CN117479838A - 杀线虫组合物 - Google Patents
杀线虫组合物 Download PDFInfo
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- CN117479838A CN117479838A CN202280042539.6A CN202280042539A CN117479838A CN 117479838 A CN117479838 A CN 117479838A CN 202280042539 A CN202280042539 A CN 202280042539A CN 117479838 A CN117479838 A CN 117479838A
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- compound
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- alkyl
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- 239000000203 mixture Substances 0.000 title claims abstract description 117
- 230000001069 nematicidal effect Effects 0.000 title claims abstract description 24
- 150000001875 compounds Chemical class 0.000 claims abstract description 291
- 150000003839 salts Chemical class 0.000 claims abstract description 68
- 239000004480 active ingredient Substances 0.000 claims abstract description 21
- 238000000034 method Methods 0.000 claims description 72
- 241000244206 Nematoda Species 0.000 claims description 54
- 125000000217 alkyl group Chemical group 0.000 claims description 48
- 229910052736 halogen Inorganic materials 0.000 claims description 42
- 150000002367 halogens Chemical class 0.000 claims description 42
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 37
- 125000000304 alkynyl group Chemical group 0.000 claims description 35
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 26
- 125000003342 alkenyl group Chemical group 0.000 claims description 24
- 125000003545 alkoxy group Chemical group 0.000 claims description 24
- 239000002689 soil Substances 0.000 claims description 21
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 19
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 19
- 125000001188 haloalkyl group Chemical group 0.000 claims description 17
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 16
- 239000005645 nematicide Substances 0.000 claims description 14
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 12
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 12
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 10
- 125000004414 alkyl thio group Chemical group 0.000 claims description 10
- 150000001923 cyclic compounds Chemical class 0.000 claims description 6
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 4
- 125000003107 substituted aryl group Chemical group 0.000 claims description 4
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- 238000005481 NMR spectroscopy Methods 0.000 description 110
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- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 32
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- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 15
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- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 12
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- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 12
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- 239000003054 catalyst Substances 0.000 description 12
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- 238000006467 substitution reaction Methods 0.000 description 11
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- 210000000582 semen Anatomy 0.000 description 10
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 9
- 239000005942 Triflumuron Substances 0.000 description 9
- 241000607479 Yersinia pestis Species 0.000 description 9
- 239000003153 chemical reaction reagent 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
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 9
- 238000009331 sowing Methods 0.000 description 9
- 239000013076 target substance Substances 0.000 description 9
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- 241000243770 Bursaphelenchus Species 0.000 description 8
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 8
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 8
- 239000002253 acid Substances 0.000 description 8
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 8
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- 241000294569 Aphelenchoides Species 0.000 description 7
- 241000193388 Bacillus thuringiensis Species 0.000 description 7
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical group C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 7
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 7
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- 229910052783 alkali metal Inorganic materials 0.000 description 7
- 239000012752 auxiliary agent Substances 0.000 description 7
- 229940097012 bacillus thuringiensis Drugs 0.000 description 7
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 7
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- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 6
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- DHTJFQWHCVTNRY-OEMAIJDKSA-N pyrisoxazole Chemical compound C1([C@@]2(C)CC(ON2C)C=2C=CC(Cl)=CC=2)=CC=CN=C1 DHTJFQWHCVTNRY-OEMAIJDKSA-N 0.000 description 1
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- 150000003248 quinolines Chemical class 0.000 description 1
- FBQQHUGEACOBDN-UHFFFAOYSA-N quinomethionate Chemical compound N1=C2SC(=O)SC2=NC2=CC(C)=CC=C21 FBQQHUGEACOBDN-UHFFFAOYSA-N 0.000 description 1
- 150000003252 quinoxalines Chemical class 0.000 description 1
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- WRIKHQLVHPKCJU-UHFFFAOYSA-N sodium bis(trimethylsilyl)amide Chemical compound C[Si](C)(C)N([Na])[Si](C)(C)C WRIKHQLVHPKCJU-UHFFFAOYSA-N 0.000 description 1
- RPACBEVZENYWOL-XFULWGLBSA-M sodium;(2r)-2-[6-(4-chlorophenoxy)hexyl]oxirane-2-carboxylate Chemical compound [Na+].C=1C=C(Cl)C=CC=1OCCCCCC[C@]1(C(=O)[O-])CO1 RPACBEVZENYWOL-XFULWGLBSA-M 0.000 description 1
- UNHKSXOTUHOTAB-UHFFFAOYSA-N sodium;sulfane Chemical compound [Na].S UNHKSXOTUHOTAB-UHFFFAOYSA-N 0.000 description 1
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- 239000012258 stirred mixture Substances 0.000 description 1
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- QAZLUNIWYYOJPC-UHFFFAOYSA-M sulfenamide Chemical compound [Cl-].COC1=C(C)C=[N+]2C3=NC4=CC=C(OC)C=C4N3SCC2=C1C QAZLUNIWYYOJPC-UHFFFAOYSA-M 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
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- 239000004094 surface-active agent Substances 0.000 description 1
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- LWLJEQHTPVPKSJ-UHFFFAOYSA-N tebufloquin Chemical compound C1=C(C(C)(C)C)C=C2C(OC(=O)C)=C(C)C(C)=NC2=C1F LWLJEQHTPVPKSJ-UHFFFAOYSA-N 0.000 description 1
- CJDWRQLODFKPEL-UHFFFAOYSA-N teflubenzuron Chemical compound FC1=CC=CC(F)=C1C(=O)NC(=O)NC1=CC(Cl)=C(F)C(Cl)=C1F CJDWRQLODFKPEL-UHFFFAOYSA-N 0.000 description 1
- DYHSDKLCOJIUFX-UHFFFAOYSA-N tert-butoxycarbonyl anhydride Chemical compound CC(C)(C)OC(=O)OC(=O)OC(C)(C)C DYHSDKLCOJIUFX-UHFFFAOYSA-N 0.000 description 1
- MLGCXEBRWGEOQX-UHFFFAOYSA-N tetradifon Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)C1=CC(Cl)=C(Cl)C=C1Cl MLGCXEBRWGEOQX-UHFFFAOYSA-N 0.000 description 1
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- WOSNCVAPUOFXEH-UHFFFAOYSA-N thifluzamide Chemical compound S1C(C)=NC(C(F)(F)F)=C1C(=O)NC1=C(Br)C=C(OC(F)(F)F)C=C1Br WOSNCVAPUOFXEH-UHFFFAOYSA-N 0.000 description 1
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- YWBFPKPWMSWWEA-UHFFFAOYSA-O triazolopyrimidine Chemical class BrC1=CC=CC(C=2N=C3N=CN[N+]3=C(NCC=3C=CN=CC=3)C=2)=C1 YWBFPKPWMSWWEA-UHFFFAOYSA-O 0.000 description 1
- REEQLXCGVXDJSQ-UHFFFAOYSA-N trichlopyr Chemical compound OC(=O)COC1=NC(Cl)=C(Cl)C=C1Cl REEQLXCGVXDJSQ-UHFFFAOYSA-N 0.000 description 1
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- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 1
- RROQIUMZODEXOR-UHFFFAOYSA-N triforine Chemical compound O=CNC(C(Cl)(Cl)Cl)N1CCN(C(NC=O)C(Cl)(Cl)Cl)CC1 RROQIUMZODEXOR-UHFFFAOYSA-N 0.000 description 1
- COIOYMYWGDAQPM-UHFFFAOYSA-N tris(2-methylphenyl)phosphane Chemical compound CC1=CC=CC=C1P(C=1C(=CC=CC=1)C)C1=CC=CC=C1C COIOYMYWGDAQPM-UHFFFAOYSA-N 0.000 description 1
- WXAZIUYTQHYBFW-UHFFFAOYSA-N tris(4-methylphenyl)phosphane Chemical compound C1=CC(C)=CC=C1P(C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 WXAZIUYTQHYBFW-UHFFFAOYSA-N 0.000 description 1
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Classifications
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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
-
- 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
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/647—Triazoles; Hydrogenated triazoles
- A01N43/653—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Environmental Sciences (AREA)
- Wood Science & Technology (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Zoology (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Dentistry (AREA)
- Agronomy & Crop Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Medicines Containing Material From Animals Or Micro-Organisms (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
提供显示优异的杀线虫活性的杀线虫组合物。涉及含有式(I):(式中,各符号如说明书所记载的那样)所示的化合物或其盐作为有效成分的杀线虫组合物。
Description
