Pr represents i-propyl.
- the present invention further relates to formula (X)
- X 3 represents a hydrogen atom, a fluorine atom or a chlorine atom.
- R 14 each independently represents a C1-20 alkyl group. R 14 together represents a 5- to 8-membered ring.
- M represents an alkali metal.
- This boronic acid derivative is also useful as an intermediate for producing the compound of the present invention.
- Examples of the “C1-20 alkyl group” for R 14 in formula (X) include the same “group” as the C1-20 alkyl group exemplified for X. Preferably, it is a C1-6 alkyl group, and examples thereof include a methyl group, an ethyl group, an n-propyl group, and an i-propyl group. Furthermore, the formula (X ′) in which all three R 14s together form a ring (In the formula, X 3 represents a hydrogen atom, a fluorine atom or a chlorine atom. R 15 represents a C1-20 alkyl group. M represents an alkali metal.) A boronic acid derivative represented by the formula is more preferred.
- Examples of the “C1-20 alkyl group” for R 15 in the formula (X ′) include the same “group” as the C1-20 alkyl group exemplified for X.
- it is a C1-6 alkyl group, and examples thereof include a methyl group, an ethyl group, an n-propyl group, and an i-propyl group.
- the boronic acid derivative represented by the formula (X ′) can be produced by the method described in Non-Patent Document 7 and the like.
- boronic acid derivative represented by the formula (X ′) include compounds shown in the following table [Table 19].
- the present invention further contains at least one nitrogen-containing heterocyclic compound represented by the formula (I), formula (IV) or formula (IX) of the present invention or a salt thereof as an active ingredient.
- the present invention relates to an agricultural and horticultural disinfectant (hereinafter sometimes referred to as “the present disinfectant”).
- the fungicide of the present invention contains the compound of the present invention as an active ingredient, and a wide variety of filamentous fungi such as algae (Omycetes), Ascomycetes, Deuteromycetes, basidiomycetes It has excellent bactericidal power against bacteria belonging to (Basidiomycetes).
- filamentous fungi such as algae (Omycetes), Ascomycetes, Deuteromycetes, basidiomycetes). It has excellent bactericidal power against bacteria belonging to (Basidiomycetes).
- the fungicide of the present invention can be used by seed treatment, foliage spraying, soil application, water application, etc., for the control of various diseases that occur during the cultivation of agricultural and horticultural crops including flowers, turf and grass.
- Sugar beet brown spot (Cercospora beticola) Black root disease (Aphanomyces cochlloides) Root rot (Thanatephorus cucumeris) Leaf rot (Thanatephorus cucumeris) Peanut brown spot (Mycosphaerella arachidis) Black astringent disease (Mycosphaerella berkeleyi) Cucumber powdery mildew (Sphaerotheca furiginea) Downy mildew (Pseudoperonospora cubensis) Vine Blight (Mycosphaella melonis) Vine split disease (Fusarium oxysporum) Sclerotinia sclerotiorum Gray mold disease (Botrytis cinerea) Anthracnose (Colletotrichum orbiculare) Black star disease (Cladosporium cucumerinum) Brown spot disease (Corynespora casiccola) Seedling Blight (Phythium debaryanam, Rhizoctonia
- Tomato gray mold (Botrytis cinerea) Leaf mold (Cladosporium fulvum) Phytophthora infestans Eggplant gray mold (Botrytis cinerea) Black blight (Corynespora melogenae) Powdery mildew (Erysiphe cichoracerarum) Susmolder disease (Mycovellosi natrassii) Strawberry Gray mold disease (Botrytis cinerea) Powdery mildew (Sohaerotheca humuli) Anthracnose (Colletotrichum acutatum, Colletotrichum fragariae) Phytophthora catarum Onion gray rot (Botrytis allii) Gray mold disease (Botrytis cinerea) White spotted leaf blight (Botrytis squamosa) Downy mildew (Peronospora destructor) Cabbage root-knot disease (Plasmodiophora brassicae) Soft rot (
- Citri Wheat powdery mildew (Erysiphe graminis f. Sp. Tritici) Red mold disease (Gibberella zeae) Red rust (Puccinia recondita) Brown snow rot (Pythium iwayamai) Scarlet Snow Rot (Monographella nivalis) Eye disease (Pseudocercosporella herpotriochoides) Leaf blight (Septoria tritici) Blight disease (Leptosphaeria nodorum) Typhula incarnata (Typhula incarnata) Snow rot large mycobacterial disease (Myriosclerotinia borealis) Blight (Gaeumanomyces graminis)
- Barley leaf spot (Pyrenophora graminea) Rhynchosporium secalis Bare Scab (Ustilago tritici, U. nuda) Rice blast disease (Pyricularia oryzae) Rhizoctonia solani Idiot Seedling (Gibberella fujikuroi) Sesame leaf blight (Cochliobolus niyabeanus) Seedling blight (Pythium gramicolium) Xanthomonas oryzae Seedling Bacterial Disease (Burkholderia plantarii) Brown stripe disease (Acidovorax avenae) Burkholderia glumae Tobacco sclerotia (Sclerotinia sclerotiorum) Powdery mildew (Erysiphe cichoracerarum) Botrytis cinerea Bentgrass Snow rot large sclerotia nuclear disease (Sclerotinia boreali
- the bactericidal agent of the present invention has an excellent bactericidal effect not only on pathogenic bacteria sensitive to these drugs but also on resistant bacteria.
- gray mold fungus (Botrytis cinerea), sugar beet brown fungus (Cercospora beticola), Venturia inaequalis, Venturia inaquali (Venturia inaequalis), Nent black urinaria (Venturia inaequilis)
- the fungicides of the present invention are also effective against).
- the fungicides of the present invention are also effective against gray mold fungi (Botrytis cinerea) that are resistant to dicarboximide fungicides (for example, vinclozolin, procymidone, iprodione).
- Favorable diseases that can be applied include black scab of apple, gray mold of cucumber, powdery mildew of wheat, plague of tomato, red rust of wheat, rice blast of rice, and cucumber vine split.
- the fungicide of the present invention is a highly safe drug with little phytotoxicity, low toxicity to fish and warm-blooded animals.
- a form that can be taken by a general pesticide for the purpose of use as an agrochemical, , Wettable powders, granules, powders, emulsions, aqueous solvents, suspensions, granular wettable powders and the like.
- Additives and carriers that can be added to the agrochemical formulation include vegetable powders such as soybean flour and wheat flour, diatomaceous earth, apatite, gypsum, talc, bentonite, and pyrophyllite for solid dosage forms.
- Organic and inorganic compounds such as mineral fine powders such as clay, sodium benzoate, urea, and sodium sulfate are used.
- kerosene, xylene and petroleum aromatic hydrocarbons, cyclohexane, cyclohexanone, dimethylformamide, dimethyl sulfoxide, alcohol, acetone, trichloroethylene, methyl isobutyl ketone, mineral oil, vegetable oil, Water or the like can be used as a solvent.
- a surfactant may be added as necessary.
- the surfactant that can be added is not particularly limited.
- alkylphenyl ether added with polyoxyethylene alkyl ether added with polyoxyethylene, higher fatty acid ester added with polyoxyethylene, polyoxyethylene Sorbitan higher fatty acid ester added with polyoxyethylene, nonionic surfactant such as tristyryl phenyl ether added with polyoxyethylene, sulfate ester salt of alkylphenyl ether added with polyoxyethylene, alkylbenzene sulfonate, sulfuric acid of higher alcohol
- ester salts alkyl naphthalene sulfonates, polycarboxylates, lignin sulfonates, formaldehyde condensates of alkyl naphthalene sulfonates, and isobutylene-maleic anhydride copolymers.
- the wettable powder, emulsion, flowable powder, aqueous solvent, and granular wettable powder thus obtained are diluted with water to a predetermined concentration to obtain a powder, granule as a solution, suspension or emulsion. Is used as it is by spraying on plants.
- the amount of the active ingredient in the fungicide of the present invention is usually preferably 0.01 to 90% by weight, more preferably 0.05 to 85% by weight, based on the entire composition (formulation).
- the application amount of the fungicide of the present invention varies depending on weather conditions, formulation form, application time, application method, application location, disease to be controlled, target crop, etc., but usually 1 to 1,000 g in terms of the amount of the active ingredient compound per hectare. It is preferably 10 to 100 g.
- the applied concentration is 1 to 1000 ppm, preferably 10 to 250 ppm.
- one or two or more of various fungicides, insecticides / miticides, and synergists can be mixed with the fungicide of the present invention.
- fungicides insecticides, acaricides, and plant growth regulators that can be used in combination with the compounds of the present invention are shown below.
- Fungicide Benzimidazoles such as benomyl, carbendazim, fuberidazole, thiabendazole, thiophanate methyl; Dicarboximides such as clozolinate, iprodione, procymidone, vinclozolin; Imazaril, oxpoconazole, pefazoate, prochloraz, triflumizole, triphorin, pyrifenox, fenarimol, nuarimol, azaconazole, viteltanol, bromconazole, cyproconazole, difenoconazole, diniconazole, epoxiconazole, fenbuconazole, full Quinconazole, flusilazole, flutriazole, hexaconazole, imibenconazole, ipconazole, metconazole, microbutanyl, penconazole, propiconazole, prothioconazole, cimeconazole,
- Phenylamides such as benalaxyl, furaxyl, metalaxyl, metalaxyl-M, oxadixyl, and ophthalase; Amines such as aldimorph, dodemorph, fenpropimorph, tridemorph, fenpropidin, piperalin, spiroxamine; Phosphorothiolate systems such as EDDP, iprobenphos, pyrazophos; Dithiolanes such as isoprothiolane; Carboxamides such as benodanyl, boscalid, carboxin, fenfuran, flutolanil, furametopyr, mepronyl, oxycarboxyl, penthiopyrad, tifluzamide; hydroxy- (2-amino) pyrimidines such as buprimate, dimethylylmol, ethylimyl; AP fungicide (anilinopyrimidine); N-phenylc
- Insecticides and acaricides Organophosphorus and carbamate insecticides: Fenthion, fenitrothion, diazinon, chlorpyrifos, ESP, bamidthione, phentoate, dimethoate, formothione, marathon, trichlorfone, thiometone, phosmet, dichlorvos, acephate, EPBP, methyl parathion, oxydimethone methyl, ethion, salicione, cyanophos, isoxathione, cyanophos, isoxathione Methidathione, Sulprophos, Chlorfenvinphos, Tetrachlorbinphos, Dimethylvinphos, Propafos, Isophenphos, Ethylthiomethone, Profenofos, Piracrofos, Monocrotophos, Adinfosmethyl, Aldicarb, Mesomil, Thiodicarb, Carbofuran, Carbo
- Pyrethroid insecticides Permethrin, cypermethrin, deltamethrin, fenvalerate, fenpropatoline, pyrethrin, allethrin, tetramethrin, resmethrin, dimethrin, propraslin, phenothrin, protorin, fulvalinate, cyfluthrin, cyhalothrin, flucitrinate, etofenprox, cycloprotorin, thoramethrin , Silafluophene, brofenprox, aclinasrin, etc.
- Benzoylurea and other insecticides Diflubenzuron, Chlorfluazuron, Hexaflumuron, Triflumuron, Tetrabenzuron, Flufenoxuron, Flucycloxuron, Buprofezin, Pyriproxyfen, Metoprene, Benzoepine, Diafenthiuron, Acetamiprid, Imidacloprid, Nitenpyram, Fipronil, Cartap Thiocyclam, bensultap, nicotine sulfate, rotenone, metaldehyde, machine oil, microbial pesticides such as BT and entomopathogenic viruses.
- Nematicides Phenamifos, phostiazates, etc.
- Acaricide Chlorbenzilate, phenisobromolate, dicofol, amitraz, BPPS, benzomate, hexithiazox, fenbutazin oxide, polynactin, quinomethionate, CPCBS, tetradiphone, avermectin, milbemectin, clofentedin, cihexatin, pyridaben, fenpyroximate, tebufenpyrad, thiomidibene Dienochlor etc.
