TW202316966A - 殺線蟲組成物 - Google Patents
殺線蟲組成物 Download PDFInfo
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- TW202316966A TW202316966A TW111125136A TW111125136A TW202316966A TW 202316966 A TW202316966 A TW 202316966A TW 111125136 A TW111125136 A TW 111125136A TW 111125136 A TW111125136 A TW 111125136A TW 202316966 A TW202316966 A TW 202316966A
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- Prior art keywords
- compound
- alkyl
- formula
- salt
- substituted
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- 239000000203 mixture Substances 0.000 title claims abstract description 85
- 230000001069 nematicidal effect Effects 0.000 title claims abstract description 18
- 150000001875 compounds Chemical class 0.000 claims abstract description 314
- 150000003839 salts Chemical class 0.000 claims abstract description 72
- 239000004480 active ingredient Substances 0.000 claims abstract description 21
- 241000244206 Nematoda Species 0.000 claims description 97
- 238000000034 method Methods 0.000 claims description 63
- 125000000217 alkyl group Chemical group 0.000 claims description 40
- 150000002367 halogens Chemical class 0.000 claims description 39
- 229910052736 halogen Inorganic materials 0.000 claims description 38
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 37
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 26
- 239000002689 soil Substances 0.000 claims description 25
- 125000003342 alkenyl group Chemical group 0.000 claims description 22
- 125000000304 alkynyl group Chemical group 0.000 claims description 22
- 239000005645 nematicide Substances 0.000 claims description 22
- 125000003545 alkoxy group Chemical group 0.000 claims description 19
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 17
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 15
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 14
- 125000001188 haloalkyl group Chemical group 0.000 claims description 14
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 13
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 12
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 12
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 12
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 12
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 11
- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims description 10
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 9
- 125000004738 (C1-C6) alkyl sulfinyl group Chemical group 0.000 claims description 7
- 125000004739 (C1-C6) alkylsulfonyl group Chemical group 0.000 claims description 6
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 5
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 5
- 125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 5
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 5
- 125000004414 alkyl thio group Chemical group 0.000 claims description 5
- 150000003254 radicals Chemical class 0.000 claims description 4
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 3
- 150000001350 alkyl halides Chemical group 0.000 claims 2
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims 2
- 230000001747 exhibiting effect Effects 0.000 abstract description 3
- -1 hydrazone compound Chemical group 0.000 description 127
- 238000006243 chemical reaction Methods 0.000 description 100
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- 235000002639 sodium chloride Nutrition 0.000 description 59
- 239000003795 chemical substances by application Substances 0.000 description 40
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- 238000002360 preparation method Methods 0.000 description 32
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- 125000001424 substituent group Chemical group 0.000 description 29
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 27
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- 239000000243 solution Substances 0.000 description 21
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- 239000011541 reaction mixture Substances 0.000 description 20
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- 239000000126 substance Substances 0.000 description 18
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- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 16
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- 230000015572 biosynthetic process Effects 0.000 description 16
- 230000000694 effects Effects 0.000 description 16
- 238000003786 synthesis reaction Methods 0.000 description 16
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- 239000007788 liquid Substances 0.000 description 15
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- 238000005481 NMR spectroscopy Methods 0.000 description 14
- 230000035484 reaction time Effects 0.000 description 13
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 12
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 12
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 12
- UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 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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- 238000004440 column chromatography Methods 0.000 description 11
- 239000003480 eluent Substances 0.000 description 11
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 11
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- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 10
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- 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
- 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
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 9
- 230000004044 response Effects 0.000 description 9
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 8
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-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
- 239000007900 aqueous suspension Substances 0.000 description 8
- 239000008187 granular material Substances 0.000 description 8
- 230000000887 hydrating effect Effects 0.000 description 8
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 8
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 7
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 7
- RPNREKIDKKUKFT-UHFFFAOYSA-K P(=O)([O-])([O-])[O-].[K+].C1(=CC=CC=C1)OC1=CC=CC=C1.[K+].[K+] Chemical compound P(=O)([O-])([O-])[O-].[K+].C1(=CC=CC=C1)OC1=CC=CC=C1.[K+].[K+] RPNREKIDKKUKFT-UHFFFAOYSA-K 0.000 description 7