技术领域
本发明涉及新的含有与季碳结合的甲腙(ホルムヒドラゾン)化合物或其盐作为有效成分的杀线虫组合物。
背景技术
已知具有特定的腙结构的化合物对于各种有害生物的防除是有用的。在专利文献1中,记载了作为农业园艺用杀虫剂或农业园艺用杀线虫剂而有用的具有由叔碳构成的-CH(Me)-或-CH(i-Pr)-那样的化学结构的腙衍生物及其使用方法。然而,在该文献中,并未记载与后述式(I)的化合物,即,具有以季碳作为特征的化学结构的腙衍生物、以其作为有效成分的杀线虫组合物和它们的使用方法有关的具体例。
现有技术文献
专利文献
专利文献1:国际公开第2020/179910号
发明内容
发明所要解决的课题
对农业和园艺等的作物生产带来损害的线虫存在各种种类,以它们的防除作为目的的农业园艺用杀线虫剂的开发进展了。进而,通过长期持续使用相同农业园艺用药剂,从而可能促进作为对象的线虫获得抗药性。因此,殷切期望与施用场合无关地,具有对线虫的高防除效果的新的农业园艺用杀线虫剂的创制。
因此,本发明的课题是提供显示优异的杀线虫活性的含有后述式(I)所示的化合物或其盐作为有效成分的杀线虫组合物。
用于解决课题的手段
本发明人等为了解决上述课题而进行了深入研究,结果发现,含有后述式(I)所示的化合物或其盐作为有效成分的组合物对线虫表现优异的防除效果。
即本发明如下所述。
[1]一种杀线虫组合物(以下,也称为本组合物),其以式(I)所示的化合物或其盐(以下,也称为化合物(I))作为有效成分。
[式中,X为N、CH或CR4,
A为未被取代的苯基或被1个~5个R1取代了的苯基,
R1为卤素、烷基、卤代烷基、烯基、炔基、环烷基、烷氧基、或卤代烷氧基,在R1存在2个的情况下,2个R1可以一起形成可以被1个或2个Z1取代的环,
Z1为卤素、或烷基,
R2和R3各自为烷基,或R2和R3一起形成(C3-C6)-碳环,
R4为卤素、烷基、卤代烷基、烯基、炔基、环烷基、烷氧基、卤代烷氧基、烷硫基、烷基亚磺酰基、烷基磺酰基、硝基或氰基,
R5为CHO,
R6为H、-SO2CF3、-C(=O)OZ3、烷基、烯基、炔基或烷氧基烷基、或可以被Z2取代的芳烷基,
Z2为烷氧基,
Z3为可以被Z2取代的芳烷基、或烷基,
m为0~2的整数。]
[2]一种线虫的防除方法,将含有有效量的式(I)所示的化合物或其盐的杀线虫组合物施用于土壤、线虫或植物体。
[式中,X为N、CH或CR4,
A为未被取代的苯基或被1个~5个R1取代了的苯基,
R1为卤素、烷基、卤代烷基、烯基、炔基、环烷基、烷氧基、或卤代烷氧基,在R1存在2个的情况下,2个R1可以一起形成可以被1个或2个Z1取代的环,
Z1为卤素、或烷基,
R2和R3各自为烷基,或R2和R3一起形成(C3-C6)碳环,
R4为卤素、烷基、卤代烷基、烯基、炔基、环烷基、烷氧基、卤代烷氧基、烷硫基、烷基亚磺酰基、烷基磺酰基、硝基或氰基,
R5为CHO,
R6为H、-SO2CF3、-C(=O)OZ3、烷基、烯基、炔基或烷氧基烷基、或可以被Z2取代的芳烷基,
Z2为烷氧基,
Z3为可以被Z2取代的芳烷基、或烷基,
m为0~2的整数]
[3]根据上述[1]所述的杀线虫组合物,式(I)所示的化合物或其盐是,A为被1个~5个R1取代了的苯基,R1为卤素、烷基、卤代烷基、烯基、炔基、环烷基、烷氧基、或卤代烷氧基,在R1存在2个的情况下,2个R1可以一起形成可以被1个或2个Z1取代的环的化合物或其盐。
[4]根据上述[2]所述的线虫的防除方法,式(I)所示的化合物或其盐是,A为被1个~5个R1取代了的苯基,R1为卤素、烷基、卤代烷基、烯基、炔基、环烷基、烷氧基、或卤代烷氧基,在R1存在2个的情况下,2个R1可以一起形成可以被1个或2个Z1取代的环的化合物或其盐。
[5]式(IA)所示的化合物或其盐。
[式中,X为N、CH或CR4A,
R1A为卤素、(C1-C6)-烷基、(C1-C6)-卤代烷基、(C2-C6)-烯基、(C2-C6)-炔基、(C3-C6)-环烷基、(C1-C6)-烷氧基、或(C1-C6)-卤代烷氧基,在R1A存在2个的情况下,2个R1A可以一起形成可以被1个或2个Z1A取代的环,
Z1A为卤素、或(C1-C6)-烷基,
R2A和R3A各自为(C1-C6)-烷基,或R2A和R3A一起形成(C3-C6)-碳环,
R4A为卤素、(C1-C6)-烷基、(C1-C6)-卤代烷基、(C2-C6)-烯基、(C2-C6)-炔基、(C3-C6)-环烷基、(C1-C6)-烷氧基、(C1-C6)-卤代烷氧基、(C1-C6)-烷硫基、(C1-C6)-烷基亚磺酰基、(C1-C6)-烷基磺酰基、硝基或氰基,
R6A为H、-SO2CF3、-C(=O)OZ3A、(C1-C6)-烷基、(C2-C6)-烯基、(C2-C6)-炔基或(C1-C6)-烷氧基-(C1-C6)-烷基、或可以被Z2A取代的(C7-C12)-芳烷基,
Z2A为(C1-C6)-烷氧基,
Z3A为可以被Z2A取代的(C7-C12)-芳烷基、或(C1-C6)-烷基,
n为1~5的整数,
m为0~2的整数]
[6]式(IB)所示的化合物或其盐。
[式中,X为N、CH或CR4A,
R2A和R3A各自为(C1-C6)-烷基,或R2A和R3A一起形成(C3-C6)-碳环,
R4A为卤素、(C1-C6)-烷基、(C1-C6)-卤代烷基、(C2-C6)-烯基、(C2-C6)-炔基、(C3-C6)-环烷基、(C1-C6)-烷氧基、(C1-C6)-卤代烷氧基、(C1-C6)-烷硫基、(C1-C6)-烷基亚磺酰基、(C1-C6)-烷基磺酰基、硝基或氰基,
R6A为H、-SO2CF3、-C(=O)OZ3A、(C1-C6)-烷基、(C2-C6)-烯基、(C2-C6)-炔基或(C1-C6)-烷氧基-(C1-C6)-烷基、或可以被Z2A取代的(C7-C12)-芳烷基,
Z2A为(C1-C6)-烷氧基,
Z3A为可以被Z2A取代的(C7-C12)-芳烷基、或(C1-C6)-烷基,
m为0~2的整数]
[7]一种线虫的防除方法,将含有有效量的上述[5]或上述[6]所述的化合物或其盐的杀线虫组合物施用于土壤、线虫或植物体。
[8]一种农业园艺用杀线虫剂,其含有上述[5]或上述[6]所述的化合物或其盐作为有效成分。
以下,有时将式(I)所示的化合物或其盐记为“化合物(I)”,将式(IA)所示的化合物或其盐记为“化合物(IA)”,将式(IB)所示的化合物或其盐记为“化合物(IB)”。
发明的效果
本组合物由于可以对线虫发挥优异的防除效果,因此作为农业园艺用杀线虫剂是有用的。
具体实施方式
对化合物(I)、化合物(IA)和化合物(IB)的取代基和化学结构的形态进行说明。
作为化合物(I)的苯基上的取代基的R1的取代数可以为1个,也可以为2个以上,在2个以上的情况下,R1各自可以相同也可以不相同。作为化合物(IA)的苯基上的取代基的R1A的取代数可以为1个,也可以为2个以上,在2个以上的情况下,R1A各自可以相同也可以不相同。
在化合物(I)中,在作为吡唑(X为CR4)的取代基的R4的取代数为2个或3个的情况下,R4各自可以相同也可以不相同。在化合物(I)中,在作为1,2,4-三唑(X为N)的取代基的R4的取代数为2个的情况下,R4各自可以相同也可以不相同。在化合物(IA)或化合物(IB)中,在作为吡唑(X为CR4A)的取代基的R4A的取代数为2个或3个的情况下,R4A各自可以相同也可以不相同。在化合物(IA)或化合物(IB)中在作为1,2,4-三唑的取代基的R4A的取代数为2个的情况下,R4A各自可以相同也可以不相同。
在本说明书中,“n-”是指“正”,“s-”是指“仲”,“tert-”是指“叔”。
卤素或作为取代基的卤素可举出氟、氯、溴、或碘的各原子。作为取代基的卤素的数目可以为1或2以上,在2以上的情况下,各卤原子各自可以相同也可以不相同。
此外,卤素的取代基的位置可以为任何位置。
在化合物(I)、化合物(IA)和化合物(IB)中,“CP-CT”是指碳原子数为P~T。例如“C1-C3”是指碳原子数为1~3。此外,“可以被取代”的表述是指取代或未取代。
作为烷基、烷基部分、或(C1-C6)-烷基,可举出例如,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、新戊基、或正己基那样的直链或支链状的基团。
作为烯基、或(C2-C6)-烯基,可举出例如,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、3-甲基-2-丁烯基、1-己烯基、或2,3-二甲基-2-丁烯基那样的直链或支链状的基团。此外,在具有几何异构体的情况下,为E体或Z体的仅任何一者、或E体与Z体的任意的比例的混合物,只要为被指定的碳原子数的范围,就没有特别限定。
作为炔基、或(C2-C6)-炔基,可举出例如,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、1-己炔基、2-己炔基、3-己炔基、4-己炔基、或5-己炔基那样的直链或支链状的基团。
作为环烷基、或(C3-C6)-环烷基,可举出例如,环丙基、环丁基、环戊基、或环己基那样的基团。
作为卤代烷基、或(C1-C6)-卤代烷基,可举出例如,氯甲基二氟甲基、三氟甲基、三氯甲基、1,1-二氯-1-氟甲基、1-氟乙基、2,2-二氟乙基、2,2,2-三氟乙基、2,2,2-三氯乙基、1,1,2,2-四氟乙基、1,1,2,2-四氯乙基、1,1,2,2,2-五氟乙基、3,3,3-三氟丙基、2,2,3,3,3-五氟丙基、或1,1,1,2,3,3,3-七氟丙烷-2-基那样的、通过1~7个相同的或不同的卤原子而部分地或完全被取代了的直链状或支链状的烷基。
作为烷氧基、或(C1-C6)-烷氧基,可举出例如甲氧基、乙氧基、正丙氧基、异丙氧基、正丁氧基、异丁氧基、仲丁氧基、叔丁氧基、正戊氧基、新戊氧基、或正己氧基那样的直链状或支链状的基团。
作为卤代烷氧基、或(C1-C6)-卤代烷氧基,可举出例如,二氟甲氧基、三氟甲氧基、2-氯乙氧基、2,2-二氟乙氧基、2,2,2-三氟乙氧基、1,1,2,2-四氟乙氧基、1,1,2,2,2-五氟乙氧基、2,2,3,3,3-五氟丙氧基、或(1,1,1,3,3,3-六氟丙烷-2-基)氧基那样的、通过1~6个相同的或不同的卤原子而部分地或完全被取代了的直链状或支链状的基团。
作为碳环、或(C3-C6)-碳环,可举出例如,环丙烷、环丁烷、环戊烷、或环己烷那样的饱和的环。
作为烷硫基、或(C1-C6)-烷硫基,可举出例如甲硫基、乙硫基、异丙硫基、正丁硫基、异丁硫基、仲丁硫基、叔丁硫基、正戊硫基、新戊硫基、或正己硫基那样的直链状或支链状的基团。
作为烷基亚磺酰基、或(C1-C6)-烷基亚磺酰基,可举出例如甲基亚磺酰基、乙基亚磺酰基、异丙基亚磺酰基、正丁基亚磺酰基、异丁基亚磺酰基、仲丁基亚磺酰基、叔丁基亚磺酰基、正戊基亚磺酰基、新戊基亚磺酰基、或正己基亚磺酰基那样的直链状或支链状的基团。
作为烷基磺酰基、或(C1-C6)-烷基磺酰基,可举出例如甲基磺酰基、乙基磺酰基、异丙基磺酰基、正丁基磺酰基、异丁基磺酰基、仲丁基磺酰基、叔丁基磺酰基、正戊基磺酰基、新戊基磺酰基、或正己基磺酰基那样的直链状或支链状的基团。
在化合物(I)中,作为2个R1一起形成环的方案中的A,可举出可以被1个或2个Z1取代的、苯并二氧杂环戊烷基或苯并二氧杂环己烷基等。此外,在式(IA)化合物中,作为2个R1A一起形成环的方案中的苯基,可举出可以被1个或2个Z1A取代的、苯并二氧杂环戊烷基或苯并二氧杂环己烷基等。在Z1或Z1A为2个的情况下,Z1或Z1A各自可以相同也可以不相同。
作为芳烷基、或(C7-C12)-芳烷基,可举出例如,苄基、1-苯基乙基、或萘基甲基等。作为可以被Z2取代的芳烷基、或可以被Z2取代的(C7-C12)-芳烷基,可举出对甲氧基苄基、2,3-二甲氧基苄基、或2,4-二甲氧基苄基等。
Z2、或Z2A的取代数可以为2个以上,在2个以上的情况下,各自可以相同也可以不相同。此外,Z2或Z2A的取代基位置可以为任何位置。
在化合物(I)中,“被1个~5个R1取代了的苯基”是指被1、2、3、4或5个R1取代了的苯基,所谓“未被取代的苯基”是指不具有作为取代基的R1的苯基。此外,在化合物(I)的特定的方案中,R1的取代数也有为1~2、1~3、1~4、2~3、2~4、2~5、3~4、3~5、4~5的整数的情况。
在化合物(IA)中,所谓“n为1~5的整数”,是指n为1、2、3、4或5的整数。此外,在化合物(IA)的特定的方案中,n也有为1~2、1~3、1~4、2~3、2~4、2~5、3~4、3~5、4~5的整数的情况。
在化合物(IA)中,如显示以下化学结构式的取代基位置那样,R1A基的取代基位置可以为苯环上的任何位置。在m为1以上时,如显示以下化学结构式的取代基位置那样,R4A基的取代基位置可以为杂五元环的3位和5位的任一位置或两个位置。
例如,在化合物(IA)中,在n为1时,R1的取代基位置为以下式(IAa)~式(IAc)所示的化合物那样的取代基位置。
式(IAa):
式(IAb):
式(IAc):
在化合物(IB)中,在m为1以上时,如显示以下化学结构式的取代基位置那样,R4A基的取代基位置可以为杂五元环的3位和5位的任一位置或两个位置。
在化合物(I)、化合物(IA)和化合物(IB)中,“m为0~2的整数”的表述是指m为0、1或2的整数。此外,在化合物(I)、化合物(IA)和化合物(IB)的特定的方案中,m也有为0~1、1~2的整数的情况。
需要说明的是,在化合物(I)、化合物(IA)和化合物(IB)中,在m为0时,(R4)m和(R4A)m为H,即是指杂五元环的3位和5位都为未取代。
以下,关于对化合物(I)进行说明的记载,由于在化合物(I)中包含化合物(IA)和化合物(IB),因此也包含与化合物(IA)和化合物(IB)有关的说明。
作为式(I)所示的化合物的盐,只要是农业上可容许的盐,就包含所有盐,可举出例如,碱金属盐(例如,钠盐、钾盐等)、碱土金属盐(例如,镁盐、钙盐等)、无机酸盐(例如,盐酸盐、高氯酸盐、硫酸盐、硝酸盐等)、有机酸盐(例如乙酸盐、甲磺酸盐等)等。
本发明的化合物(I)有时存在各种异构体,例如光学异构体、几何异构体等,但在本发明中包含各异构体和异构体混合物两者。
更具体而言,本发明的化合物(I)根据结构式中的双键(碳-碳或碳-氮)的数目而存在2种以上几何异构体。因此,在本发明中,包含能够想到的全部几何异构体和它们以任意的比例被包含的混合物。
例如,在本说明书所记载的化合物中,由结构式中的波浪线表示的键合是指也包含来源于双键(碳-碳或碳-氮)的2种以上几何异构体之中的任意几何异构体。
需要说明的是,在本发明的化合物(I)中,也包含在该技术领域中的技术常识的范围内,除上述物质以外的各种异构体。进一步,可以使用该技术领域中的技术常识和一般的实验方法,分开制作各种异构体。
此外,根据异构体的种类,有时成为与记载了的结构式不同的化学结构,但只要是本领域技术人员,就可以充分认识到它们处于异构体的关系,因此显然在本发明的范围内。
接下来对本组合物所包含的化合物(I)的制造方法进行说明。
化合物(I)可以按照以下所示的反应A~反应O和通常的盐的制造方法来制造,但获得化合物(I)的方法不限定于这些方法。例如,也能够通过在苯基、和/或吡唑、或1,2,4-三唑上的取代基,应用在本领域中周知的各种取代基转变反应(例如,水解、氧化、还原、酯化、酰胺化、烷基化、卤化等)来制造。此外,在化合物(I)的制造中,可以根据需要应用在本领域中通常被使用的保护和脱保护反应。
方案(Scheme)1
方案1为通过反应A或反应B由式(4)的化合物获得式(I-2)或式(2)的化合物的方法、和通过反应A或反应B由式(I-2)或式(2)的化合物获得化合物(I-1)的方法。
式中,A、X、m、R2、R3、R4、和R5如上所述。R6A为-SO2CF3、-C(=O)OZ3、烷基、烯基、炔基或烷氧基烷基、或可以被Z2取代的芳烷基,Z2和Z3如上所述。L为离去基团,更具体而言为氯原子、溴原子、碘原子、三氟甲磺酰基。
反应A
反应A为使式(2)的化合物与甲酰化试剂反应而获得化合物(I-1)的方法、或使式(4)的化合物与甲酰化试剂反应而获得式(I-2)的化合物的方法。
反应A通常可以在甲酰化试剂和溶剂的存在下进行。
甲酰化试剂只要反应进行就没有特别限定,可举出甲酸、N-甲酰基糖精等。甲酰化试剂相对于式(2)或式(4)的化合物可以使用1~10当量、期望1~2当量。这里,所谓“当量”是指摩尔当量,以下同样。
溶剂只要反应进行就没有特别限定,可以从例如苯、甲苯、二甲苯、氯苯那样的芳香族烃类;己烷、庚烷、石油醚、挥发油、环己烷那样的脂肪族烃类;氯仿、二氯甲烷、四氯化碳、1,2-二氯乙烷那样的卤代烃类;甲酸甲酯、甲酸乙酯、乙酸甲酯、乙酸乙酯那样的酯类;甲醇、乙醇、丙醇、叔丁醇那样的醇类;二甲亚砜、环丁砜、二甲基乙酰胺、N,N-二甲基甲酰胺(以下,也称为DMF)、N-甲基吡咯烷酮、吡啶、乙腈、丙腈那样的极性非质子性溶剂;丙酮、甲基乙基酮那样的酮类;乙酸等中适当选择1种或2种以上。
反应A可以根据需要在甲酸甲酯、甲酸乙酯那样的甲酸酯类的存在下进行。
甲酸酯类相对于式(2)或式(4)的化合物,可以使用1~50当量、期望1~30当量。
反应A可以根据需要在脱水缩合剂和碱的存在下进行。
脱水缩合剂可举出N,N’-二环己基碳二亚胺、氯磺酰异氰酸酯、N,N’-羰基二咪唑、三氟乙酸酐等。脱水缩合剂相对于式(2)或式(4)的化合物,可以使用1~5当量、期望1~2当量。
碱可以从例如钠、钾那样的碱金属;甲醇钠、乙醇钠、叔丁醇钾那样的碱金属醇盐;碳酸钠、碳酸钾那样的碳酸盐;碳酸氢钠、碳酸氢钾那样的碳酸氢盐;氢氧化钠、氢氧化钾那样的金属氢氧化物;氢化钠、氢化钾那样的金属氢化物;单甲基胺、二甲基胺、三乙胺那样的胺类;吡啶、4-二甲基氨基吡啶那样的吡啶类;甲基锂、正丁基锂、二异丙基氨基锂那样的有机锂化合物等中适当选择1种或2种以上。碱相对于式(2)或式(4)的化合物,可以使用1~5当量、期望1~2当量。
反应温度通常为约0℃~200℃,期望为约0℃~100℃。反应时间通常为约1小时~24小时。
在反应A中被使用的式(2)的化合物可以按照以下反应B来制造。
反应B
反应B为使式(I-2)的化合物与式(3)的化合物或保护化试剂反应而获得化合物(I-1)的方法、或使式(4)的化合物与式(3)的化合物或保护化试剂反应而获得式(2)的化合物的方法。
反应B通常可以在碱和溶剂的存在下进行。式(3)的化合物或保护化试剂相对于式(I-2)的化合物或式(4)的化合物,可以使用1~5当量、期望1~2当量。
碱可以使用在上述反应A中举出的物质。碱相对于式(I-2)的化合物或式(4)的化合物,可以使用1~5当量,期望1~2当量。
上述保护化试剂可以从甲氧基甲基氯、苄基溴、对甲氧基苄基氯、二碳酸二-叔丁酯、氯甲酸苄酯等中适当选择。
溶剂只要反应进行就没有特别限定,可以从例如苯、甲苯、二甲苯、氯苯那样的芳香族烃类;己烷、庚烷、石油醚、挥发油、环己烷那样的脂肪族烃类;氯仿、二氯甲烷、四氯化碳、1,2-二氯乙烷那样的卤代烃类;二烷、四氢呋喃、二乙基醚、二甲氧基乙烷那样的醚类;乙酸甲酯、乙酸乙酯那样的酯类;甲醇、乙醇、丙醇、叔丁醇那样的醇类;二甲亚砜、环丁砜、二甲基乙酰胺、N,N-二甲基甲酰胺、N-甲基吡咯烷酮、吡啶、乙腈、丙腈那样的极性非质子性溶剂;丙酮、甲基乙基酮那样的酮类;水等中适当选择1种或2种以上。
反应温度通常为约-78℃~200℃,期望为约0℃~100℃。反应时间通常为约1小时~48小时。
式(3)的化合物可以按照公知的方法来制造,或可以使用市售品。
式(4)的化合物可以按照以下反应H来制造。
反应C
反应C为使用式(b-1)的化合物,从式(I-3)的化合物转变为式(I-4)的化合物的方法。
反应C
式中,X、m、R2、R3、R4、和R5如上所述。A1为被氟取代了的苯基,A2为被羟基取代了的苯基。R6a为甲氧基甲基、苄基、对甲氧基苄基、叔丁氧基羰基、或苄基氧基羰基。式(b-1)中的Me为甲基。
反应C通常可以在碱和溶剂的存在下进行。式(b-1)的化合物相对于式(I-3)的化合物,可以使用1~10当量、期望1~5当量。
碱可以使用在上述反应A中举出的物质。碱相对于式(I-3)的化合物,可以使用1~10当量、期望1~5当量。
溶剂只要反应进行就没有特别限定,可以从例如苯、甲苯、二甲苯、氯苯那样的芳香族烃类;四氯化碳、氯仿、二氯甲烷、二氯乙烷、三氯乙烷、己烷、环己烷那样的脂肪族烃类;二烷、四氢呋喃、二乙基醚、二甲氧基乙烷那样的醚类;乙酸甲酯、乙酸乙酯那样的酯类;二甲亚砜、环丁砜、二甲基乙酰胺、N,N-二甲基甲酰胺、N-甲基吡咯烷酮、吡啶、乙腈、丙腈那样的极性非质子性溶剂;丙酮、甲基乙基酮那样的酮类等中适当选择1种或2种以上。
反应温度通常为约0~150℃,期望为约50~100℃,反应时间通常为约1~24小时左右,期望为约1~12小时左右。
反应D
反应D为使用式(b-2)的化合物、式(b-3)的化合物或卤代烷基化剂,将式(I-4)的化合物转变为式(I-5)的化合物的方法。
反应D
式中,X、m、R2、R3、R4、R5、R6a、L和A2如上所述,A3为被-ORA-1取代了的苯基,RA-1为烷基、或卤代烷基。