- Plant growth regulator Abscisic acid, indole butyric acid, uniconazole, etiquelozate, etephone, cloxiphonac, chlormecote, chlorella extract, calcium peroxide, cyanamide, dichlorprop, gibberellin, daminozide, decyl alcohol, trinexapac ethyl, mepicoat chloride, pack Lobutrazole, paraffin, wax, piperonyl butoxide, pyraflufenethyl, flurprimidol, prohydrojasmon, prohexadione calcium salt, benzylaminopurine, pendimethalin, forchlorphenuron, potassium hydrazide maleate, 1- Naphtylacetamide, 4-CPA, MCPB, choline, oxyquinoline sulfate, ethiclozeate, butorualine, 1-methylcyclopropene, abiglycine hydrochloride.
- corresponds to the compound number in the table
- Example 75 Example of synthesis using triol salt (another method of Example 51) (Process 1) Synthesis of trifluoromethanesulfonic acid 7-chloro-2,2-dimethyl-3,4-dihydro-2H-benzo [f] [1,4] oxazepin-5-yl ester Dissolve 1.6 g (7.09 mmol) of 7-chloro-2,2-dimethyl-3,4-dihydro-2H-benzo [f] [1,4] oxazepin-5-one in 50 mL of dichloromethane at -10 ° C.
- Example of this invention disinfectant is shown a few, an additive and an addition ratio should not be limited to these Examples, and can be changed in a wide range. Moreover, the part in a formulation Example shows a weight part.
- Formulation Example 1 Wetting agent Compound of the present invention 40 parts Clay 48 parts Dioctylsulfosuccinate sodium salt 4 parts Lignin sulfonic acid sodium salt 8 parts or more are uniformly mixed and finely pulverized, and 40% active ingredient wettable powder Get.
- Emulsion Compound of the present invention 10 parts Solvesso 200 53 parts Cyclohexanone 26 parts Calcium dodecylbenzenesulfonate 1 part Polyoxyethylene alkylallyl ether 10 parts or more are mixed and dissolved to obtain an emulsion containing 10% active ingredient.
- Formulation Example 3 Powder A compound of the present invention 10 parts Clay 90 parts or more are mixed uniformly and finely pulverized to obtain a powder of 10% active ingredient.
- Formulation Example 4 Granules Compound of the present invention 5 parts Clay 73 parts Bentonite 20 parts Dioctyl sulfosuccinate sodium salt 1 part Potassium phosphate 1 part or more is pulverized and mixed well, and after adding water and kneading well, granulation drying As a result, granules containing 5% of the active ingredient are obtained.
- Formulation Example 5 Suspension Compound of the present invention 10 parts Polyoxyethylene alkyl allyl ether 4 parts Polycarboxylic acid sodium salt 2 parts Glycerin 10 parts Xanthan gum 0.2 parts Water 73.8 parts or more are mixed and the particle size is 3 microns or less The suspension is wet-pulverized until a suspension of 10% active ingredient is obtained.
- Granule wettable powder Compound of the present invention 40 parts Clay 36 parts Potassium chloride 10 parts Alkylbenzenesulfonic acid sodium salt 1 part Lignin sulfonic acid sodium salt 8 parts Formaldehyde condensate of alkylbenzenesulfonic acid sodium salt 5 parts or more uniformly mixed After finely pulverizing, add an appropriate amount of water and knead to make clay. The clay-like product is granulated and then dried to obtain a granule wettable powder containing 40% of the active ingredient.
- test (Test Example 1) Apple scab control test An emulsion of the compound of the present invention was sprayed at a concentration of 100 ppm active ingredient on apple seedlings (variety “Kokumitsu”, 3-4 leaf stage) cultivated in an unglazed pot. After natural drying at room temperature, conidia spores of Venturia inaequalis were inoculated and kept in a room of 20 ° C. and high humidity for 2 weeks, repeating light and dark every 12 hours. The lesion appearance state on the leaf was compared with no treatment, and the control effect was obtained.
- Compound numbers (corresponding to the compound numbers in Tables 1 to 12): A1-19, A1-20, B1-1, B1-3, B1-9, B1-11, B1-29 to B1-49, B1 -51, B1-53, B1-54, B1-56, B1-62 to B1-67, B1-70, B1-79, B1-82, B2-6, B2-13 to B2-15, B4-47 ⁇ B4-49, B4-50, B5-34, B6-34
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Abstract
Description
本願は、2008年8月12日に日本に出願された特願2008-207759号、及び2009年1月14日に日本に出願された特願2009-005997号に基づき優先権を主張し、その内容をここに援用する。
本発明は、さらに上記化合物の製造中間体であるボロン酸誘導体、及びその製造方法を提供する。
R1とR2は一緒になって、置換基を有してもよい5~8員環を形成してもよい。
R3~R6は、夫々独立して、水素原子、置換基を有してもよいC1~20アルキル基、置換基を有してもよいC2~20アルケニル基、置換基を有してもよいC2~20アルキニル基、置換基を有してもよいC3~20シクロアルキル基、置換基を有してもよいC4~20シクロアルケニル基、置換基を有してもよいC8~20シクロアルキニル基、置換基を有してもよいC6~10アリール基、置換基を有してもよいヘテロ環基、置換基を有してもよいC1~20アシル基、置換基を有してもよい(1-イミノ)C1~20アルキル基、置換基を有してもよい水酸基、置換基を有してもよいアミノ基、置換基を有してもよいメルカプト基、置換基を有するスルホニル基、ハロゲノ基、又はシアノ基を示す。
R3~R6から複数を選択して、一緒になって、置換基を有してもよい3~8員環を形成してもよい。
R3とR4、又はR5とR6は一緒になって、オキソ基、チオキソ基、置換基を有してもよいイミノ基を形成してもよい。
式中、A-Bは、Aは炭素原子であり、Bは窒素原子であり、
式:C=N 、式:CR7-NR8 、下記式(II)又は式(III)を示す。
R7は、水素原子、置換基を有してもよいC1~20アルキル基、置換基を有してもよいC2~20アルケニル基、置換基を有してもよいC2~20アルキニル基、置換基を有してもよいC1~20アシル基、置換基を有してもよい水酸基、置換基を有してもよいアミノ基、置換基を有してもよいメルカプト基、ハロゲノ基、又はシアノ基を示す。
R8は、水素原子、置換基を有してもよいC1~20アルキル基、置換基を有してもよいC2~20アルケニル基、置換基を有してもよいC2~20アルキニル基、又は置換基を有してもよいC1~20アシル基を示す。
Yは、酸素原子、硫黄原子、又はスルフィニル基を示す。
X及びX’は、夫々独立して、置換基を有してもよいC1~20アルキル基、置換基を有してもよいC2~20アルケニル基、置換基を有してもよいC2~20アルキニル基、置換基を有してもよいC3~20シクロアルキル基、置換基を有してもよいC4~20シクロアルケニル基、置換基を有してもよいC8~20シクロアルキニル基、置換基を有してもよいC6~10アリール基、置換基を有してもよいヘテロ環基、置換基を有してもよいC1~20アシル基、置換基を有してもよい(1-イミノ)C1~20アルキル基、置換基を有してもよい水酸基、置換基を有してもよいアミノ基、置換基を有してもよいメルカプト基、置換基を有するスルホニル基、ハロゲノ基、シアノ基、又はニトロ基を示す。
mは、0~2のいずれかの整数を示す。
nは、0~4のいずれかの整数を示す。)
式中、pは0~6のいずれかの整数を示す。)
即ち、C1~6アルキルマグネシウムハライドとC1~6アルキルリチウムを反応させ、次いで、式(V)
(式中、X”は、夫々独立して、置換基を有してもよいC1~20アルキル基、置換基を有してもよいC2~20アルケニル基、置換基を有してもよいC2~20アルキニル基、置換基を有してもよいC3~20シクロアルキル基、置換基を有してもよいC4~20シクロアルケニル基、置換基を有してもよいC8~20シクロアルキニル基、置換基を有してもよいC6~10アリール基、置換基を有してもよいヘテロ環基、置換基を有してもよい水酸基、置換基を有してもよいアミノ基、置換基を有してもよいメルカプト基、フッ素原子、塩素原子又はニトロ基を示す。
qは、0~6のいずれかの整数を示す。X1は、臭素原子又はヨウ素原子を示す。)で表される化合物を反応させて、次いで、
式(VI): B(OR12)3
(式中、R12は、夫々独立して、C1~6アルキル基を示す。)