- 229910052783 alkali metal Inorganic materials 0.000 description 7
- 150000002148 esters Chemical class 0.000 description 7
- XZBIXDPGRMLSTC-UHFFFAOYSA-N formohydrazide Chemical compound NNC=O XZBIXDPGRMLSTC-UHFFFAOYSA-N 0.000 description 7
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- 229910019142 PO4 Inorganic materials 0.000 description 6
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 6
- 241000607479 Yersinia pestis Species 0.000 description 6
- 229910052801 chlorine Inorganic materials 0.000 description 6
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 6
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- 230000036571 hydration Effects 0.000 description 6
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- TZIHFWKZFHZASV-UHFFFAOYSA-N methyl formate Chemical compound COC=O TZIHFWKZFHZASV-UHFFFAOYSA-N 0.000 description 6
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- 238000006467 substitution reaction Methods 0.000 description 6
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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
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
-
- 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
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Abstract
本發明係提供一種顯示優異之殺線蟲活性的殺線蟲組成物。
本發明係關於一種殺線蟲組成物,其係含有將式(I)表示之化合物或其鹽作為有效成分,
Description
本發明係關於將與新穎之4級碳鍵結之甲腙(Form hydrazone)化合物或其鹽作為有效成分含有之殺線蟲組成物。
具有特定之腙構造的化合物已知對各式各樣之有害生物的防除為有用。專利文獻1中作為農園藝用殺蟲劑或農園藝用殺線蟲劑,記載有具有如由有用之3級碳所構成之-CH(Me)-或-CH(i-Pr)-之化學構造的腙衍生物,及其使用方法。然而,此文獻中並未記載後述式(I)之化合物,亦即並未記載關於將具有4級碳作為特徵之化學構造的腙衍生物、將其作為有效成分之殺線蟲組成物及該等之使用方法的具體例。
[先前技術文獻]
[專利文獻]
[專利文獻1]國際公開第2020/179910號
[發明欲解決之課題]
對農業及園藝等之作物生產帶來被害之線蟲中存在各式各樣的種類,並進展將該等之防除作為目的之農園藝用殺線蟲劑的開發。而且,藉由通過長期間持續使用相同之農園藝用藥劑,恐有促進對象之線蟲獲得藥劑抵抗性之虞。因此,無論施用場面,期望的是具有對於線蟲之高防除效果的新穎之農園藝用殺線蟲劑的創建。
據此,本發明之課題係提供一種將顯示優異之殺線蟲活性的後述式(I)表示之化合物或其鹽作為有效成分含有之殺線蟲組成物。
[用以解決課題之手段]
本發明者們為了解決上述課題,經努力研究的結果,發現將後述式(I)表示之化合物或其鹽作為有效成分含有之組成物,對於線蟲表現優異之防除效果。
亦即,本發明係如以下。
[1]一種殺線蟲組成物(以下,亦稱為本組成物),其係將式(I)表示之化合物或其鹽(以下,亦稱為化合物(I))作為有效成分,
[式中,X為N、CH或CR
4,
A為未被取代之苯基或被1個至5個之R
1取代之苯基,
R
1為鹵素、烷基、鹵烷基、烯基、炔基、環烷基、烷氧基或鹵烷氧基,存在2個R
1的情況下,2個之R
1可成為一起,形成可被1個或2個之Z
1取代之環,
Z
1為鹵素或烷基,
R
2及R
3分別為烷基,或R
2及R
3成為一起,形成(C
3-C
6)-碳環,
R
4為鹵素、烷基、鹵烷基、烯基、炔基、環烷基、烷氧基、鹵烷氧基、烷硫基、烷基亞磺醯基、烷基磺醯基、硝基或氰基,
R
5為CHO,
R
6為H、-SO
2CF
3、-C(=O)OZ
3、烷基、烯基、炔基或烷氧基烷基,或為可被Z
2取代之芳烷基,
Z
2為烷氧基,
Z
3為可被Z
2取代之芳烷基或烷基,
m為0至2之整數]。
[2]一種線蟲之防除方法,其係將有效量含有式(I)表示之化合物或其鹽之殺線蟲組成物施用在土壤、線蟲或植物體,
[式中,X為N、CH或CR
4,
A為未被取代之苯基或被1個至5個之R
1取代之苯基,
R
1為鹵素、烷基、鹵烷基、烯基、炔基、環烷基、烷氧基或鹵烷氧基,存在2個R
1的情況下,2個之R
1可成為一起,形成可被1個或2個之Z
1取代之環,
Z
1為鹵素或烷基,
R
2及R
3分別為烷基,或R
2及R
3成為一起形成(C
3-C
6)碳環,
R
4為鹵素、烷基、鹵烷基、烯基、炔基、環烷基、烷氧基、鹵烷氧基、烷硫基、烷基亞磺醯基、烷基磺醯基、硝基或氰基,
R
5為CHO,
R
6為H、-SO
2CF
3、-C(=O)OZ
3、烷基、烯基、炔基或烷氧基烷基或為可被Z
2取代之芳烷基,
Z
2為烷氧基,
Z
3為可被Z
2取代之芳烷基或烷基,
m為0至2之整數]。
[3]如前述[1]所記載之殺線蟲組成物,其中,在式(I)表示之化合物或其鹽,A為被1個至5個之R
1取代之苯基,R
1為鹵素、烷基、鹵烷基、烯基、炔基、環烷基、烷氧基或鹵烷氧基,存在2個R
1的情況下,2個之R
1可成為一起,形成可被1個或2個之Z
1取代之環的化合物或其鹽。
[4]如前述[2]所記載之線蟲之防除方法,其中,在式(I)表示之化合物或其鹽,A為被1個至5個之R
1取代之苯基,R
1為鹵素、烷基、鹵烷基、烯基、炔基、環烷基、烷氧基或鹵烷氧基,存在2個R
1的情況下,2個之R
1可成為一起,形成可被1個或2個之Z
1取代之環的化合物或其鹽。
[5]一種式(IA)表示之化合物或其鹽,
[式中,X為N、CH或CR
4A,
R
1A為鹵素、(C
1-C
6)-烷基、(C
1-C
6)-鹵烷基、(C
2-C
6)-烯基、(C
2-C
6)-炔基、(C
3-C
6)-環烷基、(C
1-C
6)-烷氧基或(C
1-C
6)-鹵烷氧基,存在2個R
1A的情況下,2個R
1A可成為一起,形成可被1個或2個之Z
1A取代之環,
Z
1A為鹵素或(C
1-C
6)-烷基,
R
2A及R
3A分別為(C
1-C
6)-烷基,或R
2A及R
3A成為一起,形成(C
3-C
6)-碳環,
R
4A為鹵素、(C
1-C
6)-烷基、(C
1-C
6)-鹵烷基、(C
2-C
6)-烯基、(C
2-C
6)-炔基、(C
3-C
6)-環烷基、(C
1-C
6)-烷氧基、(C
1-C
6)-鹵烷氧基、(C
1-C
6)-烷硫基、(C
1-C
6)-烷基亞磺醯基、(C
1-C
6)-烷基磺醯基、硝基或氰基,
R
6A為H、-SO
2CF
3、-C(=O)OZ
3A、(C
1-C
6)-烷基、(C
2-C
6)-烯基、(C
2-C
6)-炔基或(C
1-C
6)-烷氧基-(C
1-C
6)-烷基,或為可被Z
2A取代之(C
7-C
12)-芳烷基,
Z
2A為(C
1-C
6)-烷氧基,
Z
3A為可被Z
2A取代之(C
7-C
12)-芳烷基或(C
1-C
6)-烷基,
n為1至5之整數,
m為0至2之整數]。
[6]一種式(IB)表示之化合物或其鹽,
[式中,X為N、CH或CR
4A,
R
2A及R
3A分別為(C
1-C
6)-烷基,或R
2A及R
3A成為一起,形成(C
3-C
6)-碳環,
R
4A為鹵素、(C
1-C
6)-烷基、(C
1-C
6)-鹵烷基、(C
2-C
6)-烯基、(C
2-C
6)-炔基、(C
3-C
6)-環烷基、(C
1-C
6)-烷氧基、(C
1-C
6)-鹵烷氧基、(C
1-C
6)-烷硫基、(C
1-C
6)-烷基亞磺醯基、(C
1-C
6)-烷基磺醯基、硝基或氰基,
R
6A為H、-SO
2CF
3、-C(=O)OZ
3A、(C
1-C
6)-烷基、(C
2-C
6)-烯基、(C
2-C
6)-炔基或(C
1-C
6)-烷氧基-(C
1-C
6)-烷基,或為可被Z
2A取代之(C
7-C
12)-芳烷基,
Z
2A為(C
1-C
6)-烷氧基,
Z
3A為可被Z
2A取代之(C
7-C
12)-芳烷基或(C
1-C
6)-烷基,
m為0至2之整數]。
[7]一種線蟲之防除方法,其係將有效量含有如前述[5]或前述[6]所記載之化合物或其鹽之殺線蟲組成物施用在土壤、線蟲或植物體。
[8]一種農園藝用殺線蟲劑,其係將如前述[5]或前述[6]所記載之化合物或其鹽作為有效成分含有。
以下,有將式(I)表示之化合物或其鹽記為「化合物(I)」,將式(IA)表示之化合物或其鹽記為「化合物(IA)」,將式(IB)表示之化合物或其鹽記為「化合物(IB)」的情況。
[發明效果]
本組成物由於對於線蟲可發揮優異之防除效果,故作為農園藝用殺線蟲劑為有用。
有關化合物(I)、化合物(IA)及化合物(IB)之取代基及化學構造的形態進行說明。
化合物(I)之苯基上之取代基即R
1之取代數可為1個,亦可為2個以上,為2個以上時,R
1可為分別相同,亦可為相異。化合物(IA)之苯基上之取代基即R
1A之取代數可為1個,亦可為2個以上,為2個以上時,R
1A可為分別相同,亦可為相異。
在化合物(I),吡唑(X為CR
4)之取代基即R
4之取代數為2個或3個時,R
4可為分別相同,亦可為相異。在化合物(I),1,2,4-三唑(X為N)之取代基即R
4之取代數為2個時,R
4可為分別相同,亦可為相異。在化合物(IA)或化合物(IB),吡唑(X為CR
4A)之取代基即R
4A之取代數為2個或3個時,R
4A可為分別相同,亦可為相異。在化合物(IA)或化合物(IB),1,2,4-三唑之取代基即R
4A之取代數為2個時,R
4A可為分別相同,亦可為相異。
在本說明書,「n-」係意指「正」,「s-」係意指「二级」,「tert-」係意指「三级」。
作為鹵素或取代基之鹵素可列舉氟、氯、溴或碘之各原子。作為取代基之鹵素之數可為1或2以上,為2以上時,各鹵素原子可為分別相同,亦可為相異。
又,鹵素之取代基的位置可為任一位置。
在化合物(I)、化合物(IA)及化合物(IB),「C
P-C
T」係意指碳原子數為P至T。例如「C
1-C
3」係意指碳原子數為1至3。又,「可被取代」之表記係意指取代或無取代。
作為烷基、烷基部分或(C
1-C
6)-烷基,例如可列舉如甲基、乙基、n-丙基、異丙基、n-丁基、異丁基、s-丁基、tert-丁基、n-戊基、新戊基或n-己基之直鏈或分枝鏈狀之基。
作為烯基或(C
2-C
6)-烯基,例如可列舉如乙烯基、1-丙烯基、2-丙烯基、異丙烯基、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-丁烯基之直鏈或分枝鏈狀之基。又,為幾何異構物時,僅為E體或Z體之任一者,或為E體與Z體之任意的比例之混合物,若為被指定之碳數的範圍,則並非被特別限定。
作為炔基或(C
2-C
6)-炔基,例如可列舉如乙炔基、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-己炔基之直鏈或分枝鏈狀之基。
作為環烷基或(C
3-C
6)-環烷基,例如可列舉如環丙基、環丁基、環戊基或環己基之基。
作為鹵烷基或(C
1-C
6)-鹵烷基,例如可列舉如氯甲基二氟甲基、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-基般,為藉由1~7個之相同或不同之鹵素原子,而被部分性或完全取代之直鏈狀或分枝鏈狀之烷基。
作為烷氧基或(C
1-C
6)-烷氧基,例如可列舉如甲氧基、乙氧基、n-丙氧基、異丙氧基、n-丁氧基、異丁氧基、s-丁氧基、tert-丁氧基、n-戊氧基、新戊氧基,或n-己氧基之直鏈狀或分枝鏈狀之基。
作為鹵烷氧基或(C
1-C
6)-鹵烷氧基,例如可列舉如二氟甲氧基、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)氧基般,為藉由1~6個之相同或不同之鹵素原子,而被部分性或完全取代之直鏈狀或分枝鏈狀之基。
作為碳環或(C
3-C
6)-碳環,例如可列舉如環丙烷、環丁烷、環戊烷或環己烷之飽和之環。
作為烷硫基或(C
1-C
6)-烷硫基,例如可列舉如甲硫基、乙硫基、異丙硫基、n-丁硫基、異丁硫基、s-丁硫基、tert-丁硫基、n-戊硫基、新戊硫基,或n-己硫基之直鏈狀或分枝鏈狀之基。
作為烷基亞磺醯基或(C
1-C
6)-烷基亞磺醯基,例如可列舉如甲基亞磺醯基、乙基亞磺醯基、異丙基亞磺醯基、n-丁基亞磺醯基、異丁基亞磺醯基、s-丁基亞磺醯基、tert-丁基亞磺醯基、n-戊基亞磺醯基、新戊基亞磺醯基,或n-己基亞磺醯基之直鏈狀或分枝鏈狀之基。
作為烷基磺醯基或(C
1-C
6)-烷基磺醯基,例如可列舉如甲基磺醯基、乙基磺醯基、異丙基磺醯基、n-丁基磺醯基、異丁基磺醯基、s-丁基磺醯基、tert-丁基磺醯基、n-戊基磺醯基、新戊基磺醯基,或n-己基磺醯基之直鏈狀或分枝鏈狀之基。
作為在化合物(I),可列舉在2個之R
1成為一起而形成環的態樣之A,可被1個或2個之Z
1取代之苯并二氧雜環己烷基或苯并二噁烷基等。又,在式(IA)化合物,作為在2個之R
1A成為一起而形成環的態樣之苯基,可列舉可被1個或2個之Z
1A取代之環、苯并二氧雜環己烷基或苯并二噁烷基等。Z
1或Z
1A為2個時,Z
1或Z
1A可為分別相同,亦可為相異。
作為芳烷基或(C