反应D通常可以在碱和溶剂的存在下进行。或者,可以按照一般的光延反应,在三苯基膦、偶氮二羧酸二乙酯和溶剂的存在下进行。卤代烷基化剂可举出例如溴二氟甲基三甲基硅烷、Togni试剂等。式(b-2)的化合物、式(b-3)的化合物或卤代烷基化剂相对于式(I-4)的化合物,可以使用1~3当量、期望1~2当量。三苯基膦相对于式(I-4)的化合物,可以使用1~3当量、期望1~1.5当量。偶氮二羧酸二乙酯相对于式(I-4)的化合物,可以使用1~3当量、期望1~1.5当量。
碱可以使用在上述反应A中举出的物质。碱相对于式(I-4)的化合物,可以使用1~10当量、期望1~5当量。
溶剂可以使用在上述反应B中举出的物质。
反应温度通常为约-78~100℃,期望为约0~50℃,反应时间通常为约0.1~24小时左右,期望为约0.1~12小时左右。
反应E
反应E为将式(I-5)的化合物脱保护,转变为式(I-6)的化合物的方法。
反应E
式中的符号如上所述。
反应E可以在一般的脱保护反应的条件下进行,可举出例如,酸性条件、氧化条件或接触还原条件。酸性条件通常可以在酸和溶剂的存在下进行,酸可举出盐酸、三氟乙酸等。酸相对于式(I-5)的化合物,可以使用1~10当量、期望1~3当量。氧化条件通常可以在氧化剂和溶剂的存在下进行,氧化剂可举出2,3-二氯-5,6-二氰基-1,4-苯醌等。氧化剂相对于式(I-5)的化合物,可以使用1~5当量、期望1~2当量。接触还原条件通常可以在氢气气氛下,在催化剂和溶剂的存在下进行,催化剂可举出铂、氧化铂、铂黑、雷尼镍、钯、钯-碳、铑、铑-氧化铝等。催化剂相对于式(I-5)的化合物,可以使用0.01~1当量、期望0.1~1当量。
溶剂可以使用在上述反应B中举出的物质。
反应温度通常为约-30~100℃,期望为约0~50℃,反应时间通常为约0.1~48小时左右,期望为约1~24小时左右。
反应F
反应F为将式(I-8)的化合物转变为式(I-7)的化合物的方法。
反应F
式中,X、m、R2、R3、R4、R5和R6a如上所述。A4为被Y取代了的苯基,A5为被RA-2取代了的苯基。Y为卤素,更具体而言为氯原子、溴原子、或碘原子,RA-2为烷基、烯基、炔基或环烷基。
反应F通常可以通过使式(I-8)的化合物在过渡金属催化剂、溶剂和非活性气体的存在下,根据需要添加碱而与有机金属试剂反应来进行。
有机金属试剂只要反应进行就没有特别限定,可举出例如格利雅试剂、有机锌试剂、有机硼化合物等。这些有机金属试剂可以按照公知的方法来调制,或可以使用市售品。有机金属试剂相对于式(I-8)的化合物,可以使用1~10当量、期望1~5当量。
过渡金属催化剂可举出包含钯、铑、钌、镍、钴、钼等过渡金属的催化剂。过渡金属催化剂可以使用有机卤化物的交联偶联反应所使用的公知的各种结构的物质,在本反应中包含钯的过渡金属催化剂是特别有用的。可举出例如,钯-碳、氯化钯、乙酸钯、二氯双(乙腈)钯、双(二亚苄基丙酮)钯、二氯双(三苯基膦)钯、四(三苯基膦)钯、二氯双(1,4-双(二苯基膦基)丁烷)钯等。此外,根据需要可以使用叔膦、叔亚磷酸酯作为配位体。作为叔膦、叔亚磷酸酯,可举出三苯基膦、苯基二甲基膦、三-邻甲苯基膦、三-对甲苯基膦、1,2-双(二苯基膦基)乙烷、1,3-双(二苯基膦基)丙烷、1,4-双(二苯基膦基)丁烷、1,1’-双(二苯基膦基)二茂铁、亚磷酸三苯酯等。过渡金属催化剂相对于式(I-8)的化合物可以使用0.001~0.5当量、期望0.05~0.2当量。此外,配位体相对于过渡金属催化剂1当量,通常可以使用1~50当量、期望1~10当量。但是,根据反应条件,也可以使用该范围外的量。
碱可举出例如碳酸钠、碳酸钾、碳酸铯那样的碱金属碳酸盐;甲醇钠、乙醇钠、叔丁醇钾那样的碱金属醇盐;碳酸氢钠那样的碱金属的碳酸氢盐;碳酸钙那样的碱土金属的碳酸盐;氢氧化钠、氢氧化钾那样的金属氢氧化物;氢化钠、氢化钾那样的金属氢化物;三乙胺、二异丙基乙基胺、吡啶、4-(N,N-二甲基氨基)吡啶、咪唑那样的有机胺类等。碱相对于式(I-8)的化合物,可以使用1~20当量、期望1~10当量。
溶剂只要反应进行就没有特别限定,可以从例如苯、甲苯、二甲苯、氯苯那样的芳香族烃类;四氯化碳、氯仿、二氯甲烷、二氯乙烷、三氯乙烷、己烷、环己烷那样的脂肪族烃类;二烷、四氢呋喃、二乙基醚、二甲氧基乙烷那样的醚类;乙酸甲酯、乙酸乙酯那样的酯类;二甲亚砜、环丁砜、二甲基乙酰胺、N,N-二甲基甲酰胺、N-甲基吡咯烷酮、吡啶那样的极性非质子性溶剂;乙腈、丙腈、丙烯腈那样的腈类;丙酮、甲基乙基酮那样的酮类;甲醇、乙醇、丙醇、叔丁醇那样的醇类;水等中适当选择1种或2种以上。
非活性气体可举出例如氮气、氩气等。
反应温度通常为约-100~200℃,期望为约-78~100℃,反应时间通常为约0.5~96小时左右,期望为约1~48小时左右。
反应G
反应G为将式(I-10)的化合物转变为式(I-9)的化合物的方法。
反应G
式中,A、X、m、R2、R3、R5和R6a如上所述。R4-1为卤素,更具体而言为氯原子、溴原子、或碘原子。R4-2为烷基、烯基、炔基、或环烷基。
反应G可以按照反应F来进行。
反应H
反应H为使式(5)的化合物与式(6)的化合物或肼反应,获得式(2)的化合物或式(4)的化合物的方法。
式中的符号如上所述。
反应H通常可以在溶剂的存在下进行,或也可以根据需要在酸的存在下进行。式(6)的化合物或肼相对于式(5)的化合物,可以使用1~10当量,期望1~3当量。
酸只要反应进行就没有特别限定,可以从例如盐酸、硫酸那样的无机酸;乙酸、丙酸、甲磺酸、对甲苯磺酸那样的有机酸等中适当选择1种或2种以上。酸相对于式(5)的化合物可以使用0.01~2当量、期望0.01~1当量。
溶剂可以使用在上述反应B中举出的物质。
反应温度通常为约0℃~200℃,期望为约20℃~150℃。反应时间通常为约1小时~72小时。
在反应H中被使用的式(5)的化合物可以按照以下反应I或反应J的方法、例如美国专利第4829075号说明书等所记载的方法、或基于它们的方法来制造。式(6)的化合物可以按照公知的方法来制造,或可以使用市售品。
反应I
反应I为使式(7)的化合物与式(8)的化合物反应,获得式(5)的化合物的方法。
反应I
式中的符号如上所述。
反应I通常可以在碱和溶剂的存在下进行。碱和溶剂可以使用在上述反应B中举出的物质。式(8)的化合物相对于式(7)的化合物,可以使用1~2当量,期望1~1.2当量。碱相对于式(7)的化合物,可以使用0.5~3当量,期望0.5~1当量。
反应温度通常为约0℃~150℃,期望为0℃~100℃。反应时间通常为约1小时~48小时。
在反应I中被使用的式(7)的化合物可以按照例如日本特开2021-035913号公报、日本特开2021-035914号公报等所记载的方法、或基于它们的方法来制造,或可以使用市售品。式(8)的化合物可以按照例如国际公开第2010/029461号、国际公开第2015/095788号、国际公开第2017/019804号等所记载的方法、或基于它们的方法来制造,或可以使用市售品。
反应J
反应J为使式(9)的化合物与式(10)的化合物反应,获得式(5)的化合物的方法。
反应J
式中的符号如上所述。
反应J可以按照反应B来进行。
反应温度通常可以在约-78℃~100℃,期望在约-78℃~80℃下进行,反应时间通常可以为约1小时~48小时左右,期望为约1小时~24小时左右。
在反应J中被使用的式(9)的化合物可以按照以下反应K来制造。式(10)的化合物可以按照公知的方法来制造,或可以使用市售品。
反应K
反应K为使式(11)的化合物与式(8)的化合物反应,获得式(9)的化合物的方法。
反应K
式中的符号如上所述。
反应K可以按照反应I来进行。
在反应K中被使用的式(11)的化合物可以按照例如国际公开第2010/121022号、Eurοpean Jοurnalοf Medicinal Chemistry,148卷,86~94页(2018年)等所记载的方法、或基于它们的方法来制造,或可以使用市售品。
反应L
反应L为使式(12)的化合物与式(8)的化合物反应,获得式(I-2)的化合物的方法。
反应L
式中的符号如上所述。
反应L通常可以在碱和溶剂的存在下进行。溶剂可以使用在上述反应B中举出的物质。式(8)的化合物相对于式(12)的化合物,可以使用1~2当量,期望1~1.2当量。
碱可以从例如钠、钾那样的碱金属;甲醇钠、乙醇钠、叔丁醇钾那样的碱金属醇盐;碳酸钠、碳酸钾那样的碳酸盐;碳酸氢钠、碳酸氢钾那样的碳酸氢盐;氢氧化钠、氢氧化钾那样的金属氢氧化物;氢化钠、氢化钾那样的金属氢化物;单甲基胺、二甲基胺、三乙胺那样的胺类;吡啶、4-二甲基氨基吡啶那样的吡啶类;甲基锂、正丁基锂、二异丙基氨基锂那样的有机锂化合物;双(三甲基硅基)氨基锂、双(三甲基硅基)氨基钠、双(三甲基硅基)氨基钾那样的硅化合物等中适当选择1种或2种以上。碱相对于式(12)的化合物,可以使用0.5~5当量、期望1~2当量。
反应温度通常为约-20℃~100℃,期望为约0℃~50℃。反应时间通常为约0.1小时~48小时,期望为约0.5小时~24小时。
在反应L中被使用的式(12)的化合物可以按照以下反应M的方法来制造。
反应M
反应M为使式(13)的化合物与卤化剂反应,获得式(12)的化合物的方法。
反应M
式中的符号如上所述。
反应M通常可以在卤化剂(例如,氯化剂、溴化剂或碘化剂)和溶剂的存在下,根据需要在碱的存在下进行。卤化剂相对于式(13)的化合物,可以使用1~2当量,期望1~1.5当量。
作为氯化剂,可以从例如氯、N-氯琥珀酰亚胺、硫酰氯等中适当选择1种或2种以上,作为溴化剂,可以从例如溴、N-溴琥珀酰亚胺、三甲基苯基三溴化铵等中适当选择1种或2种以上,作为碘化剂,可以从例如碘、N-碘琥珀酰亚胺等中适当选择1种或2种以上。
溶剂只要反应进行就没有特别限定,可以从例如苯、甲苯、二甲苯、氯苯那样的芳香族烃类;己烷、庚烷、石油醚、挥发油、环己烷那样的脂肪族烃类;氯仿、二氯甲烷、四氯化碳、1,2-二氯乙烷那样的卤代烃类;甲酸甲酯、甲酸乙酯、乙酸甲酯、乙酸乙酯那样的酯类;二烷、四氢呋喃、二乙基醚、二甲氧基乙烷那样的醚类;二甲亚砜、环丁砜、二甲基乙酰胺、N,N-二甲基甲酰胺、N-甲基吡咯烷酮、吡啶那样的极性非质子性溶剂;乙酸、丙酸那样的有机酸;水等中适当选择1种或2种以上。
作为碱,可举出例如二异丙基氨基锂等。碱相对于式(13)的化合物,可以使用1~2当量,期望1~1.2当量。
在碱的存在下进行的情况下,通常溶剂可以从四氢呋喃、二乙基醚那样的醚类中适当选择1种或2种以上。
反应M根据需要可以使用乙酸、丙酸那样的有机酸或氯化铝那样的路易斯酸作为催化剂。此外,可以通过过剩地使用作为溶剂的有机酸而兼作催化剂。
反应温度通常为约-100℃~150℃,期望为约-78℃~100℃。反应时间通常为约0.1小时~48小时,期望为约0.5~24小时。在碱的存在下进行的情况下,反应温度通常为约-100℃~50℃,期望为约-78℃~20℃,反应时间通常为约0.1~12小时,期望为约0.5~6小时,此外,在酸的存在下进行的情况下,反应温度通常为约0℃~150℃,期望为约20℃~120℃,反应时间通常为约0.1~48小时,期望为约1~24小时。
在反应M中被使用的式(13)的化合物可以按照以下反应N或反应Ο的方法来制造。
反应N
反应N为使式(14)的化合物与甲酰化试剂反应,获得式(13)的化合物的方法。
反应N
式中的符号如上所述。
反应N可以按照反应A来进行。此外,作为在反应N中被使用的甲酰化试剂,可举出在反应A中例示了的化合物。
在反应N中被使用的式(14)的化合物可以按照以下反应Ο的方法来制造。
反应Ο
反应Ο为使式(15)的化合物与式(16)的化合物或肼反应而获得式(13)的化合物或式(14)的化合物的方法。
反应Ο
式中的符号如上所述。
反应Ο可以按照反应H来进行。
在反应Ο中被使用的式(15)的化合物可以按照例如日本特开2021-035913号公报、日本特开2021-035914号公报、国际公开第2006/016708号等所记载的方法、或基于它们的方法来制造,或可以使用市售品。式(16)的化合物可以按照公知的方法来制造,或可以使用市售品。
对本组合物的施用场合、施用形态、处理方法等进行说明。
可以通过对线虫直接、和/或对作为线虫的栖息场所的土壤或植物体施用有效量的本组合物来防除线虫。上述栖息场所不仅包含线虫栖息的场所,而且也包含预想栖息的场所。上述植物体是指施用本组合物的植物的地上部(例如,茎、叶、干)、地下部(例如,根部)或种子。上述种子是指通过有性生殖而被形成的散布体(所谓种子)、植物的器官(例如,块茎、鳞茎、球茎、根茎、种薯)、或果树类、花木类或花卉类的接穗(例如,作为果树类的葡萄的枝等)等。
本组合物可以防除属于例如根结线虫属(Meloidogyne属)线虫、短体线虫属(Pratylenchus属)线虫、茎线虫属(Ditylenchus属)线虫、胞囊线虫属(Heterodera属)线虫、球胞囊线虫属(Globodera属)线虫、滑刃线虫属(Aphelenchoides属)线虫、真滑刃线虫属(Aphelenchus属)线虫、穿孔线虫属(Radopholus属)线虫、小垫刃线虫属(Tylenchulus属)线虫、肾形线虫属(Rotylenchulus属)线虫、盘旋线虫属(Rotylenchus属)线虫、粒线虫属(Anguina属)线虫、刺线虫属(Belonolaimus属)线虫、伞滑刃线虫属(Bursaphelenchus属)线虫、环线虫属(Criconema属)线虫、轮线虫属(Criconemoides属)线虫、中环线虫属(Mesocriconema属)线虫、锥线虫属(Dolichodorus属)线虫、螺旋线虫属(Helicotylenchus属)线虫、潜根线虫属(Hirschmanniella属)线虫、纽带线虫属(Hoplolaimus属)线虫、珍珠线虫属(Nacobbus属)线虫、长针线虫属(Longidorus属)线虫、盾线虫属(Scutellonema属)线虫、毛刺线虫属(Trichodorus属)线虫、类毛刺线虫属(Paratrichodorus属)线虫、矮化线虫属(Tylenchorhynchus属)线虫、剑线虫属(Xiphinema属)线虫等的线虫,其中对属于根结线虫属(Meloidogyne属)线虫、短体线虫属(Pratylenchus属)线虫、胞囊线虫属(Heterodera属)线虫、球胞囊线虫属(Globodera属)线虫等的线虫的防除是特别有效的。
上述线虫的具体的例子可举出例如以下那样的例子等。
可举出南方根结线虫(Meloidogyne incognita)、北方根结线虫(Meloidogynehapla)、花生根结线虫(Meloidogyne arenaria)、爪哇根结线虫(Meloidogyne javanica)那样的根结线虫属(Meloidogyne属)线虫类、穿刺短体线虫(Pratylenchus penetrans)、咖啡短体线虫(Pratylenchus coffeae)、卢斯短体线虫(Pratylenchus loosi)、伤残短体线虫(Pratylenchus vulnus)等那样的短体线虫属(Pratylenchus属)线虫类、马铃薯腐烂线虫(Ditylenchus destructor)、鳞球茎茎线虫(Ditylenchus dipsaci)等那样的茎线虫属(Ditylenchus属)线虫类、大豆胞囊线虫(Heterodera glycines)、甜菜孢囊线虫(Heterodera schachtii)、三叶草胞囊线虫(Heterodera trifolii)等那样的胞囊线虫属(Heterodera属)线虫类、马铃薯金线虫(Globodera rostochiensis)、马铃薯白线虫(Globodera pallida)等那样的球胞囊线虫属(Globodera属)线虫类、水稻干尖线虫(Aphelenchoides besseyi)、草莓滑刃线虫(Aphelenchoides fragariae)、菊叶滑刃线虫(Aphelenchoides ritzemabosi)等那样的滑刃线虫属(Aphelenchoides属)线虫类、燕麦真滑刃线虫(Aphelenchus avenae)等那样的真滑刃线虫属(Aphelenchus属)线虫类、香蕉穿孔线虫(Radopholus similis)等那样的穿孔线虫属(Radopholus属)线虫类、半穿刺小垫刃线虫(Tylenchulus semipenetrans)等那样的小垫刃线虫属(Tylenchulus属)线虫类、肾形线虫(Rotylenchulus reniformis)等那样的肾形线虫属(Rotylenchulus属)线虫类、强壮盘旋线虫(Rotylenchus robustus)等那样的盘旋线虫属(Rotylenchus属)线虫类、小麦粒线虫(Anguina tritici)等那样的粒线虫属(Anguina属)线虫类、长尾刺线虫(Belonolaimus longicaudatus)那样的刺线虫属(Belonolaimus属)线虫类、松材线虫(Bursaphelenchus xylophilus)、椰子红环腐线虫(Bursaphelenchus cocophilus)那样的伞滑刃线虫属(Bursaphelenchus属)线虫类、Criconema jaejuense、Criconema palliatum等那样的环线虫属(Criconema属)线虫类、畸形轮线虫(Criconemoides informis)、Criconemoides morgensis等那样的轮线虫属(Criconemoides属)线虫类、异盘中环线虫(Mesocriconema xenoplax)、弯曲中环线虫(Mesocriconema curvatum)等那样的中环线虫属(Mesocriconema属)线虫类、异头锥线虫(Dolichodorus heterocephalus)等那样的锥线虫属(Dolichodorus属)线虫类、假强壮螺旋线虫(Helicotylenchus pseudorobustus)、多带螺旋线虫(Helicotylenchus multicinctus)等那样的螺旋线虫属(Helicotylenchus属)线虫类、分离潜根线虫(Hirschmanniella diversa)、水稻潜根线虫(Hirschmanniellaoryzae)等那样的潜根线虫属(Hirschmanniella属)线虫类、哥伦比亚纽带线虫(Hoplolaimus columbus)、大针纽带线虫(Hoplolaimus magnistylus)等那样的纽带线虫属(Hoplolaimus属)线虫类、异常珍珠线虫(Nacobbus aberrans)、背侧珍珠线虫(Nacobbusdorsalis)等那样的珍珠线虫属(Nacobbus属)线虫类、马蒂尼长针线虫(Longidorusmartini)、折环长针线虫(Longidorus diadecturus)等那样的长针线虫属(Longidorus属)线虫类、小尾盾线虫(Scutellonema brachyurum)、缓慢盾线虫(Scutellonema bradys)等那样的盾线虫属(Scutellonema属)线虫类、雪松毛刺线虫(Trichodorus cedarus)等那样的毛刺线虫属(Trichodorus属)线虫类、胼胝类毛刺线虫(Paratrichodorus porosus)、较小类毛刺线虫(Paratrichodorus minor)等那样的类毛刺线虫属(Paratrichodorus属)线虫类、克来顿矮化线虫(Tylenchorhynchus claytoni)等那样的矮化线虫属(Tylenchorhynchus属)线虫类、标准剑线虫(Xiphinema index)、美洲剑线虫(Xiphinemaamericanum)等那样的剑线虫属(Xiphinema属)线虫类等。
施用本组合物的植物只要在农业园艺上是有用的就没有特别限制,可举出例如,番茄、小番茄、菜椒、茄、黄瓜、西葫芦、西瓜、甜瓜、南瓜、咖啡黄葵、辣椒、菜瓜、冬瓜、苦瓜、香瓜等果菜类、莴苣、卷心莴苣、菠菜、甘蓝、洋葱、蒜、石刁柏、绿花菜、花椰菜、白菜、落葵、葱、水菜、紫苏、小松菜、旱芹等叶菜类、马铃薯、番薯、萝卜、胡萝卜、牛蒡、莲藕、芋、魔芋、日本薯蓣、姜、芜菁、藠头、蘘荷、菊牛蒡(モリアザミ)等根菜类、大豆、赤豆、豌豆、菜豆、落花生、蚕豆、大豆等豆类、稻、小麦、燕麦、黑麦、玉米等谷类、苹果、柑橘类、梨、葡萄、草莓、核桃、扁桃、香蕉、无花果、凤梨、桃、油桃、樱桃、杏、椰子、鳄梨、柿、李、阿月浑子、猕猴桃、枇杷等果树/果实/种实类、细叶结缕草、剪股颖等草类、菊、百合、蔷薇、香石竹、大丽花、非洲菊、非洲紫罗兰、郁金香、水仙、碧冬茄、欧铃兰、牡丹、仙客来、凤仙花、洋桔梗等花卉类、松、日本柳杉、日本扁柏、杜鹃花类等树木/花木类、棉、菜籽、甜菜、茶、烟草、咖啡、橄榄、甘蔗、啤酒花、芝麻、欧芹、百里香、迷迭香、罗勒、薰衣草等工艺作物类、兰、仙人掌类、蕨植物类等观叶植物、车轴草、紫苜蓿、鸭茅、石茅等牧草类等的植物。
需要说明的是,在这些植物中,包含通过传统的育种法而被赋予了对除草剂(例如,异唑草酮等HPPD抑制剂;咪唑乙烟酸、噻吩磺隆等ALS抑制剂;草甘膦等EPSP合成酶抑制剂;草铵膦等谷氨酰胺合成酶抑制剂、烯禾啶等乙酰CoA羧化酶抑制剂;溴苯腈;麦草畏;2,4-D等)的耐性的植物。进一步,在本发明的有用植物中,也包含通过基因重组技术、基因编辑技术而被制作出的转基因植物。作为转基因植物的一例,也包含对上述除草剂耐性的转基因植物、害虫抵抗性的转基因植物、与植物成分有关的转基因植物、植物病原耐性的转基因植物等。
