CN110573496A - N-(4-吡啶基)烟酰胺化合物或其盐 - Google Patents
N-(4-吡啶基)烟酰胺化合物或其盐 Download PDFInfo
- Publication number
- CN110573496A CN110573496A CN201880027250.0A CN201880027250A CN110573496A CN 110573496 A CN110573496 A CN 110573496A CN 201880027250 A CN201880027250 A CN 201880027250A CN 110573496 A CN110573496 A CN 110573496A
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- Prior art keywords
- group
- alkyl
- alkoxy
- haloalkyl
- compound
- Prior art date
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- 150000003839 salts Chemical class 0.000 title claims abstract description 52
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- 150000001875 compounds Chemical class 0.000 claims abstract description 153
- -1 N- (4-pyridyl) nicotinamide compound Chemical class 0.000 claims abstract description 83
- 241000607479 Yersinia pestis Species 0.000 claims abstract description 44
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 37
- 125000000217 alkyl group Chemical group 0.000 claims description 74
- 125000003545 alkoxy group Chemical group 0.000 claims description 58
- 125000001188 haloalkyl group Chemical group 0.000 claims description 54
- 125000005843 halogen group Chemical group 0.000 claims description 47
- 125000004414 alkyl thio group Chemical group 0.000 claims description 40
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 32
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 30
- 239000004480 active ingredient Substances 0.000 claims description 25
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 23
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 23
- 239000002689 soil Substances 0.000 claims description 18
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 17
- 125000003226 pyrazolyl group Chemical group 0.000 claims description 17
- 238000000034 method Methods 0.000 claims description 16
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 15
- 125000003342 alkenyl group Chemical group 0.000 claims description 14
- 125000004104 aryloxy group Chemical group 0.000 claims description 14
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 14
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- 125000003277 amino group Chemical group 0.000 claims description 13
- 125000006492 halo alkyl aryl group Chemical group 0.000 claims description 13
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- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 11
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 11
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 9
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 9
- 125000004692 haloalkylcarbonyl group Chemical group 0.000 claims description 9
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- 125000000304 alkynyl group Chemical group 0.000 claims description 6
- 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims description 4
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- 230000000694 effects Effects 0.000 abstract description 10
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- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 19
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 17
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical class CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 16
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
- 239000002253 acid Substances 0.000 description 15
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 14
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 14
- 238000002360 preparation method Methods 0.000 description 14
- 239000002904 solvent Substances 0.000 description 14
- 241000238631 Hexapoda Species 0.000 description 13
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- 238000012360 testing method Methods 0.000 description 11
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- 241000196324 Embryophyta Species 0.000 description 10
- JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 10
- 241000244206 Nematoda Species 0.000 description 10
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 10
- 239000003139 biocide Substances 0.000 description 10
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 10
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- 239000005840 Tetraconazole Substances 0.000 description 9