7-C
12)-芳烷基,例如列舉苄基、1-苯基乙基或萘基甲基等。作為可被Z
2取代之芳烷基或為可被Z
2取代之(C
7-C
12)-芳烷基,可列舉p-甲氧基苄基、2,3-二甲氧基苄基或2,4-二甲氧基苄基等。
Z
2或Z
2A之代數可為2個以上,為2個以上時,可分別相同亦可為相異。又,Z
2或Z
2A之取代基位置可為任一位置。
在化合物(I),「被1個至5個之R
1取代之苯基」係意指被1、2、3、4或5個之R
1取代之苯基,所謂「未被取代之苯基」,係意指不具有取代基之R
1之苯基。又,在化合物(I)之特定的態樣,R
1之取代數亦有1至2、1至3、1至4、2至3、2至4、2至5、3至4、3至5、4至5之整數的情況。
在化合物(IA),所謂「n為1至5之整數」,係意指n為1、2、3、4或5之整數。又,在化合物(IA)之特定的態樣,亦有n為1至2、1至3、1至4、2至3、2至4、2至5、3至4、3至5、4至5之整數的情況。
在化合物(IA),表示如以下之化學構造式之取代基位置,R
1A基之取代基位置可為苯基環上之任一位置。m為1以上之時,表示如以下之化學構造式之取代基位置,R
4A基之取代基位置可為雜五員環之3位及5位中之任一位置或兩者之位置。
在化合物(IB),m為1以上之時,表示如以下之化學構造式之取代基位置,R
4A基之取代基位置可為雜五員環之3位及5位中之任一位置或兩者之位置。
在化合物(I)、化合物(IA)及化合物(IB),所謂「m為0至2之整數」之表記,係意指m為0、1或2之整數。又,在化合物(I)、化合物(IA)及化合物(IB)之特定的態樣,亦有m為0至1、1至2之整數的情況。
尚,在化合物(I)、化合物(IA)及化合物(IB),m為0時,(R
4)
m及(R
4A)
m為H,亦即係意指雜五員環之3位及5位皆為無取代。
以下,有關對於化合物(I)所說明之記載,由於化合物(I)中亦包含化合物(IA)及化合物(IB),故亦包含關於化合物(IA)及化合物(IB)之說明。
作為式(I)表示之化合物之鹽,若為農業上所容許者,雖包含所有者,但例如可列舉鹼金屬鹽(例如鈉鹽、鉀鹽等)、鹼土類金屬鹽(例如鎂鹽、鈣鹽等)、無機酸鹽(例如鹽酸鹽、過氯酸鹽、硫酸鹽、硝酸鹽等)、有機酸鹽(例如乙酸鹽、甲磺酸(Methanesulfonic acid)鹽等)等。
本發明之化合物(I)雖有存在各種異構物例如光學異構物、幾何異構物等的情況,但本發明中包含各異構物及異構物混合物雙方。
更具體而言,本發明之化合物(I)因應構造式中之雙鍵(碳-碳或碳-氮)之數,存在2種類以上之幾何異構物。據此,本發明中包含可想到之全部的幾何異構物及以任意的比例包含該等之混合物。
例如,在本說明書所記載之化合物,以構造式中之波浪線表示之鍵結,係意指亦包含源自雙鍵(碳-碳或碳-氮)之2種類以上的幾何異構物當中之任一幾何異構物。
尚,本發明之化合物(I)中,在該技術領域中之技術常識的範圍內,亦包含前述者以外之各種異構物。進而,使用在該技術領域中之技術常識及一般的實驗手法,可以作出各種異構物。
又,藉由異構物的種類,雖有成為與所記載之構造式不同之化學構造的情況,但若為本發明領域中具有通常知識者,由於可充分認知該等與異構物有關係,故非常清楚為本發明的範圍內。
接著,針對本組成物所包含之化合物(I)之製造方法進行說明。
化合物(I)雖可依照以下所示之反應A~反應O及通常之鹽之製造方法製造,但得到化合物(I)之方法並非被限定於此等之方法者。例如,於苯基及/或吡唑或1,2,4-三唑上之取代基,在本領域,亦可藉由適用周知之各種的取代基變換反應(例如水解、氧化、還原、酯化、醯胺化、烷基化、鹵素化等)來製造。又,在化合物(I)之製造,如有必要可適用在本領域通常所使用之保護及脫保護反應。
Scheme1
Scheme1係藉由反應A或反應B,得到式(4)之化合物至式(I-2)或式(2)之化合物之方法,及藉由反應A或反應B,得到式(I-2)或式(2)之化合物至化合物(I-1)之方法。
式中,A、X、m、R
2、R
3、R
4及R
5係如前述。R
6A為-SO
2CF
3、-C(=O)OZ
3、烷基、烯基、炔基或烷氧基烷基,或為可被Z
2取代之芳烷基,Z
2及Z
3係如前述。L為脫離基,更具體而言,為氯原子、溴原子、碘原子、三氟甲磺醯基。
反應A
反應A為使式(2)之化合物與甲醯化試劑進行反應,而得到化合物(I-1)之方法,或使式(4)之化合物與甲醯化試劑進行反應,而得到式(I-2)之化合物之方法。
反應A通常可於甲醯化試劑及溶媒的存在下進行。
甲醯化試劑若進行反應,則並未特別限定,可列舉甲酸、N-甲醯糖精(Formylsaccharin)等。甲醯化試劑相對於式(2)或式(4)之化合物,可使用1~10當量,期望可使用1~2當量。於此,所謂「當量」,係意指莫耳當量,以下相同。
溶媒若進行反應,則並未特別限定,可從例如如苯、甲苯、二甲苯、氯苯之芳香族烴類;如己烷、庚烷、石油醚、輕汽油、環己烷之脂肪族烴類;如氯仿、二氯甲烷、四氯化碳、1,2-二氯乙烷之鹵素化烴類;如甲酸甲酯、甲酸乙酯、乙酸甲酯、乙酸乙酯之酯類;如甲醇、乙醇、丙醇、tert-丁醇之醇類;如二甲基亞碸、環丁碸、二甲基乙醯胺、N,N-二甲基甲醯胺(以下,亦稱為DMF)、N-甲基四氫吡咯酮、吡啶、乙腈、丙腈之極性非質子性溶媒;如丙酮、甲基乙基酮之酮類;乙酸等,適當選擇1種或2種以上。
反應A如有必要可於如甲酸甲酯、甲酸乙酯之甲酸酯類的存在下進行。
甲酸酯類相對於式(2)或式(4)之化合物,可使用1~50當量,期望可使用1~30當量。
反應A如有必要可於脫水縮合劑及鹼的存在下進行。
脫水縮合劑可列舉N,N’-二環己基碳二亞胺、氯磺醯基異氰酸酯、N,N’-羰基二咪唑、三氟乙酸酐等。脫水縮合劑相對於式(2)或式(4)之化合物,可使用1~5當量,期望可使用1~2當量。
鹼可從例如如鈉、鉀之鹼金屬;如甲醇鈉、乙醇鈉、三級丁酸鉀之鹼金屬醇鹽;如碳酸鈉、碳酸鉀之碳酸鹽;如碳酸氫鈉、碳酸氫鉀之碳酸氫鹽;如氫氧化鈉、氫氧化鉀之金屬氫氧化物;如氫化鈉、氫化鉀之金屬氫化物;如單甲基胺、二甲基胺、三乙基胺之胺類;如吡啶、4-二甲基胺基吡啶之吡啶類;如甲基鋰、n-丁基鋰、鋰二異丙基醯胺之有機鋰化合物等,適當選擇1種或2種以上。鹼相對於式(2)或式(4)之化合物,可使用1~5當量,期望可使用1~2當量。
反應溫度通常約為0℃~200℃,期望約為0℃~100℃。反應時間通常約為1小時~24小時。
於反應A使用之式(2)之化合物可依照以下之反應B製造。
反應B
反應B為使式(I-2)之化合物與式(3)之化合物或保護化試劑進行反應,而得到化合物(I-1)之方法,或使式(4)之化合物與式(3)之化合物或保護化試劑進行反應,而得到式(2)之化合物之方法。
反應B通常可於鹼及溶媒的存在下進行。式(3)之化合物或保護化試劑相對於式(I-2)之化合物或式(4)之化合物,可使用1~5當量,期望可使用1~2當量。
鹼可使用於前述反應A所列舉者。鹼相對於式(I-2)之化合物或式(4)之化合物,可使用1~5當量,期望可使用1~2當量。
前述保護化試劑可從甲氧基甲基氯化物、苄基溴化物、p-甲氧基苄基氯化物、二碳酸二-tert-丁酯、氯甲酸苄酯等中適當選擇。
溶媒若進行反應,則並未特別限定,可從例如如苯、甲苯、二甲苯、氯苯之芳香族烴類;如己烷、庚烷、石油醚、輕汽油、環己烷之脂肪族烴類;如氯仿、二氯甲烷、四氯化碳、1,2-二氯乙烷之鹵素化烴類;如二噁烷、四氫呋喃、二乙基醚、二甲氧基乙烷之醚類;如乙酸甲酯、乙酸乙酯之酯類;如甲醇、乙醇、丙醇、tert-丁醇之醇類;如二甲基亞碸、環丁碸、二甲基乙醯胺、N,N-二甲基甲醯胺、N-甲基四氫吡咯酮、吡啶、乙腈、丙腈之極性非質子性溶媒;如丙酮、甲基乙基酮之酮類;水等,適當選擇1種或2種以上。
反應溫度通常約為-78℃~200℃,期望約為0℃~100℃。反應時間通常約為1小時~48小時。
式(3)之化合物可依照公知之方法製造,或亦可使用市售品。
式(4)之化合物可依照以下之反應H製造。
反應C
反應C係使用式(b-1)之化合物,從式(I-3)之化合物變換成式(I-4)之化合物之方法。
式中,X、m、R
2、R
3、R
4及R
5係如前述。A
1為被氟取代之苯基,A
2為被羥基取代之苯基。R
6a為甲氧基甲基、苄基、p-甲氧基苄基、tert-丁氧基羰基或苄基氧基羰基。式(b-1)中之Me為甲基。
反應C通常可於鹼及溶媒的存在下進行。式(b-1)之化合物相對於式(I-3)之化合物,可使用1~10當量,期望可使用1~5當量。
鹼可使用於前述反應A所列舉者。鹼相對於式(I-3)之化合物,可使用1~10當量,期望可使用1~5當量。
溶媒若進行反應,則並未特別限定,可從例如如苯、甲苯、二甲苯、氯苯之芳香族烴類;如四氯化碳、氯仿、二氯甲烷、二氯乙烷、三氯乙烷、己烷、環己烷之脂肪族烴類;如二噁烷、四氫呋喃、二乙基醚、二甲氧基乙烷之醚類;如乙酸甲酯、乙酸乙酯之酯類;如二甲基亞碸、環丁碸、二甲基乙醯胺、N,N-二甲基甲醯胺、N-甲基四氫吡咯酮、吡啶、乙腈、丙腈之極性非質子性溶媒;如丙酮、甲基乙基酮之酮類等,適當選擇1種或2種以上。
反應溫度通常約為0~150℃,期望約為50~100℃,反應時間通常約為1~24小時左右,期望約為1~12小時左右。
反應D
反應D係使用式(b-2)之化合物、式(b-3)之化合物或鹵烷基化劑,將式(I-4)之化合物變換成式(I-5)之化合物之方法。
式中,X、m、R
2、R
3、R
4、R
5、R
6a、L及A
2係如前述,A
3為被-OR
A-1取代之苯基,R
A-1為烷基或鹵烷基。
反應D通常可於鹼及溶媒的存在下進行。或可依據一般的光延反應(Mitsunobu reaction),於三苯基膦、偶氮二甲酸二乙酯及溶媒的存在下進行。鹵烷基化劑例如可列舉溴二氟甲基三甲基矽烷、托尼(Togni)試劑等。式(b-2)之化合物、式(b-3)之化合物或鹵烷基化劑相對於式(I-4)之化合物,可使用1~3當量,期望可使用1~2當量。三苯基膦相對於式(I-4)之化合物,可使用1~3當量,期望可使用1~1.5當量。偶氮二甲酸二乙酯相對於式(I-4)之化合物,可使用1~3當量,期望可使用1~1.5當量。
鹼可使用於前述反應A所列舉者。鹼相對於式(I-4)之化合物,可使用1~10當量,期望可使用1~5當量。
溶媒可使用前述反應B所列舉者。
反應溫度通常約為-78~100℃,期望約為0~50℃,反應時間通常約為0.1~24小時左右,期望約為0.1~12小時左右。
反應E
反應E係脫保護式(I-5)之化合物,變換成式(I-6)之化合物之方法。
式中之記號係如前述。
反應E可於一般的脫保護反應的條件下進行,例如可列舉酸性條件、氧化條件或接觸還原條件。酸性條件通常可於酸及溶媒的存在下進行,酸可列舉鹽酸、三氟乙酸等。酸相對於式(I-5)之化合物,可使用1~10當量,期望可使用1~3當量。氧化條件通常可於氧化劑及溶媒的存在下進行,氧化劑可列舉2,3-二氯-5,6-二氰基-1,4-苯醌等。氧化劑相對於式(I-5)之化合物,可使用1~5當量,期望可使用1~2當量。接觸還原條件通常可於氫環境下,並於觸媒及溶媒的存在下進行,觸媒可列舉鉑、氧化鉑、鉑黑、雷尼鎳(Raney nickel)、鈀、鈀-碳、銠、銠-氧化鋁等。觸媒相對於式(I-5)之化合物,可使用0.01~1當量,期望可使用0.1~1當量。
溶媒可使用於前述反應B所列舉者。
反應溫度通常約為-30~100℃,期望約為0~50℃,反應時間通常約為0.1~48小時左右,期望約為1~24小時左右。
反應F
反應F係將式(I-8)之化合物變換成式(I-7)之化合物之方法。
式中,X、m、R
2、R
3、R
4、R
5及R
6a係如前述。A
4為被Y取代之苯基,A
5為被R
A-2取代之苯基。Y為鹵素,更具體而言,為氯原子、溴原子或碘原子,R
A-2為烷基、烯基、炔基或環烷基。
反應F通常可藉由將式(I-8)之化合物於過渡金屬觸媒、溶媒及惰性氣體的存在下,如有必要添加鹼,與有機金屬試劑進行反應來進行。
有機金屬試劑若進行反應,則並未特別限定,例如可列舉格氏試劑、有機鋅試劑、有機硼化合物等。此等有機金屬試劑可依照公知之方法調製,或可使用市售品。有機金屬試劑相對於式(I-8)之化合物,可使用1~10當量,期望可使用1~5當量。
過渡金屬觸媒可列舉包含鈀、銠、釕、鎳、鈷、鉬等之過渡金屬的觸媒。過渡金屬觸媒可使用有機鹵素化物之交叉耦合反應所使用之公知的各種構造者,本反應中包含鈀之過渡金屬觸媒特別有用。例如可列舉鈀-碳、氯化鈀、乙酸鈀、二氯雙(乙腈)鈀、雙(二亞苄基丙酮)鈀、二氯雙(三苯基膦)鈀、肆(三苯基膦)鈀、二氯雙(1,4-雙(二苯基膦基)丁烷)鈀等。又,如有必要可將第3級膦或第3級亞磷酸鹽作為配位子使用。作為第3級膦或第3級亞磷酸鹽,可列舉三苯基膦、苯基二甲基膦、三-o-甲苯基膦、三-p-甲苯基膦、1,2-雙(二苯基膦基)乙烷、1,3-雙(二苯基膦基)丙烷、1,4-雙(二苯基膦基)丁烷、1,1’-雙(二苯基膦基)二茂鐵、三苯基亞磷酸鹽等。過渡金屬觸媒相對於式(I-8)之化合物,可使用0.001~0.5當量,期望可使用0.05~0.2當量。又,配位子相對於過渡金屬觸媒1當量,通常可使用1~50當量,期望可使用1~10當量。惟,藉由反應條件亦可使用此範圍外的量。
鹼例如可列舉如碳酸鈉、碳酸鉀、碳酸銫之鹼金屬碳酸鹽;如甲醇鈉、乙醇鈉、三級丁酸鉀之鹼金屬醇鹽;如碳酸氫鈉之鹼金屬的碳酸氫鹽;如碳酸鈣之鹼土類金屬的碳酸鹽;如氫氧化鈉、氫氧化鉀之金屬氫氧化物;如氫化鈉、氫化鉀之金屬氫化物;如三乙基胺、二異丙基乙基胺、吡啶、4-(N,N-二甲基胺基)吡啶、咪唑之有機胺類等。鹼相對於式(I-8)之化合物,可使用1~20當量,期望可使用1~10當量。
溶媒若進行反應,則並未特別限定,可從例如如苯、甲苯、二甲苯、氯苯之芳香族烴類;如四氯化碳、氯仿、二氯甲烷、二氯乙烷、三氯乙烷、己烷、環己烷之脂肪族烴類;如二噁烷、四氫呋喃、二乙基醚、二甲氧基乙烷之醚類;如乙酸甲酯、乙酸乙酯之酯類;如二甲基亞碸、環丁碸、二甲基乙醯胺、N,N-二甲基甲醯胺、N-甲基四氫吡咯酮、吡啶之極性非質子性溶媒;如乙腈、丙腈、丙烯腈之腈類;如丙酮、甲基乙基酮之酮類;如甲醇、乙醇、丙醇、tert-丁醇之醇類;水等,適當選擇1種或2種以上。
惰性氣體例如可列舉氮氣體、氬氣氣體等。
反應溫度通常約為-100~200℃,期望約為 -78~100℃,反應時間通常約為0.5~96小時左右,期望約為1~48小時左右。
反應G
反應G係將式(I-10)之化合物變換成式(I-9)之化合物之方法。
式中,A、X、m、R
2、R
3、R
5及R
6a係如前述。R
4-1為鹵素,更具體而言,為氯原子、溴原子或碘原子。R
4-2為烷基、烯基、炔基或環烷基。
反應G可依照反應F進行。
反應H
反應H係使式(5)之化合物與式(6)之化合物或肼進行反應,而得到式(2)之化合物或式(4)之化合物之方法。
式中之記號係如前述。