で表される化合物を反応させて、式(VII)
(式中、X” 及びqは、上記と同じ意味を示す。)
で表されるボロン酸誘導体を製造する。
(式中、X2は、フッ素原子又は塩素原子を示す。R13は、夫々独立して、水素原子、又はC1~20アルキル基を示す。R13同士は一緒になって、5~8員環を形成してもよい。)
(式中、X3は、水素原子、フッ素原子又は塩素原子を示す。R14は、夫々独立して、C1~20アルキル基を示す。R14同士は一緒になって、5~8員環を形成してもよい。Mは、アルカリ金属を示す。)
本発明の農園芸用殺菌剤は優れた防除効果を有し、植物体に薬害を生じることがなく、人畜魚類に対する毒性や環境への影響が少ない薬剤である。
また、本発明のボロン酸誘導体は本発明の含窒素ヘテロ環化合物等の中間体として有用である。
(式(I)で表される含窒素ヘテロ環化合物又はその塩)
本発明は、前記式(I)で表される含窒素ヘテロ環化合物又はその塩に関するものである。本発明化合物又はその塩には、水和物、各種溶媒和物や結晶多形等も含まれる。さらに、本発明化合物は、不斉炭素原子、二重結合などに基づく立体異性体及びそれらの混合物を包含する。
R1~R8、X及びX’の「置換基を有してもよいC1~20アルキル基」の「C1~20アルキル基」とは、直鎖、又は分岐鎖の炭素数1~20のアルキル基を意味する。例えば、メチル基、エチル基、n-プロピル基、n-ブチル基、n-ペンチル基、n-ヘキシル基、n-ヘプチル基、n-オクチル基、ノニル基、n-デシル基、ドデシル基、トリデシル基、テトラデシル基、ペンタデシル基、ヘキサデシル基、ヘプタデシル基、オクタデシル基、ノナデシル基、イコシル基、i-プロピル基、i-ブチル基、s-ブチル基、t-ブチル基、イソペンチル基、ネオペンチル基、2-メチルブチル基、2,2-ジメチルプロピル基、イソヘキシル基、イソノニル基、2-エチルオクチル基、3-エチルオクチル基、2,3-ジメチルオクチル基、4-プロピルオクチル基、4-エチルデシル基、6-エチルドデシル基、3,5-ジメチルデシル基、2,5-ジメチルデシル基、6-プロピルノニル基、4-ブチルオクチル基、2,4,6,8-テトラメチルデシル基、2,2-ジエチルデシル基、2,5-ジエチルデシル基、4-ブチルデシル基、2,4,6,8-テトラエチルデシル基等が挙げられる。これらのうち、C1~6アルキル基が好ましい。
アジリジン-1-イル基、アジリジン-2-イル基、エポキシ基;
テトラヒドロフラン-2-イル基、テトラヒドロフラン-3-イル基、ピロリジン-1-イル基、ピロリジン-2-イル基、ピロリジン-3-イル基;
ピロ-ル-1-イル基、ピロ-ル-2-イル基、ピロ-ル-3-イル基、フラン-2-イル基、フラン-3-イル基、チオフェン-2-イル基、チオフェン-3-イル基、イミダゾール-1-イル基、イミダゾール-2-イル基、イミダゾール-4-イル基、イミダゾール-5-イル基、ピラゾール-1-イル基、ピラゾール-3-イル基、ピラゾール-4-イル基、ピラゾール-5-イル基、オキサゾール-2-イル基、オキサゾール-4-イル基、オキサゾール-5-イル基、チアゾール-2-イル基、チアゾール-4-イル基、チアゾール-5-イル基、イソオキサゾール-3-イル基、イソオキサゾール-4-イル基、イソオキサゾール-5-イル基、イソチアゾール-3-イル基、イソチアゾール-4-イル基、イソチアゾール-5-イル基、1,2,3-トリアゾール-1-イル基、1,2,3-トリアゾール-4-イル基、1,2,3-トリアゾール-5-イル基、1,2,4-トリアゾール-1-イル基、1,2,4-トリアゾール-3-イル基、1,2,4-トリアゾール-5-イル基、1,3,4-オキサジアゾール-2-イル基、1,2,4-オキサジアゾール-3-イル基、1,3,4-チアジアゾール-2-イル基、1,2,4-チアジアゾール-3-イル基、テトラゾール-1-イル基、テトラゾール-2-イル基;
ピリジン-2-イル基、ピリジン-3-イル基、ピリジン-4-イル基、ピラジン-2-イル基、ピリミジン-2-イル基、ピリミジン-4-イル基、ピリミジン-5-イル基、ピリダジン-3-イル基、ピリダジン-4-イル基、トリアジニル基;
インドール-1-イル基、インドール-2-イル基、インドール-3-イル基、インドール-4-イル基、インドール-5-イル基、インドール-6-イル基、インドール-7-イル基、ベンゾフラン-2-イル基、ベンゾフラン-3-イル基、ベンゾフラン-4-イル基、ベンゾフラン-5-イル基、ベンゾフラン-6-イル基、ベンゾフラン-7-イル基、ベンゾチオフェン-2-イル基、ベンゾチオフェン-3-イル基、ベンゾチオフェン-4-イル基、ベンゾチオフェン-5-イル基、ベンゾチオフェン-6-イル基、ベンゾチオフェン-7-イル基、イソインドール-1-イル基、イソインドール-2-イル基、イソインドール-4-イル基、イソインドール-5-イル基、イソインドール-6-イル基、イソインドール-7-イル基、イソベンゾフラン-1-イル基、イソベンゾフラン-4-イル基、イソベンゾフラン-5-イル基、イソベンゾフラン-6-イル基、イソベンゾフラン-7-イル基、ベンゾイミダゾール-1-イル基、ベンゾイミダゾール-2-イル基、ベンゾイミダゾール-4-イル基、ベンゾイミダゾール-5-イル基、ベンゾオキサゾール-2-イル基、ベンゾオキサゾール-4-イル基、ベンゾオキサゾール-5-イル基、ベンゾチアゾール-2-イル基、ベンゾチアゾール-4-イル基、ベンゾチアゾール-5-イル基;
クロメン-2-イル基、クロメン-3-イル基、クロメン-4-イル基、クロメン-5-イル基、クロメン-6-イル基、クロメン-7-イル基、クロメン-8-イル基、キノリン-2-イル基、キノリン-3-イル基、キノリン-4-イル基、キノリン-5-イル基、キノリン-6-イル基、キノリン-7-イル基、キノリン-8-イル基、イソキノリン-1-イル基、イソキノリン-3-イル基、イソキノリン-4-イル基、イソキノリン-5-イル基、イソキノリン-6-イル基、イソキノリン-7-イル基、イソキノリン-8-イル基;
ピペリジン-1-イル基、ピペリジン-2-イル基、ピペリジン-3-イル基、ピペリジン-4-イル基、ピペラジン-1-イル基、ピペラジン-2-イル基、ピペラジン-3-イル基、モルホリン-2-イル基、モルホリン-3-イル基、モルホリン-4-イル基;1,3-ベンゾジオキソール-4-イル基、1,3-ベンゾジオキソール-5-イル基、1,4-ベンゾジオキサン-5-イル基、1,4-ベンゾジオキサン-6-イル基、3,4-ジヒドロ-2H-1,5-ベンゾジオキセピン-6-イル基、3,4-ジヒドロ-2H-1,5-ベンゾジオキセピン-7-イル基、2,3-ジヒドロベンゾフラン-4-イル基、2,3-ジヒドロベンゾフラン-5-イル基、2,3-ジヒドロベンゾフラン-6-イル基、2,3-ジヒドロベンゾフラン-7-イル基;
等が挙げられる。
これらのうち、5~10員のヘテロ環基が好ましい。
例えば、ホルミル基、アセチル基、プロピオニル基、n-プロピルカルボニル基、n-ブチルカルボニル基、ペンタノイル基、バレリル基、オクタノイル基、ノナノイル基、デカノイル基、ウンデカノイル基、ドデカノイル基、トリデカノイル基、テトラデカノイル基、ペンタデカノイル基、ヘキサデカノイル基、ヘプタデカノイル基、オクタデカノイル基、ノナデカノイル基、アイコサノイル基及びヘナイコサノイル基、i-プロピルカルボニル基、i-ブチルカルボニル基、ピバロイル基、イソバレリル基、3-メチルノナノイル基、8-メチルノナノイル基、3-エチルオクタノイル基、3,7-ジメチルオクタノイル基、1-メチルペンタデカノイル基、14-メチルペンタデカノイル基、13,13-ジメチルテトラデカノイル基、15-メチルヘキサデカノイル基、1-メチルヘプタデカノイル基等のアルキルカルボニル基;アクリロイル基、メタクリロイル基等のアルケニルカルボニル基;プロピオロイル基等のアルキニルカルボニル基;ベンゾイル基、ナフチルカルボニル基、ビフェニルカルボニル基、アントラニルカルボニル基等のアリールカルボニル基;2-ピリジルカルボニル基、チエニルカルボニル基等のヘテロ環カルボニル基等が挙げられる。これらのうち、C1~7アシル基が好ましい。
具体的には、芳香族炭化水素環としては、ベンゼン環が挙げられ、芳香族ヘテロ環としては、フラン環、チオフェン環、ピロ-ル環、ピリジン環、ピラジン環、ピリミジン環、ピリダジン環、イミダゾール環、ピラゾール環、チアゾール環、オキサゾール環、イソオキサゾール環等が挙げられる。
脂肪族炭化水素環としては、シクロアルケン環があり、シクロペンテン環、シクロヘキセン環、シクロヘプテン環、シクロオクテン環等が挙げられる。
不飽和ヘテロ環としては、ジヒドロ-2H-ピラン環、ジヒドロ-2H-チオピラン環、テトラヒドロピリジン環等が挙げられる。
これらのうち、ベンゼン環が好ましい。すなわち、本発明化合物は、式(I)中のピリジン環とベンゼン環が縮合してキノリン環を形成するのが好ましい。
具体的には、脂肪族炭化水素環としては、シクロアルカン環があり、シクロプロパン環、シクロペンタン環、シクロヘキサン環、シクロヘプタン環、シクロオクタン環等が挙げられる。
芳香族炭化水素環としては、ベンゼン環が挙げられ、芳香族ヘテロ環としては、フラン環、チオフェン環、ピロ-ル環、ピリジン環、ピラジン環、ピリミジン環、ピリダジン環、イミダゾール環、ピラゾール環、チアゾール環、オキサゾール環、イソオキサゾール環等が挙げられる。
不飽和ヘテロ環としては、ジヒドロ-2H-ピラン環、ジヒドロ-2H-チオピラン環、テトラヒドロピリジン環等が挙げられる。
本発明化合物は、X及びX’としては、様々に選択することが可能であるが、ハロゲノ基が好ましい。
式:C=N 、式:CR7-NR8 、下記式(II)又は式(III)を示す。
R7は、水素原子、置換基を有してもよいC1~20アルキル基、置換基を有してもよいC2~20アルケニル基、置換基を有してもよいC2~20アルキニル基、置換基を有してもよいC1~20アシル基、置換基を有してもよい水酸基、置換基を有してもよいアミノ基、置換基を有してもよいメルカプト基、ハロゲノ基、又はシアノ基を示す。
R8は、水素原子、置換基を有してもよいC1~20アルキル基、置換基を有してもよいC2~20アルケニル基、置換基を有してもよいC2~20アルキニル基、又は置換基を有してもよいC1~20アシル基を示す。
A-Bは、好ましくは、式:C=N、である。
本明細書において、「置換基を有する」又は「置換基を有してもよい」とは、上記のそれぞれの「基」のいずれかの水素原子と、「置換基」が置換していること、又は置換していてもよいことをいう。「置換基」としては、例えば上記のそれぞれの「基」を挙げることができるが、それら「置換基」はさらに「別の基」で置換された「置換基」であってもよい。「別の基」としては、例えば上記のそれぞれの「基」を挙げることができる。
以下に、上記のそれぞれの「基」において、上記のいずれかの「基」により置換された例を示す。
また、「置換基を有してもよい(1-ヒドロキシイミノ)C1~20アルキル基」において、水酸基上の水素原子が、「置換基を有してもよいC1~20アルキル基」により置換された「基」としては、例えば、メトキシイミノメチル基、(1-エトキシイミノ)メチル基、(1-エトキシイミノ)エチル基等が挙げられる。これらのうち、(1-(C1~6アルコキシ)イミノ)C1~6アルキル基が好ましい。
また、アミノ基上の2つの水素原子が、「置換基を有してもよいC1~20アルキル基」の同一の炭素原子で置換された「基」としては、例えば、メチリデンアミノ基、エチリデンアミノ基等が挙げられる。これらのうち、モノC1~6アルキリデンアミノ基が好ましい。
また、上記以外にも、例えば、フェニルアミノ基、4-メチルフェニルアミノ基等のモノアリールアミノ基(好ましくはモノC6~10アリールアミノ基);ジ1-ナフチルアミノ基等のジアリールアミノ基(好ましくはジC6~10アリールアミノ基);アセチルアミノ基、ベンゾイルアミノ基等のアシルアミノ基(好ましくはC1~6アシルアミノ基)等が挙げられる。
また、上記以外にも、例えば、カルバモイル基;フェニルカルバモイル基、4-メチルフェニルカルバモイル基等のモノアリールカルバモイル基(好ましくはモノC6~10アリールカルバモイル基);アセチルカルバモイル基、ベンゾイルカルバモイル基等のアシルカルバモイル基(好ましくはC1~6アシルカルバモイル基)等が挙げられる。
また、上記以外にも、例えば、トリフロロメチルスルホニル基等のハロアルキルスルホニル基(好ましくはC1~6ハロアルキルスルホニル基);フェニルスルホニル基、4-メチルフェニルスルホニル基等のアリールスルホニル基(好ましくはC6~10アリールスルホニル基);スルフォ基;メトキシスルホニル基、エトキシスルホニル基等のアルコキシスルホニル基(好ましくはC1~6アルコキシスルホニル基);スルファモイル基;N-メチルスルファモイル基、N-エチルスルファモイル基、N,N-ジメチルスルファモイル基、N,N-ジエチルスルファモイル基等のスルファモイル基(好ましくは、モノC1~6アルキルスルファモイル基又はジC1~6アルキルスルファモイル基);フェニルスルファモイル基、4-メチルフェニルスルファモイル基等のモノアリールスルファモイル基(好ましくはモノC6~10アリールスルファモイル基)等が挙げられる。