- 235000014113 dietary fatty acids Nutrition 0.000 description 9
- 239000000194 fatty acid Substances 0.000 description 9
- 229930195729 fatty acid Natural products 0.000 description 9
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 8
- 230000015572 biosynthetic process Effects 0.000 description 8
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 8
- 238000002156 mixing Methods 0.000 description 8
- 230000003071 parasitic effect Effects 0.000 description 8
- 238000003786 synthesis reaction Methods 0.000 description 8
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- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 7
- 241000237858 Gastropoda Species 0.000 description 7
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 7
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 7
- 239000002585 base Substances 0.000 description 7
- OISVCGZHLKNMSJ-UHFFFAOYSA-N 2,6-dimethylpyridine Chemical compound CC1=CC=CC(C)=N1 OISVCGZHLKNMSJ-UHFFFAOYSA-N 0.000 description 6
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 6
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 6
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000005857 Trifloxystrobin Substances 0.000 description 6
- 150000002148 esters Chemical class 0.000 description 6
- 150000002170 ethers Chemical class 0.000 description 6
- 239000007788 liquid Substances 0.000 description 6
- 239000011541 reaction mixture Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- 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 6
- 239000008096 xylene Substances 0.000 description 6
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
- 241000254127 Bemisia tabaci Species 0.000 description 5
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 4
- CXBDYQVECUFKRK-UHFFFAOYSA-N 1-methoxybutane Chemical compound CCCCOC CXBDYQVECUFKRK-UHFFFAOYSA-N 0.000 description 4
- RQDJADAKIFFEKQ-UHFFFAOYSA-N 4-(4-chlorophenyl)-2-phenyl-2-(1,2,4-triazol-1-ylmethyl)butanenitrile Chemical compound C1=CC(Cl)=CC=C1CCC(C=1C=CC=CC=1)(C#N)CN1N=CN=C1 RQDJADAKIFFEKQ-UHFFFAOYSA-N 0.000 description 4
- ZOCSXAVNDGMNBV-UHFFFAOYSA-N 5-amino-1-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-[(trifluoromethyl)sulfinyl]-1H-pyrazole-3-carbonitrile Chemical compound NC1=C(S(=O)C(F)(F)F)C(C#N)=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl ZOCSXAVNDGMNBV-UHFFFAOYSA-N 0.000 description 4
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- 239000003242 anti bacterial agent Substances 0.000 description 4
- 229940088710 antibiotic agent Drugs 0.000 description 4
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- TWFZGCMQGLPBSX-UHFFFAOYSA-N carbendazim Chemical compound C1=CC=C2NC(NC(=O)OC)=NC2=C1 TWFZGCMQGLPBSX-UHFFFAOYSA-N 0.000 description 4
- GCKZANITAMOIAR-XWVCPFKXSA-N dsstox_cid_14566 Chemical compound [O-]C(=O)C1=CC=CC=C1.C1=C[C@H](C)[C@@H]([C@@H](C)CC)O[C@]11O[C@H](C\C=C(C)\[C@@H](O[C@@H]2O[C@@H](C)[C@H](O[C@@H]3O[C@@H](C)[C@H]([NH2+]C)[C@@H](OC)C3)[C@@H](OC)C2)[C@@H](C)\C=C\C=C/2[C@]3([C@H](C(=O)O4)C=C(C)[C@@H](O)[C@H]3OC\2)O)C[C@H]4C1 GCKZANITAMOIAR-XWVCPFKXSA-N 0.000 description 4
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Classifications
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- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/12—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, neither directly attached to a ring nor the nitrogen atom being a member of a heterocyclic ring
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings linked by a chain containing hetero atoms as chain links
-
- 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
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
- A01P5/00—Nematocides
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
- C07D213/81—Amides; Imides
- C07D213/82—Amides; Imides in position 3
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
Abstract
虽长年累月使用了多种有害生物防治剂,但具有效力不充分、害虫等获得抗药性而导致其使用受限等各种课题的有害生物防治剂并不少。因此,期望开发出所述缺点少的新型有害生物防治剂。本发明的目的是提供对于有害生物具有高活性的化合物或其盐。本发明涉及下述式(I)所示的N‑(4‑吡啶基)烟酰胺化合物或其盐。〔式(I)中,各取代基参照说明书〕。
Description
技术领域
本发明涉及新型的N-(4-吡啶基)烟酰胺化合物或其盐。
另外,本发明涉及含有该化合物或其盐作为有效成分的有害生物防治剂、农业园艺用杀虫剂、杀蜱螨剂、杀线虫剂或杀土壤害虫剂。
进而,本发明涉及使用有效量的该化合物或其盐来防治有害生物的方法。
背景技术
专利文献1记载了杀虫剂用途的范围广的杂芳基酰胺化合物,专利文献2记载了医药用途的范围广的具有吡啶骨架的化合物。