本组合物通常将化合物(I)与各种农业园艺用的助剂混合,制剂为粉剂、颗粒剂、水分散性粒剂、可湿性粉剂、水性悬浮剂、油性悬浮剂、水溶性粉剂、乳油、可溶液体制剂、膏剂、气雾剂、超低容量剂等各种形态而被使用,但只要适合于本发明的目的,就可以为通常的该领域所使用的所有制剂形态。其中,从向土壤的施用方法方面考虑,优选颗粒剂、水性悬浮剂、油性悬浮剂、乳油或可溶液体制剂。作为制剂所使用的助剂,可举出硅藻土、消石灰、碳酸钙、滑石、白炭墨、高岭土、膨润土、高岭石、绢云母、粘土、碳酸钠、碳酸氢钠、芒硝、沸石、淀粉等固体载体;水、甲苯、二甲苯、溶剂石脑油、二烷、丙酮、异佛尔酮、甲基异丁基酮、氯苯、环己烷、二甲亚砜、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、多元羧酸盐、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、聚氧乙烯烷基醚硫酸酯盐、聚氧乙烯烷基芳基醚硫酸盐、聚氧乙烯烷基芳基醚硫酸酯盐、聚氧乙烯烷基醚磷酸盐、聚氧乙烯烷基芳基磷酸酯盐、萘磺酸盐甲醛缩合物那样的阴离子系的表面活性剂;失水山梨糖醇脂肪酸酯、脂肪酸甘油酯、脂肪酸聚甘油酯、脂肪酸醇聚二醇醚、乙炔二醇、炔属醇、氧化烯嵌段聚合物、聚氧乙烯烷基醚、聚氧乙烯烷基芳基醚、聚氧乙烯苯乙烯基芳基醚、聚氧乙二醇烷基醚、聚乙二醇、聚氧乙烯脂肪酸酯、聚氧乙烯失水山梨糖醇脂肪酸酯、聚氧乙烯甘油脂肪酸酯、聚氧乙烯氢化蓖麻油、聚氧丙烯脂肪酸酯那样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、落花生油、棉籽油、豆油、菜籽油、亚麻仁油、桐油、液体石蜡等植物油、矿物油;等。这些助剂的各成分只要不超出本发明的目的,就可以适当选择1种或2种以上而使用。此外,除上述助剂以外还可以从在该领域中已知的物质中适当选择而使用,也可以使用例如,增量剂、增稠剂、抗沉降剂、防冻剂、分散稳定剂、安全剂、防霉剂等通常被使用的各种助剂。化合物(I)与各种助剂的混配比例(化合物(I):助剂)以聚合比计一般为0.001:99.999~95:5,期望为0.005:99.995~90:10。在这些制剂的实际使用时,可以直接使用,或使用水等稀释剂稀释为规定浓度,根据需要添加各种展着剂(表面活性剂、植物油、矿物油等)而使用。
本组合物的施用根据气象条件、制剂形态、对象作物、施用时期、施用场所、线虫的种类、发生状况等的不同而不能笼统地规定,但通常,可以通过一般进行的施用方法即土壤处理、茎叶处理、灌注处理、种子处理、树干注入处理、或水稻育苗箱施用等,来进行本组合物或其稀释物的施用。一般在土壤处理、茎叶处理、灌注处理的情况下,其施用适量是每1公顷,本组合物可以为约0.01g~50,000g、期望为约1g~30,000g。在种子处理的情况下,其施用适量是每1kg的种子,可以为约0.01g~200g、期望为约0.05~100g。在水稻育苗箱施用的情况下,其施用适量是每1个育苗箱,本组合物可以为约0.001g~3,000g、期望为约0.01g~1,000g。在树干注入处理的情况下,其施用适量是每1颗树,本组合物可以为约0.001g~5,000g、期望为约0.01g~3,000g左右。
所谓土壤处理,可举出例如,调制为液体制剂(可溶液体制剂、水性悬浮剂、油性悬浮剂、乳油等)或固体制剂(颗粒剂、粉剂、可湿性粉剂、水溶性粉剂、水分散性粒剂、可溶性粒剂等)等,直接或在水中稀释,在植物体的移栽前或播种前散布于土壤整面进行混合的方法;散布于为了种植植物体而挖开了的孔中(种植孔)的方法;或散布于为了播种或种植植物体而挖成一定宽度的浅沟的方法等。
所谓茎叶处理,可举出例如,将本组合物调制为液体制剂(可溶液体制剂、水性悬浮剂、油性悬浮剂、乳油等)或固体制剂(可湿性粉剂、水溶性粉剂、水分散性粒剂、可溶性粒剂等)等,在水中稀释而散布于植物体整体的方法等。
所谓灌注处理,可举出例如,将本组合物调制为液体制剂(可溶液体制剂、水性悬浮剂、油性悬浮剂等)或固体制剂(可湿性粉剂、水溶性粉剂、水分散性粒剂、可溶性粒剂等)等,直接或在水中稀释而灌注于育苗用的栽培容器、栽培中的植物体的根或其附近等的方法等。
所谓种子处理,可举出例如,将本组合物调制为液体制剂(水性悬浮剂、油性悬浮剂、乳油、可溶液体制剂等)或固体制剂(粉剂、可湿性粉剂、水溶性粉剂、水分散性粒剂、可溶性粒剂等),直接或在水中稀释,与种子进行搅拌而附着于种子表面的方法;与涂布材料一起混合而附着于种子的表面的方法;向种子喷射而使其附着的方法;将种子浸渍而使药剂渗透的方法等。
所谓水稻育苗箱施用,可举出例如,将本组合物调制为固体制剂(颗粒剂、粉剂等)或液体制剂(水性悬浮剂、油性悬浮剂、可溶液体制剂等)等,直接或在水中稀释,在播种之前、播种之后、播种的前后两者、育苗箱中的生长时、或向水田的移栽前向育苗箱散布的方法。进而,也可举出在向育苗箱播种时与培土的混合、例如将本组合物调制为固体制剂(颗粒剂、粉剂、水分散性粒剂等)而混合在床土、覆土或培土的整体的方法等。
所谓树干注入处理,可举出例如,将本组合物调制为液体制剂(可溶液体制剂等)等而直接从在树干开出的孔注入到植物体的方法等。
本组合物可以与选自其它农业园艺用药剂、肥料、安全剂等中的其它成分混用或并用,在该情况下有时显示更加优异的效果、作用性。
所谓上述混用或并用,是指将本组合物与其它成分同时、分开或空出时间间隔而使用。
其它农业园艺用药剂可举出除草剂、杀虫剂、杀螨剂、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。特别是,将本组合物、以及其它杀虫剂和/或杀线虫剂的有效成分化合物的1种或2种以上混用或并用而成的混合杀线虫组合物有时将应用范围、药剂处理的时期、防除活性等向优选的方向改良。需要说明的是,本组合物、以及其它杀虫剂、和/或杀线虫剂的有效成分化合物可以将各自分开制剂了的物质在散布时混合使用,也可以将两者一起制剂而使用。在本发明中,也包含这样的混合杀线虫组合物。
化合物(I)、以及其它杀虫剂、和/或杀线虫剂的有效成分化合物的混合比(化合物(I):有效成分化合物)根据气象条件、制剂形态、对象作物、施用时期、施用场所、线虫的种类、发生状况等的不同而不能笼统地规定,但以重量比计一般可以为1:300~300:1,期望为1:100~100:1。此外,施用适量是每1公顷的总有效成分化合物量可以为0.1~70,000g、期望为5~50,000g。在本发明中,也包含基于这样的混合杀线虫组合物的施用的线虫的防除方法、或根据情况的线虫和害虫的防除方法。
上述害虫的更具体的例子可举出例如以下那样的例子等。
可举出桃蚜、棉蚜等那样的蚜虫类;菜蛾、甘蓝夜蛾、斜纹夜蛾、苹果蠹蛾、螟蛉虫(ボールワーム)、棉铃虫(オオタバコガ)、烟毒蛾、稻纵卷叶野螟、棉褐带卷蛾、小地老虎、黄地老虎等那样的鳞翅目害虫类;马铃薯叶甲、黄守瓜、亮绿彩丽金龟类等那样的鞘翅目害虫类;褐飞虱、白背飞虱等那样的飞虱类;叶蝉类;蚧类;蝽类;甘薯粉虱等那样的粉虱类;蓟马类;蝗类;花蝇类;蚁类;双线蛞蝓、真厚螺(マイマイ)等那样的腹足类;二点叶螨、朱砂叶螨、神泽叶螨、柑桔全爪螨、苹果全爪螨、侧多食跗线螨、桔刺皮瘿蜱、赤足根螨(ネダニ)、粉螨(コナダニ)等那样的植物寄生性螨类;寻常球鼠妇、粗糙鼠妇等那样的等足类;等害虫等。
在含有化合物(I)的杀线虫组合物的施用时,也可以进一步将其它农业园艺用药剂例如杀菌剂、杀虫剂、杀螨剂、杀线虫剂、杀土壤害虫剂、抗病毒剂、引诱剂、除草剂、植物生长调节剂等一并处理。
所谓上述其它农业园艺用药剂中的、杀虫剂、杀线虫剂、杀螨剂、或杀土壤害虫剂的有效成分化合物(通用名或日本植物防疫协会试验码),可以从例如下述化合物组中适当选择。即使在没有特别记载的情况下,在这些化合物中存在盐、烷基酯、光学异构体那样的各种结构异构体等的情况下,当然也包含它们。
丙溴磷(profenofos)、敌敌畏(dichlorvos)、苯线磷(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)、噻唑膦(fosthiazate)、硫线磷(cadusafos)、乙拌磷(disulfoton)、唑磷(isoxathion)、异柳磷(isofenphos)、乙硫磷(ethion)、乙嘧硫磷(etrimfos)、喹硫磷(quinalphos)、甲基毒虫畏(dimethylvinphos)、乐果(dimethoate)、硫丙磷(sulprofos)、甲基乙拌磷(thiometon)、蚜灭磷(vamidothion)、吡唑硫磷(pyraclofos)、哒嗪硫磷(pyridaphenthion)、甲基嘧啶磷(pirimiphos-methyl)、丙虫磷(propaphos)、伏杀硫磷(phosalone)、安硫磷(formothion)、马拉硫磷(malathion)、杀虫畏(tetrachlorvinphos)、毒虫畏(chlorfenvinphos)、杀螟腈(cyanophos)、敌百虫(trichlorfon)、杀扑磷(methidathion)、稻丰散(phenthoate)、ESP(异亚砜磷,oxydeprofos)、保棉磷(azinphos-methyl)、倍硫磷(fenthion)、庚烯磷(heptenophos)、甲氧滴滴涕(methoxychlor)、对硫磷(parathion)、磷虫威(phosphocarb)、S-甲基内吸磷(demeton-S-methyl)、久效磷(monocrotophos)、甲胺磷(methamidophos)、氰咪唑硫磷(imicyafos)、甲基对硫磷(parathion-methyl)、特丁硫磷(terbufos)、磷胺(phosphamidon)、亚胺硫磷(phosmet)、甲拌磷(phorate)那样的有机磷酸酯系化合物;
甲萘威(carbaryl)、残杀威(propoxur)、涕灭威(aldicarb)、克百威(carbofuran)、硫双威(thiodicarb)、灭多威(methomyl)、杀线威(oxamyl)、乙硫苯威(ethiofencarb)、抗蚜威(pirimicarb)、仲丁威(fenobucarb)、丁硫克百威(carbosulfan)、丙硫克百威(benfuracarb)、丙硫克百威(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)那样的氨基甲酸酯系化合物;
杀螟丹(cartap)、杀虫环(thiocyclam)、杀虫环盐酸盐(thiocyclamhydrochloride)、杀虫磺(bensultap)、杀虫磺丙烷(thiosultap)、杀虫单(monosultap;别名杀虫单(thiosultap-monosodium)、杀虫双(bisultap;别名杀虫双(thiosultap-disodium)、多噻烷(polythialan)那样的沙蚕毒素衍生物;
三氯杀螨醇(dicofol)、三氯杀螨砜(tetradifon)、硫丹(endosulfan)、遍地克(dienochlor)、狄氏剂(dieldrin)那样的有机氯系化合物;
氰戊菊酯(fenvalerate)、氯菊酯(permethrin)、氯氰菊酯(cypermethrin)、α-氯氰菊酯(alpha-cypermethrin)、zeta-氯氰菊酯(zeta-cypermethrin)、theta-氯氰菊酯(theta-cypermethrin)、高效氯氰菊酯(beta-cypermethrin)、溴氰菊酯(deltamethrin)、氯氟氰菊酯(cyhalothrin)、精高效氯氟氰菊酯(gamma-cyhalothrin)、高效氯氟氰菊酯(lambda-cyhalothrin)、七氟菊酯(tefluthrin)、R-七氟菊酯(kappa-tefluthrin)、醚菊酯(ethofenprox)、三氟醚菊酯(flufenprox)、氟氯氰菊酯(cyfluthrin)、高效氟氯氰菊酯(beta-cyfluthrin)、甲氰菊酯(fenpropathrin)、氟氰戊菊酯(flucythrinate)、氟胺氰菊酯(fluvalinate)、乙氰菊酯(cycloprothrin)、除虫菊素(pyrethrins)、S-氰戊菊酯(esfenvalerate)、胺菊酯(tetramethrin)、苄呋菊酯(resmethrin)、氟苯醚菊酯(protrifenbute)、联苯菊酯(bifenthrin)、R-联苯菊酯(kappa-bifenthrin)、氟丙菊酯(acrinathrin)、烯丙菊酯(allethrin)、τ-氟胺氰菊酯(tau-fluvalinate)、四溴菊酯(tralomethrin)、丙氟菊酯(profluthrin)、甲氧苄氟菊酯(metofluthrin)、ε-甲氧苄氟菊酯(epsilon-metofluthrin)、七氟甲醚菊酯(heptafluthrin)、苯醚菊酯(phenothrin)、氟氯苯菊酯(flumethrin)、甲氧氟菊酯(momfluorothrin)、氟硅菊酯(silafluofen)那样的拟除虫菊酯系化合物;
除虫脲(diflubenzuron)、氟啶脲(chlorfluazuron)、氟苯脲(teflubenzuron)、氟虫脲(flufenoxuron)、虱螨脲(lufenuron)、氟酰脲(novaluron)、杀铃脲(triflumuron)、氟铃脲(hexaflumuron)、双三氟虫脲(bistrifluron)、多氟脲(noviflumuron)、啶蜱脲(fluazuron)、氟虫脲(flufenoxuron)那样的苯甲酰脲系化合物;
烯虫酯(methoprene)、吡丙醚(pyriproxyfen)、苯氧威(fenoxycarb)、苯虫醚(diofenolan)那样的保幼激素样化合物;
哒螨灵(pyridaben)那样的哒嗪酮系化合物;
唑螨酯(fenpyroximate)、氟虫腈(fipronil)、乙虫腈(ethiprole)、乙酰虫腈(acetoprole)、啶吡唑虫胺(pyrafluprole)、吡唑虫啶(pyriprole)、腈吡螨酯(cyenopyrafen)、丁烯氟虫腈(flufiprole)、吡螨胺(tebufenpyrad)、唑虫酰胺(tolfenpyrad)那样的吡唑系化合物;
氯虫酰胺(chlorantraniliprole)、氰虫酰胺(cyantraniliprole)、环溴虫酰胺(cyclaniliprole)、四唑虫酰胺(tetraniliprole)、氟苯虫酰胺(flubendiamide)、四氯虫酰胺(tetrachlorantraniliprole)、氯氟氰虫酰胺(cyhalodiamide)、氟氯虫酰胺(fluchlordiniliprole)、硫虫酰胺(tiorantraniliprole)那样的二酰胺系化合物;
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(dinotefuran)、硝虫噻嗪(nithiazine)那样的新烟碱系化合物;
虫酰肼(tebufenozide)、甲氧虫酰肼(methoxyfenozide)、环虫酰肼(chromafenozide)、氯虫酰肼(halofenozide)那样的肼系化合物;
啶虫醚(pyridalyl)、氟啶虫酰胺(flonicamid)那样的吡啶系化合物;
螺螨酯(spirodiclofen)、螺甲螨酯(spiromesifen)、螺螨双酯(spirobudifen)那样的季酮酸系化合物;
螺虫乙酯(spirotetramat)、甲氧哌啶乙酯(spiropidion)那样的特拉姆酸系化合物;
嘧螨酯(fluacrypyrim)、嘧螨胺(pyriminostrobin)那样的嗜球果伞素系化合物;
嘧虫胺(flufenerim)、嘧螨醚(pyrimidifen)那样的嘧啶胺系化合物;
灭蝇胺(cyromazine)那样的三嗪系化合物;
氟蚁腙(hydramethylnon)那样的腙系化合物;
丁醚脲(diafenthiuron)、灭虫脲(chloromethiuron)那样的硫脲系化合物;
双甲脒(amitraz)、杀虫脒(chlordimeform)、灭螨脒(chloromebuform)那样的甲脒系化合物;
吡蚜酮(pymetrozine)、吡氟喹虫唑(pyrifluquinazone)那样的吡啶偶氮甲碱系化合物;
阿福拉纳(afoxolaner)、氟雷拉纳(fluralaner)、氟唑酰胺(fluxametamide)、沙罗拉纳(sarolaner)那样的异/>唑啉系化合物;
此外,作为其它化合物,噻嗪酮(buprofezin)、噻螨酮(hexythiazox)、唑蚜威(triazamate)、虫螨腈(chlorfenapyr)、茚虫威(indoxacarb)、灭螨醌(acequinocyl)、乙螨唑(etoxazole)、1,3-二氯丙烯(1,3-dichloropropene)、杀线噻唑(benclothiaz)、联苯肼酯(bifenazate)、快螨特(propargite)、四螨嗪(clofentezine)、氰氟虫腙(metaflumizone)、丁氟螨酯(cyflumetofen)、喹螨醚(fenazaquin)、磺胺螨酯(amidoflumet)、氟虫胺(sulfluramid)、氟蚁腙(hydramethylnon)、四聚乙醛(metaldehyde)、砜虫啶(sulfoxaflor)、氟烯线砜(fluensulfone)、增效炔醚(verbutin)、二氯噻吡嘧啶(dicloromezotiaz)、三氟苯嘧啶(triflumezopyrim)、氟己虫腈(fluhexafon)、线噻吩(tioxazafen)、双丙环虫酯(afidopyropen)、氟虫碳酸酯(flometoquin)、氟吡呋喃酮(flupyradifurone)、三氟咪啶酰胺(fluazaindolizine)、氟螨啶(acynonapyr)、苯嘧虫烷(benzpyrimoxan)、氟虫啶胺(flupyrimin)、/>唑磺酰虫啶(oxazosulfyl)、氯吡唑虫胺(tyclopyrazoflor)、溴虫氟苯双酰胺(broflanilide)、异/>唑虫酰胺(isocycloseram)、嗪虫唑酰胺(dimpropyridaz)、氟戊螨硫醚(flupentiofenox)、唑虫烟酰胺(nicofluprole)、环丙氟虫胺(cyproflanilide)、二螺虫(spidoxamat)、三氟吡啶胺(cyclobutrifluram)、双噻唑(fenmezoditiaz)、三氟杀线酯(trifluenfuronate)那样的化合物等。
此外,本发明化合物也可以与下述化合物组合而施用。
苏云金芽孢杆菌鲇泽亚种(Bacillus thuringiensis aizawai)、苏云金芽孢杆菌库尔斯塔克亚种(Bacillus thuringiensis kurstaki)、苏云金芽孢杆菌以色列亚种(Bacillus thuringiensis israelensis)、苏云金芽孢杆菌日本亚种(Bacillusthuringiensis japonensis)、苏云金芽孢杆菌粉虫变种(Bacillus thuringiensistenebrionis)、苏云金芽孢杆菌(Bacillus thuringiensis)、淡紫拟青霉(Paecilomyceslilacinus)、甲基营养型芽孢杆菌(Bacillus methylotrophicus)、枯草芽孢杆菌(Bacillus subtilis)、解淀粉芽孢杆菌(Bacillus amyloliquefaciens)、地衣芽孢杆菌(Bacillus licheniformis)、坚强芽孢杆菌(Bacillus firmus)、巴斯德杆菌(Pasteurianishizawae)、疣孢漆斑菌(Myrothecium verrucaria)、伯克霍尔德菌(Burkholderiarinojensis)、或活性紫色细菌(Chromobacterium subtsugae)生成的晶体蛋白毒素、昆虫病原病毒剂、昆虫病原丝状菌剂、线虫病原丝状菌剂等那样的微生物农药;
阿维菌素(abamectin)、甲氨基阿维菌素苯甲酸盐(emamectin benzoate)、伊维菌素(ivermectin)、弥拜菌素(milbemectin)、米尔贝肟(milbemycin oxime)、雷皮菌素(lepimectin)、多杀霉素(spinosad)、乙基多杀菌素(spinetoram)那样的抗生素和半合成抗生素;
上述其它农业园艺用药剂中的、杀菌剂的有效成分化合物(通用名或日本植物防疫协会试验码)可以从例如下述化合物组中适当选择。即使在没有特别记载的情况下,在这些化合物中存在盐、烷基酯、光学异构体那样的各种结构异构体等的情况下,当然也包含它们。
嘧菌胺(mepanipyrim)、嘧霉胺(pyrimethanil)、嘧菌环胺(cyprodinil)那样的苯胺基嘧啶系化合物;
唑嘧菌胺(ametoctradin)那样的三唑并嘧啶系化合物;