上記のR21、R22、及びR23は、夫々独立して、C1~6アルキル基又はフェニル基を表す。C1~6アルキル基は、R1~R8、X及びX’にて例示したものと同様のものが挙げられる。
前記式(I)で表される化合物のうち、好ましくは、式(I)中、R1とR2が一緒になっている、式(IV)
(式中、X、X’、n、R3~R6、A-B及びYは、前記と同様の意味を示す。
式中、pは0~6のいずれかの整数を示す。)で表される化合物である。
前記式(IV)で表される化合物のうち、より好ましくは、式(IV)中、A-Bが式:C=Nである、式(IX)
(式中、X、X’、n、p、R3~R6、及びYは、前記と同様の意味を示す。)で表される化合物である。
前記式(I)、式(IV)及び式(IX)で表される化合物として具体的には例えば、次表[表1]~[表17]の化合物が例示できる。なお、表中、Meはメチル、Etはエチル、n-Prはn-プロピル、i-Prはi-プロピル、c-Prはシクロプロピル、t-Buはt-ブチル、Acはアセチル、Bnはベンジル、Phはフェニルを表す。
本発明の化合物は、公知の方法により製造することができるが、例えば、下記のようにして製造することができる。
(式中、R1~R6、X、X’、Y、n、mは前記と同じ意味を表す。X4はハロゲン原子を表す。)
式(1)で表される化合物は、式(2)で表されるボロン酸誘導体と、式(3)で表されるイミドイルハライド誘導体を、例えば、前記非特許文献1若しくは非特許文献2に記載されているパラジウム錯体を用いたSuzukiカップリングにより調製することができる。
場合によっては、式(3)で表されるイミドイルハライド誘導体は、X4のハロゲン原子をアルキルスルホネート基、ハロアルキルスルホネート基へと導いた後、カップリングを行ってもよい。
ここにおいて、式(2)で表されるボロン酸誘導体にかえて、下記式(2')で表されるボロン酸誘導体を用いてもよい。
(式中、R1~R2、X’、mは前記と同じ意味を表す。R'14はC1~20アルキル基を表す。Mは、リチウム、ナトリウム、カリウム等のアルカリ金属を表す。)
(式中、R3~R6、X、Y、nは前記と同じ意味を表す。X4はハロゲン原子を表す。)
式(3)で表される化合物は、式(4)で表される環状アミドを、例えば、ホスゲン、オキザリルクロライド、チオニルクロライド等の酸ハライド存在下で、反応させる方法で調製することができる。また、トリフェニルホスフィン、四塩化炭素の混合系でも同様に得られる。
(式中、R3~R6、X、Y、nは前記と同じ意味を表す。Z’は酸素原子又はN-OHを表す。)
式(4)で表される化合物は、式(5)で表される環状のアセトフェノン誘導体を、シュミット反応により、又はオキシムへと誘導した後、ベックマン転位により調製することができる。両方の反応について、様々な変法が報告されている。シュミット反応において例えば、前記非特許文献3若しくは非特許文献4に記載されているような、ケトンを、アジ化ナトリウムと強酸、例えば、濃塩酸、硫酸、トリフルオロ酢酸又はメタンスルホン酸中で、溶媒の非存在下に又はアセトニトリル、クロロホルム又は塩化メチレンのような溶媒中で反応させることができる。
本発明は、さらに、本発明化合物の製造に用いる製造中間体の製造方法に関するものである。すなわち、C1~6アルキルマグネシウムハライドとC1~6アルキルリチウムを反応させ、次いで、式(V)
qは、0~6のいずれかの整数を示す。X1は、臭素原子又はヨウ素原子を示す。)
で表される化合物を反応させて、次いで、
式(VI): B(OR12)3
(式中、R12は、夫々独立して、C1~6アルキル基を示す。)
で表される化合物(以下、「トリアルコキシボラン試薬」ということがある。)を反応させて、式(VII)
で表されるボロン酸誘導体を製造する方法に関するものである。
このボロン酸誘導体は、本発明化合物の製造中間体として用いることができる。
処理温度は、-78℃~室温の間で適宜に行うことが可能であるが、好ましくは-10℃~0℃である。
で表されるボロン酸エステル誘導体も、本発明化合物の製造中間体として用いることができる。
式(VII’)で表されるボロン酸エステル誘導体は、前記式(VII)で表されるボロン酸誘導体をエステル化することで製造することができる。エステル化の方法については、前記非特許文献5、非特許文献6等に記載された方法を用いることができる。
本発明は、本発明化合物の製造中間体にも関するものである。
すなわち、式(VIII)
(式中、X2は、フッ素原子又は塩素原子を示す。R13は、夫々独立して、水素原子、又はC1~20アルキル基を示す。R13同士は一緒になって、5~8員環を形成してもよい。)
で表されるボロン酸誘導体に関するものである。
このボロン酸誘導体は、本発明化合物の製造中間体として特に有用である。
(式中、X3は、水素原子、フッ素原子又は塩素原子を示す。R14は、夫々独立して、C1~20アルキル基を示す。R14同士は一緒になって、5~8員環を形成してもよい。Mは、アルカリ金属を示す。)
で表されるボロン酸誘導体に関するものである。
このボロン酸誘導体も、本発明化合物の製造中間体として有用である。
(式中、X3は、水素原子、フッ素原子又は塩素原子を示す。R15は、C1~20アルキル基を示す。Mは、アルカリ金属を示す。)
で表されるボロン酸誘導体が、さらに好ましい。
式(X')中のR15の「C1~20アルキル基」としては、Xにおいて例示したC1~20アルキル基と同様の「基」が挙げられる。好ましくは、C1~6アルキル基であり、例えば、メチル基、エチル基、n-プロピル基、i-プロピル基が挙げられる。
本発明は、さらに本発明の式(I)、式(IV)若しくは式(IX)で表される含窒素ヘテロ環化合物又はその塩の少なくとも1種を有効成分として含有する農園芸用殺菌剤(以下、「本発明殺菌剤」ということがある。)に関するものである。
テンサイ 褐斑病(Cercospora beticola)
黒根病(Aphanomyces cochlloides)
根腐病(Thanatephorus cucumeris)
葉腐病(Thanatephorus cucumeris)
ラッカセイ 褐斑病(Mycosphaerella arachidis)
黒渋病(Mycosphaerella berkeleyi)
キュウリ うどんこ病(Sphaerotheca fuliginea)
べと病(Pseudoperonospora cubensis)
つる枯病(Mycosphaerella melonis)
つる割病(Fusarium oxysporum)
菌核病(Sclerotinia sclerotiorum)
灰色かび病(Botrytis cinerea)
炭そ病(Colletotrichum orbiculare)
黒星病(Cladosporium cucumerinum)
褐斑病(Corynespora cassicola)
苗立枯病(Pythium debaryanam、Rhizoctonia solani Kuhn)
斑点細菌病(Pseudomonas syringae pv.Lecrymans)
トマト 灰色かび病(Botrytis cinerea)
葉かび病(Cladosporium fulvum)
疫病(Phytophthora infestans)
ナス 灰色かび病(Botrytis cinerea)
黒枯病(Corynespora melongenae)
うどんこ病(Erysiphe cichoracearum)
すすかび病(Mycovellosiella nattrassii)
イチゴ 灰色かび病(Botrytis cinerea)
うどんこ病(Sohaerotheca humuli)
炭そ病(Colletotrichum acutatum、Colletotrichum fragariae)
疫病(Phytophthora cactorum)
タマネギ 灰色腐敗病(Botrytis allii)
灰色かび病(Botrytis cinerea)
白斑葉枯病(Botrytis squamosa)
べと病(Peronospora destructor)
キャベツ 根こぶ病(Plasmodiophora brassicae)
軟腐病(Erwinia carotovora)
べと病(Peronospora parasitica)
インゲン 菌核病(Sclerotinia sclerotiorum)
灰色かび病(Botrytis cinerea)
りんご うどんこ病(Podosphaera leucotricha)
黒星病(Venturia inaequalis)
モニリア病(Monilinia mali)
黒点病(Mycosphaerella pomi)
腐らん病(Valsa mali)
斑点落葉病(Alternaria mali)
赤星病(Gymnosporangium yamadae)
輪紋病(Botryosphaeria berengeriana)
炭そ病(Glomerella cingulata、Colletotrichum acutatum)
褐斑病(Diplocarpon mali)
すす点病(Zygophiala jamaicensis)
すす斑病(Gloeodes pomigena)
カキ うどんこ病(Phyllactinia kakicola)
炭そ病(Gloeosporium kaki)
角斑落葉病(Cercospora kaki)
黒星病(Cladosporium carpophilum)
ホモプシス腐敗病(Phomopsis sp.)
オウトウ 灰星病(Monilinia fructicola)
ブドウ 灰色かび病(Botrytis cinerea)
うどんこ病(Uncinula necator)
晩腐病(Glomerella cingulata、Colletotrichum acutatum)
べと病(Plasmopara viticola)
黒とう病(Elsinoe ampelina)
褐斑病(Pseudocercospora vitis)
黒腐病(Guignardia bidwellii)
ナシ 黒星病(Venturia nashicola)
赤星病(Gymnosporangium asiaticum)
黒斑病(Alternaria kikuchiana)
輪紋病(Botryosphaeria berengeriana)
うどんこ病(Phyllactinia mali)
チャ 輪斑病(Pestalotia theae)
炭そ病(Colletotrichum theae-sinensis)
カンキツ そうか病(Elsinoe fawcetti)
青かび病(Penicillium italicum)
緑かび病(Penicillium digitatum)
灰色かび病(Botrytis cinerea)
黒点病(Diaporthe citri)
かいよう病(Xanthomonas campestris pv.Citri)
コムギ うどんこ病(Erysiphe graminis f.sp.tritici)
赤かび病(Gibberella zeae)
赤さび病(Puccinia recondita)
褐色雪腐病(Pythium iwayamai)
紅色雪腐病(Monographella nivalis)
眼紋病(Pseudocercosporella herpotrichoides)
葉枯病(Septoria tritici)
ふ枯病(Leptosphaeria nodorum)
雪腐小粒菌核病(Typhula incarnata)
雪腐大粒菌核病(Myriosclerotinia borealis)
立枯病(Gaeumanomyces graminis)
雲形病(Rhynchosporium secalis)
裸黒穂病(Ustilago tritici、U.nuda)
イネ いもち病(Pyricularia oryzae)
紋枯病(Rhizoctonia solani)
馬鹿苗病(Gibberella fujikuroi)
ごま葉枯病(Cochliobolus niyabeanus)
苗立枯病(Pythium graminicolum)
白葉枯病(Xanthomonas oryzae)
苗立枯細菌病(Burkholderia plantarii)
褐条病(Acidovorax avenae)
もみ枯細菌病(Burkholderia glumae)
タバコ 菌核病(Sclerotinia sclerotiorum)
うどんこ病(Erysiphe cichoracearum)
チューリップ灰色かび病(Botrytis cinerea)
ベントグラス雪腐大粒菌核病(Sclerotinia borealis)
赤焼病(Pythium aphanidermatum)
オーチャードグラス うどんこ病(Erysiphe graminis)
ダイズ 紫斑病(Cercospora kikuchii)
べと病(Peronospora Manshurica)
茎疫病(Phytophthora sojae)
ジャガイモ・トマト疫病(Phytophthora infestans)
等の防除に使用することができる。
本発明殺菌剤を実際に施用する際には、本発明化合物を他成分を加えることなく純粋な形で使用するものであっても、農薬として使用する目的で一般の農薬のとり得る形態、即ち、水和剤、粒剤、粉剤、乳剤、水溶剤、懸濁剤、顆粒水和剤等の農薬製剤の形態で使用するものであってもよい。