另外,专利文献3记载了医药用途的范围广的杂芳基酰胺化合物。
现有技术文献
专利文献
专利文献1:国际公开第2002/070483号
专利文献2:国际公开第2005/115986号
专利文献3:日本特开2003-73357号公报
发明内容
发明要解决的问题
虽长年累月使用了多种有害生物防治剂,但具有效力不充分、害虫等获得抗药性而导致其使用受限等各种课题的有害生物防治剂并不少。
因此,期望开发出所述缺点少的新型有害生物防治剂。
因而,本发明的目的是提供对于有害生物具有高活性的化合物或其盐,提供使用了该化合物或其盐的有害生物防治剂、农业园艺用杀虫剂、杀蜱螨剂、杀线虫剂或杀土壤害虫剂,提供施用该化合物或其盐来防治有害生物的方法。
需要说明的是,专利文献1所述的化合物和专利文献2所述的化合物与本发明化合物有所区别。另外,对于专利文献3所述的化合物,仅存在后述式(I)中的R4为氢原子的化合物的具体记载。
用于解决问题的方案
本发明人等为了发现更优异的有害生物防治剂而针对吡啶化合物进行了各种研究。其结果发现:新型的N-(4-吡啶基)烟酰胺化合物或其盐在低药量下对有害生物具有极高的防治效果,从而完成了本发明。
即,本发明涉及下述内容。
[1]一种式(I)所示的N-(4-吡啶基)烟酰胺化合物或其盐,
式(I)中,R1为氢原子、卤素原子、烷基、卤代烷基、烷氧基、卤代烷氧基、芳氧基或卤代烷基芳基;
R2为卤素原子、烷基、卤代烷基、烷氧基、卤代烷氧基、氨基、单烷基氨基、二烷基氨基、芳氧基、氰基、烷硫基、烷基亚磺酰基或烷基磺酰基;
R3为氢原子、烷基、环烷基、卤代烷基、烷氧基、烷氧基烷基、烷基羰基或烷氧基羰基;
R4为卤素原子、硝基、烷基、烯基、炔基、卤代烷基、烷氧基、烷硫基、烷基羰基、卤代烷基羰基、环烷基羰基、烷氧基羰基、(烷硫基)羰基或吡唑基;
m为0~3的整数;
存在多个前述R2时,前述R2任选彼此相同或不同。
[2]根据前述[1]所述的化合物或其盐,其中,前述式(I)中,R1为氢原子、卤素原子、烷基、卤代烷基、烷氧基、卤代烷氧基、芳氧基或卤代烷基芳基;
R2为卤素原子、烷基、卤代烷基、烷氧基、氨基、单烷基氨基、二烷基氨基、氰基、烷硫基、烷基亚磺酰基或烷基磺酰基;
R3为氢原子、烷基、环烷基、烷氧基、烷氧基烷基、烷基羰基或烷氧基羰基;
R4为卤素原子、硝基、烷基、烯基、卤代烷基、烷氧基、烷硫基、烷基羰基、卤代烷基羰基、烷氧基羰基、(烷硫基)羰基或吡唑基;
m为0或1。
[3]根据前述[1]所述的化合物或其盐,其中,前述式(I)中,R1为氢原子、卤素原子、烷基、卤代烷基、烷氧基、卤代烷氧基、芳氧基或卤代烷基芳基;
R2为卤素原子、烷基、卤代烷基、烷氧基、氨基、氰基、烷硫基、烷基亚磺酰基或烷基磺酰基;
R3为氢原子、烷基、环烷基、烷氧基或烷氧基羰基;
R4为卤素原子、硝基、烷基、烯基、卤代烷基、烷氧基、烷硫基、烷基羰基、烷氧基羰基、(烷硫基)羰基或吡唑基;
m为0或1。
[4]根据前述[1]所述的化合物或其盐,其中,前述式(I)中,R1为卤素原子、烷基、卤代烷基、烷氧基、卤代烷氧基、芳氧基或卤代烷基芳基;
R2为卤素原子、烷基、卤代烷基、烷氧基、氨基、单烷基氨基、二烷基氨基、氰基、烷硫基、烷基亚磺酰基或烷基磺酰基;
R3为氢原子、烷基、环烷基、烷氧基、烷氧基烷基、烷基羰基或烷氧基羰基;
R4为硝基、烷基、烯基、卤代烷基、烷氧基、烷硫基、烷基羰基、卤代烷基羰基、烷氧基羰基、(烷硫基)羰基或吡唑基;
m为0或1。
[5]根据前述[1]所述的化合物或其盐,其中,前述式(I)中,R1为卤素原子、烷基、卤代烷基、烷氧基、卤代烷氧基、芳氧基或卤代烷基芳基;
R2为卤素原子、烷基、卤代烷基、烷氧基、氨基、氰基、烷硫基、烷基亚磺酰基或烷基磺酰基;
R3为氢原子、烷基、环烷基、烷氧基或烷氧基羰基;
R4为硝基、烷基、烯基、卤代烷基、烷氧基、烷硫基、烷基羰基、烷氧基羰基、(烷硫基)羰基或吡唑基;
m为0或1。
[6]根据前述[1]所述的化合物或其盐,其中,前述式(I)中,R1为卤素原子、烷基、卤代烷基、烷氧基或卤代烷氧基;
R2为卤素原子、烷基、卤代烷基、烷氧基、卤代烷氧基、氨基、单烷基氨基或二烷基氨基;
R3为氢原子、烷基、烷氧基烷基、烷基羰基或烷氧基羰基;
R4为卤素原子、硝基、烷基、烯基、炔基、卤代烷基、烷氧基、烷硫基、烷基羰基、卤代烷基羰基、环烷基羰基、烷氧基羰基、(烷硫基)羰基或吡唑基;
m为0~3的整数;
存在多个前述R2时,前述R2任选彼此相同或不同。
[7]根据前述[1]所述的化合物或其盐,其中,前述式(I)中,R1为卤素原子、烷基、卤代烷基、烷氧基或卤代烷氧基;
R2为烷基、卤代烷基、烷氧基、氨基、单烷基氨基或二烷基氨基;
R3为氢原子、烷基、烷氧基烷基、烷基羰基或烷氧基羰基;
R4为卤素原子、硝基、烷基、卤代烷基、烷氧基、烷硫基、烷氧基羰基、(烷硫基)羰基或吡唑基;
m为0或1。
[8]根据前述[1]所述的化合物或其盐,其中,前述式(I)中,R1为烷基、卤代烷基或卤代烷氧基;
R2为烷基、卤代烷基或氨基;
R3为氢原子或、烷基;
R4为卤素原子、硝基、烷基、烷氧基、烷氧基羰基或吡唑基;
m为0或1。
[9]根据前述[1]~[8]中任一项所述的化合物或其盐,其中,前述式(I)中,R1为卤代烷基;R3为氢原子、烷基、环烷基或烷氧基;R4为烷基、烷氧基、烷基羰基或烷氧基羰基;m为0。
[10]根据[1]所述的化合物或其盐,其中,前述式(I)中,R1为氢原子、卤素原子、烷基、卤代烷基、烷氧基、卤代烷氧基、芳氧基或卤代烷基芳基。
[11]根据[1]所述的化合物或其盐,其中,前述式(I)中,R1为烷基、卤代烷基或卤代烷氧基。
[12]根据[1]、[10]或[11]中任一项所述的化合物或其盐,其中,前述式(I)中,R2为卤素原子、烷基、卤代烷基、烷氧基、氨基、氰基、烷硫基、烷基亚磺酰基或烷基磺酰基。
[13]根据[1]、[10]~[12]中任一项所述的化合物或其盐,其中,前述式(I)中,R2为烷基、卤代烷基或氨基。
[14]根据[1]、[10]~[13]中任一项所述的化合物或其盐,其中,前述式(I)中,R3为氢原子、烷基、环烷基、烷氧基或烷氧基羰基。
[15]根据[1]、[10]~[14]中任一项所述的化合物或其盐,其中,前述式(I)中,R3为氢原子或烷基。
[16]根据[1]、[10]~[15]中任一项所述的化合物或其盐,其中,前述式(I)中,R4为卤素原子、硝基、烷基、烯基、卤代烷基、烷氧基、烷硫基、烷基羰基、烷氧基羰基、(烷硫基)羰基或吡唑基。
[17]根据[1]、[10]~[16]中任一项所述的化合物或其盐,其中,前述式(I)中,R4为卤素原子、硝基、烷基、烷氧基、烷氧基羰基、(烷硫基)羰基或吡唑基。
[18]根据[1]、[10]~[17]中任一项所述的化合物或其盐,其中,前述式(I)中,m为0或1。
[19]根据[6]所述的化合物或其盐,其中,前述式(I)中,R1为卤素原子、烷基、卤代烷基、烷氧基或卤代烷氧基;R2为烷基、卤代烷基、烷氧基、氨基、单烷基氨基或二烷基氨基;R3为氢原子、烷基、烷氧基烷基、烷基羰基或烷氧基羰基;R4为卤素原子、硝基、烷基、卤代烷基、烷氧基、烷硫基、烷氧基羰基、(烷硫基)羰基或吡唑基;m为0或1。
[20]根据[6]所述的化合物或其盐,其中,前述式(I)中,R1为烷基、卤代烷基或卤代烷氧基;R2为烷基、卤代烷基或氨基;R3为氢原子或烷基;R4为卤素原子、硝基、烷基、烷氧基、烷氧基羰基或吡唑基;m为0或1。
[21]一种有害生物防治剂,其含有前述[1]~[20]中任一项所述的化合物或其盐作为有效成分。
[22]一种农业园艺用杀虫剂、杀蜱螨剂、杀线虫剂或杀土壤害虫剂,其含有前述[1]~[20]中任一项所述的化合物或其盐作为有效成分。
[23]一种农业园艺用杀虫剂,其含有前述[1]~[20]中任一项所述的化合物或其盐作为有效成分。
[24]一种防治有害生物的方法,其施用有效量的前述[1]~[20]中任一项所述的化合物或其盐来防治有害生物。
发明的效果
以前述式(I)所示的化合物或其盐作为有效成分的有害生物防治剂在低药量下对有害生物具有极高的防治效果。
具体实施方式
以下,针对本发明进行详述,它们表示优选实施方式的一例,本发明不限定于这些内容。
需要说明的是,本说明书中,“Cn”(n为自然数)与“碳原子数n”(n为自然数)的含义相同。作为浓度而记作“ppm”时,表示“重量ppm”。
本发明涉及下述式(I)所示的N-(4-吡啶基)烟酰胺化合物或其盐(以下有时统称为“本发明化合物”)。
〔式(I)中,R1为氢原子、卤素原子、烷基、卤代烷基、烷氧基、卤代烷氧基、芳氧基或卤代烷基芳基;
R2为卤素原子、烷基、卤代烷基、烷氧基、卤代烷氧基、氨基、单烷基氨基、二烷基氨基、芳氧基、氰基、烷硫基、烷基亚磺酰基或烷基磺酰基;
R3为氢原子、烷基、环烷基、卤代烷基、烷氧基、烷氧基烷基、烷基羰基或烷氧基羰基;
R4为卤素原子、硝基、烷基、烯基、炔基、卤代烷基、烷氧基、烷硫基、烷基羰基、卤代烷基羰基、环烷基羰基、烷氧基羰基、(烷硫基)羰基或吡唑基;
m为0~3的整数;
存在多个前述R2时,前述R2任选彼此相同或不同。〕
作为前述式(I)中的卤素原子或作为取代基的卤素,可列举出氟、氯、溴或碘各自的原子。作为取代基的卤素原子的数量可以为1或2以上,为2以上时,各卤素原子任选相同或不同。另外,卤素原子的取代位置可以为任意位置。
需要说明的是,本说明书中使用的“卤代烷基”是指:烷基所含的至少1个氢原子被卤素原子取代而得的烷基。
关于“卤代烷氧基”、“卤代烷基芳基”或“卤代烷基羰基”也同样地分别是指:各基团所含的至少1个氢原子被卤素原子取代而得的烷氧基、烷基芳基或烷基羰基。在这些卤代烷基、卤代烷氧基、卤代烷基芳基或卤代烷基羰基中,将取代氢原子的卤素原子称为“作为取代基的卤素”。
作为前述式(I)中的烷基或烷基部分,可列举出例如甲基、乙基、正丙基、异丙基、正丁基、异丁基、仲丁基、叔丁基、正戊基、异戊基、新戊基、正己基或新己基之类的直链或支链状的C1~C6的基团。