氟啶胺(fluazinam)那样的氨基吡啶系化合物;
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)、环丙唑醇(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)、咪唑富马酸盐(oxpoconazole fumarate)、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)、硅氟唑(simeconazole)、稻瘟酯(pefurazoate)、种菌唑(ipconazole)、亚胺唑(imibenconazole)、氧环唑(azaconazole)、灭菌唑(triticonazole)、抑霉唑(imazalil)、异三氟菌唑(ipfentrifluconazole)、氯氟醚菌唑(mefentrifluconazole)那样的唑系化合物;
灭螨猛(quinomethionate)那样的喹喔啉系化合物;
代森锰(maneb)、代森锌(zineb)、代森锰锌(mancozeb)、代森福美锌(polycarbamate)、代森联(metiram)、丙森锌(propineb)、福美双(thiram)那样的二硫代氨基甲酸酯系化合物;
四氯苯酞(fthalide)、百菌清(chlorothalonil)、五氯硝基苯(quintozene)那样的有机氯系化合物;
苯菌灵(benomyl)、甲基硫菌灵(thiophanate-methyl)、多菌灵(carbendazim)、噻菌灵(thiabendazole)、麦穗宁(fuberiazole)那样的咪唑系化合物;
霜脲氰(cymoxanil)那样的氰基乙酰胺系化合物;
甲霜灵(metalaxyl)、精甲霜灵(metalaxyl-M;别名精甲霜灵(mefenoxam))、霜灵(oxadixyl)、呋酰胺(ofurace)、苯霜灵(benalaxyl)、精苯霜灵(benalaxyl-M,别名精苯霜灵(kiralaxyl、chiralaxyl))、呋霜灵(furalaxyl)、缬菌胺(valifenalate)那样的酰基氨基酸系化合物;
酯菌胺(cyprofuram)、萎锈灵(carboxin)、氧化萎锈灵(oxycarboxin)、噻氟菌胺(thifluzamide)、烟酰胺(boscalid)、环酰菌胺(fenhexamid)、异噻菌胺(isotianil)、噻酰菌胺(tiadinil)、联苯吡嗪菌胺(pyraziflumid)那样的酰苯胺系化合物;
苯氟磺胺(dichlofluanid)那样的磺酰胺系化合物;
氢氧化铜(cupric hydroxide)、有机铜(oxine copper)、无水硫酸铜、壬基苯酚磺酸铜、8-羟基喹啉铜、十二烷基苯磺酸双乙二胺铜配盐(II)(别名DBEDC)那样的铜系化合物;
三乙膦酸铝(fosetyl-Al)、甲基立枯磷(tolclofos-Methyl)、敌瘟磷(edifenphos)、异稻瘟净(iprobenfos)那样的有机磷系化合物;
克菌丹(captan)、敌菌丹(captafol)、灭菌丹(folpet)那样的邻苯二甲酰亚胺系化合物;
腐霉利(procymidone)、异菌脲(iprodione)、乙烯菌核利(vinclozolin)那样的二甲酰亚胺系化合物;
氟酰胺(flutolanil)、灭锈胺(mepronil)、麦锈灵(benodanil)那样的苯甲酰苯胺系化合物;
环丙酰菌胺(carpropamid)、双氯氰菌胺(diclocymet)、硅噻菌胺(silthiopham)、稻瘟酰胺(fenoxanil)那样的酰胺系化合物;
苯并烯氟菌唑(benzovindiflupyr)、联苯吡菌胺(bixafen)、氟茚唑菌胺(fluindapyr)、氟唑菌酰胺(fluxapyroxad)、呋吡菌胺(furametpyr)、吡唑萘菌胺(isopyrazam)、氟唑菌苯胺(penflufen)、吡噻菌胺(penthiopyrad)、氟唑菌酰羟胺(pydiflumetofen)、氟唑环菌胺(sedaxane)、异丙氟吡菌胺(isoflucypram)、茚吡菌胺(inpyrfluxam)、吡炔虫酰胺(pyrapropoyne)那样的吡唑甲酰胺系化合物;
氟吡菌胺(fluopicolide)、氟吡菌酰胺(fluopyram)、苯酰菌胺(zoxamide)、氟醚菌酰胺(fluopimomide)那样的苯甲酰胺系化合物;
甲呋酰胺(fenfuram)那样的呋喃苯胺系化合物;
异丙噻菌胺(isofetamid)那样的噻吩酰胺系化合物;
嗪氨灵(triforine)那样的哌嗪系化合物;
啶斑肟(pyrifenox)、啶菌唑(pyrisoxazole)、氨吡菌酯(aminopyrifen)那样的吡啶系化合物;
氯苯嘧啶醇(fenarimol)、嘧菌腙(ferimzone)、氟苯嘧啶醇(nuarimol)那样的嘧啶系化合物;
苯锈啶(fenpropidin)那样的哌啶系化合物;
丁苯吗啉(fenpropimorph)、十三吗啉(tridemorph)那样的吗啉系化合物;
三苯基氢氧化锡(fentin hydroxide)、三苯基乙酸锡(fentin acetate)那样的有机锡系化合物;
戊菌隆(pencycuron)那样的脲系化合物;
烯酰吗啉(dimethomorph)、氟吗啉(flumorph)、丁吡吗啉(pyrimorph)、缬霉威(iprovalicarb)、苯噻菌胺异丙酯(benthiavalicarb-isopropyl)、双炔酰菌胺(mandipropamid)那样的羧酸酰胺系化合物;
乙霉威(diethofencarb)那样的苯基氨基甲酸酯系化合物;
咯菌腈(fludioxonil)、拌种咯(fenpiclonil)那样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)、稻菌胺(oryzastrobin)、醚菌胺(dimoxystrobin)、吡唑醚菌酯(pyraclostrobin)、氟嘧菌酯(fluoxastrobin)、烯肟菌酯(enestroburin)、唑菌酯(pyraoxystrobin)、唑胺菌酯(pyrametostrobin)、丁香菌酯(coumoxystrobin)、烯肟菌酯(enoxastrobin)、烯肟菌胺(fenaminstrobin)、氟菌螨酯(flufenoxystrobin)、氯啶菌酯(triclopyricarb)、甲苯醚菌酯(mandestrobin)那样的嗜球果伞素系化合物;
唑菌酮(famoxadone)、氟噻唑吡乙酮(oxathiapiprolin)那样的/>唑系化合物;
噻唑菌胺(ethaboxam)那样的噻唑甲酰胺系化合物;
咪唑菌酮(fenamidone)那样的咪唑啉酮系化合物;
磺菌胺(flusulfamide)那样的苯磺酰胺系化合物;
环氟苄酰胺(cyflufenamid)那样的肟醚系化合物;
二氰蒽醌(dithianon)那样的蒽醌系化合物;
硝苯菌酯(meptyldinocap)那样的巴豆酸系化合物;
井冈霉素(validamycin)、春雷霉素(kasugamycin)、链霉素(streptomycin)、多抗霉素(polyoxins)那样的抗生素;
双胍辛胺(iminoctadine)、多果定(dodine)那样的胍系化合物;异丁乙氧喹啉(tebufloquin)、苯氧喹啉(quinoxyfen)、氟菌喹啉(quinofumelin)、异丙菌喹啉(ipflufenoquin)那样的喹啉系化合物;
氟噻唑菌腈(flutianil)那样的噻唑烷系化合物;
霜霉威盐酸盐(propamocarb hydrochloride)、吡菌苯威(pyribencarb)、三氟甲氧威(tolprocarb)那样的氨基甲酸酯系化合物;
四唑吡氨酯(picarbutrazox)、四唑菌酮(metyltetraprole)那样的四唑系化合物;
吲唑磺菌胺(amisulbrom)、氰霜唑(cyazofamiid)那样的磺酰胺系化合物;
苯菌酮(metrafenone)、苯啶菌酮(pyriofenone)那样的烯丙基苯基酮系化合物;
烯丙苯噻唑(probenazole)、二氯菌噻(dichlobentiazox)那样的苯并噻唑系化合物;
胺苯吡菌酮(fenpyrazamine)那样的苯基吡唑系化合物;
稻瘟灵(isoprothiolane)那样的二硫戊环系化合物;
吡啶菌胺(fenpicoxamid)、二氟吡啶菌胺(florylpicoxamid)那样的皮考啉酰胺系化合物;
硫(Sulfur)、石硫合剂那样的硫系化合物;
作为其它化合物的、咯喹酮(pyroquilon)、哒菌酮(diclomezine)、氯化苦(chloropicrin)、棉隆(dazomet)、威百亩(metam-sodium)、丙氧喹啉(proquinazid)、螺环菌胺(spiroxamine)、噻英菌酮(dipymetitrone)等;
解淀粉芽孢杆菌菌株QST713(Bacillus amyloliqefaciens strain QST713)、解淀粉芽孢杆菌菌株FZB24(Bacillus amyloliqefaciens strain FZB24)、解淀粉芽孢杆菌菌株MBI600(Bacillus amyloliqefaciens strain MBI600)、解淀粉芽孢杆菌菌株D747(Bacillus amyloliqefaciens strain D747)、荧光假单胞菌(Pseudomonasfluorescens)、枯草芽孢杆菌(Bacillus subtilis)、深绿木霉SKT-1(Trichodermaatroviride SKT-1)那样的微生物杀菌剂;以及
茶树油(Tea tree oil)那样的植物提取物。
本发明的期望的方案如下所述。然而,本发明不限定于它们。
〔1〕一种杀线虫组合物,其含有式(I)所示的化合物或其盐作为有效成分。
〔2〕一种线虫的防除方法,将含有有效量的式(I)所示的化合物或其盐的杀线虫组合物施用于土壤、线虫或植物体。
〔3〕根据上述〔1〕所述的杀线虫组合物,式(I)所示的化合物或其盐是,A为被1个~5个R1取代了的苯基,R1为卤素、烷基、卤代烷基、烯基、炔基、环烷基、烷氧基、或卤代烷氧基,在R1存在2个的情况下,2个R1可以一起形成可以被1个或2个Z1取代的环的化合物或其盐。
〔4〕根据上述〔2〕所述的线虫的防除方法,式(I)所示的化合物或其盐是,A为被1个~5个R1取代了的苯基,R1为卤素、烷基、卤代烷基、烯基、炔基、环烷基、烷氧基、或卤代烷氧基,在R1存在2个的情况下,2个R1可以一起形成可以被1个或2个Z1取代的环的化合物或其盐。
〔5〕式(I)所示的化合物或其盐。
〔6〕式(IA)所示的化合物或其盐。
〔7〕式(IB)所示的化合物或其盐。
〔8〕根据上述〔6〕所述的化合物或其盐,R1A为卤素、(C1-C6)-烷基、(C1-C6)-卤代烷基、(C2-C6)-烯基、(C2-C6)-炔基、(C3-C6)-环烷基、(C1-C6)-烷氧基、或(C1-C6)-卤代烷氧基。
〔9〕根据上述〔6〕所述的化合物或其盐,R1A为卤素、(C1-C6)-烷基、(C1-C6)-卤代烷基、(C1-C6)-烷氧基、(C1-C6)-卤代烷氧基。
〔10〕根据上述〔6〕所述的化合物或其盐,R1A为卤素、(C1-C6)-烷基、(C1-C6)-卤代烷基。
〔11〕根据上述〔6〕所述的化合物或其盐,2个R1A一起形成可以被1个或2个Z1A取代的环。
〔12〕根据上述〔6〕~〔11〕所述的化合物或其盐,R2A和R3A各自为(C1-C3)-烷基。
〔13〕根据上述〔6〕~〔11〕所述的化合物或其盐,R2A和R3A都为甲基。
〔14〕根据上述〔6〕~〔13〕所述的化合物或其盐,R4A为卤素、(C1-C6)-卤代烷基、(C1-C6)-烷基亚磺酰基、(C1-C6)-烷基磺酰基、硝基或氰基。
〔15〕根据上述〔6〕~〔13〕所述的化合物或其盐,R4A为氟、氯、溴、二氟甲基、三氟甲基、硝基或氰基。
〔16〕根据上述〔6〕~〔15〕所述的化合物或其盐,R6A为氢、(C1-C6)-烷基、(C2-C6)-烯基或(C2-C6)-炔基。
〔17〕根据上述〔6〕~〔15〕所述的化合物或其盐,R6A为氢。
〔18〕根据上述〔6〕或〔8〕~〔17〕所述的化合物或其盐,n为1或2。
〔19〕根据上述〔6〕或〔8〕~〔17〕所述的化合物或其盐,n为1,1个R1A在苯基的2位或3位取代。
〔20〕根据上述〔6〕或〔8〕~〔17〕所述的化合物或其盐,n为1,1个R1A在苯基的2位取代。
〔21〕根据上述〔6〕或〔8〕~〔17〕所述的化合物或其盐,n为1,1个R1A在苯基的3位取代。
〔22〕根据上述〔6〕或〔8〕~〔17〕所述的化合物或其盐,n为2,2个R1A在苯基的2位和3位取代。
〔23〕根据上述〔6〕或〔8〕~〔17〕所述的化合物或其盐,n为2,2个R1A在苯基的2位和6位取代。
〔24〕根据上述〔6〕或〔8〕~〔17〕所述的化合物或其盐,n为2,2个R1A在苯基的2位和5位取代。
〔25〕一种线虫的防除方法,将含有有效量的上述〔6〕~〔24〕所述的化合物或其盐的杀线虫组合物施用于土壤、线虫或植物体。
〔26〕一种农业园艺用杀线虫剂,其含有上述〔6〕~〔24〕所述的化合物或其盐作为有效成分。
本发明化合物优选为式(IA)化合物或式(IB)化合物,更优选为式(IA)化合物。
实施例
接下来记载本发明的实施例,但本发明不限定于它们。
合成例1:N’-(2-甲基-1-苯基-2-(3-三氟甲基-1H-吡唑-1-基)亚丙基)甲酰肼(No.A-1)的合成
(1)2-甲基-1-苯基-2-(3-三氟甲基-1H-吡唑-1-基)丙烷-1-酮的合成
在3-三氟甲基-1H-吡唑(1.80g)的乙腈(12ml)溶液中加入碳酸钾(0.92g),在室温下进行了搅拌。30分钟后,加入2-溴-2-甲基-1-苯基丙烷-1-酮(3.01g),在室温下搅拌而获得了混合物。10分钟后,将上述混合物升温到70℃使其反应20.5小时,获得了反应混合物。在上述反应混合物中加入水,使用乙酸乙酯进行了提取。然后,将所得的提取溶液在减压下浓缩了。将所得的残渣用柱色谱(洗脱液:乙酸乙酯/庚烷)进行精制,获得了目标物质(1.23g)。
1H NMR(CDCl3/300MHz):δ(ppm)=7.50-7.40(m,2H),7.35-7.23(m,4H),6.57(d,1H),1.93(s,6H).
(2)(2-甲基-1-苯基-2-(3-三氟甲基-1H-吡唑-1-基)亚丙基)酰肼的合成
在2-甲基-1-苯基-2-(3-三氟甲基-1H-吡唑-1-基)丙烷-1-酮(0.84g)的乙醇(2.51ml)溶液中,加入肼一水合物(0.38g),回流19.5小时,获得了反应混合物。在上述反应混合物中加入水,使用乙酸乙酯进行了提取。然后,将所得的提取溶液在减压下浓缩了。将所得的残渣用柱色谱(洗脱液:乙酸乙酯/庚烷)进行精制,获得了目标物质(0.37g)。
1H NMR(CDCl3/300MHz):δ(ppm)=7.45-7.42(m,1H),7.37-7.28(m,3H),6.70-6.62(m,2H),6.45(d,1H),5.10(s,2H),1.82(s,6H).
(3)(N’-(2-甲基-1-苯基-2-(3-三氟甲基-1H-吡唑-1-基)亚丙基)甲酰肼(No.A-1)的合成
在(2-甲基-1-苯基-2-(3-三氟甲基-1H-吡唑-1-基)亚丙基)酰肼(0.20g)的甲酸乙酯(2ml)溶液中,加入甲酸(0.04g)而回流2小时,获得了反应混合物。在上述反应混合物中加入了水后,使用饱和碳酸氢钠水而获得了碱性的反应溶液。使用乙酸乙酯将上述反应溶液进行了提取后,将所得的提取溶液在减压下浓缩了。将所得的残渣用柱色谱(洗脱液:乙酸乙酯/庚烷)进行精制,获得了目标物质(No.A-1,0.20g)。
1H NMR(CDCl3/300MHz):δ(ppm)=8.73(d,1H),8.03(d,1H),7.43-7.29(m,4H),6.67-6.61(m,2H),6.45(d,1H),1.89(s,6H).
合成例2:N’-(苯基(1-(3-三氟甲基-1H-吡唑-1-基)环丙基)亚甲基)甲酰肼的2种几何异构体(No.B-1、和No.B-2)的合成
(1)2-溴-4-氯-1-苯基丁烷-1-酮的合成
在4-氯-1-苯基丁烷-1-酮(0.61g)的四氢呋喃(6.07ml)溶液中,加入三甲基苯基三溴化铵(1.28g),在室温下使其反应15.5小时而获得了反应混合物。在上述反应混合物中加入水,使用乙酸乙酯进行了提取后,将所得的提取溶液在减压下浓缩了。将所得的残渣用柱色谱(洗脱液:乙酸乙酯/庚烷)进行精制,获得了目标物质(0.86g)。
1H NMR(CDCl3/300MHz):δ(ppm)=8.08-8.01(m,2H),7.66-7.59(m,1H),7.55-7.48(m,2H),5.49(dd,1H),3.90-3.72(m,2H),2.67-2.49(m,2H).
(2)苯基(1-(3-三氟甲基-1H-吡唑-1-基)环丙基)甲酮的合成
在3-三氟甲基-1H-吡唑(0.50g)的乙腈(2.58ml)溶液中,加入碳酸钾(0.51g),在室温下进行了搅拌。50分钟后,加入2-溴-4-氯-1-苯基丁烷-1-酮(0.86g),升温到90℃而反应6小时,获得了反应混合物。在上述反应混合物中加入水,使用乙酸乙酯进行了提取后,将所得的提取溶液在减压下浓缩了。将所得的残渣用柱色谱(洗脱液:乙酸乙酯/庚烷)进行精制,获得了目标物质(0.86g)。
1H NMR(CDCl3/300MHz):δ(ppm)=7.48-7.39(m,4H),7.32-7.24(m,2H),6.43(d,1H),2.08-2.01(m,2H),1.89-1.83(m,2H).
(3)(苯基(1-(3-三氟甲基-1H-吡唑-1-基)环丙基)亚甲基)酰肼的2种几何异构体的合成
在苯基(1-(3-三氟甲基-1H-吡唑-1-基)环丙基)甲酮(1.07g)的乙醇(4.29ml)溶液中,加入肼一水合物(0.51g),回流25.5小时,获得了反应混合物。在上述反应混合物中加入水,使用乙酸乙酯进行了提取后,将所得的提取溶液在减压下浓缩了。将所得的残渣用柱色谱(洗脱液:乙酸乙酯/庚烷)进行精制,获得了主生成物(0.41g)及其几何异构体(0.23g)。
主生成物
1H NMR(CDCl3/300MHz):δ(ppm)=7.41-7.29(m,4H),7.11-7.03(m,2H),6.33(d,1H),5.15(s,2H),1.65-1.58(m,2H),1.56-1.49(m,2H).
主生成物的几何异构体
1H NMR(CDCl3/300MHz):δ(ppm)=7.80-7.74(m,2H),7.72-7.68(m,1H),7.40-7.27(m,3H),6.64(s,2H).6.50(d,1H),1.92-1.86(m,2H),1.41-1.35(m,2H).
(4)N’-(苯基(1-(3-三氟甲基-1H-吡唑-1-基)环丙基)亚甲基)甲酰肼的2种几何异构体(No.B-1、No.B-2)的合成
在(苯基(1-(3-三氟甲基-1H-吡唑-1-基)环丙基)亚甲基)酰肼(0.20g)的甲酸乙酯(2.01ml)溶液中,加入甲酸(0.05g),回流2.5小时,获得了反应混合物。在上述反应混合物中加入了水后,使用饱和碳酸氢钠水而获得了碱性的反应溶液。使用乙酸乙酯而将上述反应溶液进行了提取后,将所得的提取溶液在减压下浓缩了。将所得的残渣用柱色谱(洗脱液:乙酸乙酯/庚烷)进行精制,获得了主生成物(No.B-1,0.18g)及其几何异构体(No.B-2,0.02g)。
主生成物
1H NMR(CDCl3/300MHz):δ(ppm)=8.61(d,1H),8.17(d,1H),7.43-7.37(m,3H),7.37-7.34(m,1H),7.06-6.99(m,2H),6.33(d,1H),1.80-1.61(m,4H).
主生成物的几何异构体
1H NMR(CDCl3/300MHz):δ(ppm)=10.67(d,1H),8.84(d,1H),7.93-7.86(m,2H),7.74-7.70(m,1H),7.46-7.38(m,3H),6.55(d,1H),1.96-1.89(m,2H),1.45-1.38(m,2H).
合成例3:N’-(2-甲基-1-(3-甲基苯基)-2-(3-三氟甲基-1H-三唑-1-基)亚丙基)甲酰肼(No.A-323)的合成
(1)(2-甲基-1-(3-甲基苯基)-亚丙基)腙的合成
将使用2-甲基-1-(3-甲基苯基)-丙烷-1-酮(0.35g)、乙醇(1.05mL)和肼一水合物(0.27g)而调制出的混合物进行了脱气后,回流13.5小时,获得了反应混合物。将上述反应混合物用乙酸乙酯和庚烷进行稀释,通于包含硅藻土和硅胶的衬垫进行过滤,获得了滤液。将上述滤液在减压下浓缩,将所得的残渣用柱色谱(洗脱液:乙酸乙酯/庚烷)进行精制,获得了目标物质(0.35g)。
1H NMR(CDCl3/500MHz):δ(ppm)=7.34(t,1H),7.18(d,1H),6.98(s,1H),6.97(d,1H),4.93(brs,2H),2.71(m,1H),2.38(s,3H),1.09(d,6H).