添加することができる界面活性剤としては特に限定はないが、例えば、ポリオキシエチレンが付加したアルキルフェニルエーテル、ポリオキシエチレンが付加したアルキルエーテル、ポリオキシエチレンが付加した高級脂肪酸エステル、ポリオキシエチレンが付加したソルビタン高級脂肪酸エステル、ポリオキシエチレンが付加したトリスチリルフェニルエーテル等の非イオン性界面活性剤、ポリオキシエチレンが付加したアルキルフェニルエーテルの硫酸エステル塩、アルキルベンゼンスルホン酸塩、高級アルコールの硫酸エステル塩、アルキルナフタレンスルホン酸塩、ポリカルボン酸塩、リグニンスルホン酸塩、アルキルナフタレンスルホン酸塩のホルムアルデヒド縮合物、イソブチレン-無水マレイン酸共重合体等が挙げられる。
ベノミル、カルベンダジム、フベリダゾール、チアベンダゾール、チオファネート メチル等のベンゾイミダゾール系;
クロゾリネート、イプロジオン、プロシミドン、ビンクロゾリン等のジカルボキシイミド系;
イマザリル、オキスポコナゾール、ペフラゾエート、プロクロラズ、トリフルミゾール、トリホリン、ピリフェノックス、フェナリモル、ヌアリモル、アザコナゾール、ビテルタノール、ブロムコナゾール、シプロコナゾール、ジフェノコナゾール、ジニコナゾール、エポキシコナゾール、フェンブコナゾール、フルキンコナゾール、フルシラゾール、フルトリアホル、ヘキサコナゾール、イミベンコナゾール、イプコナゾール、メトコナゾール、ミクロブタニル、ペンコナゾール、プロピコナゾール、プロチオコナゾール、シメコナゾール、テブコナゾール、テトラコナゾール、トリアジメホン、トリアジメノール、トリチコナゾール、エタコナゾール、ファーコナゾールシス、イプコナゾール、イミベンコナゾール、等のDMI-殺菌剤;
ベナラキシル、フララキシル、メタラキシル、メタラキシル-M、オキサジキシル、オフラセ等のフェニルアミド系;
アルジモルフ、ドデモルフ、フェンプロピモルフ、トリデモルフ、フェンプロピジン、ピペラリン、スピロキサミン等のアミン系;
EDDP、イプロベンホス、ピラゾホス等のホスホロチオレート系;
イソプロチオラン等のジチオラン系;
ベノダニル、ボスカリド、カルボキシン、フェンフラン、フルトラニル、フラメトピル、メプロニル、オキシカルボキシン、ペンチオピラド、チフルザミド等のカルボキサミド;ブピリメート、ジメチリモル、エチリモル等のヒドロキシ-(2-アミノ)ピリミジン;シプロジニル、メパニピリム、ピリメタニル等のAP殺菌剤 (アニリノピリミジン) ;
ジエトフェンカルブ等のN-フェニルカーバメート;アゾキシストロビン、ピコキシストロビン、ピラクロストロビン、クレソキシム-メチル、トリフロキシストロビン、ジモキシストロビン、メトミノストロビン、オリザストロビン、ファモキサドン、フルオキサストロビン、フェンアミドン、メトミノフェン、ピリベンカルブ等のQoI-殺菌剤 (Qo阻害剤);
フェンピコニル、フルジオキソニル等のPP殺菌剤 (フェニルピロール) ;
キノキシフェン等のキノリン系 ;
ビフェニル、クロロネブ、ジクロラン、キントゼン、テクナゼン、トルクトフォス-メチル等のAH殺菌剤(芳香族炭化水素);
フサライド、ピロキロン、トリシクラゾール等のMBI-R;
カルプロパミド、ジクロシメット、フェノキサニル等のMBI-D;
フェンヘキサミド、ピリブチカルブ、タービナフィン等のSBI剤;
ペンシクロン等のフェニルウレア;
シアゾファミド等のQiI-殺菌剤(Qi阻害剤);
ゾキサミド等のベンズアミド;
ブラストサイジン、ミルディオマイシン等のエノピランウロン;
カスガマイシン等のへキソピラノシル;
ストレプトマイシン、バリダマイシン等のグルコピラノシル;
シモキサニル等のシアノアセトアミド;
プロパモカルブ、プロチオカルブ、ポリカーバメート等のカーバメート;
ビナパクリル、ジノカップ、フェリムゾン、フルアジナム等の脱共役剤;
酢酸トリフェニルスズ、塩化トリフェニルスズ、水酸化トリフェニルスズ等の有機スズ化合物;
亜リン酸、トルクロホスメチル、ホセチル等のリン酸エステル;
テクロフタラム等のフタルアミド酸;
トリアゾキシド等のベンゾトリアジン;
フルスルファミド等のベンゼンスルフォナミド;
ジクロメジン等のピリダジノン;
ジメトモルフ、フルモルフ、ベンチアバリカルブ、イプロバリカルブ、マンジプロパミド等のCAA殺菌剤(カルボン酸アミド);
オキシテトラサイクリン等のテトラサイクリン;
メタスルホカルブ等のチオカーバメート;
エトリジアゾール、ポリオキシン、オキソリニック酸、ヒドロキシイソキサゾール、オクチノリン、シルチオファム、ジフルメトリム、アシベンゾラルSメチル、プロベナゾール、チアジニル、エタボキサム、シフルフェナミド、プロキナジド、メトラフェノン、フルオピコリド、水酸化第二銅、有機銅、硫黄、ファーバム、マンゼブ、マンネブ、メチラム、プロピネブ、チウラム、ジネブ、ジラム、キャプタン、カプタホール、フォルペット、クロロタロニル、ジクロフルアニド、トリルフルアニド、ドジン、グアザチン、イミノクタジン、アニラジン、ジチアノン、クロロピクリン、ダゾメット、メタムナトリウム塩、キノメチオネート、シプロフラム、シルチオファム、アグロバクテリウム、フルオルイミド等のその他の化合物。
有機燐及びカーバメート系殺虫剤:
フェンチオン、フェニトロチオン、ダイアジノン、クロルピリホス、ESP、バミドチオン、フェントエート、ジメトエート、ホルモチオン、マラソン、トリクロルホン、チオメトン、ホスメット、ジクロルボス、アセフェート、EPBP、メチルパラチオン、オキシジメトンメチル、エチオン、サリチオン、シアノホス、イソキサチオン、ピリダフェンチオン、ホサロン、メチダチオン、スルプロホス、クロルフェンビンホス、テトラクロルビンホス、ジメチルビンホス、プロパホス、イソフェンホス、エチルチオメトン、プロフェノホス、ピラクロホス、モノクロトホス、アジンホスメチル、アルディカルブ、メソミル、チオジカルブ、カルボフラン、カルボスルファン、ベンフラカルブ、フラチオカルブ、プロポキスル、BPMC、MTMC、MIPC、カルバリル、ピリミカーブ、エチオフェンカルブ、フェノキシカルブ、EDDP等。
ピレスロイド系殺虫剤:
ペルメトリン、シペルメトリン、デルタメスリン、フェンバレレート、フェンプロパトリン、ピレトリン、アレスリン、テトラメスリン、レスメトリン、ジメスリン、プロパスリン、フェノトリン、プロトリン、フルバリネート、シフルトリン、シハロトリン、フルシトリネート、エトフェンプロクス、シクロプロトリン、トロラメトリン、シラフルオフェン、ブロフェンプロクス、アクリナスリン等。
ベンゾイルウレア系その他の殺虫剤:
ジフルベンズロン、クロルフルアズロン、ヘキサフルムロン、トリフルムロン、テトラベンズロン、フルフェノクスロン、フルシクロクスロン、ブプロフェジン、ピリプロキシフェン、メトプレン、ベンゾエピン、ジアフェンチウロン、アセタミプリド、イミダクロプリド、ニテンピラム、フィプロニル、カルタップ、チオシクラム、ベンスルタップ、硫酸ニコチン、ロテノン、メタアルデヒド、機械油、BTや昆虫病原ウイルス等の微生物農薬等。
フェナミホス、ホスチアゼート等。
殺ダニ剤:
クロルベンジレート、フェニソブロモレート、ジコホル、アミトラズ、BPPS、ベンゾメート、ヘキシチアゾクス、酸化フェンブタスズ、ポリナクチン、キノメチオネート、CPCBS、テトラジホン、アベルメクチン、ミルベメクチン、クロフェンテジン、シヘキサチン、ピリダベン、フェンピロキシメート、テブフェンピラド、ピリミジフェン、フェノチオカルブ、ジエノクロル等。
植物生長調節剤:
アブシジン酸、インドール酪酸、ウニコナゾール、エチクロゼート、エテホン、クロキシホナック、クロルメコート、クロレラ抽出液、過酸化カルシウム、シアナミド、ジクロルプロップ、ジベレリン、ダミノジッド、デシルアルコール、トリネキサパックエチル、メピコートクロリド、パクロブトラゾール、パラフィン、ワックス、ピペロニルブトキシド、ピラフルフェンエチル、フルルプリミドール、プロヒドロジャスモン、プロヘキサジオンカルシウム塩、ベンジルアミノプリン、ペンディメタリン、ホルクロルフェニュロン、マレイン酸ヒドラジドカリウム、1-ナフチルアセトアミド、4-CPA、MCPB、コリン、硫酸オキシキノリン、エチクロゼート、ブトルアリン、1-メチルシクロプロペン、アビグリシン塩酸塩。
[実施例1]
2,2-dimethyl-5-(3-quinolinyl)-2,3-dihydro-benzo[f][1,4]oxazepine(化合物番号B1-9)
(工程1)
2,2-dimethyl-3,4-dihydro-2H-benzo[f][1,4]oxazepin-5-one(合成方法は前記非特許文献3の記載を参照。)(0.60g、3.13mmol)にオキシ塩化リン(5mL)と五塩化リン(0.65g, 3.13mmol)を室温で加えた後、5.5時間加熱還流した。室温まで冷却後、減圧下で濃縮し、残渣を砕いた氷に注加した。水層を酢酸エチル(50mL)で回抽出し、合わせた有機層を[飽和炭酸水素ナトリウム水溶液(30mL)+H2O (20mL)]で2回、ブライン(30mL)で洗浄し、硫酸マグネシウムで乾燥した。濾過後、減圧下で溶媒を留去し、5-chloro-2,2-dimethyl-2,3-dihydro-benzo[f][1,4]oxazepine 0.74gを茶色油状物として得た。この物は、これ以上精製を行うことなく、次の反応に用いた。
3-キノリンボロン酸(0.70g、4.07mmol)及び2M炭酸セシウム水溶液(4.70mL、9.40mol)のジメチルホルムアミド溶液(15mL)を窒素置換後、この溶液にテトラキストリフェニルホスフィンパラジウム(0.72g、0.63mmol)及び5-chloro-2,2-dimethyl-2,3-dihydro- benzo[f][1,4]oxazepine (3.13mmol)を加えた。この溶液を90℃で14時間過熱攪拌した。その後、反応溶液を室温まで冷却し、酢酸エチル(50mL)と水(50mL)に注加し、セライトろ過を行った。ろ液を酢酸エチル(100mL)で抽出し、有機層をブライン(50mL)で洗浄し、硫酸マグネシウムで乾燥した。濾過後、減圧下で溶媒を留去し、得られた残渣をシリカゲルカラムクロマトグラフィー(ヘキサン:酢酸エチル=2:1)で精製して目的物0.50g(53%)を得た。
物性:mp134-135℃
[実施例2]
3,3-dimethyl-5-(3-quinolinyl)-2,3-dihydro-benzo[f][1,4]oxazepine(化合物番号B1-3)
物性:mp109-112℃
2-Chloro-2,3-dimethyl-5-(3-quinolinyl)-2,3-dihydro-benzo[f][1,4]oxazepine (化合物番号B1-29)
2-Ethyl-2-methyl-2,3-dihydro-4H-1,3-benzoxazin-4-one 7.7g(40.3mmol)をオキシ塩化リン30mLに溶解し、五塩化リン8.4g(40.3mmol)を加え4時間加熱還流を行った。反応液を減圧下濃縮した後、残渣を酢酸エチルに溶解し、順次炭酸水素ナトリウム水溶液、飽和食塩水で洗浄した。有機層を硫酸マグネシウムで乾燥した後、減圧下で溶媒を留去した。3-キノリンホウ酸 3.4g(22.4mmol)、炭酸セシウム 21.9g(67.2mmol)及びテトラキストリフェニルホスフィンパラジウム 5.2g(4.48mmol)をDMF120mLと水30mLの混合溶液に溶解し、得られた残渣4.7gをこの混合溶液に加えた。反応溶液を窒素置換した後、80~90℃で14時間撹拌した。反応溶液を室温に冷却後、氷水に注ぎ、酢酸エチルで抽出した。有機層を飽和食塩水で洗浄後、減圧下で溶媒を留去し、得られた残渣をシリカゲルカラムクロマトグラフィー(展開溶媒;クロロホルム:酢酸エチル=4:1)で精製し、互いに立体異性体である化合物(A)0.15g(収率2%)及び化合物(B)0.15g(収率2%)を得た。
化合物(A)物性:amorphous
1H NMR (300 MHz, CDCl3) δ1.67 (d, 2H, J= 6.8 Hz), 1.72 (s, 3H), 4.41 (q, 2H, J=6.8 Hz), 6.9-7.1 (m, 2H), 7.25 (dd, 1H, J= 7.4, 2.4 Hz), 7.44 (m, 1H), 7.62 (m,1H), 7.80 (m, 1H), 7.87 (m, 1H), 8.18 (d, 1H, J = 8.3 Hz), 8.39 (d, 1H, J = 2.0Hz), 9.14 (d, 1H, J = 2.0 Hz) ; MS (APCI, m/z) 337 ([M+1]+).
化合物(B)物性:amorphous
1H NMR (300 MHz, CDCl3) δ1.73 (d, 2H, J= 6.5 Hz), 1.72 (s, 3H), 4.38 (q, 2H, J=6.5 Hz), 6.90-7.05 (m, 2H), 7.25 (dd, 1H, J= 8.0, 1.5 Hz), 7.45 (m, 1H), 7.62 (m, 1H), 7.80 (m, 1H), 7.90 (d, 1H, J = 8.0 Hz), 8.18 (d, 1H, J = 8.6 Hz), 8.38 (d, 1H, J = 1.8 Hz), 9.14 (d, 1H, J = 2.4 Hz) ; MS (APCI, m/z) 337 ([M+1]+).