作为前述式(I)中的烯基或烯基部分,可列举出例如乙烯基、1-丙烯基、2-丙烯基、异丙烯基、2-甲基-1-丙烯基、1-甲基-1-丙烯基、2-甲基-2-丙烯基、1-甲基-2-丙烯基、1-丁烯基、2-丁烯基、3-丁烯基、1-戊烯基、2-戊烯基、2-甲基-2-丁烯基、1-己烯基或2,3-二甲基-2-丁烯基之类的直链或支链状的C2~C6的基团。
作为前述式(I)中的炔基或炔基部分,可列举出例如乙炔基、1-丙炔基、2-丙炔基、1-丁炔基、2-丁炔基、3-丁炔基、1-甲基-2-丙炔基、2-甲基-3-丁炔基、3,3-二甲基-1-丁炔基、1-己炔基、2-己炔基、3-己炔基、4-己炔基或5-己炔基之类的直链或支链状的C2~C6的基团。
作为前述式(I)中的环烷基或环烷基部分,可列举出例如环丙基、环丁基、环戊基或环己基之类的C3~C6的基团。
作为前述式(I)中的芳基或芳基部分,可列举出例如苯基、萘基之类的C6~C10的基团。
作为前述式(I)所示的化合物的盐,只要是该技术领域中允许的盐,则包含所有盐,可列举出例如二甲基铵盐、三乙基铵盐之类的铵盐;盐酸盐、高氯酸盐、硫酸盐、硝酸盐之类的无机酸盐;乙酸盐、三氟乙酸盐、草酸盐、对甲苯磺酸盐、甲磺酸盐之类的有机酸盐等。
本发明化合物中有时存在光学异构体之类的异构体,但本发明化合物包括各自的异构体和异构体混合物这两者。本申请说明书中,在没有特别提及的条件下,以混合物的形式记载异构体。另外,本发明化合物也可以在该技术领域中的技术常识范围内包含前述异构体之外的各种异构体。另外,根据异构体种类的不同,有时呈现与本发明化合物不同的化学结构,只要是本领域技术人员就能够充分认识它们处于异构体的关系,因此处于本发明的范围内是不言而喻的。
本发明化合物可按照以下的制造方法、以及通常的盐的制造方法来制造,但不限定于这些方法。
制法〔1〕
前述式(I)所示的化合物可通过使下述式(II)所示的化合物与下述式(III)所示的化合物在脱水缩合剂或碱的存在下发生反应来制造。
需要说明的是,下述式(II)所示的化合物和下述式(III)所示的化合物除了可以使用市售品之外,也可以通过公知的方法来制造。
(制法〔1〕的式中,R1、R2、R3、R4和m如上所述。)
作为脱水缩合剂,没有特别限定,可列举出例如1-乙基-3-(3-二甲基氨基丙基)碳二亚胺盐酸盐、1,3-二环己基碳二亚胺、O-(7-氮杂苯并三唑-1-基)-N,N,N’,N’-四甲基脲六氟磷酸盐等。
该反应可根据需要加入添加剂来进行。作为添加剂,可列举出例如1-羟基苯并三唑、N-羟基琥珀酰亚胺、N,N-二甲基-4-氨基吡啶等。
作为碱,没有特别限定,可列举出例如三乙胺、4-甲基吗啉、二异丙基乙胺等叔胺类、1,8-二氮杂双环[5.4.0]-7-十一碳烯、吡啶、4-(二甲基氨基)吡啶、2,6-二甲基吡啶等。
该反应可根据需要在溶剂的存在下进行。作为溶剂,没有特别限定,可以从例如二乙醚、丁基甲醚、四氢呋喃、乙二醇二甲醚、1,4-二氧杂环己烷、二甲氧基乙烷等醚类;二氯甲烷、二氯乙烷、氯仿等脂肪族卤代烃类;苯、甲苯、二甲苯、氯苯等芳香族烃类;N,N-二甲基甲酰胺、N,N-二甲基乙酰胺、N-甲基-2-吡咯烷酮、二甲基亚砜、环丁砜等非质子性极性溶剂;乙腈、丙腈等腈类;乙酸乙酯、丙酸乙酯等酯类;戊烷、己烷、庚烷、辛烷、环己烷等脂肪族烃类;丙酮、甲乙酮等酮类;水等中适当选择1种或2种以上,或者混合使用。
关于反应温度,通常可以以约0℃~在反应体系内发生加热回流的温度的范围来进行。关于反应时间,通常可以以数分钟~24小时来进行。
制法〔2〕
前述式(I)所示的化合物可通过使下述式(II-a)所示的化合物与下述式(III)所示的化合物在碱的存在下发生反应来制造。
(制法〔2〕的式中,R1、R2、R3、R4和m如上所述;X为卤素原子。)
碱可以为有机碱或无机碱。作为有机碱,没有特别限定,可列举出例如三乙胺、二异丙基乙胺之类的胺碱等。作为无机碱,没有特别限定,可列举出例如碳酸钠、碳酸钾、碳酸铯之类的碱金属碳酸盐等。
该反应可根据需要在溶剂的存在下进行。作为溶剂,没有特别限定,可以从例如二乙醚、丁基甲醚、四氢呋喃、乙二醇二甲醚、1,4-二氧杂环己烷、二甲氧基乙烷等醚类;二氯甲烷、二氯乙烷、氯仿等脂肪族卤代烃类;苯、甲苯、二甲苯、氯苯等芳香族烃类;N,N-二甲基甲酰胺、N,N-二甲基乙酰胺、N-甲基-2-吡咯烷酮、二甲基亚砜、环丁砜等非质子性极性溶剂;乙腈、丙腈等腈类;乙酸乙酯、丙酸乙酯等酯类;戊烷、己烷、庚烷、辛烷、环己烷等脂肪族烃类;丙酮、甲乙酮等酮类;水等中适当选择1种或2种以上,或者混合使用。
关于反应温度,通常可以以约0℃~在反应体系内发生加热回流的温度的范围来进行。关于反应时间,通常可以以数分钟~24小时来进行。
前述式(II-a)所示的化合物除了可使用市售品之外,还可如下述路线所示那样,通过使前述式(II)所示的化合物与卤化剂发生反应来制造。
(上述式(II-a)所示的化合物的制法的式中,R1、R2、X和m如上所述。)
作为卤化剂,没有特别限定,可列举出例如亚硫酰氯、草酰氯、磷酰氯、磺酰氯、三氯化磷、五氯化磷等。
该反应可根据需要在溶剂的存在下进行。作为溶剂,没有特别限定,可以从例如二乙醚、丁基甲醚、四氢呋喃、乙二醇二甲醚、1,4-二氧杂环己烷、二甲氧基乙烷等醚类;二氯甲烷、二氯乙烷、氯仿等脂肪族卤代烃类;苯、甲苯、二甲苯、氯苯等芳香族烃类;N,N-二甲基甲酰胺、N,N-二甲基乙酰胺、N-甲基-2-吡咯烷酮、二甲基亚砜、环丁砜等非质子性极性溶剂;乙腈、丙腈等腈类;乙酸乙酯、丙酸乙酯等酯类;戊烷、己烷、庚烷、辛烷、环己烷等脂肪族烃类;丙酮、甲乙酮等酮类等中适当选择1种或2种以上,或者混合使用。
关于反应温度,通常可以以约0℃~在反应体系内发生加热回流的温度的范围来进行。关于反应时间,通常可以以数分钟~24小时来进行。
前述式(III)所示的化合物可通过使下述式(III-a)所示的化合物与下述式(IV)所示的化合物发生反应来制造。下述式(III-a)所示的化合物和下述式(IV)所示的化合物除了可使用市售品之外,也可通过公知的方法来制造。
(上述式(III)所示的化合物的制法的式中,R3、R4、X如上所述。)
该反应可根据需要在碱的存在下进行。作为碱,可列举出例如氢化钠之类的碱金属氢化物;碳酸钠、碳酸钾、碳酸铯之类的碱金属碳酸盐;氢氧化锂、氢氧化钠、氢氧化钾之类的碱金属氢氧化物;三乙胺、4-甲基吗啉、二异丙基乙胺等叔胺类;1,8-二氮杂双环[5.4.0]-7-十一碳烯、吡啶、4-(二甲基氨基)吡啶、2,6-二甲基吡啶等。
该反应可根据需要在溶剂的存在下进行。溶剂没有特别限定,可以从例如二乙醚、丁基甲醚、四氢呋喃、乙二醇二甲醚、1,4-二氧杂环己烷、二甲氧基乙烷等醚类;二氯甲烷、二氯乙烷、氯仿等脂肪族卤代烃类;苯、甲苯、二甲苯、氯苯等芳香族烃类;N,N-二甲基甲酰胺、N,N-二甲基乙酰胺、N-甲基-2-吡咯烷酮、二甲基亚砜、环丁砜等非质子性极性溶剂;乙腈、丙腈等腈类;乙酸乙酯、丙酸乙酯等酯类;戊烷、己烷、庚烷、辛烷、环己烷等脂肪族烃类;丙酮、甲乙酮等酮类;水等中适当选择1种或2种以上,或者混合使用。
关于反应温度,通常可以以约0℃~在反应体系内发生加热回流的温度的范围来进行。关于反应时间,通常可以以数分钟~24小时来进行。
针对含有本发明化合物作为有效成分的有害生物防治剂的优选方式,以下进行记述。
含有本发明化合物作为有效成分的有害生物防治剂作为例如在农业园艺领域中成为问题的害虫、蜱螨、线虫或土壤害虫的防治剂、即农业园艺用杀虫剂、杀蜱螨剂、杀线虫剂或杀土壤害虫剂等是有用的。另外,作为动物寄生生物的防治剂、即杀动物寄生生物剂是有用的。
本发明化合物对于防治桃蚜(Myzus persicae)、棉蚜(Aphis gossypii)等之类的蚜虫类(aphids);小菜蛾(Plutella xylostella)、切根虫(Cutworm)、斜纹夜蛾(Spodoptera litura)、苹果蠹蛾(Laspeyresia pomonella)、棉铃虫(Heliothis zea)、烟芽夜蛾(Heliothis virescens)、舞毒蛾(Lymantria dispar)、稻纵卷叶螟(Cnaphalocrocis medinalis)、茶小卷叶蛾(Adoxophyes honmai)、马铃薯甲虫(Leptinotarsa decemlineata)、黄守瓜(Aulacophora femoralis)、棉铃象鼻虫(Anthonomus grandis)、褐飞虱(Nilaparvata lugens)等之类的稻飞虱类(Planthoppers);叶蝉类(leafhoppers)、蚧总类(scales)、臭虫类(stinkbugs)、烟粉虱(Bemisia tabaci)等之类的粉虱类(whiteflies)、缨翅目类(thrips);蝗虫(grasshoppers)类;花蝇(anthomyiid flies)类;墨绿彩丽金龟(scarabaeidae scarabs)类;小地老虎(Agrotis ipsilon)、黄地老虎(Agrotis segetum)、蚁类等之类的农业害虫类;蛞蝓(slugs)、蝸牛(Snail)等之类的腹足类(gastropods);柏氏禽刺螨(Ornithonyssusbacoti)、蟑螂类(cockroaches);家蝇(Musca domestica)、淡色库蚊(Culex pipiens)等之类的卫生害虫类;麦蛾(Sitotroga cerealella)、绿豆象(Callosobruchus chinensis)、赤拟谷盗(Tribolium castaneum)、黄粉虫(mealworms)类等之类的贮谷害虫类;衣蛾(Tineatranslucens)、黑毛皮蠹(Attagenus unicolor)、白蚁类(termites)等之类的服装、房屋害虫类等害虫;二斑叶螨(Tetranychus urticae)、朱砂叶螨(Tetranychus cinnabarinus)、神泽氏叶螨(Tetranychus kanzawai)、柑桔全爪螨(Panonychus citri)、苹果全爪螨(Panonychus ulmi)、侧多食跗线螨(Polyphagotarsonemus latus)、桔刺皮瘿螨(Aculopspelekassi)、刺足根螨(Rhizoglyphus echinopus)等之类的植物寄生性蜱螨类;腐食酪螨(Tyrophagus putrescentiae)、粉尘螨(Dermatophagoides farinae)、爪螨(Chelacaropsis moorei)等之类的室内尘性蜱螨类等蜱螨;根结线虫(root-knotnematodes)类、囊肿线虫(cyst nematodes)类、根病变根腐线虫(root-lesion nematodes)类、水稻干尖线虫(Aphelenchoides besseyi)、草莓芽线虫(Nothotylenchus acris)、松材线虫(Bursaphelenchus lignicolus)等之类的植物寄生性线虫类等线虫;普通卷甲虫(Armadillidium vulgare)、鼠妇虫(Porcellio scaber)之类等足类等土壤害虫是有效的。