(2)N’-(2-甲基-1-(3-甲基苯基)-亚丙基)甲酰肼的合成
在将使用(2-甲基-1-(3-甲基苯基)-亚丙基)腙(0.35g)、甲酸乙酯(1.4mL)和甲酸(0.12g)而调制出的混合物进行了氮气置换后,回流5小时而获得了反应溶液。将上述反应溶液在减压下浓缩,用柱色谱(洗脱液:乙酸乙酯/庚烷)进行精制,获得了目标物质(0.29g)。
1H NMR(CDCl3/500MHz):δ(ppm)=8.70(d,1H),8.22(d,1H),7.36(t,1H),7.24(d,1H),6.90(s,1H),6.90(d,1H),2.78(m,1H),2.39(s,3H),1.13(d,6H).
(3)N’-(2-氯-2-甲基-1-(3-甲基苯基)-亚丙基)甲酰肼的合成
将使用N’-(2-甲基-1-(3-甲基苯基)-亚丙基)甲酰肼(0.26g)、甲苯(2.5mL)、硫酰氯(0.2g)而调制出的混合物在室温下搅拌4小时,获得了反应混合物。一边将所得的反应混合物用冰冷却,一边依次加入冰水、饱和碳酸氢钠水溶液进行搅拌,用乙酸乙酯提取了3次。将通过提取而获得了的有机层通于硅藻土衬垫而过滤,获得了滤液。将上述滤液在减压下浓缩,将所得的残渣用柱色谱(洗脱液:乙酸乙酯/庚烷)进行精制,获得了目标物质(0.24g)。
1H NMR(CDCl3/500MHz):δ(ppm)=8.70(d,1H),8.05(d,1H),7.39(t,1H),7.29(d,1H),7.03(s,1H),7.03(d,1H),2.41(s,3H),1.82(s,6H).
(4)N’-(2-甲基-1-(3-甲基苯基)-2-(3-三氟甲基-1H-三唑-1-基)亚丙基)甲酰肼(No.A-323)的合成
将使用3-三氟甲基-1H-三唑(0.05g)、DMF(0.3mL)和碳酸钾(0.05g)而调制出的混合物进行了氮气置换后,在室温下搅拌了一晚。在被搅拌了的混合物中一点点地滴加N-(2-氯-2-甲基-1-(3-甲基苯基)-亚丙基)甲酰肼(0.07g)的DMF(0.3mL)溶液,在室温下搅拌1小时,获得了反应混合物。将所得的反应混合物用水进行了稀释后,用乙酸乙酯/庚烷提取了3次。将提取而获得了的有机层通于硅藻土衬垫而过滤,获得了滤液。将上述滤液在减压下浓缩,将所得的残渣用柱色谱(洗脱液:乙酸乙酯/庚烷)进行精制,获得了目标物质(No.A-323,0.09g)。
1H NMR(CDCl3/500MHz):δ(ppm)=8.68(d,1H),8.04(d,1H),8.03(s,1H),7.28(t,1H),7.22(d,1H),6.55(d,1H),6.49(s,1H),2.28(s,3H),1.94(s,6H).
接下来,将本发明的化合物(I)的代表例在第1表和第2表中具体地举出。这些化合物可以基于上述制造方法和上述合成例、以及在本技术领域中公知的方法来合成。
在各表中,No.表示化合物No.。在第1表和第2表中的物性栏中记载为NMR的化合物在第3表和第4表中显示1H-NMR光谱数据。进一步,在第1表和第2表所记载的化合物为本发明的化合物(I)的盐的情况下,在第1表和第2表中的物性栏中也显示该盐的种类。
第1表和第2表中的各A、R2、R3、R4、R6、和X栏中使用了的缩略语如下所述。Me表示甲基,Et表示乙基,nPr表示正丙基,iPr表示异丙基,cPr表示环丙基,tBu表示叔丁基,cBu表示环丁基,nHexyl表示正己基,cHexyl表示环己基,Ph表示苯基,Na盐表示钠盐,K盐表示钾盐,di表示2个,bis表示2个,tri表示3个。
在第1表和第2表中显示R5为CHO的本发明的化合物(I)。此外,在第1表和第2表中的A和R4栏中显示的各取代基的位置表示如下所述的取代基的位置。“*”表示键合位置。
例如,在A栏中被记载为“4-Cl-Ph”的化合物表示在向上述化学结构式的A(苯基)赋予了的取代基位置被1个R1基取代了,即,仅苯基的4位被氯基取代了的化合物。
此外,在R4栏中被记载为“3-CF3”、在m栏中被记载为“1”的化合物表示在向上述化学结构式的杂5元环赋予了的取代基位置被1个R4基取代了,即,仅杂5元环的3位被三氟甲基取代了的化合物。在R4栏中被记载为“3-CF3-5-Me”、在m栏中被记载为“2”的化合物表示在向上述化学结构式的杂5元环赋予了的取代基位置被2个R4基取代了,即,杂5元环的3位被三氟甲基、杂5元环的5位被甲基取代了的化合物。在R4栏中被记载为“-”、在m栏中被记载为“0”的化合物表示在上述化学结构式的杂5元环的3位和5位R4基未进行取代。
此外,第1表和第2表所记载的化合物No.A-188、A-189、B-186和B-187为A-1、A-2、B-1和B-3的钠盐,以及化合物No.A-190、A-191、B-188和B-189为A-1、A-2、B-1和B-3的钾盐。
第3表和第4表中的1H-NMR的数据的s表示单峰(singlet),brs表示宽单峰,d表示二重峰(doublet),t表示三重峰(triplet),q表示四重峰(quartet),dd表示双二重峰,dt表示双三重峰,ddd表示双双二重峰,m表示多重峰(multiplet)。
[表1]
第1表
R5=CHO
No. | A | R2 | R3 | R4 | R6 | X | m | 物性 |
A-1 | Ph | Me | Me | 3-CF3 | H | CH | 1 | NMR |
A-2 | Ph | Me | Me | 3-CF3 | H | N | 1 | NMR |
A-3 | Ph | Me | Me | 3-CF3 | Me | CH | 1 | |
A-4 | Ph | Me | Me | 3-CF3 | Me | N | 1 | |
A-5 | Ph | Me | Me | 3-CF3 | Et | CH | 1 | |
A-6 | Ph | Me | Me | 3-CF3 | Et | N | 1 | |
A-7 | Ph | Me | Me | 3-CF3 | nPr | CH | 1 | |
A-8 | Ph | Me | Me | 3-CF3 | nPr | N | 1 | |
A-9 | Ph | Me | Me | 3-CF3 | nHexyl | CH | 1 | |
A-10 | Ph | Me | Me | 3-CF3 | nHexyl | N | 1 | |
A-11 | Ph | Me | Me | 3-CF3 | iPr | CH | 1 | |
A-12 | Ph | Me | Me | 3-CF3 | iPr | N | 1 | |
A-13 | Ph | Me | Me | 3-CF3 | CH2CH=CH2 | CH | 1 | |
A-14 | Ph | Me | Me | 3-CF3 | CH2CH=CH2 | N | 1 | |
A-15 | Ph | Me | Me | 3-CF3 | CH2CH=C(Me)2 | CH | 1 | |
A-16 | Ph | Me | Me | 3-CF3 | CH2CH=C(Me)2 | N | 1 | |
A-17 | Ph | Me | Me | 3-CF3 | CH2C≡CH | CH | 1 | |
A-18 | Ph | Me | Me | 3-CF3 | CH2C≡CH | N | 1 | |
A-19 | Ph | Me | Me | 3-CF3 | CH2C≡CMe | CH | 1 | |
A-20 | Ph | Me | Me | 3-CF3 | CH2C≡CMe | N | 1 | |
A-21 | Ph | Me | Me | 3-CF3 | CH2OMe | CH | 1 | |
A-22 | Ph | Me | Me | 3-CF3 | CH2OMe | N | 1 | |
A-23 | Ph | Me | Me | 3-CF3 | CH2OEt | CH | 1 | |
A-24 | Ph | Me | Me | 3-CF3 | CH2OEt | N | 1 | |
A-25 | Ph | Me | Me | 3-CF3 | C2H4OMe | CH | 1 | |
A-26 | Ph | Me | Me | 3-CF3 | C2H4OMe | N | 1 |
[表2]
第1表(续)
No. | A | R2 | R3 | R4 | R6 | X | m | 物性 |
A-27 | Ph | Me | Me | 3-CF3 | SO2CF3 | CH | 1 | |
A-28 | Ph | Me | Me | 3-CF3 | SO2CF3 | N | 1 | |
A-29 | Ph | Me | Me | 3-CHF2 | H | CH | 1 | |
A-30 | Ph | Me | Me | 3-CF3CF3 | H | CH | 1 | |
A-31 | Ph | Me | Me | 3-OMe | H | CH | 1 | |
A-32 | Ph | Me | Me | 3-OMe | H | N | 1 | |
A-33 | Ph | Me | Me | 3-O(iPr) | H | CH | 1 | |
A-34 | Ph | Me | Me | 3-O(nHexyl) | H | CH | 1 | |
A-35 | Ph | Me | Me | 3-OCHF2 | H | CH | 1 | |
A-36 | Ph | Me | Me | 3-OCF3 | H | CH | 1 | |
A-37 | Ph | Me | Me | 3-OCF2CF3 | H | CH | 1 | |
A-38 | Ph | Me | Me | 3-OCH(CF3)2 | H | CH | 1 | |
A-39 | Ph | Me | Me | 3-OCH2CF3 | H | CH | 1 | |
A-40 | Ph | Me | Me | 3-F | H | CH | 1 | |
A-41 | Ph | Me | Me | 3-Cl | H | CH | 1 | |
A-42 | Ph | Me | Me | 3-Cl | H | N | 1 | |
A-43 | Ph | Me | Me | 3-Br | H | CH | 1 | |
A-44 | Ph | Me | Me | 3-Br | H | N | 1 | |
A-45 | Ph | Me | Me | 3-I | H | CH | 1 | |
A-46 | Ph | Me | Me | 3-NO2 | H | CH | 1 | |
A-47 | Ph | Me | Me | 3-NO2 | H | N | 1 | |
A-48 | Ph | Me | Me | 3-CN | H | CH | 1 | |
A-49 | Ph | Me | Me | 3-CN | H | N | 1 | |
A-50 | Ph | Me | Me | 3-SMe | H | CH | 1 | |
A-51 | Ph | Me | Me | 3-SMe | H | N | 1 | |
A-52 | Ph | Me | Me | 3-S(iPr) | H | N | 1 | |
A-53 | Ph | Me | Me | 3-S(nHexyl) | H | N | 1 | |
A-54 | Ph | Me | Me | 3-SOMe | H | CH | 1 | |
A-55 | Ph | Me | Me | 3-SOMe | H | N | 1 | |
A-56 | Ph | Me | Me | 3-SO2Me | H | CH | 1 | |
A-57 | Ph | Me | Me | 3-SO2Me | H | N | 1 |
[表3]
第1表(续)
No. | A | R2 | R3 | R4 | R6 | X | m | 物性 |
A-58 | Ph | Me | Me | 3-CF3 | H | CCl | 1 | |
A-59 | Ph | Me | Me | 3-CF3 | H | CBr | 1 | |
A-60 | Ph | Me | Me | 3-CF3 | H | CMe | 1 | |
A-61 | Ph | Me | Me | 3-CF3 | H | C-C≡CH | 1 | |
A-62 | Ph | Me | Me | 3-CF3 | H | C-cPr | 1 | |
A-63 | Ph | Me | Me | 3-CF3-5-Me | H | CH | 2 | |
A-64 | Ph | Me | Me | 3-Cl | H | CNO2 | 1 | |
A-65 | Ph | Me | Me | 3-Cl | H | CCl | 1 | |
A-66 | Ph | Me | Me | 3-Cl | H | CBr | 1 | |
A-67 | Ph | Me | Me | 3-Cl | H | CMe | 1 | |
A-68 | Ph | Me | Me | 3-Cl | H | CEt | 1 | |
A-69 | Ph | Me | Me | 3-Cl | H | C-iPr | 1 | |
A-70 | Ph | Me | Me | 3-Cl | H | C-nHexyl | 1 | |
A-71 | Ph | Me | Me | 3-Cl | H | C-CH=CH2 | 1 | |
A-72 | Ph | Me | Me | 3-Cl | H | C-C(Me)=CH2 | 1 | |
A-73 | Ph | Me | Me | 3-Cl | H | C-C≡CH | 1 | |
A-74 | Ph | Me | Me | 3-Cl | H | C-cPr | 1 | |
A-75 | Ph | Me | Me | 3-Cl | H | CCF3 | 1 | |
A-76 | Ph | Me | Me | - | H | CCF3 | 0 | |
A-77 | Ph | Me | Me | - | H | CCl | 0 | |
A-78 | Ph | Me | Me | - | H | CF | 0 | |
A-79 | Ph | Me | Et | 3-CF3 | H | CH | 1 | |
A-80 | Ph | Me | Et | 3-CF3 | H | N | 1 | |
A-81 | Ph | Et | Et | 3-CF3 | H | CH | 1 | |
A-82 | Ph | Et | Et | 3-CF3 | H | N | 1 | |
A-83 | Ph | Me | nPr | 3-CF3 | H | CH | 1 | |
A-84 | Ph | Me | nPr | 3-CF3 | H | N | 1 | |
A-85 | Ph | Me | iPr | 3-CF3 | H | CH | 1 | |
A-86 | Ph | Me | iPr | 3-CF3 | H | N | 1 | |
A-87 | Ph | Me | nHexyl | 3-CF3 | H | CH | 1 | |
A-88 | Ph | Me | nHexyl | 3-CF3 | H | N | 1 |
[表4]
第1表(续)
No. | A | R2 | R3 | R4 | R6 | X | m | 物性 |
A-89 | 4-Cl-Ph | Me | Me | 3-CF3 | H | CH | 1 | NMR |
A-90 | 4-Cl-Ph | Me | Me | 3-CF3 | H | N | 1 | NMR |
A-91 | 4-Cl-Ph | Me | Me | 3-CF3 | Me | CH | 1 | NMR |
A-92 | 4-Cl-Ph | Me | Me | 3-CF3 | Et | CH | 1 | NMR |
A-93 | 4-Cl-Ph | Me | Me | 3-CF3 | CH2OMe | CH | 1 | |
A-94 | 4-Cl-Ph | Me | Me | 3-CF3 | Me | N | 1 | NMR |
A-95 | 4-Cl-Ph | Me | Me | 3-CF3 | Et | N | 1 | NMR |
A-96 | 4-Cl-Ph | Me | Me | 3-CF3 | nPr | N | 1 | NMR |
A-97 | 4-Cl-Ph | Me | Me | 3-CF3 | nHexyl | N | 1 | |
A-98 | 4-Cl-Ph | Me | Me | 3-CF3 | iPr | N | 1 | |
A-99 | 4-Cl-Ph | Me | Me | 3-CF3 | CH2OMe | N | 1 | |
A-100 | 4-Cl-Ph | Me | Me | 3-CF3 | CH2OEt | N | 1 | |
A-101 | 4-Cl-Ph | Me | Me | 3-CF3 | C2H4OMe | N | 1 | NMR |
A-102 | 4-Cl-Ph | Me | Me | 3-CF3 | SO2CF3 | N | 1 | |
A-103 | 4-Cl-Ph | Me | Me | 3-OMe | H | CH | 1 | NMR |
A-104 | 4-Cl-Ph | Me | Me | 3-OMe | H | N | 1 | |
A-105 | 4-Cl-Ph | Me | Me | 3-Cl | H | CH | 1 | |
A-106 | 4-Cl-Ph | Me | Me | 3-Cl | H | N | 1 | |
A-107 | 4-F-Ph | Me | Me | 3-CF3 | H | CH | 1 | NMR |
A-108 | 4-F-Ph | Me | Me | 3-CF3 | H | N | 1 | |
A-109 | 4-F-Ph | Me | Me | 3-CF3 | CH2OMe | CH | 1 | NMR |
A-110 | 4-F-Ph | Me | Me | 3-CF3 | CH2OMe | N | 1 | |
A-111 | 4-F-Ph | Me | Me | 3-CF3 | CH2Ph | CH | 1 | |
A-112 | 4-F-Ph | Me | Me | 3-CF3 | CH2Ph | N | 1 | |
A-113 | 4-F-Ph | Me | Me | 3-CF3 | CH2-(4-OMe-Ph) | CH | 1 | |
A-114 | 4-F-Ph | Me | Me | 3-CF3 | CH2-(4-OMe-Ph) | N | 1 | |
A-115 | 4-F-Ph | Me | Me | 3-CF3 | CO2tBu | CH | 1 | |
A-116 | 4-F-Ph | Me | Me | 3-CF3 | CO2tBu | N | 1 | |
A-117 | 4-F-Ph | Me | Me | 3-CF3 | CO2CH2Ph | CH | 1 | |
A-118 | 4-F-Ph | Me | Me | 3-CF3 | CO2CH2Ph | N | 1 |
[表5]
第1表(续)
No. | A | R2 | R3 | R4 | R6 | X | m | 物性 |
A-119 | 4-F-Ph | Me | Me | 3-OMe | H | CH | 1 | |
A-120 | 4-F-Ph | Me | Me | 3-OMe | H | N | 1 | |
A-121 | 4-F-Ph | Me | Me | 3-Cl | H | CH | 1 | |
A-122 | 4-F-Ph | Me | Me | 3-Cl | H | N | 1 | |
A-123 | 4-F-Ph | Me | Me | 3-CF3 | H | CCl | 1 | |
A-124 | 4-F-Ph | Me | Me | 3-Cl | H | CBr | 1 | |
A-125 | 4-F-Ph | Me | Me | - | H | CF | 0 | |
A-126 | 4-Br-Ph | Me | Me | 3-CF3 | H | CH | 1 | |
A-127 | 4-Br-Ph | Me | Me | 3-CF3 | H | N | 1 | |
A-128 | 4-Br-Ph | Me | Me | 3-CF3 | CH2OMe | CH | 1 | |
A-129 | 4-Br-Ph | Me | Me | 3-CF3 | CH2OMe | N | 1 | |
A-130 | 4-I-Ph | Me | Me | 3-CF3 | H | CH | 1 | |
A-131 | 4-I-Ph | Me | Me | 3-CF3 | H | N | 1 | |
A-132 | 4-CF3-Ph | Me | Me | 3-CF3 | H | CH | 1 | |
A-133 | 4-CF3-Ph | Me | Me | 3-CF3 | H | N | 1 | |
A-134 | 4-OMe-Ph | Me | Me | 3-CF3 | H | CH | 1 | |
A-135 | 4-OMe-Ph | Me | Me | 3-CF3 | H | N | 1 | |
A-136 | 4-O(iPr)-Ph | Me | Me | 3-CF3 | H | CH | 1 | |
A-137 | 4-O(iPr)-Ph | Me | Me | 3-CF3 | H | N | 1 | |
A-138 | 4-O(nHexyl)Ph | Me | Me | 3-CF3 | H | CH | 1 | |
A-139 | 4-O(nHexyl)-Ph | Me | Me | 3-CF3 | H | N | 1 | |
A-140 | 4-OCHF2-Ph | Me | Me | 3-CF3 | H | CH | 1 | |
A-141 | 4-OCHF2-Ph | Me | Me | 3-CF3 | H | N | 1 | |
A-142 | 4-OCF3-Ph | Me | Me | 3-CF3 | H | CH | 1 | |
A-143 | 4-OCF3-Ph | Me | Me | 3-CF3 | H | N | 1 | |
A-144 | 4-OCF2CF3-Ph | Me | Me | 3-CF3 | H | CH | 1 | |