[実施例4]
2-Chloro-9-fluoro-2-methyl-5-(3-quinolinyl)-2,3-dihydro-benzo[f][1,4]oxazepine (化合物番号B1-30)
物性:mp123-125℃
5-(3-quinolinyl)-2,2,3,3-tetramethyl-2,3-dihydro-benzo[f][1,4]oxazepine (化合物番号B1-11)
物性:mp135-137℃
5-(3-quinolinyl)-2,3-dihydro-benzo[f][1,4]oxazepine (化合物番号B1-1)
物性: mp115-117℃
2-ethyl-2-methyl-5-(3-quinolinyl)-2,3-dihydro-benzo[f][1,4]oxazepine(化合物番号B1-31)
物性: amorphous
1H NMR (300 MHz, CDCl3) δ1.08 (t, 3H, J = 7.5 Hz), 1.43 (s, 3H), 1.74-1.90 (m, 2H), 3.60 (d, 1H, J = 11.7 Hz), 3.64 (d, 1H, J= 11.7 Hz), 7.11-7.21 (m, 3H), 7.47 (m, 1H), 7.56 (m, 1H), 7.76 (m, 1H), 7.82 (d, 1H, J = 8.1 Hz), 8.15 (d, 1H, J = 8.4 Hz), 8.31 (d, 1H, J = 2.4 Hz), 9.28 (d, 1H, J= 2.4 Hz); MS (APCI, m/z) 317 ([M+1]+).
2,2-diethyl-5-(3-quinolinyl)-2,3-dihydro-benzo[f][1,4]oxazepine(化合物番号B1-32)
物性: amorphous
1H NMR (300 MHz, CDCl3) δ1.04 (t, 3H, J = 7.5 Hz), 1.76-1.84 (m, 2H), 3.63 (s, 2H), 7.10-7.19 (m, 3H), 7.46 (m, 1H), 7.55 (m, 1H), 7.72-7.82 (m, 2H), 8.15 (d, 1H, J = 8.4 Hz), 8.29 (d, 1H, J = 2.1 Hz), 9.27 (d, 1H, J = 2.1 Hz); MS (APCI, m/z) 331 ([M+1]+).
2-isopropyl-2-methyl-5-(3-quinolinyl)-2,3-dihydro-benzo[f][1,4]oxazepine(化合物番号B1-35)
物性: amorphous
1H NMR (300 MHz, CDCl3) δ1.02 (d, 3H, J = 6.8 Hz), 1.13 (d, 3H, J = 6.8 Hz), 1.35 (s, 3H), 2.18 (m, 1H), 3.63 (d, 1H, J = 11.6 Hz), 3.74 (d, 1H, J = 11.6 Hz), 7.12-7.20 (m, 3H), 7.47 (m, 1H), 7.56 (m, 1H), 7.60 (m, 1H), 7.82 (d, 1H, J= 8.0 Hz), 8.16 (d, 1H, J = 8.6 Hz), 8.31 (d, 1H, J = 2.4 Hz), 9.27 (d, 1H, J = 2.4 Hz);MS (APCI, m/z) 331 ([M+1]+).
5-(8-fluoroquinolin-3-yl)-2,2-dimethyl-2,3-dihydro-benzo[f][1,4]oxazepine(化合物番号B1-37)
物性: mp165-167℃
2,2-dimethyl-9-fluoro-5-(8-fluoroquinolin-3-yl)-2,3-dihydro-benzo[f][1,4] oxazepine(化合物番号B1-38)
物性: mp171-173℃
2,2-dimethyl-9-chloro-5-(8-chloroquinolin-3-yl)-2,3-dihydro-benzo[f][1,4] oxazepine(化合物番号B1-41)
物性:mp214-217℃
5-(3-quinolinyl)-2,2,3-trimethyl-2,3-dihydro-benzo[f][1,4]oxazepine(化合物番号B1-42)
物性:mp139-142℃
9-fluoro-5-(3-quinolinyl)-2,2,3,3-tetramethyl-2,3-dihydro-benzo[f][1,4]oxazepine(化合物番号B1-43)
物性: mp132-133℃
9-fluoro-5-(8-fluoroquinolin-3-yl)-2,2,3,3-tetramethyl-2,3-dihydro-benzo[f][1,4]oxazepine(化合物番号B1-45)
物性: mp144-145℃
5-(8-chloroquinolin-3-yl)-2,2-dimethyl-2,3-dihydro-benzo[f][1,4]oxazepine(化合物番号B1-46)
物性: mp155-157℃
2-ethyl-5-(8-fluoroquinolin-3-yl)-2-methyl-2,3-dihydro-benzo[f][1,4]oxazepine(化合物番号B1-47)
物性:mp93-95℃
5-(8-fluoroquinolin-3-yl)-2,2,3,3-tetramethyl-2,3-dihydro-benzo[f][1,4]oxazepine(化合物番号B1-50)
物性:mp138-140℃
2,2-dimethyl-5-(3-quinolinyl)-2,3-dihydro-benzo[f][1,4]thiazepine(化合物番号B2-6)
反応に用いる2,2-dimethyl-3,4-dihydro-2H-benzo[f][1,4] thiazepin-5-oneは、前記非特許文献8記載の方法を参考に調製した。
物性:mp125-128℃
2,2-dimethyl-5-(8-fluoroquinolin-3-yl)-2,3-dihydro-benzo[f][1,4]thiazepine(化合物番号B2-13)
物性:mp181-183℃
2,2-dimethyl-9-fluoro-5-(quinolin-3-yl)-2,3-dihydro-benzo[f][1,4]oxazepine(化合物番号B1-36)
物性: amorphous
1H NMR (300 MHz, CDCl3) δ1.54 (s, 6H), 3.65 (s, 2H), 6.9-7.9 (m, 6H), 8.16 (d, 1H,J = 8.6 Hz), 8.34 (d, 1H, J= 2.1 Hz), 9.32 (d, 1H, J = 2.1 Hz)
9-chloro-2,2-dimethyl-5-(quinolin-3-yl)-2,3-dihydro-benzo[f][1,4]oxazepine(化合物番号B1-34)
物性: amorphous
1H NMR (300 MHz, CDCl3) δ1.56 (s, 6H), 3.66 (s, 2H), 7.0-7.2 (m, 2H), 7.5-7.9 (m, 4H), 8.16 (d, 1H, J = 8.6 Hz), 8.28 (d, 1H, J = 2.1 Hz), 9.26 (d, 1H, J = 2.1 Hz)
2,2-dimethyl-9-methyl-5-(quinolin-3-yl)-2,3-dihydro-benzo[f][1,4]oxazepine(化合物番号B1-33)
物性: amorphous
1H NMR (300 MHz, CDCl3) δ1.51 (s, 6H), 2.37 (s, 3H), 3.64 (s, 2H), 6.9-7.1 (m, 2H), 7.3-7.9 (m, 4H), 8.15 (d, 1H, J = 8.0 Hz), 8.29 (d, 1H, J = 2.1 Hz), 9.26 (d, 1H, J = 2.1 Hz)
2,2-dimethyl-5-(quinolin-3-yl)-9-trifluoromethyl-2,3-dihydro-benzo[f][1,4] oxazepine(化合物番号B1-44)
物性: amorphous
1H NMR (300 MHz, CDCl3) δ1.54 (s, 6H), 3.78 (s, 2H), 7.1-7.9 (m, 6H), 8.16 (d, 1H,J = 8.0 Hz), 8.22 (d, 1H, J= 2.4 Hz), 9.22 (d, 1H, J = 2.4 Hz)
9-chloro-2,2-dimethyl-5-(8-methylquinolin-3-yl)-2,3-dihydro-benzo[f][1,4] oxazepine(化合物番号B1-40)
物性: mp145-147℃
1H NMR (300 MHz, CDCl3) δ1.56 (s, 6H), 2.84 (s, 3H), 3.65 (s, 2H), 7.0 -7.2 (m, 2H), 7.4-7.7 (m, 4H), 8.30 (d, 1H, J = 2.3 Hz), 9.21 (d, 1H, J = 2.3 Hz)
2-ethyl-9-fluoro-5-(8-fluoroquinolin-3-yl)-2-methyl-2,3-dihydro-benzo[f][1,4] oxazepine(化合物番号B1-49)
物性: mp140-142℃
9-chloro-5-(8-fluoroquinolin-3-yl)-2,2-dimethyl-2,3-dihydro-benzo[f][1,4] oxazepine(化合物番号B1-39)
物性: mp190-191℃
9-chloro-2-ethyl-5-(8-fluoroquinolin-3-yl)-2-methyl-2,3-dihydro-benzo[f][1,4] oxazepine(化合物番号B1-48)
物性: mp144-146℃
9-chloro-2,2-dimethyl-5-(5’,6’,7’,8’-tetrahydroquinolin-3-yl)-2,3- dihydro-benzo [f][1,4]oxazepine(化合物番号A1-19)
物性: amorphous
1H NMR (300 MHz, CDCl3) δ1.53(s, 6H), 1.7-2.0 (m, 4H), 2.79 (t, 2H), 2.96 (t, 2H),3.56 (s, 2H), 7.0-7.1(m, 2H), 7.54 (dd, 1H, J = 2.1, 7.7 Hz), 7.65 (d, 1H, J = 2.1 Hz), 8.47 (d, 1H, J = 2.1Hz)
9-chloro-2,2-dimethyl-5-(thieno[2,3-b]pyridine-5-yl)-2,3-dihydro-benzo[f][1,4] oxazepine(化合物番号A1-20)
反応に用いる5-bromothieno[2,3-b]pyridineは、前記非特許文献8記載の方法を参考に調製した。
物性: mp169-171℃
2-Methyl-5-quinolin-3-yl-2-trifluoromethyl-2,3-dihydro-benzo[f][1,4]oxazepine(化合物番号B1-51)
物性:amorphous
1H NMR (300 MHz, CDCl3) δ1.68 (s, 3H), 3.80 (d, 1H, J = 12 Hz), 4.11 (d, 1H, J= 12 Hz), 7.16-7.26 (m, 3H), 7.49-7.61 (m, 2H), 7.76-7.85 (m, 2H), 8.17 (d, 1H, J = 8.4 Hz), 8.32 (d, 1H, J = 2.1 Hz), 9.29 (d, 1H, J = 2.1 Hz)
2-Methyl-2-phenyl-5-quinolin-3-yl-2,3-dihydro-benzo[f][1,4]oxazepine(化合物番号B1-52)
物性: mp196-197℃
2-(4-Fluorobenzyl)-2-methyl-5-quinolin-3-yl-2,3-dihydro-benzo[f][1,4] oxazepine(化合物番号B1-53)
物性:amorphous
1H NMR (300 MHz, CDCl3) δ1.33 (s, 3H), 3.10 (s, 2H), 3.47 (d, 1H, J= 12.0 Hz), 3.76 (d, 1H, J = 12.0 Hz), 6.97-7.05 (m, 2H), 7.14-7.26 (m, 3H), 7.32-7.38 (m, 2H), 7.45-7.60 (m, 2H), 7.74-7.85 (m, 2H), 8.17 (d 1H, J= 8.4 Hz), 8.33 (d, 1H, J = 2.1 Hz), 9.63 (d, 1H, J = 2.1 Hz)
2,2-Dimethyl-5-quinolin-3-yl-2,3-dihydro-benzo[f][1,4]oxazepine-9-carbonitrile (化合物番号B1-54)
物性:amorphous
9-Methoxy-2,2-dimethyl-5-quinolin-3-yl-2,3-dihydro-benzo[f][1,4]oxazepine (化合物番号B1-55)
物性:mp153-155℃
5-(8-Fluoro-quinolin-3-yl)-2-methyl-2-trifluoromethyl-2,3-dihydro-benzo[f][1,4]oxazepine(化合物番号B1-56)
物性:mp103-105℃
9-Chloro-5-(5-chloro-quinolin-3-yl)-2,2-dimethyl-2,3-dihydro-benzo[f][1,4]oxazepine(化合物番号B1-57)
物性:mp157-159℃