含有本发明化合物作为有效成分的有害生物防治剂对于防治植物寄生性蜱螨类、农业害虫类、植物寄生性线虫类等是特别有效的。其中,对于植物寄生性蜱螨类、农业害虫类的防治显示更优异的效果,因此,作为杀虫剂或杀蜱螨剂非常有用。
另外,含有本发明化合物作为有效成分的农业园艺用杀虫剂、杀蜱螨剂、杀线虫剂或杀土壤害虫剂对于防治针对有机磷剂、氨酯剂、合成乙氰菊酯剂、类尼古丁剂等药剂的各种抗药性害虫也是有效的。
进而,本发明化合物具有优异的浸透转移性,因此,通过用含有本发明化合物作为有效成分的农业园艺用杀虫剂、杀蜱螨剂、杀线虫剂或杀土壤害虫剂对土壤进行处理,从而能够在防治土壤有害昆虫类、蜱螨类、线虫类、腹足类等足类的同时,还防治茎叶部的害虫类。
作为含有本发明化合物作为有效成分的有害生物防治剂的其它优选方式,可列举出综合性地防治前述植物寄生性蜱螨类、农业害虫类、植物寄生性线虫类、腹足类、土壤害虫类等的农业园艺用杀虫剂、杀蜱螨剂、杀线虫剂或杀土壤害虫剂。
含有本发明化合物作为有效成分的有害生物防治剂通常可将该化合物与各种辅助剂混合而制成粉剂、粒剂、颗粒水合剂、水合剂、水性悬浮剂、油性悬浮剂、颗粒水溶剂、水溶剂、乳剂、液剂、糊剂、气雾剂、微量散布剂等各种形态来使用,只要符合本发明的目的,则可以制成该领域中通常使用的所有制剂形态。
作为制剂中使用的辅助剂,可列举出硅藻土、消石灰、碳酸钙、滑石、白碳、高岭土、皂土、高岭石、绢云母、粘土、碳酸钠、碳酸氢钠、芒硝、沸石、淀粉等固型载体;水、甲苯、二甲苯、溶剂石脑油、二氧杂环己烷、丙酮、异佛尔酮、甲基异丁基酮、氯苯、环己烷、二甲基亚砜、N,N-二甲基甲酰胺、N,N-二甲基乙酰胺、N-甲基-2-吡咯烷酮、醇等溶剂;脂肪酸盐、苯甲酸盐、烷基磺基琥珀酸盐、二烷基磺基琥珀酸盐、多羧酸盐、烷基硫酸酯盐、烷基硫酸盐、烷基芳基硫酸盐、烷基二甘醇醚硫酸盐、醇硫酸酯盐、烷基磺酸盐、烷基芳基磺酸盐、芳基磺酸盐、木质素磺酸盐、烷基二苯基醚二磺酸盐、聚苯乙烯磺酸盐、烷基磷酸酯盐、烷基芳基磷酸盐、苯乙烯基芳基磷酸盐、聚氧亚乙基烷基醚硫酸酯盐、聚氧亚乙基烷基芳基醚硫酸盐、聚氧亚乙基烷基芳基醚硫酸酯盐、聚氧亚乙基烷基醚磷酸盐、聚氧亚乙基烷基芳基磷酸酯盐、萘磺酸盐甲醛缩合物之类的阴离子系表面活性剂;脱水山梨糖醇脂肪酸酯、甘油脂肪酸酯、脂肪酸聚甘油酯、脂肪酸醇聚二醇醚、乙炔二醇、乙炔醇、氧亚烷基嵌段聚合物、聚氧亚乙基烷基醚、聚氧亚乙基烷基芳基醚、聚氧亚乙基苯乙烯基芳基醚、聚氧乙二醇烷基醚、聚乙二醇、聚氧亚乙基脂肪酸酯、聚氧亚乙基脱水山梨糖醇脂肪酸酯、聚氧亚乙基甘油脂肪酸酯、聚氧亚乙基氢化蓖麻油、聚氧亚丙基脂肪酸酯之类的非离子系的表面活性剂;橄榄油、木棉油、蓖麻油、棕榈油、山茶油、椰子油、芝麻油、玉米油、米糠油、花生油、棉籽油、大豆油、菜籽油、亚麻仁油、桐油、液体石蜡等植物油、矿物油等。
这些辅助剂的各成分可以在不脱离本发明目的的范围内适当选择1种或2种以上并使用。另外,除了前述辅助剂之外,也可以从该领域中公知的辅助剂中适当选择并使用,还可以使用例如增量剂、增稠剂、防沉降剂、防冻剂、分散稳定剂、药害减轻剂、防霉剂等通常使用的各种辅助剂。
本发明化合物与各种辅助剂的配混比例(重量比)为0.001:99.999~95:5、优选为0.005:99.995~90:10。实际使用这些制剂时,可以直接使用,或者用水等稀释剂稀释至规定浓度,并根据需要添加各种展着剂(表面活性剂、植物油、矿物油等)并使用。
含有本发明化合物作为有效成分的农业园艺用杀虫剂、杀蜱螨剂、杀线虫剂或杀土壤害虫剂的施用因气象条件、制剂形态、施用时期、施用场所、病害虫的种类、发生状況等的差异而无法一概而论,通常以0.05~800000ppm、优选以0.5~500000ppm的有效成分浓度来进行,关于其平均单位面积的施用量,平均1公顷的本发明化合物为0.05~50000g、理想的是1~30000g。
另外,本发明还包括基于这种施用方法的有害生物的防治方法,其中,还包括在农业园艺领域中成为问题的害虫、蜱螨、线虫或土壤害虫的防治方法,尤其是植物寄生性蜱螨类、农业害虫类、植物寄生性线虫类的防治方法。
含有本发明化合物作为有效成分的有害生物防治剂的各种制剂或其稀释物的施用通常可通过一般进行的施用方法、即散布(例如喷雾、雾化、粉化、散粒、水面施用等)、土壤施用(混入、灌注等)、表面施用(涂布、粉衣、覆盖等)、浸渍毒饵等来进行。另外,将前述有效成分混合至饵料并对家畜进行施用,利用其排泄物也能够阻碍害虫、尤其是有害昆虫的发生和生育。另外,也可通过所谓的超高浓度少量散布法(ultra low volume applicationmethod)来施用。在该方法中,可以含有100%的活性成分。
另外,含有本发明化合物作为有效成分的农业园艺用杀虫剂、杀蜱螨剂、杀线虫剂或杀土壤害虫剂可以与其它农药、肥料、药害减轻剂等进行混用或组合使用,在该情况下,有时显示出更优异的效果、作用性。作为其它农药,可列举出除草剂、杀虫剂、杀蜱螨剂、杀线虫剂、杀土壤害虫剂、杀菌剂、抗病毒剂、引诱剂、抗生素、植物激素、植物生长调节剂等。尤其是,将本发明化合物与其它农药的有效成分化合物中的1种或2种以上混用或组合使用而得的杀虫用组合物、杀蜱螨用组合物、杀线虫用组合物或杀土壤害虫用组合物可以将应用范围、药剂处理时期、防治活性等向优选方向改良。另外,将本发明化合物和其它农药的有效成分化合物各自分别制剂而得的物质可以在施用时混合使用,也可以将两者一同制剂而使用。本发明还包括这种杀虫用组合物、杀蜱螨用组合物、杀线虫用组合物或杀土壤害虫用组合物。
作为上述其它农药中的杀虫剂、杀蜱螨剂、杀线虫剂或杀土壤害虫剂的有效成分化合物(通用名;包括一部分正在申请中或者日本植物防疫协会试验编码),可列举出例如丙溴磷(profenofos)、敌敌畏(dichlorvos)、克线磷(fenamiphos)、杀螟硫磷(fenitrothion)、EPN(O-乙基-O-4-硝基苯基苯基硫代膦酸酯,O-ethyl O-4-nitrophenylphenylphosphonothioate)、二嗪磷(diazinon)、毒死蜱(chlorpyrifos)、甲基毒死蜱(chlorpyrifos-methyl)、乙酰甲胺磷(acephate)、丙硫磷(prothiofos)、噻唑磷(fosthiazate)、硫线磷(cadusafos)、乙拌磷(disulfoton)、异恶唑磷(isoxathion)、异丙胺磷(isofenphos)、乙硫磷(ethion)、乙嘧硫磷(etrimfos)、喹硫磷(quinalphos)、二甲基亚硝胺(dimethylvinphos)、乐果(dimethoate)、硫丙磷(sulprofos)、二甲硫吸磷(thiometon)、蚜灭多(vamidothion)、吡唑硫磷(pyraclofos)、哒嗪硫磷(pyridaphenthion)、甲基嘧啶磷(pirimiphos-methyl)、丙虫磷(propaphos)、伏杀磷(phosalone)、安果(formothion)、马拉硫磷(malathion)、杀虫威(tetrachlorvinphos)、毒虫畏(chlorfenvinphos)、杀螟腈(cyanophos)、敌百虫(trichlorfon)、杀扑磷(methidathion)、稻丰散(phenthoate)、ESP(异砜磷、oxydeprofos)、保棉磷(azinphos-methyl)、倍硫磷(fenthion)、庚烯磷(heptenophos)、甲氧滴滴涕(methoxychlor)、对硫磷(parathion)、乙丙磷威(phosphocarb)、甲基内吸磷(demeton-S-methyl)、久效磷(monocrotophos)、甲胺磷(methamidophos)、新烟磷(imicyafos)、甲基对硫磷(parathion-methyl)、特丁磷(terbufos)、磷胺(phosphamidon)、亚胺硫膦(phosmet)、甲拌磷(phorate)、辛硫磷(phoxim)、三唑磷(triazophos)之类的有机磷酸酯系化合物;
西维因(carbaryl)、残杀威(propoxur)、涕灭威(aldicarb)、呋喃丹(carbofuran)、硫双灭多威(thiodicarb)、灭多威(methomyl)、杀线威(oxamyl)、杀虫丹(ethiofencarb)、抗蚜威(pirimicarb)、仲丁威(fenobucarb)、丁硫克百威(carbosulfan)、丙硫克百威(benfuracarb)、苯恶威(bendiocarb)、呋线威(furathiocarb)、异丙威(isoprocarb)、速灭威(metolcarb)、灭杀威(xylylcarb)、XMC(3,5-二甲苯基甲基氨基甲酸酯,3,5-xylyl methylcarbamate)、苯硫威(fenothiocarb)之类的氨基甲酸酯系化合物;