反應H通常可於溶媒的存在下進行,或如有必要亦可於酸的存在下進行。式(6)之化合物或肼相對於式(5)之化合物,可使用1~10當量,期望可使用1~3當量。
酸若進行反應,則並未特別限定,可從例如如鹽酸、硫酸之無機酸;如乙酸、丙酸、甲磺酸、p-甲苯磺酸之有機酸等,適當選擇1種或2種以上。酸相對於式(5)之化合物,可使用0.01~2當量,期望可使用0.01~1當量。
溶媒可使用於前述反應B所列舉者。
反應溫度通常約為0℃~200℃,期望約為20℃~150℃。反應時間通常約為1小時~72小時。
於反應H使用之式(5)之化合物可依照以下之反應I或反應J之方法,例如依照美國專利第4829075號說明書等所記載之方法,或依據該等之方法製造。式(6)之化合物可依照公知之方法製造,或亦可使用市售品。
反應I
反應I使式(7)之化合物與式(8)之化合物進行反應,而得到式(5)之化合物之方法。
式中之記號係如前述。
反應I通常可於鹼及溶媒的存在下進行。鹼及溶媒可使用於前述反應B所列舉者。式(8)之化合物相對於式(7)之化合物,可使用1~2當量,期望可使用1~1.2當量。鹼相對於式(7)之化合物,可使用0.5~3當量,期望可使用0.5~1當量。
反應溫度通常約為0℃~150℃,期望可使用0℃~100℃。反應時間通常約為1小時~48小時。
於反應I使用之式(7)之化合物可依照例如日本特開2021-035913號公報、日本特開2021-035914號公報等所記載之方法,或依據該等之方法製造,或亦可使用市售品。式(8)之化合物可依照例如國際公開第2010/029461號、國際公開第2015/095788號、國際公開第2017/019804號等所記載之方法,或依據該等之方法製造,或亦可使用市售品。
反應J
反應J為使式(9)之化合物與式(10)之化合物進行反應,而得到式(5)之化合物之方法。
式中之記號係如前述。
反應J可依照反應B進行。
反應溫度通常約可定為於-78℃~100℃,期望約可定為於-78℃~80℃進行,反應時間通常約可定為1小時~48小時左右,期望約可定為1小時~24小時左右。
於反應J使用之式(9)之化合物可依照以下之反應K製造。式(10)之化合物可依照公知之方法製造,或亦可使用市售品。
反應K
反應K為使式(11)之化合物與式(8)之化合物進行反應,而得到式(9)之化合物之方法。
反應K可依照反應I進行。
於反應K使用之式(11)之化合物,可依照例如國際公開第2010/121022號、European Journal of Medicinal Chemistry、148卷、86~94頁(2018年)等所記載之方法,或依據該等之方法製造,或亦可使用市售品。
反應L
反應L為使式(12)之化合物與式(8)之化合物進行反應,而得到式(I-2)之化合物之方法。
式中之記號係如前述。
反應L通常可於鹼及溶媒的存在下進行。溶媒可使用於前述反應B所列舉者。式(8)之化合物相對於式(12)之化合物,可使用1~2當量,期望可使用1~1.2當量。
鹼可從例如如鈉、鉀之鹼金屬;如甲醇鈉、乙醇鈉、三級丁酸鉀之鹼金屬醇鹽;如碳酸鈉、碳酸鉀之碳酸鹽;如碳酸氫鈉、碳酸氫鉀之碳酸氫鹽;如氫氧化鈉、氫氧化鉀之金屬氫氧化物;如氫化鈉、氫化鉀之金屬氫化物;如單甲基胺、二甲基胺、三乙基胺之胺類;如吡啶、4-二甲基胺基吡啶之吡啶類;如甲基鋰、n-丁基鋰、鋰二異丙基醯胺之有機鋰化合物;如鋰雙(三甲基矽烷基)醯胺、鈉雙(三甲基矽烷基)醯胺、鉀雙(三甲基矽烷基)醯胺之矽化合物等,適當選擇1種或2種以上。鹼相對於式(12)之化合物,可使用0.5~5當量,期望可使用1~2當量。
反應溫度通常約為-20℃~100℃,期望約為0℃~50℃。反應時間通常約為0.1小時~48小時,期望約為0.5小時~24小時。
於反應L使用之式(12)之化合物可依照以下之反應M之方法製造。
反應M
反應M為使式(13)之化合物與鹵素化劑進行反應,而得到式(12)之化合物之方法。
式中之記號係如前述。
反應M通常可於鹵素化劑(例如氯化劑、溴化劑或碘化劑)及溶媒的存在下,如有必要亦可於鹼的存在下進行。鹵素化劑相對於式(13)之化合物,可使用1~2當量,期望可使用1~1.5當量。
作為氯化劑,例如可從氯、N-氯琥珀酸醯亞胺、硫醯氯等適當選擇1種或2種以上,作為溴化劑,例如可從溴、N-溴琥珀酸醯亞胺、三甲基苯基銨三溴化物等適當選擇1種或2種以上,作為碘化劑,例如可從碘、N-碘琥珀酸醯亞胺等適當選擇1種或2種以上。
溶媒若進行反應,則並未特別限定,可從例如如苯、甲苯、二甲苯、氯苯之芳香族烴類;如己烷、庚烷、石油醚、輕汽油、環己烷之脂肪族烴類;如氯仿、二氯甲烷、四氯化碳、1,2-二氯乙烷之鹵素化烴類;如甲酸甲酯、甲酸乙酯、乙酸甲酯、乙酸乙酯之酯類;如二噁烷、四氫呋喃、二乙基醚、二甲氧基乙烷之醚類;如二甲基亞碸、環丁碸、二甲基乙醯胺、N,N-二甲基甲醯胺、N-甲基四氫吡咯酮、吡啶之極性非質子性溶媒;如乙酸、丙酸之有機酸;水等,適當選擇1種或2種以上。
作為鹼,例如可列舉鋰二異丙基醯胺等。鹼相對於式(13)之化合物,可使用1~2當量,期望可使用1~1.2當量。
於鹼的存在下進行時,作為通常溶媒可從如四氫呋喃、二乙基醚之醚類,適當選擇1種或2種以上。
反應M如有必要可將如乙酸、丙酸之有機酸或如氯化鋁之路易斯酸作為觸媒使用。又,藉由過剩使用作為溶媒之有機酸,可兼任觸媒。
反應溫度通常約為-100℃~150℃,期望約為-78℃~100℃。反應時間通常約為0.1小時~48小時,期望約為0.5~24小時。於鹼的存在下進行時,反應溫度通常約為-100℃~50℃,期望約為-78℃~20℃,反應時間通常約為0.1~12小時,期望約為0.5~6小時,又,於酸的存在下進行時,反應溫度通常約為0℃~150℃,期望約為20℃~120℃,反應時間通常約為0.1~48小時,期望約為1~24小時。
於反應M使用之式(13)之化合物可依照以下之反應N或反應О之方法製造。
反應N
反應N為使式(14)之化合物與甲醯化試劑進行反應,而得到式(13)之化合物之方法。
式中之記號係如前述。
反應N可依照反應A進行。又,作為於反應N使用之甲醯化試劑,可列舉於反應A例示之化合物。
於反應N使用之式(14)之化合物可依照以下之反應О之方法製造。
反應О
反應О為使式(15)之化合物與式(16)之化合物或肼進行反應,而得到式(13)之化合物或式(14)之化合物之方法。
式中之記號係如前述。
反應О可依據反應H進行。
於反應О使用之式(15)之化合物,可依照例如日本特開2021-035913號公報、日本特開2021-035914號公報、國際公開第2006/016708號等所記載之方法,或依據該等之方法製造,或亦可使用市售品。式(16)之化合物可依照公知之方法製造,或亦可使用市售品。
針對本組成物之施用場面、施用形態、處理方法等進行說明。
可藉由對線蟲直接及/或線蟲之棲息場所的土壤或植物體,施用有效量之本組成物,防除線蟲。前述棲息場所不僅是線蟲棲息中的場所,亦包含預想到棲息的場所。前述植物體係意指施用本組成物之植物的地上部(例如莖、葉、樹幹)、地下部(例如根部)或種子。前述種子係意指藉由有性生殖所形成之散布體(即所謂種子)、植物之器官(例如塊莖、鱗莖、球莖、根莖、種芋),或果樹類、花木類或花卉類之插穗(例如果樹類之葡萄枝等)等。
本組成物可防除例如屬於根結線蟲(Meloidogyne)屬線蟲、短體線蟲(Pratylenchus)屬線蟲、莖線蟲(Ditylenchus)屬線蟲、異皮線蟲(Heterodera)屬線蟲、球異皮線蟲(Globodera)屬線蟲、葉芽線蟲(Aphelenchoides)屬線蟲、真滑刃線蟲(Aphelenchus)屬線蟲、穿孔線蟲(Radopholus)屬線蟲、小墊刃(Tylenchulus)屬線蟲、腎形線蟲(Rotylenchulus)屬線蟲、盤旋線蟲(Rotylenchus)屬線蟲、Anguina屬線蟲、刺線蟲(Belonolaimus)屬線蟲、傘滑刃(Bursaphelenchus)屬線蟲、Criconema屬線蟲、輪線蟲(Criconemoides)屬線蟲、Mesocriconema屬線蟲、錐線蟲(Dolichodorus)屬線蟲、螺旋線蟲(Helicotylenchus)屬線蟲、潛根線蟲(Hirschmanniella)屬線蟲、紐帶線蟲(Hoplolaimus)屬線蟲、珍珠線蟲(Nacobbus)屬線蟲、長針線蟲(Longidorus)屬線蟲、盾線蟲(Scutellonema)屬線蟲、毛刺線蟲(Trichodorus)屬線蟲、擬毛刺線蟲(Paratrichodorus)屬線蟲、矮化線蟲(Tylenchorhynchus)屬線蟲、劍線蟲(Xiphinema)屬線蟲等之線蟲,其中,對屬於根結線蟲(Meloidogyne)屬線蟲、短體線蟲(Pratylenchus)屬線蟲、異皮線蟲(Heterodera)屬線蟲、球異皮線蟲(Globodera)屬線蟲等之線蟲的防除特別有效。
前述線蟲之具體的例,例如可列舉如以下者等。
如根結線蟲(Meloidogyne incognita)、北方根瘤線蟲(Meloidogyne hapla)、花生根結線蟲(Meloidogyne arenaria)、根瘤線蟲(Meloidogyne javanica)之根結線蟲(Meloidogyne)屬線蟲類、如穿刺短體線蟲(Pratylenchus penetrans)、根腐線蟲(Pratylenchus coffeae)、盧斯短體線蟲(Pratylenchus loosi)、核桃根腐線蟲(Pratylenchus vulnus)等之短體線蟲(Pratylenchus)屬線蟲類、如甘薯莖線蟲(Ditylenchus destructor)、鱗球莖莖線蟲(Ditylenchus dipsaci)等之莖線蟲(Ditylenchus)屬線蟲類、如大豆異皮線蟲(Heterodera glycines)、甜菜包囊線蟲(Heterodera schachtii)、三葉草包囊線蟲(Heterodera trifolii)等之異皮線蟲(Heterodera)屬線蟲類、如馬鈴薯金線蟲(Globodera rostochiensis)、馬鈴薯白線蟲(Globodera pallida)等之球異皮線蟲(Globodera)屬線蟲類、如貝西滑刃線蟲(Aphelenchoides besseyi)、草莓滑刃線蟲(Aphelenchoides fragariae)、菊花滑刃線蟲(Aphelenchoides ritzemabosi)等之葉芽線蟲(Aphelenchoides)屬線蟲類、如燕麥真滑刃線蟲(Aphelenchus avenae)等之真滑刃線蟲(Aphelenchus)屬線蟲類、如香蕉穿孔線蟲(Radopholus similis)等之穿孔線蟲(Radopholus)屬線蟲類、如柑桔線蟲(Tylenchulus semipenetrans)等之小墊刃(Tylenchulus)屬線蟲類、如腎形線蟲(Rotylenchulus reniformis)等之腎形線蟲(Rotylenchulus)屬線蟲類、如Rotylenchus robustus等之盤旋線蟲(Rotylenchus)屬線蟲類、如小麥腫癭線蟲(Anguina tritici)等之Anguina屬線蟲類、如長尾刺線蟲(Belonolaimus longicaudatus)之刺線蟲(Belonolaimus)屬線蟲類、如松材線蟲(Bursaphelenchus xylophilus)、挪子紅環腐線蟲(Bursaphelenchus cocophilus)之傘滑刃(Bursaphelenchus)屬線蟲類、如Criconema jaejuense、Criconema palliatum等之環紋線蟲(Criconema)屬線蟲類、如Criconemoides informis、Criconemoides morgensis等之輪線蟲(Criconemoides)屬線蟲類、如環腐線蟲(Mesocriconema xenoplax)、Mesocriconema curvatum等之中環線蟲(Mesocriconema)屬線蟲類、如隱鼠錐線蟲(Dolichodorus heterocephalus)等之錐線蟲(Dolichodorus)屬線蟲類、如偽強螺旋線蟲(Helicotylenchus pseudorobustus)、多節螺旋線蟲(Helicotylenchus multicinctus)等之螺旋線蟲(Helicotylenchus)屬線蟲類、如Hirschmanniella diversa、稻根線蟲(Hirschmanniella oryzae)等之潛根線蟲(Hirschmanniella)屬線蟲類、如哥倫布冠線蟲(Hoplolaimus columbus)、棉花長矛冠線蟲(Hoplolaimus magnistylus)等之紐帶線蟲(Hoplolaimus)屬線蟲類、如異常珍珠線蟲(Nacobbus aberrans)、Nacobbus dorsalis等之珍珠線蟲(Nacobbus)屬線蟲類、如水稻矮化線蟲(Longidorus martini)、Longidorus diadecturus等之長針線蟲(Longidorus)屬線蟲類、如卡羅萊納螺旋形線蟲(Scutellonema brachyurum)、山藥螺旋性線蟲(Scutellonema bradys)等之盾線蟲(Scutellonema)屬線蟲類、如Trichodorus cedarus等之毛刺線蟲(Trichodorus)屬線蟲類、如多孔擬針線蟲(Paratrichodorus porosus)、次要擬針線蟲(Paratrichodorus minor)等之擬毛刺線蟲(Paratrichodorus)屬線蟲類、如菸草矮化線蟲(Tylenchorhynchus claytoni)等之矮化線蟲(Tylenchorhynchus)屬線蟲類、如匕首線蟲(Xiphinema index)、美洲劍線蟲(Xiphinema americanum)等之劍線蟲(Xiphinema)屬線蟲類等。
施用本組成物之植物若為農園藝上有用者,雖並未特別限制,但例如可列舉蕃茄、小蕃茄、青椒、茄子、黃瓜、夏南瓜、西瓜、甜瓜、南瓜、秋葵、胡椒、越瓜、冬瓜、苦瓜、東方甜瓜等之果菜類、萵苣、橡葉萵苣、菠菜、甘藍、洋蔥、大蒜、蘆筍、青花菜、花椰菜、白菜、落葵、大蔥、水菜、紫蘇、小松菜、芹菜等之葉菜類、馬鈴薯、甘藷、白蘿蔔、胡蘿蔔、牛蒡、蓮藕、芋頭、蒟蒻、日本薯蕷、薑、蕪菁、薤、蘘荷、森薊等之根菜類、大豆、紅豆、豌豆、菜豆、花生、蠶豆、毛豆等之豆類、稻、小麥、燕麥、黑麥、玉蜀黍等之穀類、蘋果、柑橘類、梨、葡萄、草莓、核桃、杏仁、香蕉、無花果、鳳梨、桃、油桃、櫻桃、杏、椰子、酪梨、柿子、李子、開心果、奇異果、枇杷等之果樹・果實・種實類、細葉結縷草、翦股穎草等之草類、菊花、百合、玫瑰、康乃馨、大麗花、非洲菊、非洲堇、鬱金香、水仙、矮牽牛、鈴蘭、牡丹、仙客來、鳳仙花、洋桔梗等之花卉類、松樹、杉樹、柏樹、杜鵑花等之樹木・花木類、棉花、菜種、甜菜、茶、煙草、咖啡、橄欖、甘蔗、蛇麻、芝麻、香芹、百里香、迷迭香、羅勒、薰衣草等之工藝作物類、蘭花、仙人掌類、蕨類植物類等之觀葉植物、三葉草、苜蓿、鴨茅、石茅等之牧草類等之植物。