9-Chloro-2,2-dimethyl-5-(5-methyl-quinolin-3-yl)-2,3-dihydro-benzo[f][1,4]oxazepine(化合物番号B1-58)
物性:mp160-162℃
9-Chloro-5-(6-chloro-quinolin-3-yl)-2,2-dimethyl-2,3-dihydro-benzo[f][1,4]oxazepine(化合物番号B1-59)
物性:amorphous
1H NMR (300 MHz, CDCl3) δ1.56 (s, 6H), 3.66 (s, 2H), 7.03 (m, 1H), 7.13 (m, 1H), 7.59 (m, 1H), 7.69 (m, 1H), 7.79 (m, 1H), 8.09 (d, 1H, J = 9.0 Hz), 8.18 (d, 1H, J = 2.4 Hz), 9.25 (d, 1H, J = 2.4 Hz)
9-Chloro-2,2-dimethyl-5-(6-methyl-quinolin-3-yl)-2,3-dihydro-benzo[f][1,4]oxazepine(化合物番号B1-60)
物性:mp166-168℃
9-Chloro-5-(7-chloro-quinolin-3-yl)-2,2-dimethyl-2,3-dihydro-benzo[f][1,4]oxazepine(化合物番号B1-61)
物性:amorphous
1H NMR (300 MHz, CDCl3) δ1.56 (s, 6H), 3.65 (s, 2H), 7.04 (m, 1H), 7.13 (m, 1H), 7.51-7.60 (m, 2H), 7.75 (d, 1H, J = 8.7 Hz), 8.15 (d, 1H, J = 1.8 Hz), 8.25 (d, 1H, J = 1.5 Hz), 9.25 (d, 1H, J = 2.1 Hz)
9-Chloro-2,2-dimethyl-5-(7-methyl-quinolin-3-yl)-2,3-dihydro-benzo[f][1,4]oxazepine(化合物番号B1-62)
物性:amorphous
1H NMR (300 MHz, CDCl3) δ1.55 (s, 6H), 2.58 (s, 3H), 3.63 (s, 2H), 7.03-7.13 (m, 2H), 7.39 (m, 1H), 7.57 (m, 1H), 7.69 (d, 1H, J = 8.0 Hz), 7.91 (s, 1H), 8.22 (s, 1H), 9.18 (d, 1H, J= 2.1 Hz)
9-Chloro-5-(6,8-difluoro-quinolin-3-yl)-2,2-dimethyl-2,3-dihydro-benzo[f][1,4]oxazepine(化合物番号B1-63)
物性:amorphous
1H NMR (300 MHz, CDCl3) δ1.55 (s, 6H), 3.66 (s, 2H), 7.06 (m, 1H), 7.13 (m, 1H), 7.24-7.31 (m, 2H), 7.59 (m, 1H), 8.24 (s, 1H), 9.23 (d, 1H, J = 1.8 Hz)
9-Chloro-2,2-dimethyl-5-quinolin-3-yl-2,3-dihydro-benzo[f][1,4]oxazepine hydrochloride salt(化合物番号B1-64)
物性:mp149-151℃
9-Chloro-2,2-dimethyl-5-quinolin-3-yl-2,3-dihydro-benzo[f][1,4]oxazepine, trifluoroacetic acid salt(化合物番号B1-65)
物性:mp129-131℃
9-Fluoro-5-(8-fluoro-quinolin-3-yl)-2,2-dimethyl-2,3-dihydro-benzo[f][1,4]oxazepine, trifluoroacetic acid salt(化合物番号B1-66)
物性:mp174-176℃
9-Fluoro-5-(8-fluoro-quinolin-3-yl)-2,2-dimethyl-2,3-dihydro-benzo[f][1,4]oxazepine hydrochloride salt(化合物番号B1-67)
物性:mp164-166℃
2-Cyclopropyl-2-methyl-5-quinolin-3-yl-2,3-dihydro-benzo[f][1,4]oxazepine(化合物番号B1-70)
物性:amorphous
1H NMR (300 MHz, CDCl3) δ0.48-0.61 (m, 4H), 1.24-1.38 (m, 4H), 3.69 (d, 1H,J = 11.6 Hz), 3.81 (d, 1H, J = 11.6 Hz), 7.10-7.83 (m, 7H), 8.16 (d, 1H, J= 8.3 Hz), 8.31 (d, 1H, J = 2.1 Hz), 9.26 (d, 1H, J = 2.1 Hz)
5-quinolin-3-yl-2,3-dihydro-benzo[f][1,4]oxazepine-2-spiro-cyclopropane(化合物番号B1-72)
物性:mp102-104℃
9-benzyl-2,2-dimethyl-5-quinolin-3-yl-2,3-dihydro-benzo[f][1,4]oxazepine(化合物番号B1-74)
物性:amorphous
1H NMR (300 MHz, CDCl3) δ1.53 (s, 6H), 3.61 (s, 2H), 4.13 (s, 2H), 6.95-7.85 (m, 11H), 8.15 (d, 1H, J = 8.1 Hz), 8.28 (d, 1H, J = 2.1 Hz), 9.28 (d, 1H, J = 2.1 Hz)
7-Chloro-2,2-dimethyl-5-quinolin-3-yl-2,3-dihydro-benzo[f][1,4]oxazepine(化合物番号B1-77)
物性:amorphous
1H NMR (300 MHz, CDCl3) δ1.48 (s, 6H), 3.61 (s, 2H), 7.09 (d, 1H, J= 8.7 Hz), 7.15 (d, 1H, J = 2.7 Hz), 7.44 (dd, 1H, J =8.7, 2.7Hz), 7.56-7.62 (m, 1H), 7.75-7.87 (m, 2H), 8.17 (d, 1H, J= 8.4 Hz), 8.31 (d, 1H, J = 2.4 Hz), 9.27 (d, 1H, J = 2.1 Hz)
5-(8-Fluoro-quinolin-3-yl)-2,2,9-trimethyl-2,3-dihydro-benzo[f][1,4] oxazepine(化合物番号B1-79)
物性:mp151-153℃
2,2-Dimethyl-9-phenoxy-5-quinolin-3-yl-2,3-dihydro-benzo[f][1,4]oxazepine(化合物番号B1-82)
物性:amorphous
1H NMR (300 MHz, CDCl3) δ1.48 (s, 6H), 3.67 (s, 2H), 6.9-7.9 (m, 11H), 8.17 (d, 1H, J = 8.1 Hz), 8.36 (d, 1H, J= 1.8 Hz), 9.31 (d, 1H, J = 2.1 Hz)
11-Quinolin-3-yl-dibenzo[b,f][1,4]oxazepine(化合物番号B1-83)
物性:mp182-184℃
5-Quinolin-3-yl-benzo[f][1,4]oxazepin-3-one(化合物番号B1-84)
物性:mp169-170℃
8-Fluoro-3,3-dimethyl-5-quinolin-3-yl-2,3-dihydro-benzo[f][1,4]oxazepine(化合物番号B1-85)
物性:mp133-135℃
6-Fluoro-5-quinolin-3-yl-2,3-dihydro-benzo[f][1,4]oxazepine(化合物番号B1-86)
物性:mp126-128℃
4-Fluoro-6,6-dimethyl-9-quinolin-3-yl-6,7-dihydro-5-thia-8-aza-benzocy cloheptene(化合物番号B2-14)
物性:mp119-122℃
4-Fluoro-9-(8-fluoro-quinolin-3-yl)-6,6-dimethyl-6,7-dihydro-5-thia-8-aza-benzocycloheptene(化合物番号B2-15)
物性:mp179-181℃
6,6-Dimethyl-9-quinolin-3-yl-6,7-dihydro-5-thia-8-aza-benzocycloheptene 5-oxide(化合物番号B2-16)
物性:mp118-120℃
9-Chloro-5-(5,6-dimethyl-pyridin-3-yl)-2,3-dihydro-benzo[f][1,4]oxazepine(化合物番号A1-21)
物性:mp142-143℃
9-Chloro-5-(6,7-dihydro-5H-[1]pyrindin-3-yl)-2,2,3,3-tetramethyl-2,3-dihydro-benzo[f][1,4]oxazepine(化合物番号A1-22)
物性:mp132-133℃
5-Quinolin-3-yl-4,5-dihydro-benzo[f][1,4]oxazepin-3-one(化合物番号B4-46)
物性:mp225-227℃
9-Fluoro-5-(8-fluoro-quinolin-3-yl)-2,2-dimethyl-2,3,4,5-tetrahydro-benzo[f][1,4]oxazepine(化合物番号B4-47)
物性:mp130-131℃
4-Ethyl-9-fluoro-5-(8-fluoro-quinolin-3-yl)-2,2-dimethyl-2,3,4,5-tetrahydro-benzo[f][1,4]oxazepine(化合物番号B4-48)
物性:mp117-118℃
9-Chloro-5-(8-fluoro-quinolin-3-yl)-2,2-dimethyl-2,3,4,5-tetrahydro-benzo[f][1,4]oxazepine(化合物番号B4-49)
物性:mp133-134℃
4-Benzyl-9-chloro-5-(8-fluoro-quinolin-3-yl)-2,2-dimethyl-2,3,4,5-tetrahydro-benzo[f][1,4]oxazepine(化合物番号B4-50)
物性:mp138-141℃
9-Fluoro-5-(8-fluoro-quinolin-3-yl)-2,2-dimethyl-2,3-dihydro-5H-benzo[f][1,4]oxazepine-4-carbaldehyde(化合物番号B4-51)
物性:mp131-133℃
1-[9-Fluoro-5-(8-fluoro-quinolin-3-yl)-2,2-dimethyl-2,3-dihydro-5H-benzo[f][1,4]oxazepin-4-yl]-ethanone(化合物番号B4-52)
物性:mp132-134℃
2,2-Dimethyl-5-quinolin-3-yl-4,5-dihydro-benzo[f][1,4]oxazepin-3-one(化合物番号B4-53)
物性:mp225-227℃
8b-(8-Fluoro-quinolin-3-yl)-3,3-dimethyl-2,3-dihydro-8bH-1,4-dioxa-1a-aza-benzo[a]cyclopropa[c]cycloheptene(化合物番号B6-34)
5-(8-fluoroquinolin-3-yl)-2,2-dimethyl-2,3-dihydro-benzo[f][1,4]oxazepineを原料に、前記特許文献1に記載のC法を参考に合成した。
物性:mp113-115℃
5-(8-Fluoro-quinolin-3-yl)-2,2-dimethyl-2,3-dihydro-benzo[f][1,4] oxazepine 4-oxide(化合物番号B5-34)
8b-(8-Fluoro-quinolin-3-yl)-3,3-dimethyl-2,3-dihydro-8bH-1,4-dioxa-1a-aza-benzo[a]cyclopropa[c]cyclohepteneを原料に、前記特許文献1に記載のD法を参考に合成した。
物性:mp179-181℃
[実施例73]
8-fluoro-3-quinolineboronic acid(化合物番号C1-1)
窒素ガスで置換した300mL のフラスコに無水のTHF溶液(130mL)をシリンジで加え反応容器を塩-氷浴で冷却した。その後、0.91M N-BuMgCl (20.72mL、18.86mmol) のTHF溶液、及び2.63M N-BuLi(14.73mL、38.74mmol)のヘキサン溶液を順次加え、この温度で30分間攪拌した。 この溶液に8-fluoro-3-iodoquinoline (13.92g,50.98mmol)を固体のまま加え、同様の温度で1.5時間攪拌した後、B(OMe)3(6.36g,61.18mmol)を加え、さらに2時間攪拌した。この反応溶液にH2O(27.8g)、1M NaOH (27.8g)を順次加え室温で30分攪拌した。反応溶液を1M HCl水溶液を用いてpHを6-7とし、この溶液を酢酸エチル(300mL X 2)で抽出し、合わせた有機層をブライン(100mL)で洗浄し、硫酸マグネシウムで乾燥した。濾過後、減圧下で溶媒を留去し、得られた残渣をヘキサン、ジエチルエーテルで順次洗浄することにより目的物8.89g(91%)をベージュ色の個体として得た。 反応に用いる8-fluoro-3-iodoquinolineは、前記非特許文献9と特許文献3に記載の方法を参考に調製した。