杀螟丹(cartap)、杀虫环(thiocyclam)、杀虫磺(bensultap)、1-硫代磺酸钠基-2-二甲氨基-3-硫代磺酸基丙烷(thiosultap-sodium)、2-二甲氨基-1,3-双硫代磺酸钠基丙烷(thiosultap-disodium)、杀虫单(monosultap)、杀虫双(bisultap)、杀虫环草酸盐(thiocyclam hydrogen oxalate)之类的沙蚕毒素(nereistoxin)衍生物;
三氯杀螨醇(dicofol)、四氯杀螨砜(tetradifon)、硫丹(endosulfan)、除螨灵(dienochlor)、狄氏剂(dieldrin)之类的有机氯系化合物;
六苯丁锡氧(fenbutatin oxide)、三环锡(cyhexatin)之类的有机金属系化合物;
氰戊菊酯(fenvalerate)、氯菊酯(permethrin)、氯氰菊酯(cypermethrin)、溴氰菊酯(deltamethrin)、三氟氯氰菊酯(cyhalothrin)、七氟菊酯(tefluthrin)、醚菊酯(ethofenprox)、三氟醚菊酯(flufenprox)、氟氯氰菊酯(cyfluthrin)、甲氰菊酯(fenpropathrin)、氟氰戊菊酯(flucythrinate)、氟胺氰菊酯(fluvalinate)、乙氰菊酯(cycloprothrin)、高效氯氟氰菊酯(lambda-cyhalothrin)、除虫菊酯(pyrethrins)、高氰戊菊酯(esfenvalerate)、胺菊酯(tetramethrin)、苄呋菊酯(resmethrin)、丙苯烃菊酯(protrifenbute)、联苯菊脂(bifenthrin)、ζ-氯氰菊酯(zeta-cypermethrin)、氟丙菊酯(acrinathrin)、α-氯氰菊酯(alpha-cypermethrin)、丙烯菊酯(allethrin)、超高效三氟氯氰菊酯(gamma-cyhalothrin)、反式氯氰菊酯(theta-cypermethrin)、氟胺氰菊酯(tau-fluvalinate)、四溴菊酯(tralomethrin)、丙氟菊酯(profluthrin)、高效氯氰菊酯(beta-cypermethrin)、高效氟氯氰菊酯(beta-cyfluthrin)、甲氧苄氟菊酯(metofluthrin)、苯醚菊酯(phenothrin)、氟氯苯氰菊酯(flumethrin)、溴氰菊脂(decamethrin)之类的乙氰菊酯系化合物;
除虫脲(diflubenzuron)、定虫隆(chlorfluazuron)、伏虫隆(teflubenzuron)、氟虫脲(flufenoxuron)、杀虫脲(triflumuron)、除虫脲(hexaflumuron)、氯虱螨脲(lufenuron)、双苯氟脲(novaluron)、多氟脲(noviflumuron)、双三氟虫脲(bistrifluron)、啶蜱脲(fluazuron)之类的苯甲酰基脲系化合物;
烯虫酯(methoprene)、蚊蝇醚(pyriproxyfen)、苯醚威(fenoxycarb)、苯虫醚(diofenolan)之类的类保幼激素化合物;
哒螨灵(pyridaben)之类的哒嗪酮系化合物;
唑螨酯(fenpyroximate)、芬普尼(fipronil)、吡螨胺(tebufenpyrad)、吡螨胺(ethiprole)、唑虫酰胺(tolfenpyrad)、乙酰虫腈(acetoprole)、吡嗪氟虫腈(pyrafluprole)、吡啶氟虫腈(pyriprole)之类的吡唑系化合物;
吡虫啉(imidacloprid)、烯啶虫胺(nitenpyram)、啶虫脒(acetamiprid)、噻虫啉(thiacloprid)、噻虫嗪(thiamethoxam)、噻虫胺(clothianidin)、呋虫胺(nidinotefuran)、呋虫胺(dinotefuran)、硝虫噻嗪(nithiazine)之类的类尼古丁系化合物;
虫酰肼(tebufenozide)、甲氧虫酰肼(methoxyfenozide)、环虫酰肼(chromafenozide)、氯虫酰肼(halofenozide)之类的肼系化合物;
啶虫丙醚(pyridalyl)、氟啶虫酰胺(flonicamid)之类的吡啶系化合物;
螺螨酯(spirodiclofen)、螺甲螨酯(spiromesifen)、螺虫乙酯(spirotetramat)、先正达(spiropidion)之类的环状酮烯醇系化合物;
嘧螨酯(fluacrypyrim)之类的甲氧基丙烯酸酯系化合物;
嘧虫胺(flufenerim)之类的嘧啶胺系化合物;
二硝基系化合物、有机硫化合物、脲系化合物、三嗪系化合物、腙系化合物;另外,作为其它化合物,可列举出2-乙基-3,7-二甲基-6-[4-(三氟甲氧基)苯氧基]-4-喹啉基碳酸甲酯(flometoquin)、噻嗪酮(buprofezin)、噻螨酮(hexythiazox)、阿米曲士(amitraz)、杀虫脒(chlordimeform)、氟硅菊酯(silafluofen)、唑蚜威(triazamate)、吡蚜酮(pymetrozine)、嘧螨醚(pyrimidifen)、虫螨腈(chlorfenapyr)、茚虫威(indoxacarb)、灭螨醌(acequinocyl)、乙螨唑(etoxazole)、环丙马秦(cyromazine)、1,3-二氯丙烯(1,3-dichloropropene)、杀螨隆(diafenthiuron)、异噻虫唑(benclothiaz)、联苯肼酯(bifenazate)、克螨特(propargite)、四螨嗪(clofentezine)、氰氟虫腙(metaflumizone)、氟虫双酰胺(flubendiamide)、丁氟螨酯(cyflumetofen)、氯虫苯甲酰胺(chlorantraniliprole)、氰虫酰胺(cyantraniliprole)、环溴虫酰胺(cyclaniliprole)、腈吡螨酯(cyenopyrafen)、氟虫吡喹(pyrifluquinazon)、喹螨醚(fenazaquin)、磺胺螨酯(amidoflumet)、氟虫胺(sulfluramid)、氟蚁腙(hydramethylnon)、四聚乙醛(metaldehyde)、莱诺啶(ryanodine)、增效炔醚(verbutin)、氯代苯甲酸(chlorobenzoate)、噻唑基肉桂腈(thiazolylcinnanonitrile)、氟啶虫胺腈(sulfoxaflor)、氟噻虫砜(fluensulfone)、三氟苯嘧啶(triflumezopyrim)、双丙环虫酯(afidopyropen)、氟吡呋喃酮(flupyradifuron)、氟恶唑酰胺(fluxametamide)、氟氰虫酰胺(tetraniliprole)、氟雷拉纳(fluralaner)、溴虫氟苯双酰胺(broflanilide)、3'-异丁基-N-异丁酰基-1,3,5-三甲基-4'-[2,2,2-三氟-1-甲氧基-1-(三氟甲基)乙基]吡唑-4-甲酰苯胺(pyflubumide)、二氯噻吡嘧啶(dicloromezotiaz)、fluhexafon、3-苯基-5-(噻吩-2-基)-1,2,4-恶二唑(tioxazafen)、三氟咪啶酰胺(fluazaindolizine)、3-内-[2-丙氧基-4-(三氟甲基)苯氧基]-9-[5-(三氟甲基)-2-吡啶氧基]-9-氮杂双环[3.3.1]壬烷(acynonapyr)、5-(1,3-二恶烷-2-基)-4-[4-(三氟甲基)苄氧基]嘧啶(benzpyrimoxan)、2-[3-(乙基磺酰基)-2-吡啶基]-5-[(三氟甲基)磺酰基]苯并恶唑(oxazosulfyl)、N-[(E)-1-(6-氯-3-吡啶甲基)吡啶-2(1H)-亚基]-2,2,2-三氟乙酰胺(flupyrimin)、:N-[3-氯-1-(3-吡啶基)-1H-吡唑-4-基]-N-乙基-3-[(3,3,3-三氟丙基)硫代]丙酰胺(tyclopyrazoflor)之类的化合物等。
进而,也可以与苏云金杆菌鲇泽变种(Bacillus thuringiensisaizawai)、苏云金杆菌戈氏变种(Bacillus thuringiensiskurstaki)、苏云金杆菌以色列变种(Bacillusthuringiensisisraelensis)、苏云金杆菌日本变种(Bacillusthuringiensisjaponensis)、苏云金杆菌粉甲变种(Bacillusthuringiensistenebrionis)等苏云金杆菌(Bacillus thuringiensis)所生成的结晶蛋白毒素、昆虫病原病毒剂、昆虫病原丝状菌剂、线虫病原丝状菌剂等之类的微生物农药;除虫菌素(avermectin)、甲氨基阿维菌素苯甲酸盐(emamectin benzoate)、弥拜菌素(milbemectin)、倍脉心(milbemycin)、多杀菌素(spinosad)、伊维菌素(ivermectin)、乐平霉素(lepimectin)、DE-175、阿维菌素(abamectin)、埃玛菌素(emamectin)、乙基多杀菌素(spinetoram)之类的抗生素和半合成抗生素、印楝素(azadirachtin)、鱼藤酮(rotenone)之类的天然物、避蚊胺(deet)之类的拒虫剂等混用、组合使用。
作为上述其它农药中的杀菌剂的有效成分化合物(通用名;包括一部分正在申请中或者日本植物防疫协会试验编码),可列举出例如嘧菌胺(mepanipyrim)、嘧霉胺(pyrimethanil)、嘧菌环胺(cyprodinil)、嘧菌腙(ferimzone)之类的苯胺基嘧啶系化合物;
5-氯-7-(4-甲基哌啶-1-基)-6-(2,4,6-三氟苯基)[1,2,4]三唑并[1,5-a]嘧啶之类的三唑嘧啶系化合物;