尚,此等植物中包含將對於除草劑(例如抑殺特(Isoxaflutol)等之HPPD抑制劑;依滅草(Imazethapyr)、噻吩磺隆(Thifensulfuron Methyl)等之ALS抑制劑;嘉磷塞等之EPSP合成酶抑制劑;草銨膦等之麩醯胺酸合成酶抑制劑、西殺草(Sethoxydim)等之乙醯輔酶A羧化酶抑制劑;溴苯腈;麥草畏;2,4-D等)之耐性藉由古典的育種法所賦予之植物。進而,本發明之有用植物中亦包含藉由基因重組技術或基因編集技術所作出之轉基因植物。作為轉基因植物之一例,亦包含對前述除草劑有耐性之轉基因植物、害蟲抵抗性之轉基因植物、關於植物成分之轉基因植物、植物病原耐性之轉基因植物等。
本組成物雖通常混合化合物(I)與各種農園藝用之輔助劑,製劑成粉劑、粒劑、顆粒水合劑、水合劑、水性懸濁劑、油性懸濁劑、水溶劑、乳劑、液劑、膏劑、氣溶膠劑、微量散布劑等之各種的形態來使用,但只要適合本發明之目的,可成為使用在通常之該領域每一個製劑形態。其中,從對土壤之施用方法的點來看,較佳為粒劑、水性懸濁劑、油性懸濁劑、乳劑或液劑。作為使用在製劑之輔助劑,可列舉如矽藻土、消石灰、碳酸鈣、滑石、白碳、高嶺土、膨潤土、高嶺石、絹雲母、黏土、碳酸鈉、小蘇打、芒硝、沸石、澱粉等之固形載體;水、甲苯、二甲苯、溶劑石腦油、二噁烷、丙酮、異佛爾酮、甲基異丁基酮、氯苯、環己烷、二甲基亞碸、N,N-二甲基甲醯胺、N,N-二甲基乙醯胺、N-甲基-2-四氫吡咯酮、醇等之溶劑;脂肪酸鹽、苯甲酸鹽、烷基磺基琥珀酸鹽、二烷基磺基琥珀酸鹽、聚羧酸鹽、烷基硫酸酯鹽、烷基硫酸鹽、烷基芳基硫酸鹽、烷基二甘醇醚硫酸鹽、醇硫酸酯鹽、烷基磺酸鹽、烷基芳基磺酸鹽、芳基磺酸鹽、木質素磺酸鹽、烷基二苯基醚二磺酸鹽、聚苯乙烯磺酸鹽、烷基磷酸酯鹽、烷基芳基磷酸鹽、苯乙烯基芳基磷酸鹽、聚氧乙烯烷基醚硫酸酯鹽、聚氧乙烯烷基芳基醚硫酸鹽、聚氧乙烯烷基芳基醚硫酸酯鹽、聚氧乙烯烷基醚磷酸鹽、聚氧乙烯烷基芳基磷酸酯鹽、萘磺酸鹽甲醛縮合物之陰離子系的界面活性劑;如山梨糖醇脂肪酸酯、甘油脂肪酸酯、脂肪酸甘油酯、脂肪酸醇聚甘醇醚、乙炔二醇、乙炔醇、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、聚氧乙烯甘醇烷基醚、聚乙二醇、聚氧乙烯脂肪酸酯、聚氧乙烯山梨糖醇脂肪酸酯、聚氧乙烯甘油脂肪酸酯、聚氧乙烯硬化蓖麻油、聚氧丙烯脂肪酸酯之非離子系的界面活性劑;橄欖油、木棉油、蓖麻油、棕櫚油、茶籽油、椰子油、芝麻油、玉米油、米糠油、花生油、棉籽油、大豆油、菜籽油、亞麻籽油、桐油、液狀石蠟等之植物油或礦物油;等。此等輔助劑之各成分只要不脫離本發明之目的,可適當選擇1種或2種以上使用。又,亦可於前述之輔助劑以外從該領域所知悉者當中適當選擇使用,例如亦可使用增量劑、增黏劑、防沉劑、防凍劑、分散安定劑、藥害減輕劑、防黴劑等通常所使用之各種輔助劑。化合物(I)與各種輔助劑的摻合比例(化合物(I):輔助劑)以聚合比,一般為0.001:99.999~ 95:5,期望可使用0.005:99.995~90:10。進行此等製劑之實際的使用時,可直接使用,或使用水等之稀釋劑,稀釋成指定濃度,如有必要亦可添加各種展著劑(界面活性劑、植物油、礦物油等)來使用。
本組成物的施用雖因氣象條件、製劑形態、對象作物、施用時期、施用場所、線蟲的種類或產生狀況等之差異無法一概而定,但通常一般進行之施用方法,亦即可藉由土壤處理、莖葉處理、灌溉處理、種子處理、樹幹注入處理或水稻育苗箱施用等,進行本組成物或其稀釋物之施用。一般而言,為土壤處理、莖葉處理、灌溉處理時,其施用適量為每1公頃,本組成物約可定為0.01g~ 50,000g,期望約可定為1g~30,000g。為種子處理時,其施用適量可定為每1kg之種子約為0.01g~200g,期望約可定為0.05~100g。為水稻育苗箱施用時,其施用適量可定為每1個育苗箱,本組成物約可定為0.001g~3,000g,期望約可定為0.01g~1,000g。為樹幹注入處理時,其施用適量每1樹,本組成物約可定為0.001g~5,000g,期望約可定為0.01g~3,000g左右。
所謂土壤處理,例如可列舉調製成液體製劑(液劑、水性懸濁劑、油性懸濁劑、乳劑等)或固形製劑(粒劑、粉劑、水合劑、水溶劑、顆粒水合劑、顆粒水溶劑等)等,直接或稀釋在水,並於植物體之移植前或播種前,散布並混和在土壤全面之方法、為了種植植物體,而散布在打開之孔當中(種植孔)之方法,或為了播種或種植植物體,而散布在挖出一定寬度的淺溝之方法等。
所謂莖葉處理,例如可列舉將本組成物調製成液體製劑(液劑、水性懸濁劑、油性懸濁劑、乳劑等)或固形製劑(水合劑、水溶劑、顆粒水合劑、顆粒水溶劑等)等,並稀釋在水,散布在植物體全體之方法等。
所謂灌溉處理,例如可列舉將本組成物調製成液體製劑(液劑、水性懸濁劑、油性懸濁劑等)或固形製劑(水合劑、水溶劑、顆粒水合劑、顆粒水溶劑等)等,並直接或稀釋在水,灌溉在育苗用之栽培容器、栽培中之植物體的植株源頭或其附近等之方法等。
所謂種子處理,例如可列舉將本組成物調製成液體製劑(水性懸濁劑、油性懸濁劑、乳劑、液劑等)或固形製劑(粉劑、水合劑、水溶劑、顆粒水合劑、顆粒水溶劑等),並直接或稀釋在水,與種子進行攪拌而附著在種子表面之方法;與塗佈資材一起混和,並附著在種子的表面之方法;吹附在種子並使其附著之方法;浸漬種子,並浸透藥劑之方法等。
所謂水稻育苗箱施用,例如亦可列舉將本組成物調製成固形製劑(粒劑、粉劑等)或液體製劑(水性懸濁劑、油性懸濁劑、液劑等)等,並直接或稀釋在水,於播種之前、播種之後、播種之前後兩者、於育苗箱之生育時,或對水田之移植前,對育苗箱散布之方法。而且,對育苗箱播種時與培土的混和,例如將本組成物調製成固形製劑(粒劑、粉劑、顆粒水合劑等),並混和在床土、覆土或培土的全體之方法等。
所謂樹幹注入處理,例如可列舉將本組成物調製成液體製劑(液劑等)等,直接從開在樹幹之孔,注入在植物體之方法等。
本組成物可與選自其他農園藝用藥劑、肥料、藥害減輕劑等中之其他成分混用或併用,此情況下,有顯示更為優異之效果、作用性的情況。
前述所謂混用或併用,係意指將本組成物與其他成分在同時、分別或時間間隔上使用。
其他農園藝用藥劑,可列舉除草劑、殺蟲劑、殺蟎劑、殺線蟲劑、殺土壤害蟲劑、殺菌劑、抗病毒劑、引誘劑、抗生物質、植物荷爾蒙、植物成長調整劑等。特別是混用或併用本組成物以及其他殺蟲劑及/或殺線蟲劑的有效成分化合物之1種或2種以上的混合殺線蟲組成物,有將適用範圍、藥劑處理的時期、防除活性等往較佳之方向改良的情況。尚,可將本組成物以及其他殺蟲劑,及/或殺線蟲劑的有效成分化合物,於散布時混合各自分別製劑者來使用,亦可一起製劑兩者來使用。本發明中亦包含這般的混合殺線蟲組成物。
與化合物(I)以及其他殺蟲劑,及/或殺線蟲劑的有效成分化合物之混合比(化合物(I):有效成分化合物),雖因氣象條件、製劑形態、對象作物、施用時期、施用場所、線蟲的種類或產生狀況等之差異無法一概而定,但以重量比,一般可定為1:300~300:1,期望可定為1:100~100:1。又,施用適量可定為每1公頃之總有效成分化合物量為0.1~70,000g,期望可定為5~50,000g。本發明中亦包含藉由這般的混合殺線蟲組成物的施用之線蟲之防除方法,或視情況,亦包含線蟲及害蟲之防除方法。
前述害蟲之更具體的例,例如可列舉如以下者等。
如桃蚜、綿蚜等之蚜蟲類;如小菜蛾、甘藍夜蛾、斜紋夜盜蛾、蘋果蠹蛾、棉鈴蟲、番茄夜蛾、舞毒蛾、瘤野螟、捲葉蛾、小地老虎、鬱金香蛾等之鱗翅目害蟲類;如科羅拉多金花蟲、黃守瓜、艷金龜類等之甲蟲目害蟲類;如褐飛蝨、白背飛蝨等之飛蝨類;如葉蟬類;如介殼蟲類;椿象類;菸草粉蝨等之粉蝨類;如薊馬類;蚱蜢類;如花蠅類;蟻類;蛞蝓、蝸牛等之腹足類;如二斑葉蟎、赤葉蟎、神澤氏葉蟎、柑桔葉蟎、歐洲葉蟎、多食細蟎、桔刺皮節蜱、紅蜱、粉蟎等之植物寄生性蟎類;如鼠婦、糙瓷鼠婦等之等足類;等之害蟲等。
通過含有化合物(I)之殺線蟲組成物的施用,亦可進一步合併其他農園藝用藥劑、例如殺菌劑、殺蟲劑、殺蟎劑、殺線蟲劑、殺土壤害蟲劑、抗病毒劑、引誘劑、除草劑、植物成長調整劑等進行處理。
所謂上述其他農園藝用藥劑中之殺蟲劑、殺線蟲劑、殺蟎劑或殺土壤害蟲劑的有效成分化合物(一般名或日本植物防疫協會試驗代碼),例如可適當選自下述之化合物群組中。即使為未特別記載的情況,於此等化合物存在如鹽、烷基酯、光學異構物之各種構造異構物等時,當然亦包含該等。
如佈飛松(profenofos)、二氯松(dichlorvos)、芬滅松(fenamiphos)、撲滅松(fenitrothion)、EPN(O-乙基-O-4-硝基苯基苯基硫代磷酸酯、O-ethyl-O-4-nitrophenyl phenylphosphonothioate)、二嗪農(diazinon)、陶斯松(chlorpyrifos)、陶斯松・甲基(chlorpyrifos-methyl)、毆殺松(acephate)、普硫松(prothiofos)、福賽絕(fosthiazate)、硫線磷(cadusafos)、二硫松(disulfoton)、加福松(isoxathion)、亞芬松(isofenphos)、愛殺松(ethion)、益多松(etrimfos)、拜裕松(quinalphos)、甲基毒蟲畏(dimethylvinphos)、大滅松(dimethoate)、海羅松(sulprofos)、硫滅松(thiometon)、繁米松(vamidothion)、白克松(pyraclofos)、必芬松(pyridaphenthion)、亞特松(pirimiphos-methyl)、加護松(propaphos)、裕必松(phosalone)、福木松(formothion)、馬拉松(malathion)、樂本松(tetrachlorvinphos)、克芬松(chlorfenvinphos)、氰乃松(cyanophos)、三氯松(trichlorfon)、滅大松(methidathion)、賽達松(phenthoate)、ESP(異亞碸磷、oxydeprofos)、谷速松・甲基(azinphos-methyl)、芬殺松(fenthion)、飛達松(heptenophos)、甲氧基氯(methoxychlor)、巴拉松(parathion)、磷蟲威(phosphocarb)、滅賜松(demeton-S-methyl)、亞速靈(monocrotophos)、達馬松(methamidophos)、依米賽松(imicyafos)、巴拉松-甲基(parathion-methyl)、托福松(terbufos)、福賜米松(phosphamidon)、益滅松(phosmet)、福瑞松(phorate)之有機磷酸酯系化合物;
如加保利(carbaryl)、安丹(propoxur)、得滅克(aldicarb)、加保扶(carbofuran)、硫敵克(thiodicarb)、納乃得(methomyl)、歐殺滅(oxamyl)、愛芬克(ethiofencarb)、比加普(pirimicarb)、仲丁威(fenobucarb)、丁基加保扶(carbosulfan)、免扶克(benfuracarb)、免敵克(bendiocarb)、扶線威(furathiocarb)、滅必蝨(isoprocarb)、治滅蝨(metolcarb)、滅殺威(xylylcarb)、XMC(3,5-二甲苯基胺基甲酸甲酯、3,5-xylyl methylcarbamate)、苯硫威(fenothiocarb)之胺基甲酸酯系化合物;
如培丹(cartap)、硫賜安(thiocyclam)、硫賜安鹽酸鹽(thiocyclam hydrochloride)、免速達(bensultap)、硫速達(thiosultap)、殺蟲單(monosultap;別名硫速達單鈉(thiosultap-monosodium)、殺蟲雙(bisultap;別名硫速達二鈉(thiosultap-disodium)、多噻烷(polythialan)之沙蠶毒素衍生物;
如大克蟎(dicofol)、四氯殺蟎碸(tetradifon)、安殺番(endosulfan)、得氯蟎(dienochlor)、特地靈(dieldrin)之有機氯系化合物;
如芬化利(fenvalerate)、百滅靈(permethrin)、賽滅寧(cypermethrin)、α-賽滅寧(alpha-cypermethrin)、ζ-賽滅寧(zeta-cypermethrin)、θ-賽滅寧(theta-cypermethrin)、β-賽滅寧(beta-cypermethrin)、第滅靈(deltamethrin)、三氟氯氰菊酯(cyhalothrin)、γ-三氟氯氰菊酯(gamma-cyhalothrin)、λ-三氟氯氰菊酯(lambda-cyhalothrin)、七氟菊酯(tefluthrin)、κ-七氟菊酯(kappa-tefluthrin)、依芬寧(ethofenprox)、三氟醚菊酯(flufenprox)、氟氯氰菊酯(cyfluthrin)、β-氟氯氰菊酯(beta-cyfluthrin)、甲氰菊酯(fenpropathrin)、氟氰戊菊酯(flucythrinate)、氟氰胺菊酯(fluvalinate)、乙氰菊酯(cycloprothrin)、除蟲菊素(pyrethrins)、氰戊菊酯(esfenvalerate)、胺菊酯(tetramethrin)、苄呋菊酯(resmethrin)、普提芬布(protrifenbute)、畢芬寧(bifenthrin)、κ-畢芬寧(kappa-bifenthrin)、氟丙菊酯(acrinathrin)、丙烯菊酯(allethrin)、氟胺氰戊菊酯(tau-fluvalinate)、四溴菊酯(tralomethrin)、丙氟菊酯(profluthrin)、甲氧苄氟甲酯(metofluthrin)、ε-甲氧苄氟甲酯(epsilon-metofluthrin)、右旋七氟甲醚菊酯(heptafluthrin)、苯醚菊酯(phenothrin)、氯苯菊酯(flumethrin)、沒氟菊酯(momfluorothrin)、矽護芬(silafluofen)之除蟲菊酯系化合物;
如二福隆(diflubenzuron)、克福隆(chlorfluazuron)、得福隆(teflubenzuron)、氟芬隆(flufenoxuron)、祿芬隆(lufenuron)、諾伐隆(novaluron)、三褔隆(triflumuron)、六褔隆(hexaflumuron)、雙三氟蟲脲(bistrifluron)、諾唯褔隆(noviflumuron)、氟札隆(fluazuron)、氟芬隆(flufenoxuron)之苯甲醯脲系化合物;