物性:mp198-201℃
3-キノリンボロン酸トリオール塩(化合物番号C2-12)
トルエン50mLに、3-キノリンボロン酸 8.65g(50mmol)、1,1,1-Tris(hydroxymethyl)ethane 6.0g(50mmol)を加え、加熱還流を1時間行った。反応液を50℃まで冷却した後、水酸化カリウム2.66g(47.5mmol)を徐々に加え、ジーンスターク装置で脱水を行いながら、さらに4時間加熱還流を行った。反応液を室温まで冷却した後、析出した結晶を濾取し、トルエン50mL、アセトン20mLで順次洗浄を行い、減圧下で12時間乾燥し、目的物とするトリオール塩10.4g(収率71%)を得た。
1H NMR (300 MHz, DMSO) δ0.53 (s, 3H), 3.66 (s, 6H), 7.37-7.56 (m, 2H), 7.73-7.85 (m, 2H), 8.13 (s, 1H), 8.83 (d, 1H, J = 1.5 Hz)
同様の方法で化合物番号C2-4の化合物も製造できる。
1H NMR (300 MHz, DMSO) δ0.54 (s, 3H), 3.69 (s, 6H), 7.25-7.40 (m, 2H), 7.56-7.59 (m, 1H), 8.16 (s, 1H), 8.93 (s, 1H)
トリオール塩を用いた合成例(実施例51の別法)
(工程1)
trifluoromethanesulfonic acid 7-chloro-2,2-dimethyl-3,4-dihydro- 2H-benzo [f][1,4]oxazepin-5-yl esterの合成
7-chloro-2,2-dimethyl-3,4-dihydro-2H-benzo[f][1,4]oxazepin-5-one 1.6g(7.09mmol)をジクロロメタン50mLに溶解し、-10℃冷却下、無水トリフルオロメタンスルホン酸3.0g(10.6mmol)を滴下し、同温度にて1時間攪拌した。さらに-10℃冷却下、反応溶液に2,6-ルチジン1.13g(10.6mmol)を加え、1時間攪拌した後、反応液を氷水に注ぎ、クロロホルムで抽出した。有機層を飽和食塩水で洗浄後、減圧下で溶媒を留去し、得られた残渣をシリカゲルカラムクロマトグラフィー(展開溶媒;n-ヘキサン:酢酸エチル=9:1)で精製し、目的物 2.25g(収率89%)を得た。
(工程2)
7-chloro-2,2-dimethyl-5-(3-quinolinyl)-2,3-dihydro-benzo[f][1,4]oxazepineの製造(化合物番号B1-77)
3-キノリンボロン酸トリオール塩(化合物番号C2-12の化合物)1.33g(3.76mmol)、trifluoromethanesulfonic acid 7-chloro-2,2-dimethyl- 3,4-dihydro-2H-benzo[f][1,4]oxazepin-5-yl ester 1.0gおよびPd(PPh3)4 0.86g(0.68mmol)をトルエン40mLに加え、反応溶液を窒素置換した後、14時間加熱還流した。反応溶液を室温に冷却後、氷水に注ぎ、酢酸エチルで抽出した。有機層を飽和食塩水で洗浄後、減圧下で溶媒を留去し、得られた残渣をシリカゲルカラムクロマトグラフィー(展開溶媒;n-ヘキサン:酢酸エチル=3:1)で精製し、目的物 0.1g(収率10%)を得た。
次に、本発明殺菌剤の実施例を若干示すが、添加物及び添加割合は、これら実施例に限定されるべきものではなく、広範囲に変化させることが可能である。また、製剤実施例中の部は重量部を示す。
本発明化合物 40部
クレー 48部
ジオクチルスルホサクシネートナトリウム塩 4部
リグニンスルホン酸ナトリウム塩 8部
以上を均一に混合して微細に粉砕し、有効成分40%の水和剤を得る。
本発明化合物 10部
ソルベッソ200 53部
シクロヘキサノン 26部
ドデシルベンゼンスルホン酸カルシウム塩 1部
ポリオキシエチレンアルキルアリルエーテル 10部
以上を混合溶解し、有効成分10%の乳剤を得る。
本発明化合物 10部
クレー 90部
以上を均一に混合して微細に粉砕し、有効成分10%の粉剤を得る。
本発明化合物 5部
クレー 73部
ベントナイト 20部
ジオクチルスルホサクシネートナトリウム塩 1部
リン酸カリウム 1部
以上をよく粉砕混合し、水を加えてよく練り合せた後、造粒乾燥して有効成分5%の粒剤を得る。
本発明化合物 10部
ポリオキシエチレンアルキルアリルエーテル 4部
ポリカルボン酸ナトリウム塩 2部
グリセリン 10部
キサンタンガム 0.2部
水 73.8部
以上を混合し、粒度が3ミクロン以下になるまで湿式粉砕し、有効成分10%の懸濁剤を得る。
本発明化合物 40部
クレー 36部
塩化カリウム 10部
アルキルベンゼンスルホン酸ナトリウム塩 1部
リグニンスルホン酸ナトリウム塩 8部
アルキルベンゼンスルホン酸ナトリウム塩のホルムアルデヒド縮合物
5部
以上を均一に混合して微細に粉砕後,適量の水を加えてから練り込んで粘土状にする。粘土状物を造粒した後乾燥し、有効成分40%の顆粒水和剤を得る。
(試験例1)リンゴ黒星病防除試験
素焼きポットで栽培したリンゴ幼苗(品種「国光」、3~4葉期)に、本発明化合物の乳剤を有効成分100ppmの濃度で散布した。室温で自然乾燥した後、リンゴ黒星病菌(Venturia inaequalis)の分生胞子を接種し、明暗を12時間毎に繰り返す20℃、高湿度の室内に2週間保持した。葉上の病斑出現状態を無処理と比較調査し、防除効果を求めた。
化合物番号(第1表~第12表の化合物番号に対応):A1-19、A1-20、B1-1、B1-3、B1-9、B1-11、B1-29~B1-49、B1-51、B1-53、B1-54、B1-56、B1-62~B1-67、B1-70、B1-79、B1-82、B2-6、B2-13~B2-15、B4-47~B4-49、B4-50、B5-34、B6-34
素焼きポットで栽培したキュウリ幼苗(品種「相模半白」、子葉期)に、本発明化合物の乳剤を有効成分100ppmの濃度で散布した。室温で自然乾燥した後、キュウリ灰色かび病菌(Botrytis cinerea)の分生胞子懸濁液を滴下接種し、暗所、20℃、高湿度の室内に4日間保持した。葉上の病斑出現状態を無処理と比較調査し、防除効果を求めた。
化合物番号:A1-19~A1-22、B1-3、B1-9、B1-11、B1-29~B1-62、B1-63~B1-67、B1-70、B1-72、B1-74、B1-77、B1-79、B1-82、B1-84、B2-6、B2-13~B2-15、B4-47~B4-51、B5-34、B6-34
市販の培土を詰めたポットでイネ幼苗を栽培し(品種「ひとめぼれ」、1葉期)、本発明化合物の乳剤を有効成分200ppmの濃度で土壌へ点滴処理した。14日間湛水条件で管理した後、イネいもち病菌(Pyricularia oryzae)の分生胞子懸濁液を噴霧接種し、暗所、25℃、高湿度の室内に2日間保持した後、明暗を12時間毎に繰り返す25℃の室内に8日間保持した。葉上の病斑出現状態を無処理と比較調査し、下記の基準で防除効果を判定した。
A(防除価60%以上)
B(防除価40以上60%未満)
化合物番号:A1-20、B1-1、B1-38、B1-39
また、下記の化合物の防除効果はBであった。
化合物番号:B1-3、B1-37
キュウリつる割病菌(Fusarium oxysporum)によって汚染されたキュウリ種子(品種「相模半白」)に対して本発明化合物の乳剤を有効成分1g/kg種子となるように種子処理した。これら種子を播種し、3週間後に発病程度を無処理と比較調査し、防除効果を求めた。
化合物番号:A1-19、B1-1、B1-3、B1-9、B1-11、B1-34、B1-37~B1-39、B2-6
Claims (8)
- 式(I)
(式中、R1及びR2は、夫々独立して、水素原子、置換基を有してもよいC1~20アルキル基、置換基を有してもよいC2~20アルケニル基、置換基を有してもよいC2~20アルキニル基、置換基を有してもよいC3~20シクロアルキル基、置換基を有してもよいC4~20シクロアルケニル基、置換基を有してもよいC8~20シクロアルキニル基、置換基を有してもよいC6~10アリール基、置換基を有してもよいヘテロ環基、置換基を有してもよいC1~20アシル基、置換基を有してもよい(1-イミノ)C1~20アルキル基、置換基を有してもよい水酸基、置換基を有してもよいアミノ基、置換基を有してもよいメルカプト基、置換基を有するスルホニル基、ハロゲノ基、シアノ基、又はニトロ基を示す。
R1とR2は一緒になって、置換基を有してもよい5~8員環を形成してもよい。
R3~R6は、夫々独立して、水素原子、置換基を有してもよいC1~20アルキル基、置換基を有してもよいC2~20アルケニル基、置換基を有してもよいC2~20アルキニル基、置換基を有してもよいC3~20シクロアルキル基、置換基を有してもよいC4~20シクロアルケニル基、置換基を有してもよいC8~20シクロアルキニル基、置換基を有してもよいC6~10アリール基、置換基を有してもよいヘテロ環基、置換基を有してもよいC1~20アシル基、置換基を有してもよい(1-イミノ)C1~20アルキル基、置換基を有してもよい水酸基、置換基を有してもよいアミノ基、置換基を有してもよいメルカプト基、置換基を有するスルホニル基、ハロゲノ基、又はシアノ基を示す。
R3~R6から複数を選択して、一緒になって、置換基を有してもよい3~8員環を形成してもよい。
R3とR4、又はR5とR6は一緒になって、オキソ基、チオキソ基、置換基を有してもよいイミノ基を形成してもよい。
式中、A-Bは、Aは炭素原子であり、Bは窒素原子であり、
式:C=N 、式:CR7-NR8 、下記式(II)、又は式(III)を示す。
R7は、水素原子、置換基を有してもよいC1~20アルキル基、置換基を有してもよいC2~20アルケニル基、置換基を有してもよいC2~20アルキニル基、置換基を有してもよいC1~20アシル基、置換基を有してもよい水酸基、置換基を有してもよいアミノ基、置換基を有してもよいメルカプト基、ハロゲノ基、又はシアノ基を示す。
R8は、水素原子、置換基を有してもよいC1~20アルキル基、置換基を有してもよいC2~20アルケニル基、置換基を有してもよいC2~20アルキニル基、又は置換基を有してもよいC1~20アシル基を示す。
Yは、酸素原子、硫黄原子、又はスルフィニル基を示す。
X及びX’は、夫々独立して、置換基を有してもよいC1~20アルキル基、置換基を有してもよいC2~20アルケニル基、置換基を有してもよいC2~20アルキニル基、置換基を有してもよいC3~20シクロアルキル基、置換基を有してもよいC4~20シクロアルケニル基、置換基を有してもよいC8~20シクロアルキニル基、置換基を有してもよいC6~10アリール基、置換基を有してもよいヘテロ環基、置換基を有してもよいC1~20アシル基、置換基を有してもよい(1-イミノ)C1~20アルキル基、置換基を有してもよい水酸基、置換基を有してもよいアミノ基、置換基を有してもよいメルカプト基、置換基を有するスルホニル基、ハロゲノ基、シアノ基、又はニトロ基を示す。
mは、0~2のいずれかの整数を示す。
nは、0~4のいずれかの整数を示す。)
で表される含窒素ヘテロ環化合物、又はその塩。 - C1~6アルキルマグネシウムハライドとC1~6アルキルリチウムを反応させ、次いで、式(V)
(式中、X”は、夫々独立して、置換基を有してもよいC1~20アルキル基、置換基を有してもよいC2~20アルケニル基、置換基を有してもよいC2~20アルキニル基、置換基を有してもよいC3~20シクロアルキル基、置換基を有してもよいC4~20シクロアルケニル基、置換基を有してもよいC8~20シクロアルキニル基、置換基を有してもよいC6~10アリール基、置換基を有してもよいヘテロ環基、置換基を有してもよい水酸基、置換基を有してもよいアミノ基、置換基を有してもよいメルカプト基、フッ素原子、塩素原子又はニトロ基を示す。
qは、0~6のいずれかの整数を示す。X1は、臭素原子又はヨウ素原子を示す。)
で表される化合物を反応させて、次いで、
式(VI): B(OR12)3
(式中、R12は、夫々独立して、C1~6アルキル基を示す。)
で表される化合物を反応させて、式(VII)
(式中、X”及びqは、上記と同じ意味を示す。)
で表されるボロン酸誘導体を製造する方法。 - 請求項1~3のいずれかに記載の化合物又はその塩の少なくとも1種を有効成分として含有する農園芸用殺菌剤。
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Publication number | Publication date |
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EP2314583A4 (en) | 2011-11-09 |
JP5696177B2 (ja) | 2015-04-08 |
JPWO2010018686A1 (ja) | 2012-01-26 |
JP2013209411A (ja) | 2013-10-10 |
EP2314583B1 (en) | 2015-02-25 |
KR20110036611A (ko) | 2011-04-07 |
KR101315628B1 (ko) | 2013-10-08 |
US20110136782A1 (en) | 2011-06-09 |
US8557738B2 (en) | 2013-10-15 |
JP5303561B2 (ja) | 2013-10-02 |
EP2314583A1 (en) | 2011-04-27 |
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