A-145 | 4-OCF2CF3-Ph | Me | Me | 3-CF3 | H | N | 1 | |
A-146 | 4-OCH(CF3)2-Ph | Me | Me | 3-CF3 | H | CH | 1 | |
A-147 | 4-OCH(CF3)2-Ph | Me | Me | 3-CF3 | H | N | 1 |
[表6]
第1表(续)
No. | A | R2 | R3 | R4 | R6 | X | m | 物性 |
A-148 | 4-OCH2CF3-Ph | Me | Me | 3-CF3 | H | CH | 1 | |
A-149 | 4-OCH2CF3-Ph | Me | Me | 3-CF3 | H | N | 1 | |
A-150 | 2-Cl-Ph | Me | Me | 3-CF3 | H | CH | 1 | NMR |
A-151 | 2-Cl-Ph | Me | Me | 3-CF3 | H | N | 1 | NMR |
A-152 | 2-F-Ph | Me | Me | 3-CF3 | H | CH | 1 | NMR |
A-153 | 2-F-Ph | Me | Me | 3-CF3 | H | N | 1 | NMR |
A-154 | 2,4-diCl-Ph | Me | Me | 3-CF3 | H | CH | 1 | NMR |
A-155 | 2,4-diCl-Ph | Me | Me | 3-CF3 | H | N | 1 | |
A-156 | 2,4-diF-Ph | Me | Me | 3-CF3 | H | CH | 1 | NMR |
A-157 | 2,4-diF-Ph | Me | Me | 3-CF3 | H | N | 1 | NMR |
A-158 | 3,5-diF-Ph | Me | Me | 3-CF3 | H | CH | 1 | |
A-159 | 3,5-diF-Ph | Me | Me | 3-CF3 | H | N | 1 | |
A-160 | 2,6-diF-Ph | Me | Me | 3-CF3 | H | CH | 1 | NMR |
A-161 | 2,6-diF-Ph | Me | Me | 3-CF3 | H | N | 1 | NMR |
A-162 | 3,4,5-triF-Ph | Me | Me | 3-CF3 | H | CH | 1 | |
A-163 | 3,4,5-triF-Ph | Me | Me | 3-CF3 | H | N | 1 | |
A-164 | 4-Et-Ph | Me | Me | 3-CF3 | H | CH | 1 | |
A-165 | 4-Et-Ph | Me | Me | 3-CF3 | H | N | 1 | |
A-166 | 4-iPr-Ph | Me | Me | 3-CF3 | H | CH | 1 | |
A-167 | 4-iPr-Ph | Me | Me | 3-CF3 | H | N | 1 | |
A-168 | 4-CH2CH(Me)2-Ph | Me | Me | 3-CF3 | H | CH | 1 | |
A-169 | 4-CH2CH(Me)2-Ph | Me | Me | 3-CF3 | H | N | 1 | |
A-170 | 4-nHexyl-Ph | Me | Me | 3-CF3 | H | CH | 1 | |
A-171 | 4-nHexyl-Ph | Me | Me | 3-CF3 | H | N | 1 | |
A-172 | 4-CH=CH2-Ph | Me | Me | 3-CF3 | H | CH | 1 | |
A-173 | 4-CH=CH2-Ph | Me | Me | 3-CF3 | H | N | 1 | |
A-174 | 4-C(Me)=CH2-Ph | Me | Me | 3-CF3 | H | CH | 1 | |
A-175 | 4-C(Me)=CH2-Ph | Me | Me | 3-CF3 | H | N | 1 | |
A-176 | 4-CH=C(Me)2-Ph | Me | Me | 3-CF3 | H | CH | 1 | |
A-177 | 4-CH=C(Me)2-Ph | Me | Me | 3-CF3 | H | N | 1 | |
A-178 | 4-C≡CH-Ph | Me | Me | 3-CF3 | H | CH | 1 | |
A-179 | 4-C≡CH-Ph | Me | Me | 3-CF3 | H | N | 1 | |
A-180 | 4-cPr-Ph | Me | Me | 3-CF3 | H | CH | 1 | |
A-181 | 4-cPr-Ph | Me | Me | 3-CF3 | H | N | 1 | |
A-182 | 2-Me-4-Cl-Ph | Me | Me | 3-CF3 | H | CH | 1 | NMR |
A-183 | 2-Me-4-Cl-Ph | Me | Me | 3-CF3 | H | N | 1 |
[表7]
第1表(续)
[表8]
第1表(续)
No. | A | R2 | R3 | R4 | R6 | X | m | 物性 |
A-214 | 2-Cl-Ph | Me | Me | 3-OMe | H | CH | 1 | NMR |
A-215 | 2-Cl-Ph | Me | Me | 3-S(nPr) | H | CH | 1 | NMR |
A-216 | 2-Cl-Ph | Me | Me | - | H | CCF3 | 0 | NMR |
A-217 | 2-Cl-Ph | Me | Me | - | H | CF | 0 | NMR |
A-218 | 2-Cl-Ph | Me | Me | - | H | CCl | 0 | |
A-219 | 2-Cl-Ph | Me | Me | - | H | CNO2 | 0 | |
A-220 | 2-Cl-Ph | Me | Me | 3-CF3 | H | CCN | 1 | |
A-221 | 2-Cl-Ph | Me | Me | 3-CF3-5-Me | H | CH | 2 | NMR |
A-222 | 2-Cl-Ph | Me | Me | 3-CF3-5-CF3 | H | CH | 2 | NMR |
A-223 | 2-Cl-Ph | Me | Me | 3-Br-5-Br | H | CBr | 2 | NMR |
A-224 | 2-Cl-Ph | Me | Me | 3-Br-5-Br | H | N | 2 | NMR |
A-225 | 2-Cl-Ph | Et | Et | 3-CF3 | H | CH | 1 | NMR |
A-226 | 2-Cl-Ph | Et | Et | 3-CF3 | H | N | 1 | NMR |
A-227 | 2-Cl-Ph | Et | Et | 3-Cl | H | CH | 1 | |
A-228 | 2-Cl-Ph | Et | Et | 3-Cl | H | N | 1 | |
A-229 | 2-Cl-Ph | Et | Et | 3-Br | H | CH | 1 | |
A-230 | 2-Cl-Ph | Et | Et | 3-Br | H | N | 1 | |
A-231 | 2-Cl-Ph | nPr | nPr | 3-CF3 | H | CH | 1 | |
A-232 | 2-Cl-Ph | nPr | nPr | 3-CF3 | H | N | 1 | |
A-233 | 2-Br-Ph | Me | Me | 3-CF3 | H | CH | 1 | NMR |
A-234 | 2-Br-Ph | Me | Me | 3-CF3 | H | N | 1 | NMR |
A-235 | 2-Br-Ph | Me | Me | 3-CF3 | CH2OMe | CH | 1 | NMR |
A-236 | 2-Br-Ph | Me | Me | 3-Cl | H | CH | 1 | |
A-237 | 2-Br-Ph | Me | Me | 3-Cl | H | N | 1 | |
A-238 | 2-Br-Ph | Me | Me | 3-Br | H | CH | 1 | |
A-239 | 2-Br-Ph | Me | Me | 3-Br | H | N | 1 | |
A-240 | 2-I-Ph | Me | Me | 3-CF3 | H | CH | 1 | NMR |
A-241 | 2-I-Ph | Me | Me | 3-CF3 | H | N | 1 | NMR |
A-242 | 2-I-Ph | Me | Me | 3-CF3 | CH2OMe | CH | 1 | |
A-243 | 2-I-Ph | Me | Me | 3-CF3 | CO2tBu | CH | 1 | NMR |
[表9]
第1表(续)
No. | A | R2 | R3 | R4 | R6 | X | m | 物性 |
A-244 | 2-Me-Ph | Me | Me | 3-CF3 | H | CH | 1 | NMR |
A-245 | 2-Me-Ph | Me | Me | 3-CF3 | H | N | 1 | NMR |
A-246 | 2-Me-Ph | Me | Me | 3-CHF2 | H | N | 1 | |
A-247 | 2-Me-Ph | Me | Me | 3-Cl | H | CH | 1 | NMR |
A-248 | 2-Me-Ph | Me | Me | 3-Cl | H | N | 1 | NMR |
A-249 | 2-Me-Ph | Me | Me | 3-Br | H | CH | 1 | NMR |
A-250 | 2-Me-Ph | Me | Me | 3-Br | H | N | 1 | |
A-251 | 2-Me-Ph | Me | Me | 3-NO2 | H | CH | 1 | NMR |
A-252 | 2-Me-Ph | Me | Me | 3-NO2 | H | N | 1 | NMR |
A-253 | 2-Me-Ph | Me | Me | 3-CN | H | CH | 1 | NMR |
A-254 | 2-Me-Ph | Me | Me | 3-CN | H | N | 1 | |
A-255 | 2-Me-Ph | Me | Me | - | H | CF | 0 | NMR |
A-256 | 2-Me-Ph | Me | Me | - | H | CNO2 | 0 | NMR |
A-257 | 2-Me-Ph | Me | Me | 3-CF3 | H | CCN | 1 | NMR |
A-258 | 2-Me-Ph | Me | Me | 3-Br-5-Br | H | CBr | 2 | |
A-259 | 2-Me-Ph | Me | Me | 3-Br-5-Br | H | N | 2 | |
A-260 | 2-CF3-Ph | Me | Me | 3-CF3 | H | CH | 1 | NMR |
A-261 | 2-CF3-Ph | Me | Me | 3-CF3 | H | N | 1 | NMR |
A-262 | 2-CHF2-Ph | Me | Me | 3-CF3 | H | CH | 1 | |
A-263 | 2-CHF2-Ph | Me | Me | 3-CF3 | H | N | 1 | |
A-264 | 2-OMe-Ph | Me | Me | 3-CF3 | H | CH | 1 | NMR |
A-265 | 2-OMe-Ph | Me | Me | 3-CF3 | H | N | 1 | NMR |
A-266 | 2-OMe-Ph | Me | Me | 3-Cl | H | CH | 1 | |
A-267 | 2-OMe-Ph | Me | Me | 3-Cl | H | N | 1 | |
A-268 | 2-OMe-Ph | Me | Me | 3-Br | H | CH | 1 | |
A-269 | 2-OMe-Ph | Me | Me | 3-Br | H | N | 1 | |
A-270 | 2-OCF3-Ph | Me | Me | 3-CF3 | H | CH | 1 | NMR |
A-271 | 2-OCF3-Ph | Me | Me | 3-CF3 | H | N | 1 | NMR |
A-272 | 2-OCF3-Ph | Me | Me | 3-Br | H | CH | 1 | NMR |
A-273 | 2-OCF3-Ph | Me | Me | 3-CN | H | N | 1 | NMR |
[表10]
第1表(续)
No. | A | R2 | R3 | R4 | R6 | X | m | 物性 |
A-274 | 3-F-Ph | Me | Me | 3-CF3 | H | CH | 1 | NMR |
A-275 | 3-F-Ph | Me | Me | 3-CF3 | H | N | 1 | NMR |
A-276 | 3-F-Ph | Me | Me | 3-CHF2 | H | N | 1 | NMR |
A-277 | 3-F-Ph | Me | Me | 3-Cl | H | CH | 1 | NMR |
A-278 | 3-F-Ph | Me | Me | 3-Cl | H | N | 1 | NMR |
A-279 | 3-F-Ph | Me | Me | 3-Br | H | CH | 1 | NMR |
A-280 | 3-F-Ph | Me | Me | 3-Br | H | N | 1 | |
A-281 | 3-F-Ph | Me | Me | 3-I | H | CH | 1 | |
A-282 | 3-F-Ph | Me | Me | 3-I | H | N | 1 | |
A-283 | 3-F-Ph | Me | Me | 3-NO2 | H | CH | 1 | |
A-284 | 3-F-Ph | Me | Me | 3-NO2 | H | N | 1 | |
A-285 | 3-F-Ph | Me | Me | 3-CN | H | CH | 1 | |
A-286 | 3-F-Ph | Me | Me | 3-CN | H | N | 1 | |
A-287 | 3-F-Ph | Me | Me | 3-Me | H | CH | 1 | NMR |
A-288 | 3-F-Ph | Me | Me | 3-Me | H | N | 1 | |
A-289 | 3-F-Ph | Me | Me | 3-cPr | H | CH | 1 | NMR |
A-290 | 3-F-Ph | Me | Me | 3-cBu | H | CH | 1 | |
A-291 | 3-F-Ph | Me | Me | 3-cHexyl | H | CH | 1 | NMR |
A-292 | 3-F-Ph | Me | Me | 3-OMe | H | CH | 1 | |
A-293 | 3-F-Ph | Me | Me | 3-S(nPr) | H | CH | 1 | |
A-294 | 3-F-Ph | Me | Me | 3-SOMe | H | CH | 1 | NMR |
A-295 | 3-F-Ph | Me | Me | 3-SO2Me | H | CH | 1 | NMR |
A-296 | 3-F-Ph | Me | Me | - | H | CCF3 | 0 | |
A-297 | 3-F-Ph | Me | Me | - | H | CF | 0 | |
A-298 | 3-F-Ph | Me | Me | - | H | CCl | 0 | |
A-299 | 3-F-Ph | Me | Me | - | H | CBr | 0 | |
A-300 | 3-F-Ph | Me | Me | - | H | CI | 0 | |
A-301 | 3-F-Ph | Me | Me | - | H | CNO2 | 0 | |
A-302 | 3-F-Ph | Me | Me | 3-CF3-5-Me | H | CH | 2 | |
A-303 | 3-F-Ph | Me | Me | 3-CF3-5-CF3 | H | CH | 2 |
[表11]
第1表(续)
No. | A | R2 | R3 | R4 | R6 | X | m | 物性 |
A-304 | 3-F-Ph | Me | Me | 3-Br-5-Br | H | CBr | 2 | |
A-305 | 3-F-Ph | Me | Me | 3-Br-5-Br | H | N | 2 | |
A-306 | 3-F-Ph | Me | Me | 3-CF3 | Me | CH | 1 | |
A-307 | 3-F-Ph | Me | Me | 3-CF3 | Et | CH | 1 | |
A-308 | 3-F-Ph | Me | Me | 3-CF3 | nPr | CH | 1 | |
A-309 | 3-F-Ph | Me | Me | 3-CF3 | nHexyl | CH | 1 | |
A-310 | 3-F-Ph | Me | Me | 3-CF3 | iPr | CH | 1 | |
A-311 | 3-F-Ph | Me | Me | 3-CF3 | CH2CH=CH2 | CH | 1 | |
A-312 | 3-F-Ph | Me | Me | 3-CF3 | CH2CH=C(Me)2 | CH | 1 | |
A-313 | 3-F-Ph | Me | Me | 3-CF3 | CH2C≡CH | CH | 1 | |
A-314 | 3-F-Ph | Me | Me | 3-CF3 | CH2C≡CMe | CH | 1 | |
A-315 | 3-F-Ph | Me | Me | 3-CF3 | CH2OMe | CH | 1 | |
A-316 | 3-F-Ph | Me | Me | 3-CF3 | CH2OEt | CH | 1 | |
A-317 | 3-F-Ph | Me | Me | 3-CF3 | C2H4OMe | CH | 1 | |
A-318 | 3-Cl-Ph | Me | Me | 3-CF3 | H | CH | 1 | NMR |
A-319 | 3-Cl-Ph | Me | Me | 3-CF3 | H | N | 1 | NMR |
A-320 | 3-Cl-Ph | Me | Me | 3-Cl | H | CH | 1 | |
A-321 | 3-Cl-Ph | Me | Me | 3-Cl | H | N | 1 | |
A-322 | 3-Me-Ph | Me | Me | 3-CF3 | H | CH | 1 | NMR |
A-323 | 3-Me-Ph | Me | Me | 3-CF3 | H | N | 1 | NMR |
A-324 | 3-Me-Ph | Me | Me | 3-Cl | H | CH | 1 | NMR |
A-325 | 3-Me-Ph | Me | Me | 3-CHF2 | H | N | 1 | |
A-326 | 3-CF3-Ph | Me | Me | 3-CF3 | H | CH | 1 | |
A-327 | 3-CF3-Ph | Me | Me | 3-CF3 | H | N | 1 | NMR |
A-328 | 3-OMe-Ph | Me | Me | 3-CF3 | H | CH | 1 | NMR |
A-329 | 3-OMe-Ph | Me | Me | 3-CF3 | H | N | 1 | NMR |
A-330 | 3-OMe-Ph | Me | Me | 3-Cl | H | CH | 1 | NMR |
A-331 | 3-OMe-Ph | Me | Me | 3-CHF2 | H | N | 1 | |
A-332 | 2,3-diCl-Ph | Me | Me | 3-CF3 | H | CH | 1 | NMR |
A-333 | 2,3-diCl-Ph | Me | Me | 3-CF3 | H | N | 1 | NMR |
[表12]
第1表(续)
No. | A | R2 | R3 | R4 | R6 | X | m | 物性 |
A-334 | 2,5-diCl-Ph | Me | Me | 3-CF3 | H | CH | 1 | NMR |
A-335 | 2,5-diCl-Ph | Me | Me | 3-CF3 | H | N | 1 | NMR |
A-336 | 2,3-diF-Ph | Me | Me | 3-CF3 | H | CH | 1 | NMR |
A-337 | 2,3-diF-Ph | Me | Me | 3-CF3 | H | N | 1 | NMR |
A-338 | 2,5-diF-Ph | Me | Me | 3-CF3 | H | CH | 1 | |
A-339 | 2,5-diF-Ph | Me | Me | 3-CF3 | H | N | 1 | |
A-340 | 2,3-diMe-Ph | Me | Me | 3-CF3 | H | CH | 1 | NMR |
A-341 | 2,3-diMe-Ph | Me | Me | 3-CF3 | H | N | 1 | NMR |
A-342 | 2,5-diMe-Ph | Me | Me | 3-CF3 | H | CH | 1 | |
A-343 | 2,5-diMe-Ph | Me | Me | 3-CF3 | H | N | 1 | |
A-344 | 2,4-diF-Ph | Me | Me | 3-Cl | H | CH | 1 | NMR |
A-345 | 2,6-diCl-Ph | Me | Me | 3-CF3 | H | CH | 1 | |