如美賜平(methoprene)、百利普芬(pyriproxyfen)、芬諾克(fenoxycarb)、二苯丙醚(diofenolan)之幼年荷爾蒙類化合物;
如嗒蟎酮(pyridaben)之噠嗪系化合物;
如芬普蟎(fenpyroximate)、芬普尼(fipronil)、乙蟲腈(ethiprole)、乙醯蟲腈(acetoprole)、吡蟲腈(pyrafluprole)、吡瑞蟲腈(pyriprole)、塞比芬(cyenopyrafen)、丁烯氟蟲腈(flufiprole)、吡蟎胺(tebufenpyrad)、唑蟲醯胺(tolfenpyrad)之吡唑系化合物;
如氯蟲醯胺(chlorantraniliprole)、氰蟲醯胺
(cyantraniliprole)、環溴蟲醯胺(cyclaniliprole)、氟氰蟲醯胺(tetraniliprole)、氟蟲胺(flubendiamide)、四氯蟲醯胺(tetrachlorantraniliprole)、氯氟氰蟲醯胺(cyhalodiamide)、氟氯蟲雙醯胺(fluchlordiniliprole)、tiorantraniliprole之二醯胺系化合物;
如益達胺(imidacloprid)、烯啶蟲胺(nitenpyram)、亞滅培(acetamiprid)、噻蟲啉(thiacloprid)、噻蟲嗪(thiamethoxam)、可尼丁(clothianidin)、呋蟲胺(dinotefuran)、硝蟲噻嗪(nithiazine)之新菸鹼系化合物;
如得芬諾(tebufenozide)、美芬諾(methoxyfenozide)、可芬諾(chromafenozide)、氯蟲醯肼(halofenozide)之肼系化合物;
如三氟甲吡醚(pyridalyl)、氟尼胺(flonicamid)之吡啶系化合物;
如賜派芬(spirodiclofen)、螺甲蟎酯(spiromesifen)、spirobudifen之丁炔酸系化合物;
如螺蟲乙酯(spirotetramat)、賜派酮(spiropidion)之四胺酸系化合物;
如嘧蟎酯(fluacrypyrim)、嘧蟎胺(pyriminostrobin)之甲氧基丙烯酸酯(Strobilurin)系化合物;
如氟芬林(flufenerim)、嘧蟎醚(pyrimidifen)之嘧啶胺(Pyrimidinamine)系化合物;
如賽滅淨(cyromazine)之三嗪系化合物;
如愛美松(hydramethylnon)之腙系化合物;
如殺蟎隆(diafenthiuron)、滅蟲脲(chloromethiuron)之硫脲系化合物;
如三亞蟎(amitraz)、殺蟲脒(chlordimeform)、滅蟎脒(chloromebuform)之甲脒(Formamidine)系化合物;
如吡蚜酮(pymetrozine)、哌氟喹腙(pyrifluquinazone)之吡啶偶氮甲鹼(Azomethine)系化合物;
如福沙那(afoxolaner)、氟拉尼(fluralaner)、氟米塔麥(fluxametamide)、賽蘭(sarolaner)之異㗁唑啉(Isoxazoline)系化合物;
又,作為其他化合物,有如布酚淨(buprofezin)、噻蟎酮(hexythiazox)、唑蚜威(triazamate)、蟲蟎腈(chlorfenapyr)、茚蟲威(indoxacarb)、亞醌蟎(acequinocyl)、依殺蟎(etoxazole)、1,3-二氯丙烯(1,3-dichloropropene)、苯克提(benclothiaz)、聯苯肼(bifenazate)、毆蟎多(propargite)、克芬蟎(clofentezine)、氰氟蟲腙metaflumizone)、丁氟蟎酯(cyflumetofen)、芬殺蟎(fenazaquin)、醯胺氟美(amidoflumet)、氟蟲胺(sulfluramid)、愛美松(hydramethylnon)、介乙醛(metaldehyde)、速殺氟(sulfoxaflor)、氟速芬(fluensulfone)、唯布汀(verbutin)、二克滅(dicloromezotiaz)、三氟苯嘧啶(triflumezopyrim)、氟殺逢(fluhexafon)、替奧沙芬(tioxazafen)、雙丙環蟲酯(afidopyropen)、氟米克(flometoquin)、氟吡呋喃酮(flupyradifurone)、氯氟氰蟲醯胺(fluazaindolizine)、阿克那比(acynonapyr)、苯吡莫賽(benzpyrimoxan)、氟必靈(flupyrimin)、歐賽菲(oxazosulfyl)、吡啶菌醯胺(tyclopyrazoflor)、溴氟苯胺(broflanilide)、異環賽蘭(isocycloseram)、吡蟲啉(dimpropyridaz)、氟戊芬諾(flupentiofenox)、尼可氟酮(nicofluprole)、吉伏苯胺(cyproflanilide)、螺環季酮酸酯(spidoxamat)、環丁三氟胺(cyclobutrifluram)、芬米地佐(fenmezoditiaz)、trifluenfuronate之化合物等。
又,本發明化合物可與下述化合物組合來施用。
如蘇力菌之Bacillus thuringiensis aizawai、Bacillus thuringiensis kurstaki、Bacillus thuringiensis israelensis、Bacillus thuringiensis japonensis、Bacillus thuringiensis tenebrionis、Bacillus thuringiensis、淡紫色擬青黴(Paecilomyces lilacinus)、甲基營養型芽孢桿菌(Bacillus methylotrophicus)、枯草桿菌(Bacillus subtilis)、液化澱粉芽孢桿菌(Bacillus amyloliquefaciens)、地衣芽孢桿菌(Bacillus licheniformis)、堅強芽孢桿菌(Bacillus firmus)、西澤巴氏桿菌(Pasteuria nishizawae)、疣孢漆斑菌(Myrothecium verrucaria)、伯克氏菌(Burkholderia rinojensis),或沙加色桿菌(Chromobacterium subtsugae)所生成之結晶蛋白毒素、昆蟲病原病毒劑、昆蟲病原糸狀菌劑、線蟲病原糸狀菌劑等之微生物農藥;
如阿巴汀(abamectin)、因滅汀苯甲酸鹽(emamectin benzoate)、伊維菌素(ivermectin)、密滅汀(milbemectin)、倍脈心(milbemycin oxime)、列比美汀(lepimectin)、賜諾殺(spinosad)、賜諾特(spinetoram)之抗生物質及半合成抗生物質;
上述其他農園藝用藥劑中之殺菌劑的有效成分化合物(一般名或日本植物防疫協會試驗代碼),例如可適當選自下述之化合物群組中。即使為未特別記載的情況,於此等化合物存在如鹽、烷基酯、光學異構物之各種構造異構物等時,當然亦包含該等。
如滅派林(mepanipyrim)、嘧黴胺(pyrimethanil)、賽普洛(cyprodinil)之苯胺嘧啶(Anilinopyrimidine)系化合物;
如愛特丁(ametoctradin)之三唑并嘧啶(Triazolopyrimidine)系化合物;
如扶吉胺(fluazinam)之吡啶胺(Pyridinamine)系化合物;
如三泰芬(triadimefon)、比多農(bitertanol)、氟菌唑(triflumizole)、乙環唑(etaconazole)、丙環唑(propiconazole)、戊菌唑(penconazole)、氟矽唑(flusilazole)、邁克尼(myclobutanil)、環克唑(cyproconazole)、戊唑醇(tebuconazole)、己唑醇(hexaconazole)、順呋醚唑(furconazole-cis)、咪鮮安(prochloraz)、滅特唑(metconazole)、氟環唑(epoxiconazole)、氟醚唑(tetraconazole)、反丁烯二酸噁咪唑(oxpoconazole fumarate)、丙硫菌唑(prothioconazole)、三唑醇(triadimenol)、粉唑醇(flutriafol)、待克利(difenoconazole)、氟喹唑(fluquinconazole)、腈苯唑(fenbuconazole)、糠菌唑(bromuconazole)、烯唑醇(diniconazole)、三環唑(tricyclazole)、矽氟唑(simeconazole)、稻瘟酯(pefurazoate)、種菌唑(ipconazole)、醯胺唑(imibenconazole)、戊環唑(azaconazole)、滅菌唑(triticonazole)、依滅列(imazalil)、抑吩伏唑(ipfentrifluconazole)、甲分三康唑
(mefentrifluconazole)之唑系化合物;
如滅蟎猛(quinomethionate)之喹喔啉系化合物;
如代森猛(maneb)、代森鋅(zineb)、代森錳鋅(mancozeb)、聚胺基甲酸酯(polycarbamate)、代森聯(metiram)、丙森鋅(propineb)、福美雙(thiram)之二硫代胺基甲酸酯系化合物;
如四氯苯酞(fthalide)、四氯異苯(chlorothalonil)、五氯硝基苯(quintozene)之有機氯系化合物;
如苯菌靈(benomyl)、甲基硫菌靈(thiophanate-methyl)、多菌靈(carbendazim)、噻菌靈(thiabendazole)、福貝唑(fuberiazole)之咪唑系化合物;
如霜脲氰(cymoxanil)之氰基乙醯胺系化合物;
如甲霜靈(metalaxyl)、甲霜靈-M(metalaxyl-M;別名精甲霜靈(mefenoxam))、悉霜靈(oxadixyl)、甲呋醯胺(ofurace)、苯霜靈(benalaxyl)、精苯霜靈(benalaxyl-M、別名可瑞西(kiralaxyl、chiralaxyl))、呋霜靈(furalaxyl)、精高效氯氟氰菊酯(valifenalate)之醯基胺基酸系化合物;
如酯菌胺(cyprofuram)、萎銹靈(carboxin)、氧化萎銹靈(oxycarboxin)、噻呋醯胺(thifluzamide)、白克列(boscalid)、環醯菌胺(fenhexamid)、異噻菌胺(isotianil)、噻醯菌胺(tiadinil)、必福滅(pyraziflumid)之苯胺系化合物;
如苯氟醯胺(dichlofluanid)之磺醯胺系化合物;
如氫氧化銅(cupric hydroxide)、有機銅(oxine copper)、無水硫酸銅、壬基酚磺酸銅、8-羥基喹啉銅、十二烷基苯磺酸雙乙二胺銅錯合物(II)(別名DBEDC)之銅系化合物;
如疫霜靈鋁(fosetyl-Al)、甲基立枯磷(tolclofos-Methyl)、護粒松(edifenphos)、異稻瘟淨(iprobenfos)之有機磷系化合物;
如克菌丹(captan)、四氯丹(captafol)、滅菌丹(folpet)之鄰苯二甲醯亞胺系化合物;
如撲滅寧(procymidone)、依普同(iprodione)、免克寧(vinclozolin)之二碳二亞胺(Dicarboximide)系化合物;
如福多寧(flutolanil)、滅普寧(mepronil)、麥銹靈(benodanil)之苯甲醯苯胺系化合物;
如加普胺(carpropamid)、雙氯氰菌胺(diclocymet)、矽噻菌胺(silthiopham)、芬諾尼fenoxanil)之醯胺系化合物;
如苯并烯氟菌唑(benzovindiflupyr)、比沙吩(bixafen)、氟茚唑菌胺(fluindapyr)、氟克殺(fluxapyroxad)、福拉比(furametpyr)、亞派占(isopyrazam)、平氟芬(penflufen)、吡噻菌胺(penthiopyrad)、護汰派滅芬(pydiflumetofen)、環苯吡菌胺(sedaxane)、異氟西波(isoflucypram)、應吡福安(inpyrfluxam)、吡普洛潑尼(pyrapropoyne)之吡唑甲醯胺系化合物;
如氟比拔克(fluopicolide)、氟派瑞(fluopyram)、座賽胺(zoxamide)、氟醚菌醯胺(fluopimomide)之苯甲醯胺系化合物;
如甲呋醯苯胺(fenfuram)之糠苯胺(furanilide)系化合物;
如異丙噻菌胺(isofetamid)之噻吩醯胺系化合物;
如賽福寧(triforine)之哌嗪系化合物;
如比芬諾(pyrifenox)、啶菌唑(pyrisoxazole)、胺基吡芬(aminopyrifen)之吡啶系化合物;
如芬瑞莫(fenarimol)、富米綜(ferimzone)、尼瑞莫(nuarimol)之嘧啶系化合物;
如苯銹啶(fenpropidin)之哌啶系化合物;
如丁基嗎啉(fenpropimorph)、十三嗎啉(tridemorph)之嗎啉系化合物;
如羥化三苯基錫(fentin hydroxide)、三苯基乙酸錫(fentin acetate)之有機錫系化合物;
如戊菌隆(pencycuron)之脲系化合物;
如達滅芬(dimethomorph)、氟嗎啉(flumorph)、丁吡嗎啉(pyrimorph)、丙森鋅(iprovalicarb)、苯噻菌胺
(benthiavalicarb-isopropyl)、曼普胺(mandipropamid)之羧酸醯胺系化合物;
如乙黴威(diethofencarb)之苯基胺基甲酸酯系化合物;
如護汰寧(fludioxonil)、拌種咯(fenpiclonil)之氰基吡咯系化合物;
如亞托敏(azoxystrobin)、克收欣(kresoxim-methyl)、苯氧菌胺(metominostrobin)、三氟敏(trifloxystrobin)、啶氧菌酯(picoxystrobin)、肟醚菌胺(oryzastrobin)、醚菌胺(dimoxystrobin)、百克敏(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)、氟菌蟎酯(flufenoxystrobin)、氯啶菌酯(triclopyricarb)、杏仁菌酯(mandestrobin)之甲氧基丙烯酸酯(Strobilurin)系化合物;
如凡殺同(famoxadone)、歐西比(oxathiapiprolin)之噁唑系化合物;
如噻唑菌胺(ethaboxam)之噻唑甲醯胺系化合物;
如咪唑菌酮(fenamidone)之咪唑啉酮系化合物;
如氟硫滅(flusulfamide)之苯磺醯胺系化合物;
如賽芬胺(cyflufenamid)之肟醚系化合物;