氟啶胺(fluazinam)之类的吡啶胺系化合物;
三唑酮(triadimefon)、联苯三唑醇(bitertanol)、氟菌唑(triflumizole)、乙环唑(etaconazole)、丙环唑(propiconazole)、戊菌唑(penconazole)、氟硅唑(flusilazole)、腈菌唑(myclobutanil)、环唑醇(cyproconazole)、戊唑醇(tebuconazole)、己唑醇(hexaconazole)、呋醚唑(furconazole-cis)、咪鲜胺(prochloraz)、叶菌唑(metconazole)、氟环唑(epoxiconazole)、四氟醚唑(tetraconazole)、富马酸恶咪唑(oxpoconazole fumarate)、硅氟唑(sipconazole)、丙硫菌唑(prothioconazole)、三唑醇(triadimenol)、粉唑醇(flutriafol)、苯醚甲环唑(difenoconazole)、氟喹唑(fluquinconazole)、腈苯唑(fenbuconazole)、糠菌唑(bromuconazole)、烯唑醇(diniconazole)、三环唑(tricyclazole)、噻菌灵(probenazole)、硅氟唑(simeconazole)、稻瘟酯(pefurazoate)、种菌唑(ipconazole)、亚胺唑(imibenconazole)之类的唑系化合物;
灭螨猛(quinomethionate)之类的喹喔啉系化合物;
代森锰(maneb)、代森锌(zineb)、代森锰锌(mancozeb)、聚氨酯(polycarbamate)、代森联(metiram)、甲基代森锌(propineb)、福美双(thiram)之类的二硫代氨酯系化合物;
稻瘟酞(fthalide)、百菌清(chlorothalonil)、五氯硝基苯(quintozene)之类的有机氯系化合物;
苯菌灵(benomyl)、氰霜唑(cyazofamid)、甲基托布津(thiophanate-methyl)、多菌灵(carbendazim)、噻苯咪唑(thiabendazole)、麦穗宁(fuberiazole)之类的咪唑系化合物;
霜脲氰(cymoxanil)之类的氰基乙酰胺系化合物;
甲霜灵(metalaxyl)、甲霜灵-M(metalaxyl-M)、精甲霜灵(mefenoxam)、恶霜灵(oxadixyl)、甲呋酰胺(ofurace)、苯霜灵(benalaxyl)、苯霜灵-M(benalaxyl-M、别称:精苯霜灵(kiralaxyl、chiralaxyl))、呋霜灵(furalaxyl)、酯菌胺(cyprofuram)、萎锈灵(carboxin)、氧化萎锈灵(oxycarboxin)、噻呋酰胺(thifluzamide)、啶酰菌胺(boscalid)、联苯吡菌胺(bixafen)、异噻菌胺(isothianil)、噻酰菌胺(tiadinil)、氟唑环菌胺(sedaxane)之类的酰替苯胺系化合物;
抑菌灵(dichlofluanid)之类的磺酰胺系化合物;
氢氧化铜(cupric hydroxide)、有机铜(oxine copper)之类的铜系化合物;
恶霉灵(hymexazol)之类的异恶唑系化合物;
乙磷铝(fosetyl-Al)、甲基立枯磷(tolclofos-methyl)、O,O-二异丙基硫代磷酸S-苄酯、S,S-二苯基二硫代磷酸O-乙酯、以及乙膦酸铝、敌瘟磷(edifenphos)、异稻瘟净(iprobenfos)之类的有机磷系化合物;
克菌丹(captan)、敌菌丹(captafol)、灭菌丹(folpet)之类的邻苯二甲酰亚胺系化合物;
速克灵(procymidone)、异菌脲(iprodione)、乙烯菌核利(vinclozolin)之类的二甲酰亚胺系化合物;
氟酰胺(flutolanil)、灭锈胺(mepronil)之类的苯酰替苯胺系化合物;
吡噻菌胺(penthiopyrad)、3-(二氟甲基)-1-甲基-N-[(1RS,4SR,9RS)-1,2,3,4-四氢-9-异丙基-1,4-甲代萘-5-基]吡唑-4-羧酰胺与3-(二氟甲基)-1-甲基-N-[(1RS,4SR,9SR)-1,2,3,4-四氢-9-异丙基-1,4-甲代萘-5-基]吡唑-4-羧酰胺的混合物(吡唑萘菌胺(isopyrazam))、硅噻菌胺(silthiopham)、氰菌胺(fenoxanil)、呋吡菌胺(furametpyr)之类的酰胺系化合物;
氟吡菌酰胺(fluopyram)、苯酰菌胺(zoxamide)之类的苯甲酰胺系化合物;
嗪胺灵(triforine)之类的哌嗪系化合物;
啶斑肟(pyrifenox)之类的吡啶系化合物;
氯苯嘧啶醇(fenarimol)之类的甲醇系化合物;
苯锈啶(fenpropidin)之类的哌啶系化合物;
丁苯吗啉(fenpropimorph)、十三吗啉(tridemorph)之类的吗啉系化合物;
毒菌锡(fentin hydroxide)、薯瘟锡(fentin acetate)之类的有机锡系化合物;
戊菌隆(pencycuron)之类的脲系化合物;
烯酰吗啉(dimethomorph)、氟吗啉(flumorph)之类的肉桂酸系化合物;
乙霉威(diethofencarb)之类的苯基氨酯系化合物;
氟咯菌腈(fludioxonil)、拌种咯(fenpiclonil)之类的氰基吡咯系化合物;
嘧菌酯(azoxystrobin)、醚菌酯(kresoxim-methyl)、苯氧菌胺(metominostrobin)、肟菌酯(trifloxystrobin)、啶氧菌酯(picoxystrobin)、肟醚菌胺(oryzastrobin)、醚菌胺(dimoxystrobin)、吡唑醚菌酯(pyraclostrobin)、氟嘧菌酯(fluoxastrobin)之类的甲氧基丙烯酸酯系化合物;
恶唑菌酮(famoxadone)之类的恶唑烷酮系化合物;
噻唑菌胺(ethaboxam)之类的噻唑羧酰胺系化合物;
丙森锌(iprovalicarb)、苯噻菌胺酯(benthiavalicarb-isopropyl)之类的缬氨酰胺系化合物;
N-(异丙氧基羰基)-L-缬氨酰基-(3RS)-3-(4-氯苯基)-β-丙氨酸甲酯(valiphenalate)之类的酰基氨基酸系化合物;
咪唑菌酮(fenamidone)之类的咪唑烷酮系化合物;
环酰菌胺(fenhexamid)之类的羟基苯胺系化合物;
磺菌胺(flusulfamide)之类的苯磺酰胺系化合物;
环氟菌胺(cyflufenamid)之类的肟醚系化合物;
蒽醌系化合物;
巴豆酸系化合物;
有效霉素(validamycin)、春日霉素(kasugamycin)、多氧菌素(polyoxins)之类的抗生素;
双胍辛胺(iminoctadine)、多果定(dodine)之类的胍系化合物;
6-叔丁基-8-氟-2,3-二甲基喹啉-4-基-乙酸酯(异丁乙氧喹啉(tebufloquin))之类的喹啉系化合物;
(Z)-2-(2-氟-5-(三氟甲基)苯硫基)-2-(3-(2-甲氧基苯基)噻唑烷-2-亚基)乙腈(氟噻菌净(flutianil))之类的噻唑烷系化合物;
作为其它化合物,可列举出吡菌苯威(pyribencarb)、稻瘟灵(isoprothiolane)、咯喹酮(pyroquilon)、哒菌酮(diclomezine)、喹氧灵(quinoxyfen)、霜霉威(propamocarbhydrochloride)、氯化苦(chloropicrin)、棉隆(dazomet)、威百亩(metam-sodium)、啶酰菌胺(nicobifen)、苯菌酮(metrafenone)、UBF-307、双氯氰菌胺(diclocymet)、丙氧喹啉(proquinazid)、安美速(amisulbrom;别称:amibromdole)、3-(2,3,4-三甲氧基-6-甲基苯甲酰基)-5-氯-2-甲氧基-4-甲基吡啶、4-(2,3,4-三甲氧基-6-甲基苯甲酰基)-2,5-二氯-3-三氟甲基吡啶、吡啶苯菌酮(pyriofenone)、异丙噻菌胺(isofetamid)、双炔酰菌胺(mandipropamid)、氟吡酰菌胺(fluopicolide)、环丙酰菌胺(carpropamid)、硝苯菌酯(meptyldinocap)、葚孢菌素(spiroxamine)、胺苯吡菌酮(fenpyrazamine)、2-[(2,5-二甲基苯氧基)甲基]-α-甲氧基-N-甲基苯乙酰胺(mandestrobin)、ZF-9646、BCF-051、BCM-061、BCM-062等。
其它,作为能够与本发明化合物混用或组合使用的农药,有例如The PesticideManual(第15版)中记载那样的除草剂的有效成分化合物、尤其是土壤处理型的农药等。
实施例
接着记载本发明的实施例,但本发明不限定于它们。首先,记载本发明化合物的合成例。
合成例1
4-(6-(三氟甲基)烟酰胺)烟酸甲酯(化合物No.I-9)的合成
将4-氨基-烟酸甲酯(366mg、2.4mmol)、O-(7-氮杂苯并三唑-1-基)-N,N,N’,N’-四甲基脲六氟磷酸盐(997mg、2.6mmol)和三乙胺(1.22mL、8.7mmol)添加至6-(三氟甲基)烟酸(418mg、2.2mmol)的N,N-二甲基甲酰胺(15mL)溶液中,在室温下搅拌24小时。将反应混合物投入至水(50mL)中,过滤所产生的固体,得到目标物(426mg、收率为60%)。
合成例2
4-(N-乙基-6-(三氟甲基)烟酰胺)烟酸甲酯(化合物No.I-11)的合成
(1)向4-氯烟酸甲酯(3.3g、19.2mmol)的N,N-二甲基甲酰胺(40mL)溶液中添加70%乙胺水溶液(9.9g、153.9mmol),以70℃搅拌2小时。将反应混合物投入至水(200mL)中,用乙酸乙酯进行萃取。将有机层用饱和食盐水清洗,添加无水硫酸钠并进行干燥。通过过滤而去除无水硫酸钠后,在减压下馏去溶剂,得到4-(乙基氨基)烟酸甲酯(3.0g、收率为87%)。