A-346 | 2,6-diCl-Ph | Me | Me | 3-CF3 | H | N | 1 | |
A-347 | 2,6-diMe-Ph | Me | Me | 3-CF3 | H | CH | 1 | |
A-348 | 2,6-diMe-Ph | Me | Me | 3-CF3 | H | N | 1 | |
A-349 | 2-Cl-3-F-Ph | Me | Me | 3-CF3 | H | CH | 1 | NMR |
A-350 | 2-Cl-3-F-Ph | Me | Me | 3-CF3 | H | N | 1 | NMR |
A-351 | 2-Cl-5-F-Ph | Me | Me | 3-CF3 | H | CH | 1 | NMR |
A-352 | 2-Cl-5-F-Ph | Me | Me | 3-CF3 | H | N | 1 | NMR |
A-353 | 2-Me-3-F-Ph | Me | Me | 3-CF3 | H | CH | 1 | |
A-354 | 2-Me-3-F-Ph | Me | Me | 3-CF3 | H | N | 1 | |
A-355 | 2-Me-5-F-Ph | Me | Me | 3-CF3 | H | CH | 1 | |
A-356 | 2-Me-5-F-Ph | Me | Me | 3-CF3 | H | N | 1 | |
A-357 | 2-CF3-3-F-Ph | Me | Me | 3-CF3 | H | CH | 1 | |
A-358 | 2-CF3-3-F-Ph | Me | Me | 3-CF3 | H | N | 1 | |
A-359 | 3,5-bis(CF3)-Ph | Me | Me | 3-CF3 | H | CH | 1 | |
A-360 | 3,5-bis(CF3)-Ph | Me | Me | 3-CF3 | H | N | 1 | NMR |
A-361 | 2-Et-Ph | Me | Me | 3-CF3 | H | CH | 1 | |
A-362 | 2-Et-Ph | Me | Me | 3-CF3 | H | N | 1 | |
A-363 | 2-iPr-Ph | Me | Me | 3-CF3 | H | CH | 1 | NMR |
[表13]
第1表(续)
No. | A | R2 | R3 | R4 | R6 | X | m | 物性 |
A-364 | 2-iPr-Ph | Me | Me | 3-CF3 | H | N | 1 | NMR |
A-365 | 2-CH2CH(Me)2-Ph | Me | Me | 3-CF3 | H | CH | 1 | |
A-366 | 2-CH2CH(Me)2-Ph | Me | Me | 3-CF3 | CH2OMe | CH | 1 | |
A-367 | 2-CH2CH(Me)2-Ph | Me | Me | 3-CF3 | CO2tBu | CH | 1 | |
A-368 | 2-nBu-Ph | Me | Me | 3-CF3 | H | CH | 1 | |
A-369 | 2-nBu-Ph | Me | Me | 3-CF3 | CH2OMe | CH | 1 | |
A-370 | 2-nBu-Ph | Me | Me | 3-CF3 | CO2tBu | CH | 1 | |
A-371 | 2-CH=CH2-Ph | Me | Me | 3-CF3 | H | CH | 1 | |
A-372 | 2-CH=CH2-Ph | Me | Me | 3-CF3 | CH2OMe | CH | 1 | |
A-373 | 2-CH=CH2-Ph | Me | Me | 3-CF3 | CO2tBu | CH | 1 | |
A-374 | 2-C(Me)=CH2-Ph | Me | Me | 3-CF3 | H | CH | 1 | |
A-375 | 2-C(Me)=CH2-Ph | Me | Me | 3-CF3 | CH2OMe | CH | 1 | |
A-376 | 2-C(Me)=CH2-Ph | Me | Me | 3-CF3 | CO2tBu | CH | 1 | |
A-377 | 2-CH=C(Me)2-Ph | Me | Me | 3-CF3 | CH | 1 | ||
A-378 | 2-CH=C(Me)2-Ph | Me | Me | 3-CF3 | CH2OMe | CH | 1 | |
A-379 | 2-CH=C(Me)2-Ph | Me | Me | 3-CF3 | CO2tBu | CH | 1 | |
A-380 | 2-C≡CH-Ph | Me | Me | 3-CF3 | H | CH | 1 | |
A-381 | 2-C≡CH-Ph | Me | Me | 3-CF3 | CH2OMe | CH | 1 | |
A-382 | 2-C≡CH-Ph | Me | Me | 3-CF3 | CO2tBu | CH | 1 | |
A-383 | 2-C≡C(Me)-Ph | Me | Me | 3-CF3 | H | CH | 1 | |
A-384 | 2-C≡C(Me)-Ph | Me | Me | 3-CF3 | CH2OMe | CH | 1 | |
A-385 | 2-C≡C(Me)-Ph | Me | Me | 3-CF3 | CO2tBu | CH | 1 | |
A-386 | 2-C≡C(tBu)-Ph | Me | Me | 3-CF3 | H | CH | 1 | |
A-387 | 2-C≡C(tBu)-Ph | Me | Me | 3-CF3 | CH2OMe | CH | 1 | |
A-388 | 2-C≡C(tBu)-Ph | Me | Me | 3-CF3 | CO2tBu | CH | 1 | |
A-389 | 2-cPr-Ph | Me | Me | 3-CF3 | H | CH | 1 | NMR |
A-390 | 2-cPr-Ph | Me | Me | 3-CF3 | CH2OMe | CH | 1 | |
A-391 | 2-cPr-Ph | Me | Me | 3-CF3 | CO2tBu | CH | 1 | |
A-392 | 2-OEt-Ph | Me | Me | 3-CF3 | H | CH | 1 | |
A-393 | 2-OEt-Ph | Me | Me | 3-CF3 | H | N | 1 |
[表14]
第1表(续)
[表15]
第1表(续)
[表16]
第1表(续)
No. | A | R2 | R3 | R4 | R6 | X | m | 物性 |
A-426 | 2-Cl-Ph | Me | Me | 3-CF3 | CH2Ph | CH | 1 | |
A-427 | 2-Cl-Ph | Me | Me | 3-NO2 | H | CCN | 1 | |
A 428 | 2-Cl-Ph | Me | Me | 3-CHF2-5-CHF2 | H | CH | 2 | |
A-429 | 2-Me-Ph | Me | Me | 3-CF3-5-CF3 | H | CH | 2 | |
A-430 | 3-F-Ph | Me | Me | 3-SMe | H | CH | 1 | NMR |
A-431 | 3-F-Ph | Me | Me | 3-Et | H | CH | 1 | |
A-432 | 3-F-Ph | Me | Me | 3-CH=CH2 | H | CH | 1 | |
A-433 | 3-F-Ph | Me | Me | 3-trans-CH=CHCH3 | H | CH | 1 | |
A-434 | 3-F-Ph | Me | Me | 3-nPr | H | CH | 1 | |
A-435 | 3-F-Ph | Me | Me | 3-C≡CH | H | CH | 1 | |
A-436 | 3-F-Ph | Me | Me | 3-C≡C(CH2)3CH3 | H | CH | 1 | |
A-437 | 3-F-Ph | Me | Me | 3-nHex | H | CH | 1 |
[表17]
第2表
[表18]第2(续)
[表19]
第2表(续)
[表20]
第2表(续)
[表21]
第2表(续)
[表22]
第2表(续)
[表23]
第2表(续)
[表24]
第3表
[表25]
第3表(续)
[表26]
第3表(续)
[表27]
第3表(续)
[表28]
第3表(续)
[表29]
第3表(续)
[表30]
第3表(续)
[表31]
第3表(续)
[表32]
第3表(续)
[表33]
第3表(续)
[表34]
第3表(续)
[表35]
第4表
[表36]
第4表(续)
[表37]
试验例1:对南方根结线虫的效果试验
在南方根结线虫污染土壤200mL中,灌注了使用水以化合物(I)的浓度成为400ppm或200ppm的方式调制出的本组合物10mL后,以本组合物均匀地分散的方式混合了。在将处理土壤装填于盆后,播种3粒黄瓜种子,放置在温室内。在从上述黄瓜种子的播种起2~3周后,按照第5表所示的根结指数而判定了被形成在根部的根结的着生程度。其结果,包含上述化合物No.A-1、A-2、A-89、A-90、A-94、A-95、A-96、A-107、A-150、A-151、A-152、A-156、A-157、A-160、A-161、A-193、A-195、A-198、A-199、A-200、A-201、A-202、A-203、A-205、A-206、A-216、A-217、A-224、A-233、A-234、A-235、A-240、A-241、A-244、A-245、A-247、A-248、A-249、A-251、A-252、A-253、A-255、A-256、A-257、A-260、A-261、A-264、A-265、A-270、A-271、A-272、A-273、A-274、A-275、A-277、A-278、A-279、A-318、A-319、A-322、A-323、A-324、A-327、A-328、A-329、A-330、A-332、A-333、A-334、A-335、A-336、A-337、A-344、A-349、A-350、A-351、A-352、A-410、A-411、A-412、A-413、A-414、A-416、A-417、A-419、A-424、A-430、B-1、B-2、B-3、B-4、B-81、B-87、B-105、B-106、B-148、B-190、B-192或B-196的各组合物以400ppm、包含上述化合物No.A-153的组合物以200ppm显示根结指数1以下的高防除效果。
[表38]
第5表
根结指数 | 根结的着生程度 |
0 | 根整体完全未确认到根结 |
1 | 略微确认到结 |
2 | 结数为中等程度 |
3 | 结数多 |
4 | 结数特别多,并且大 |
试验例2:对穿刺短体线虫的效果试验
在穿刺短体线虫污染土壤200mL中,灌注了使用水将化合物(I)的浓度调制为800ppm的本组合物10mL后,以本组合物均匀地分散的方式混合了。在将处理土壤装填于盆后,播种3粒牛蒡种子,放置在温室内。在从上述牛蒡种子的播种起约1个月后,按照第6表所示的损害指数而判定了根部的损害程度。其结果,包含上述化合物No.A-1、A-318、B-1或B-192的各组合物显示出损害指数1以下的高防除效果。
[表39]
第6表
损害指数 | 根部的损害程度 |
0 | 无 |
1 | 小 |
2 | 中 |
3 | 大 |
4 | 很大 |
试验例3:对大豆胞囊线虫的效果试验
在大豆胞囊线虫污染土壤200mL中,灌注了用水将化合物(I)的浓度调制为800ppm或400ppm的本组合物10mL后,以本组合物均匀地分散的方式混合了。在将处理土壤装填于盆后,播种3粒大豆种子,放置在温室内。在从上述大豆种子的播种起约1个月后,按照第7表所示的寄生指数而判定了孢囊对根部的寄生度。其结果,包含上述化合物No.A-1、A-2、A-89、A-91、A-107、A-109、A-271、A-274、A-279、A-318、A-319、A-322、A-323、A-328、A-333、A-352、A-411、A-416、B-1、B-3、B-4、B-6、B-24、B-192或B-196的各组合物以800ppm、包含上述化合物No.A-260、B-106或B-193的组合物以400ppm显示出寄生指数1以下的高防除效果。
[表40]
第7表
寄生指数 | 寄生度 |
0 | 根整体完全未确认到孢囊的寄生 |
1 | 略微确认到孢囊的寄生 |
2 | 孢囊的寄生为中等程度 |
3 | 孢囊的寄生多 |
4 | 孢囊在根整体密集地寄生 |
接下来,通过以下比较试验而显示本组合物和包含国际公开第2020/179910号所记载的化合物的组合物对南方根结线虫的效果。
比较试验
使用化合物No.A-1、A-2、和A-318作为本组合物的有效成分,使用国际公开第2020/179910号所记载的化合物No.A-1、A-3、和A-58作为比较对照的有效成分,将有效成分浓度调制为50ppm,除此以外,通过与上述试验例1相同方法而进行了对南方根结线虫的效果试验。将试验结果示于第8表和第9表中。
试验的结果是,包含国际公开第2020/179910号所记载的化合物(化合物No.A-1、A-3、或A-58)的各组合物的根结指数为2。与此相对,包含本发明化合物(化合物No.A-1、A-2、或A-318)的各本组合物的根结指数为1或0。
所谓根结指数2,表示健全的根的比率为整体的50%以下,限于试验对象作物的黄瓜不能健全地生长的防除效果的状态。与此相对,所谓根结指数1或0,表示健全的根的比率为整体的75%以上,发挥黄瓜可以健全地生长的高防除效果的状态。
[表41]
第8表
[表42]
第9表
以下对本组合物的制剂具体地说明,但混配比例、剂型等不限定于以下制剂例。
接下来记载制剂例。
制剂例1
(1)化合物(I)20重量份
(2)粘土70重量份
(3)白炭墨5重量份
(4)多元羧酸钠3重量份
(5)烷基萘磺酸钠2重量份
将以上物质均匀地混合而制成可湿性粉剂。
制剂例2
(1)化合物(I)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
将以上物质均匀地混合而制成粉剂。
制剂例3
(1)化合物(I)20重量份
(2)N,N-二甲基乙酰胺20重量份
(3)聚氧乙烯三苯乙烯基苯基醚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
将以上物质均匀地混合、溶解而制成乳油。
制剂例4
(1)粘土68重量份
(2)木质素磺酸钠2重量份
(3)聚氧乙烯烷基芳基硫酸酯5重量份
(4)白炭墨25重量份
将以上各成分的混合物、与化合物(I)以4:1的重量比例混合,制成可湿性粉剂。
制剂例5
(1)化合物(I)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
在将以上物质均匀地混合、粉碎了的原液中进一步加入
(5)多元羧酸钠5重量份
(6)无水硫酸钠42.8重量份,
均匀地混合、造粒、干燥而制成水分散性粒剂。
制剂例6
(1)化合物(I)5重量份
(2)聚氧乙烯辛基苯基醚1重量份
(3)聚氧乙烯烷基醚磷酸酯0.1重量份
(4)粒状碳酸钙93.9重量份
将(1)~(3)预先均匀地混合,用适量的丙酮进行了稀释后,向(4)喷射,除去丙酮而制成颗粒剂。
制剂例7
(1)化合物(I)2.5重量份
(2)N,N-二甲基乙酰胺2.5重量份
(3)豆油95重量份
将以上物质均匀地混合、溶解而制成超低容量剂(ultra low volumeformulation)。
制剂例8
(1)化合物(I)40重量份
(2)聚氧乙烯三苯乙烯基苯基醚磷酸钾4重量份
(3)硅油0.2重量份
(4)黄原胶0.1重量份
(5)乙二醇5重量份
(6)水50.7重量份
将以上物质均匀地混合、粉碎而制成水性悬浮剂。
制剂例9
(1)化合物(I)10重量份
(2)二甘醇单乙基醚80重量份
(3)聚氧乙烯烷基醚10重量份
将以上成分均匀地混合而制成可溶液体制剂。
需要说明的是,将在2021年7月8日申请的日本专利申请2021-113233号的说明书、权利要求书、和摘要的全部内容引用到本文中,作为本发明的说明书的公开而被采用。
Claims (14)
1.一种杀线虫组合物,其含有式(I)所示的化合物或其盐作为有效成分,
式中,X为N、CH或CR4,
A为未被取代的苯基或被1个~5个R1取代了的苯基,
R1为卤素、烷基、卤代烷基、烯基、炔基、环烷基、烷氧基、或卤代烷氧基,在R1存在2个的情况下,2个R1可以一起形成可以被1个或2个Z1取代的环,
Z1为卤素、或烷基,
R2和R3各自为烷基,或R2和R3一起形成(C3-C6)-碳环,
R4为卤素、烷基、卤代烷基、烯基、炔基、环烷基、烷氧基、卤代烷氧基、烷硫基、烷基亚磺酰基、烷基磺酰基、硝基或氰基,
R5为CHO,
R6为H、-SO2CF3、-C(=O)OZ3、烷基、烯基、炔基或烷氧基烷基、或可以被Z2取代的芳烷基,
Z2为烷氧基,
Z3为可以被Z2取代的芳烷基、或烷基,
m为0~2的整数。
2.一种线虫的防除方法,将含有有效量的式(I)所示的化合物或其盐的杀线虫组合物施用于土壤、线虫或植物体,
式中,X为N、CH或CR4,
A为未被取代的苯基或被1个~5个R1取代了的苯基,
R1为卤素、烷基、卤代烷基、烯基、炔基、环烷基、烷氧基、或卤代烷氧基,在R1存在2个的情况下,2个R1可以一起形成可以被1个或2个Z1取代的环,
Z1为卤素、或烷基,
R2和R3各自为烷基,或R2和R3一起形成(C3-C6)-碳环,
R4为卤素、烷基、卤代烷基、烯基、炔基、环烷基、烷氧基、卤代烷氧基、烷硫基、烷基亚磺酰基、烷基磺酰基、硝基或氰基,
R5为CHO,
R6为H、-SO2CF3、-C(=O)OZ3、烷基、烯基、炔基或烷氧基烷基、或可以被Z2取代的芳烷基,
Z2为烷氧基,
Z3为可以被Z2取代的芳烷基、或烷基,
m为0~2的整数。
3.选自下述式中的化合物或其盐,
以及
4.根据权利要求1所述的杀线虫组合物,式(I)所示的化合物或其盐是,A为被1个~5个R1取代了的苯基,R1为卤素、烷基、卤代烷基、烯基、炔基、环烷基、烷氧基、或卤代烷氧基,在R1存在2个的情况下,2个R1可以一起形成可以被1个或2个Z1取代的环的化合物或其盐。
5.根据权利要求2所述的线虫的防除方法,式(I)所示的化合物或其盐是,A为被1个~5个R1取代了的苯基,R1为卤素、烷基、卤代烷基、烯基、炔基、环烷基、烷氧基、或卤代烷氧基,在R1存在2个的情况下,2个R1可以一起形成可以被1个或2个Z1取代的环的化合物或其盐。
6.式(IA)所示的化合物或其盐,
式中,X为N、CH或CR4A,
R1A为卤素、(C1-C6)-烷基、(C1-C6)-卤代烷基、(C2-C6)-烯基、(C2-C6)-炔基、(C3-C6)-环烷基、(C1-C6)-烷氧基、或(C1-C6)-卤代烷氧基,在R1A存在2个的情况下,2个R1A可以一起形成可以被1个或2个Z1A取代的环,
Z1A为卤素、或(C1-C6)-烷基,
R2A和R3A各自为(C1-C6)-烷基,或R2A和R3A一起形成(C3-C6)-碳环,
R4A为卤素、(C1-C6)-烷基、(C1-C6)-卤代烷基、(C2-C6)-烯基、(C2-C6)-炔基、(C3-C6)-环烷基、(C1-C6)-烷氧基、(C1-C6)-卤代烷氧基、(C1-C6)-烷硫基、(C1-C6)-烷基亚磺酰基、(C1-C6)-烷基磺酰基、硝基或氰基,
R6A为H、-SO2CF3、-C(=O)OZ3A、(C1-C6)-烷基、(C2-C6)-烯基、(C2-C6)-炔基或(C1-C6)-烷氧基-(C1-C6)-烷基、或可以被Z2A取代的(C7-C12)-芳烷基,
Z2A为(C1-C6)-烷氧基,
Z3A为可以被Z2A取代的(C7-C12)-芳烷基、或(C1-C6)-烷基,
n为1~5的整数,
m为0~2的整数。
7.式(IB)所示的化合物或其盐,
式中,X为N、CH或CR4A,
R2A和R3A各自为(C1-C6)-烷基,或R2A和R3A一起形成(C3-C6)-碳环,
R4A为卤素、(C1-C6)-烷基、(C1-C6)-卤代烷基、(C2-C6)-烯基、(C2-C6)-炔基、(C3-C6)-环烷基、(C1-C6)-烷氧基、(C1-C6)-卤代烷氧基、(C1-C6)-烷硫基、(C1-C6)-烷基亚磺酰基、(C1-C6)-烷基磺酰基、硝基或氰基,
R6A为H、-SO2CF3、-C(=O)OZ3A、(C1-C6)-烷基、(C2-C6)-烯基、(C2-C6)-炔基或(C1-C6)-烷氧基-(C1-C6)-烷基、或可以被Z2A取代的(C7-C12)-芳烷基,
Z2A为(C1-C6)-烷氧基,
Z3A为可以被Z2A取代的(C7-C12)-芳烷基、或(C1-C6)-烷基,
m为0~2的整数。
8.根据权利要求6所述的化合物或其盐,在式(IA)所示的化合物或其盐中,R1A为卤素、(C1-C6)-烷基、(C1-C6)-卤代烷基、(C2-C6)-烯基、(C2-C6)-炔基、(C3-C6)-环烷基、(C1-C6)-烷氧基、或(C1-C6)-卤代烷氧基。
9.根据权利要求6所述的化合物或其盐,在式(IA)所示的化合物或其盐中,R2A和R3A各自为(C1-C3)-烷基。
10.根据权利要求6所述的化合物或其盐,在式(IA)所示的化合物或其盐中,R4A为卤素、(C1-C6)-卤代烷基、(C1-C6)-烷基亚磺酰基、(C1-C6)-烷基磺酰基、硝基或氰基。
11.根据权利要求7所述的化合物或其盐,在式(IB)所示的化合物或其盐中,R2A和R3A各自为(C1-C3)-烷基。
12.根据权利要求7所述的化合物或其盐,在式(IB)所示的化合物或其盐中,R4A为卤素、(C1-C6)-卤代烷基、(C1-C6)-烷基亚磺酰基、(C1-C6)-烷基磺酰基、硝基或氰基。
13.一种线虫的防除方法,将含有有效量的权利要求6或7所述的化合物或其盐的杀线虫组合物施用于土壤、线虫或植物体。
14.一种农业园艺用杀线虫剂,其含有权利要求6或7所述的化合物或其盐作为有效成分。
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