如腈硫醌(dithianon)之蒽醌系化合物;
如硝苯菌酯(meptyldinocap)之巴豆酸系化合物;
如維利黴素(validamycin)、嘉賜徵素(kasugamycin)、鏈黴素(streptomycin)、保粒黴素(polyoxins)之抗生物質;
如克熱淨(iminoctadine)、多果定(dodine)之胍系化合物;如特布弗喹(tebufloquin)、快諾芬(quinoxyfen)、昆諾浮美林(quinofumelin)、艾氟芬喹啉(ipflufenoquin)之喹啉系化合物;
如氟噻菌淨(flutianil)之四氫噻唑系化合物;
如普拔克(propamocarb hydrochloride)、派本克
(pyribencarb)、三氟甲氧威(tolprocarb)之胺基甲酸酯系化合物;
如四唑吡氨酯(picarbutrazox)、美特洛(metyltetraprole)之四唑系化合物;
如安美速(amisulbrom)、賽座滅(cyazofamiid)之磺醯胺系化合物;
如滅芬農(metrafenone)、甲氧苯啶菌(pyriofenone)之烯丙基苯基酮系化合物;
如烯丙苯噻唑(probenazole)、二氯苯賽鐸
(dichlobentiazox)之苯并噻唑系化合物;
如胺苯吡菌酮(fenpyrazamine)之苯基吡唑系化合物;
如亞賜圃(isoprothiolane)之二硫戊環系化合物;
如芬庇科米得(fenpicoxamid)、吡啶醯菌胺
(florylpicoxamid)之吡咯啉醯胺系化合物;
如硫(Sulfur)、石灰硫劑之硫系化合物;
作為其他化合物,如咯喹酮(pyroquilon)、達滅淨(diclomezine)、氯化苦(chloropicrin)、棉隆(dazomet)、威百畝(metam-sodium)、丙氧喹啉(proquinazid)、螺環菌胺(spiroxamine)、大芬滅替松(dipymetitrone)等;
如Bacillus amyloliqefaciens strain QST713、Bacillus amyloliqefaciens strain FZB24、Bacillus amyloliqefaciens strain MBI600、Bacillus amyloliqefaciens strain D747、螢光假單孢菌(pseudomonas fluorescens)、枯草桿菌(Bacillus subtilis)、深綠木黴(trichoderma atroviride) SKT-1之微生物殺菌劑;及
如茶樹油(Tea tree oil)之植物萃取物。
本發明所期望的態樣係如以下。惟,本發明並非被限定於此等者。
[1]一種殺線蟲組成物,其係將式(I)表示之化合物或其鹽作為有效成分含有。
[2]一種線蟲之防除方法,其係將有效量含有式(I)表示之化合物或其鹽之殺線蟲組成物施用在土壤、線蟲或植物體。
[3]如前述[1]所記載之殺線蟲組成物,其中,在式(I)表示之化合物或其鹽,A為被1個至5個之R
1取代之苯基,R
1為鹵素、烷基、鹵烷基、烯基、炔基、環烷基、烷氧基或鹵烷氧基,存在2個R
1的情況下,2個之R
1可成為一起,形成可被1個或2個之Z
1取代之環的化合物或其鹽。
[4]如前述[2]所記載之線蟲之防除方法,其中,在式(I)表示之化合物或其鹽,A為被1個至5個之R
1取代之苯基,R
1為鹵素、烷基、鹵烷基、烯基、炔基、環烷基、烷氧基或鹵烷氧基,存在2個R
1的情況下,2個之R
1可成為一起,形成可被1個或2個之Z
1取代之環的化合物或其鹽。
[5]一種式(I)表示之化合物或其鹽。
[6]一種式(IA)表示之化合物或其鹽。
[7]一種式(IB)表示之化合物或其鹽。
[8]如前述[6]所記載之化合物或其鹽,其中,R
1A為鹵素、(C
1-C
6)-烷基、(C
1-C
6)-鹵烷基、(C
2-C
6)-烯基、(C
2-C
6)-炔基、(C
3-C
6)-環烷基、(C
1-C
6)-烷氧基或(C
1-C
6)-鹵烷氧基。
[9]如前述[6]所記載之化合物或其鹽,其中,R
1A為鹵素、(C
1-C
6)-烷基、(C
1-C
6)-鹵烷基、(C
1-C
6)-烷氧基、(C
1-C
6)-鹵烷氧基。
[10]如前述[6]所記載之化合物或其鹽,其中,R
1A為鹵素、(C
1-C
6)-烷基、(C
1-C
6)-鹵烷基。
[11]如前述[6]所記載之化合物或其鹽,其中,2個之R
1A成為一起,形成可被1個或2個之Z
1A取代之環。
[12]如前述[6]~[11]所記載之化合物或其鹽,其中,R
2A及R
3A分別為(C
1-C
3)-烷基。
[13]如前述[6]~[11]所記載之化合物或其鹽,其中,R
2A及R
3A一同為甲基。
[14]如前述[6]~[13]所記載之化合物或其鹽,其中,R
4A為鹵素、(C
1-C
6)-鹵烷基、(C
1-C
6)-烷基亞磺醯基、(C
1-C
6)-烷基磺醯基、硝基或氰基。
[15]如前述[6]~[13]所記載之化合物或其鹽,其中,R
4A為氟、氯、溴、二氟甲基、三氟甲基、硝基或氰基。
[16]如前述[6]~[15]所記載之化合物或其鹽,其中,R
6A為氫、(C
1-C
6)-烷基、(C
2-C
6)-烯基或(C
2-C
6)-炔基。
[17]如前述[6]~[15]所記載之化合物或其鹽,其中,R
6A為氫。
[18]如前述[6]或[8]~[17]所記載之化合物或其鹽,其中,n為1或2。
[19]如前述[6]或[8]~[17]所記載之化合物或其鹽,其中,n為1,1個之R
1A被苯基之2位或3位取代。
[20]如前述[6]或[8]~[17]所記載之化合物或其鹽,其中,n為1,1個之R
1A被苯基之2位取代。
[21]如前述[6]或[8]~[17]所記載之化合物或其鹽,其中,n為1,1個之R
1A被苯基之3位取代。
[22]如前述[6]或[8]~[17]所記載之化合物或其鹽,其中,n為2,2個之R
1A被苯基之2位及3位取代。
[23]如前述[6]或[8]~[17]所記載之化合物或其鹽,其中,n為2,2個之R
1A被苯基之2位及6位取代。
[24]如前述[6]或[8]~[17]所記載之化合物或其鹽,其中,n為2,2個之R
1A被苯基之2位及5位取代。
[25]一種線蟲之防除方法,其係將有效量含有如前述[6]~[24]所記載之化合物或其鹽之殺線蟲組成物施用在土壤、線蟲或植物體。
[26]一種農園藝用殺線蟲劑,其係將如前述[6]~[24]所記載之化合物或其鹽作為有效成分含有。
本發明化合物較佳為式(IA)化合物或式(IB)化合物,更佳為式(IA)化合物。
[實施例]
接著,雖記載本發明之實施例,但本發明並非被限定於此等者。
合成例1:N’-(2-甲基-1-苯基-2-(3-三氟甲基-1H-吡唑-1-基)亞丙基)甲醯肼(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
於3-三氟甲基-1H-吡唑(1.80g)之乙腈(12ml)溶液加入碳酸鉀(0.92g),並在室溫攪拌。30分鐘後,加入2-溴-2-甲基-1-苯基丙烷-1-酮(3.01g),並在室溫攪拌,而得到混合物。10分鐘後,將前述混合物昇溫至70℃,並使其反應20.5小時,而得到反應混合物。於前述反應混合物加入水,並使用乙酸乙酯萃取。然後,減壓下濃縮所得之萃取溶液。將所得之殘渣以管柱層析(溶離液:乙酸乙酯/庚烷)純化,而得到目的物(1.23g)。
1H NMR (CDCl
3/300MHz):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)亞丙基)醯肼的合成
於2-甲基-1-苯基-2-(3-三氟甲基-1H-吡唑-1-基)丙烷-1-酮(0.84g)之乙醇(2.51ml)溶液,加入肼一水合物(0.38g),並回流19.5小時,而得到反應混合物。於前述反應混合物加入水,並使用乙酸乙酯萃取。然後,減壓下濃縮所得之萃取溶液。將所得之殘渣以管柱層析(溶離液:乙酸乙酯/庚烷)純化,而得到目的物(0.37g)。
1H NMR (CDCl
3/300MHz):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)亞丙基)甲醯肼(No.A-1)的合成
於(2-甲基-1-苯基-2-(3-三氟甲基-1H-吡唑-1-基)亞丙基)醯肼(0.20g)之甲酸乙酯(2ml)溶液,加入甲酸(0.04g),回流2小時,而得到反應混合物。於前述反應混合物加入水後,使用飽和小蘇打水,而得到鹼性之反應溶液。使用乙酸乙酯,萃取前述反應溶液後,減壓下濃縮所得之萃取溶液。將所得之殘渣以管柱層析(溶離液:乙酸乙酯/庚烷)純化,而得到目的物(No.A-1、0.20g)。
1H NMR (CDCl
3/300MHz):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)環丙基)亞甲基)甲醯肼的2種類之幾何異構物(No.B-1及No.B-2)的合成
(1)2-溴-4-氯-1-苯基丁烷-1-酮的合成
於4-氯-1-苯基丁烷-1-酮(0.61g)之四氫呋喃(6.07ml)溶液,加入三甲基苯基銨三溴化物(1.28g),於室溫使其反應15.5小時,而得到反應混合物。於前述反應混合物加入水,使用乙酸乙酯萃取後,減壓下濃縮所得之萃取溶液。將所得之殘渣以管柱層析(溶離液:乙酸乙酯/庚烷)純化,而得到目的物(0.86g)。
1H NMR (CDCl
3/300MHz):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)環丙基)甲酮的合成
於3-三氟甲基-1H-吡唑(0.50g)之乙腈(2.58ml)溶液,加入碳酸鉀(0.51g),並在室溫攪拌。50分鐘後,加入2-溴-4-氯-1-苯基丁烷-1-酮(0.86g),並昇溫至90℃反應6小時,而得到反應混合物。於前述反應混合物加入水,使用乙酸乙酯萃取後,減壓下濃縮所得之萃取溶液。將所得之殘渣以管柱層析(溶離液:乙酸乙酯/庚烷)純化,而得到目的物(0.86g)。
1H NMR (CDCl
3/300MHz):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)環丙基)亞甲基)醯肼的2種類之幾何異構物的合成
於苯基(1-(3-三氟甲基-1H-吡唑-1-基)環丙基)甲酮(1.07g)之乙醇(4.29ml)溶液,加入肼一水合物(0.51g),並回流25.5小時,而得到反應混合物。於前述反應混合物加入水,使用乙酸乙酯萃取後,減壓下濃縮所得之萃取溶液。將所得之殘渣以管柱層析(溶離液:乙酸乙酯/庚烷)純化,而得到主生成物(0.41g)、與其幾何異構物(0.23g)。
主生成物
1H NMR (CDCl
3/300MHz):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).
主生成物之幾何異構物
1H NMR (CDCl
3/300MHz):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)環丙基)亞甲基)甲醯肼的2種類之幾何異構物(No.B-1、No.B-2)的合成
於(苯基(1-(3-三氟甲基-1H-吡唑-1-基)環丙基)亞甲基)醯肼(0.20g)之甲酸乙酯(2.01ml)溶液,加入甲酸(0.05g),並回流2.5小時,而得到反應混合物。於前述反應混合物加入水後,使用飽和小蘇打水,而得到鹼性之反應溶液。使用乙酸乙酯,萃取前述反應溶液後,減壓下濃縮所得之萃取溶液。將所得之殘渣以管柱層析(溶離液:乙酸乙酯/庚烷)純化,而得到主生成物(No.B-1、0.18g)、與其幾何異構物(No.B-2、0.02g)。
主生成物
1H NMR (CDCl
3/300MHz):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).
主生成物之幾何異構物
1H NMR (CDCl
3/300MHz):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)亞丙基)甲醯肼(No.A-323)的合成
(1)(2-甲基-1-(3-甲基苯基)-亞丙基)腙的合成
脫氣使用2-甲基-1-(3-甲基苯基)-丙烷-1-酮(0.35g)、乙醇(1.05mL)與肼一水合物(0.27g)所調製之混合物後,回流13.5小時,而得到反應混合物。將前述反應混合物以乙酸乙酯與庚烷稀釋,並通過包含矽藻土與二氧化矽凝膠之墊進行過濾,而得到濾液。將減壓下濃縮前述濾液所得之殘渣以管柱層析(溶離液:乙酸乙酯/庚烷)純化,而得到目的物(0.35g)。
1H NMR (CDCl
3/500MHz):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)-亞丙基)甲醯肼的合成
氮取代使用(2-甲基-1-(3-甲基苯基)-亞丙基)腙(0.35g)、甲酸乙酯(1.4mL)與甲酸(0.12g)所調製之混合物後,回流5小時,而得到反應溶液。減壓下濃縮前述反應溶液,並以管柱層析(溶離液:乙酸乙酯/庚烷)純化,而得到目的物(0.29g)。
1H NMR (CDCl
3/500MHz):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)-亞丙基)甲醯肼的合成
將使用N’-(2-甲基-1-(3-甲基苯基)-亞丙基)甲醯肼(0.26g)、甲苯(2.5mL)、硫醯氯(0.2g)所調製之混合物於室溫攪拌4小時,而得到反應混合物。一邊冰冷所得之反應混合物,一邊依序加入冰水、飽和碳酸氫鈉水溶液並攪拌,並以乙酸乙酯萃取3次。將於萃取所得之有機層通過矽藻土墊進行過濾,而得到濾液。將減壓下濃縮前述濾液所得之殘渣以管柱層析(溶離液:乙酸乙酯/庚烷)純化,而得到目的物(0.24g)。
1H NMR (CDCl
3/500MHz):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)亞丙基)甲醯肼(No.A-323)的合成
氮取代使用3-三氟甲基-1H-三唑(0.05g)、DMF(0.3mL)與碳酸鉀(0.05g)所調製之混合物後,於室溫下攪拌一晩。於經攪拌之混合物一點一點地滴下N-(2-氯-2-甲基-1-(3-甲基苯基)-亞丙基)甲醯肼(0.07g)之DMF(0.3mL)溶液,並於室溫攪拌1小時,而得到反應混合物。將所得之反應混合物以水稀釋後,以乙酸乙酯/庚烷萃取3次。將萃取所得之有機層通過矽藻土墊進行過濾,而得到濾液。將減壓下濃縮前述濾液所得之殘渣以管柱層析(溶離液:乙酸乙酯/庚烷)純化,而得到目的物(No.A-323、0.09g)。
1H NMR (CDCl
3/500MHz):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).