(2)向四氢呋喃(6mL)中的4-(乙基氨基)烟酸甲酯(300mg、1.7mmol)、二异丙基乙胺(0.85mL、5.0mmol)的混合物中添加6-(三氟甲基)烟酰氯(350mg、1.7mmol),以65℃搅拌5小时。将反应混合物投入至水(20mL)中,用乙酸乙酯进行萃取。将有机层用饱和食盐水清洗,添加无水硫酸钠并进行干燥。通过过滤而去除无水硫酸钠后,在减压下馏去溶剂。将残渣用急骤层析法(洗脱液:正庚烷/乙酸乙酯)进行精制,得到目标物(437mg、收率为74%)。
合成例3
4-(N-甲氧基-6-(三氟甲基)烟酰胺)烟酸甲酯(化合物No.I-131)的合成
(1)向O-甲基羟胺盐酸盐(8.4g、100.5mmol)的N-甲基-2-吡咯烷酮(67mL)溶液中依次添加水(13mL)、氢氧化钠(2.7g、67.0mmol)、三乙胺(4.7mL、33.5mmol),在室温下搅拌15分钟。向所得反应混合物中添加4-氯烟酸甲酯(5.75g、33.5mmol),以75℃搅拌15小时。将反应混合物投入至水(300mL)中,用乙酸乙酯进行萃取。将有机层用饱和食盐水清洗,添加无水硫酸钠并进行干燥。通过过滤而去除无水硫酸钠后,在减压下馏去溶剂。将残渣用急骤层析法(洗脱液:正庚烷/乙酸乙酯)进行精制,得到4-(甲氧基氨基)烟酸甲酯(1.7g、收率为28%)。
(2)向四氢呋喃(9mL)中的4-(甲氧基氨基)烟酸甲酯(500mg、2.7mmol)、二异丙基乙胺(1.44mL、8.2mmol)的混合物中添加6-((三氟甲基)烟酰氯(863mg、4.1mmol),以65℃搅拌16小时。将反应混合物投入至水(45mL)中,用乙酸乙酯进行萃取。将有机层用饱和食盐水清洗,添加无水硫酸钠并进行干燥。通过过滤而去除无水硫酸钠后,在减压下馏去溶剂。将残渣用急骤层析法(洗脱液:正庚烷/乙酸乙酯)进行精制,得到目标物(330mg、收率为34%)。
接着,将本发明所述的式(I)所示的化合物的代表例列举在表1中。另外,这些化合物可基于前述合成例或前述各种制造方法来合成。表1中,物性栏中记载的数值表示熔点(℃),针对记为“NMR”的化合物,将它们的1H-NMR光谱数据列举在表2中。
另外,表1中的No.表示化合物编号。
另外,表中,Me表示甲基,Et表示乙基,Pr表示丙基,Bu表示丁基,“cyc-”表示“环”,“i-”表示“异”,“t-”表示“叔”,“n-”表示“正”。
另外,在(R2)m一栏中,例如记为“6-NH2”的化合物表示:仅表中的化学结构式上赋予的取代位置被R2取代、即仅6位被氨基取代的“m=1”的化合物。另一方面,记为“m=0”的化合物表示未被R2取代的化合物。其它相同的记载也基于此。
化合物No.I-54的1H-NMR光谱以光学异构体的混合物的形式测定各自的峰。
[表1]
[表2]
[表3]
[表4]
[表5]
[表6]
[表7]
[表8]
[表9]
[表10]
[表11]
试验例1对于稻褐飞虱的效果试验
将稻幼苗在以本发明化合物的浓度达到200ppm的方式制备的药液中进行浸渍处理。待药液风干后,用湿润的脱脂棉包裹根部并放入试管中。向其中投放约10只稻褐飞虱2~3龄幼虫,管口用纱布封住,静置在25℃的附带照明的恒温室内。处理5天后判断稻褐飞虱的生死,利用下述计算式求出死虫率(%)。针对前述化合物No.I-4、I-8、I-9、I-10、I-11和I-94进行试验的结果,任意化合物均显示90%以上的死虫率。
死虫率(%)=(死虫数/放虫数)×100
试验例2对于烟粉虱(Bemisia tabaci)的效果试验
对钵植的黄瓜苗投放烟粉虱(Bemisia tabaci)成虫。使其产卵1天后,取出黄瓜苗,静置在25℃的附带照明的恒温室内。7天后,调查寄生于黄瓜苗的1~2龄幼虫数,使用手动喷雾器将以本发明化合物的浓度达到200ppm的方式制备的药液进行散布处理。待药液风干后,静置在25℃的附带照明的恒温室内。处理7天后,调查老龄幼虫数,利用下述计算式求出防治值。针对前述化合物No.I-7、I-8、I-9、I-10、I-11、I-12、I-13、I-15、I-25、I-27、I-29、I-30和I-94进行试验的结果,任意化合物均显示90以上的防治值。
防治值=(1-(Ta×Cb)/(Tb×Ca))×100
Ta:处理黄瓜苗在处理后的老龄幼虫数
Tb:处理黄瓜苗在处理前的1~2龄幼虫数
Ca:无处理黄瓜苗在处理后的老龄幼虫数
Cb:无处理黄瓜苗在处理前的1~2龄幼虫数
试验例3对于桃蚜的效果试验
向灌水插入至试管内的萝卜叶上投放5只桃蚜成虫。在1天后去除成虫后,数出寄生在萝卜叶上的幼虫数,在以本发明化合物的浓度达到200ppm的方式制备的药液中进行浸渍处理。待药液风干后,静置在25℃的附带照明的恒温室内。处理5天后,判断桃蚜的生死,利用下述计算式求出死虫率。另外,脱离虫和异常虫视作死虫。针对前述化合物No.I-3、I-7、I-8、I-9、I-10、I-11、I-15、I-25、I-30和I-94进行试验的结果,任意化合物均显示90%以上的死虫率。
死虫率(%)=(死虫数/供试虫数)×100
以下记载制剂例。
制剂例1
(1)本发明化合物20重量份
(2)粘土70重量份
(3)白碳5重量份
(4)多羧酸钠3重量份
(5)烷基萘磺酸钠2重量份
将以上的成分均匀混合而制成水合剂。
制剂例2
(1)本发明化合物5重量份
(2)滑石60重量份
(3)碳酸钙34.5重量份
(4)液体石蜡0.5重量份
将以上的成分均匀混合而制成粉剂。
制剂例3
(1)本发明化合物20重量份
(2)N,N-二甲基乙酰胺20重量份
(3)聚氧亚乙基三苯乙烯基苯基醚10重量份
(4)十二烷基苯磺酸钙2重量份
(5)二甲苯48重量份
将以上的成分均匀混合、溶解而制成乳剂。
制剂例4
(1)粘土68重量份
(2)木质素磺酸钠2重量份
(3)聚氧亚乙基烷基芳基硫酸酯5重量份
(4)白碳25重量份
将上述各成分的混合物与本发明化合物以4:1的重量比例进行混合而制成水合剂。
制剂例5
(1)本发明化合物50重量份
(2)烷基萘磺酸钠甲醛缩合物2重量份
(3)硅油0.2重量份
(4)水47.8重量份
将以上的成分均匀混合并粉碎,向由此得到的原液中进一步添加:
(5)多羧酸钠5重量份
(6)无水硫酸钠42.8重量份,
并均匀混合、造粒、干燥而制成颗粒水合剂。
制剂例6
(1)本发明化合物5重量份
(2)聚氧亚乙基辛基苯基醚1重量份
(3)聚氧亚乙基烷基醚磷酸酯0.1重量份
(4)粒状碳酸钙93.9重量份
将前述(1)~(3)预先均匀混合,利用适量的丙酮进行稀释后,吹送至前述(4),去除丙酮而制成粒剂。
制剂例7
(1)本发明化合物2.5重量份
(2)N,N-二甲基乙酰胺2.5重量份
(3)大豆油95.0重量份
将以上的成分均匀混合并溶解,制成微量散布剂(ultra low volumeformulation)。
制剂例8
(1)本发明化合物10重量份
(2)二乙二醇单乙醚80重量份
(3)聚氧亚乙基烷基醚10重量份
将以上的成分均匀混合而制成液体制剂。
参照特定的实施方式详细地说明了本发明,但对于本领域技术人员而言,能够不超脱本发明的精神和范围地施加各种变更、修改是不言而喻的。本申请基于2017年4月27日提交的日本专利申请(日本特愿2017-088847),将其内容作为参照而援引至此。
Claims (7)
1.一种式(I)所示的N-(4-吡啶基)烟酰胺化合物或其盐,
式(I)中,R1为氢原子、卤素原子、烷基、卤代烷基、烷氧基、卤代烷氧基、芳氧基或卤代烷基芳基;
R2为卤素原子、烷基、卤代烷基、烷氧基、卤代烷氧基、氨基、单烷基氨基、二烷基氨基、芳氧基、氰基、烷硫基、烷基亚磺酰基或烷基磺酰基;
R3为氢原子、烷基、环烷基、卤代烷基、烷氧基、烷氧基烷基、烷基羰基或烷氧基羰基;
R4为卤素原子、硝基、烷基、烯基、炔基、卤代烷基、烷氧基、烷硫基、烷基羰基、卤代烷基羰基、环烷基羰基、烷氧基羰基、(烷硫基)羰基或吡唑基;
m为0~3的整数;
存在多个所述R2时,所述R2任选彼此相同或不同。
2.根据权利要求1所述的化合物或其盐,其中,所述式(I)中,R1为氢原子、卤素原子、烷基、卤代烷基、烷氧基、卤代烷氧基、芳氧基或卤代烷基芳基;
R2为卤素原子、烷基、卤代烷基、烷氧基、氨基、单烷基氨基、二烷基氨基、氰基、烷硫基、烷基亚磺酰基或烷基磺酰基;
R3为氢原子、烷基、环烷基、烷氧基、烷氧基烷基、烷基羰基或烷氧基羰基;
R4为卤素原子、硝基、烷基、烯基、卤代烷基、烷氧基、烷硫基、烷基羰基、卤代烷基羰基、烷氧基羰基、(烷硫基)羰基或吡唑基;
m为0或1。
3.根据权利要求1所述的化合物或其盐,其中,所述式(I)中,R1为氢原子、卤素原子、烷基、卤代烷基、烷氧基、卤代烷氧基、芳氧基或卤代烷基芳基;
R2为卤素原子、烷基、卤代烷基、烷氧基、氨基、氰基、烷硫基、烷基亚磺酰基或烷基磺酰基;
R3为氢原子、烷基、环烷基、烷氧基或烷氧基羰基;
R4为卤素原子、硝基、烷基、烯基、卤代烷基、烷氧基、烷硫基、烷基羰基、烷氧基羰基、(烷硫基)羰基或吡唑基;
m为0或1。
4.根据权利要求1所述的化合物或其盐,其中,所述式(I)中,R1为卤素原子、烷基、卤代烷基、烷氧基、卤代烷氧基、芳氧基或卤代烷基芳基;
R2为卤素原子、烷基、卤代烷基、烷氧基、氨基、氰基、烷硫基、烷基亚磺酰基或烷基磺酰基;
R3为氢原子、烷基、环烷基、烷氧基或烷氧基羰基;
R4为硝基、烷基、烯基、卤代烷基、烷氧基、烷硫基、烷基羰基、烷氧基羰基、(烷硫基)羰基或吡唑基;
m为0或1。
5.一种有害生物防治剂,其含有权利要求1所述的化合物或其盐作为有效成分。
6.一种农业园艺用杀虫剂、杀蜱螨剂、杀线虫剂或杀土壤害虫剂,其含有权利要求1所述的化合物或其盐作为有效成分。
7.一种防治有害生物的方法,其施用有效量的权利要求1所述的化合物或其盐来防治有害生物。
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