其次,將本發明之化合物(I)之代表例具體列舉於第1表及第2表。此等化合物可根據前述製造方法及前述合成例,以及在本技術領域公知之方法合成。
各表中,No.表示化合物No.。於第1表及第2表中之物性欄,表示記載為NMR之化合物,於第3表及第4表中表示
1H-NMR光譜數據。進而,第1表及第2表所記載之化合物為本發明之化合物(I)之鹽時,於第1表及第2表中之物性欄亦表示其鹽的種類。
於第1表及第2表中之各A、R
2、R
3、R
4、R
6及X欄所使用之簡稱係如以下。Me表示甲基,Et表示乙基,nPr表示正丙基,iPr表示異丙基,cPr表示環丙基,tBu表示三级丁基,cBu表示環丁基,nHexyl表示正己基,cHexyl表示環己基,Ph表示苯基,Na鹽表示鈉鹽,K鹽表示鉀鹽,di表示2個,bis表示2個,及tri表示3個。
於第1表及第2表,表示R
5為CHO之本發明的化合物(I)。又,於第1表及第2表中之A及R
4欄表示之各取代基之位置,表示如以下之取代基的位置。「*」表示鍵結位置。
例如,在A欄,記載為「4-Cl-Ph」之化合物,係表示於賦予在上述之化學構造式之A(苯基)的取代基位置,被1個R
1基取代,亦即表示僅苯基之4位被氯基取代之化合物。
又,在R
4欄,記載為「3-CF
3」,在m欄,記載為「1」之化合物,係表示於賦予在上述之化學構造式之雜5員環的取代基位置,被1個R
4基取代,亦即表示僅雜5員環之3位被三氟甲基取代之化合物。在R
4欄,記載為「3-CF
3-5-Me」,在m欄,記載為「2」之化合物,係表示於賦予在上述之化學構造式之雜5員環的取代基位置,被2個R
4基取代,亦即表示雜5員環之3位被三氟甲基取代,雜5員環之5位被甲基取代之化合物。在R
4欄,記載為「-」,在m欄,記載為「0」之化合物,係表示於上述之化學構造式的雜5員環之3位及5位未被R
4基取代。
又,第1表及第2表所記載之化合物No.A-188、A-189、B-186及B-187為A-1、A-2、B-1及B-3之鈉鹽,以及化合物No.A-190、A-191、B-188及B-189為A-1、A-2、B-1及B-3之鉀鹽。
第3表及第4表中之
1H-NMR的數據之s表示單線(Singlet)(一重線),brs表示經擴大之單線,d表示雙線(Doublet)(二重線),t表示三線(三重線),q表示四線(四重線),dd表示雙雙線(Double Doublet),dt表示雙三線,ddd表示雙雙雙線(Double Double Doublet),m表示多線(Multilet)(多重線)。
試驗例1:對於根結線蟲之效果試驗
於根結線蟲污染土壤200mL,使用水,灌溉以化合物(I)的濃度成為400ppm或200ppm的方式調製之本組成物10mL後,以本組成物均一分散的方式混和。將處理土壤集中在盆後,播種3粒黃瓜種子,放置在溫室內。從前述黃瓜種子的播種2~3週後,將形成在根部之根瘤的著生程度依照第5表所示之根瘤指數判定。其結果,將包含前述化合物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之各組成物於400ppm顯示,包含前述化合物No.A-153之組成物於200ppm顯示根瘤指數1以下之高防除效果。
[表38]
第5表 | |
根瘤指數 | 根瘤的著生程度 |
0 | 根全體完全未觀察到根瘤 |
1 | 觀察到些微根瘤 |
2 | 根瘤之數為中程度 |
3 | 根瘤之數多 |
4 | 根瘤之數特別多且大 |
試驗例2:對於穿刺短體線蟲之效果試驗
於穿刺短體線蟲污染土壤200mL,使用水,灌溉將化合物(I)的濃度調製成800ppm之本組成物10mL後,以本組成物均一分散的方式混和。將處理土壤集中在盆後,播種3粒牛蒡種子,放置在溫室內。從前述牛蒡種子的播種後約1個月後,將根部的被害程度依照第6表所示之被害指數判定。其結果,包含前述化合物No.A-1、A-318、B-1或B-192之各組成物顯示被害指數1以下之高防除效果。
[表39]
第6表 | |
被害指數 | 根部之被害程度 |
0 | 無 |
1 | 小 |
2 | 中 |
3 | 大 |
4 | 甚大 |
試驗例3:對於大豆異皮線蟲之效果試驗
於大豆異皮線蟲污染土壤200mL,使用水,灌溉將化合物(I)的濃度調製成800ppm或400ppm之本組成物10mL後,以本組成物均一分散的方式混和。將處理土壤集中在盆後,播種3粒大豆種子,放置在溫室內。從前述大豆種子的播種後約1個月後,將對根部之囊腫的寄生度依照第7表所示之寄生指數判定。其結果,包含前述化合物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之各組成物於800ppm顯示,包含前述化合物No.A-260、B-106或B-193之組成物於400ppm顯示寄生指數1以下之高防除效果。
[表40]
第7表 | |
寄生指數 | 寄生度 |
0 | 於根全體完全未觀察到囊腫的寄生 |
1 | 觀察到些微囊腫的寄生 |
2 | 囊腫的寄生為中程度 |
3 | 囊腫的寄生多 |
4 | 於根全體密集寄生囊腫 |
其次,將包含本組成物及國際公開第2020/179910號所記載之化合物之組成物對於根結線蟲的效果用以下之比較試驗表示。
比較試驗
除了使用化合物No.A-1、A-2及A-318作為本組成物的有效成分,使用國際公開第2020/179910號所記載之化合物No.A-1、A-3及A-58作為比較對照的有效成分,並將有效成分濃度調製成50ppm之外,其他以與上述試驗例1相同之方法,進行對於根結線蟲之效果試驗。將試驗結果示於第8表及第9表。
試驗的結果,包含國際公開第2020/179910號所記載之化合物(化合物No.A-1、A-3或A-58)之各組成物為根瘤指數2。對此,包含本發明化合物(化合物No.A-1、A-2或A-318)之各本組成物為根瘤指數1或0。
所謂根瘤指數2,係表示健全之根的比率為全體之50%以下,試驗對象作物的黃瓜停留在無法健全生育之防除效果的狀態。對此,所謂根瘤指數1或0,係表示健全根的比率為全體之75%以上,發揮黃瓜可健全生育之高防除效果的狀態。
於以下雖針對本組成物的製劑具體說明,但摻合比例、劑型等並非被限定於以下之製劑例者。
以下記載製劑例。
製劑例1
(1)化合物(I) 20重量份
(2)黏土 70重量份
(3)白碳 5重量份
(4)聚羧酸鈉 3重量份
(5)烷基萘磺酸鈉 2重量份
將以上者均一混合,作為水合劑。
製劑例2
(1)化合物(I) 5重量份
(2)滑石 60重量份
(3)碳酸鈣 34.5重量份
(4)流動石蠟 0.5重量份
將以上者均一混合,作為粉劑。
製劑例3
(1)化合物(I) 20重量份
(2)N,N-二甲基乙醯胺 20重量份
(3)聚氧乙烯三苯乙烯基苯基醚 10重量份
(4)十二烷基苯磺酸鈣 2重量份
(5)二甲苯 48重量份
將以上者均一混合溶解,作為乳劑。
製劑例4
(1)黏土 68重量份
(2)木質素磺酸鈉 2重量份
(3)聚氧乙烯烷基芳基硫酸鹽 5重量份
(4)白碳 25重量份
將以上之各成分的混合物、與化合物(I)以4:1之重量比例混合,作為水合劑。
製劑例5
(1)化合物(I) 50重量份
(2)烷基萘磺酸鈉甲醛縮合物 2重量份
(3)聚矽氧油 0.2重量份
(4)水 47.8重量份
將以上者均一混合,於經粉碎之原液進一步加入
(5)聚羧酸鈉 5重量份
(6)無水硫酸鈉 42.8重量份
並均一混合、造粒、乾燥,作為顆粒水合劑。
製劑例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)粒狀碳酸鈣 93.9重量份
預先將(1)~(3)均一混合,並以適量的丙酮稀釋後,吹附在(4),去除丙酮,作為粒劑。
製劑例7
(1)化合物(I) 2.5重量份
(2)N,N-二甲基乙醯胺 2.5重量份
(3)大豆油 95重量份
將以上者均一混合,進行溶解,作為微量散布劑(ultra low volume formulation)。
製劑例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鉀 4重量份
(3)聚矽氧油 0.2重量份
(4)黃原膠 0.1重量份
(5)乙二醇 5重量份
(6)水 50.7重量份
將以上者均一混合,進行粉碎,作為水性懸濁劑。
製劑例9
(1)化合物(I) 10重量份
(2)二乙二醇單乙基醚 80重量份
(3)聚氧乙烯烷基醚 10重量份
將以上之成分均一混合,而成為液劑。
尚,將2021年7月8日所申請之日本特許出願2021-113233號之說明書、申請專利範圍,及摘要之全內容引用於此,並作為本發明之說明書的揭示而納入者。
Claims (14)
- 一種殺線蟲組成物,其係將式(I)表示之化合物或其鹽作為有效成分含有, [式中,X為N、CH或CR 4, A為未被取代之苯基或被1個至5個之R 1取代之苯基, R 1為鹵素、烷基、鹵烷基、烯基、炔基、環烷基、烷氧基或鹵烷氧基,存在2個R 1的情況下,2個之R 1可成為一起,形成可被1個或2個之Z 1取代之環, Z 1為鹵素或烷基, R 2及R 3分別為烷基,或R 2及R 3成為一起,形成(C 3-C 6)-碳環, R 4為鹵素、烷基、鹵烷基、烯基、炔基、環烷基、烷氧基、鹵烷氧基、烷硫基、烷基亞磺醯基、烷基磺醯基、硝基或氰基, R 5為CHO, R 6為H、-SO 2CF 3、-C(=O)OZ 3、烷基、烯基、炔基或烷氧基烷基,或為可被Z 2取代之芳烷基, Z 2為烷氧基, Z 3為可被Z 2取代之芳烷基或烷基, m為0至2之整數]。
- 一種線蟲之防除方法,其係將有效量含有式(I)表示之化合物或其鹽之殺線蟲組成物施用在土壤、線蟲或植物體, [式中,X為N、CH或CR 4, A為未被取代之苯基或被1個至5個之R 1取代之苯基, R 1為鹵素、烷基、鹵烷基、烯基、炔基、環烷基、烷氧基或鹵烷氧基,存在2個R 1的情況下,2個之R 1可成為一起,形成可被1個或2個之Z 1取代之環, Z 1為鹵素或烷基, R 2及R 3分別為烷基,或R 2及R 3成為一起,形成(C 3-C 6)-碳環, R 4為鹵素、烷基、鹵烷基、烯基、炔基、環烷基、烷氧基、鹵烷氧基、烷硫基、烷基亞磺醯基、烷基磺醯基、硝基或氰基, R 5為CHO, R 6為H、-SO 2CF 3、-C(=O)OZ 3、烷基、烯基、炔基或烷氧基烷基,或為可被Z 2取代之芳烷基, Z 2為烷氧基, Z 3為可被Z 2取代之芳烷基或烷基, m為0至2之整數]。
- 如請求項1之殺線蟲組成物,其中,在式(I)表示之化合物或其鹽,A為被1個至5個之R 1取代之苯基,R 1為鹵素、烷基、鹵烷基、烯基、炔基、環烷基、烷氧基或鹵烷氧基,存在2個R 1的情況下,2個之R 1可成為一起,形成可被1個或2個之Z 1取代之環的化合物或其鹽。
- 如請求項2之線蟲之防除方法,其中,在式(I)表示之化合物或其鹽,A為被1個至5個之R 1取代之苯基,R 1為鹵素、烷基、鹵烷基、烯基、炔基、環烷基、烷氧基或鹵烷氧基,存在2個R 1的情況下,2個之R 1可成為一起,形成可被1個或2個之Z 1取代之環的化合物或其鹽。
- 一種式(IA)表示之化合物或其鹽, [式中,X為N、CH或CR 4A, R 1A為鹵素、(C 1-C 6)-烷基、(C 1-C 6)-鹵烷基、(C 2-C 6)-烯基、(C 2-C 6)-炔基、(C 3-C 6)-環烷基、(C 1-C 6)-烷氧基或(C 1-C 6)-鹵烷氧基,存在2個R 1A的情況下,2個R 1A可成為一起,形成可被1個或2個之Z 1A取代之環, Z 1A為鹵素或(C 1-C 6)-烷基, R 2A及R 3A分別為(C 1-C 6)-烷基,或R 2A及R 3A成為一起,形成(C 3-C 6)-碳環, R 4A為鹵素、(C 1-C 6)-烷基、(C 1-C 6)-鹵烷基、(C 2-C 6)-烯基、(C 2-C 6)-炔基、(C 3-C 6)-環烷基、(C 1-C 6)-烷氧基、(C 1-C 6)-鹵烷氧基、(C 1-C 6)-烷硫基、(C 1-C 6)-烷基亞磺醯基、(C 1-C 6)-烷基磺醯基、硝基或氰基, R 6A為H、-SO 2CF 3、-C(=O)OZ 3A、(C 1-C 6)-烷基、(C 2-C 6)-烯基、(C 2-C 6)-炔基或(C 1-C 6)-烷氧基-(C 1-C 6)-烷基,或為可被Z 2A取代之(C 7-C 12)-芳烷基, Z 2A為(C 1-C 6)-烷氧基, Z 3A為可被Z 2A取代之(C 7-C 12)-芳烷基或(C 1-C 6)-烷基, n為1至5之整數, m為0至2之整數]。
- 一種式(IB)表示之化合物或其鹽, [式中,X為N、CH或CR 4A, R 2A及R 3A分別為(C 1-C 6)-烷基,或R 2A及R 3A成為一起,形成(C 3-C 6)-碳環, R 4A為鹵素、(C 1-C 6)-烷基、(C 1-C 6)-鹵烷基、(C 2-C 6)-烯基、(C 2-C 6)-炔基、(C 3-C 6)-環烷基、(C 1-C 6)-烷氧基、(C 1-C 6)-鹵烷氧基、(C 1-C 6)-烷硫基、(C 1-C 6)-烷基亞磺醯基、(C 1-C 6)-烷基磺醯基、硝基或氰基, R 6A為H、-SO 2CF 3、-C(=O)OZ 3A、(C 1-C 6)-烷基、(C 2-C 6)-烯基、(C 2-C 6)-炔基或(C 1-C 6)-烷氧基-(C 1-C 6)-烷基,或為可被Z 2A取代之(C 7-C 12)-芳烷基, Z 2A為(C 1-C 6)-烷氧基, Z 3A為可被Z 2A取代之(C 7-C 12)-芳烷基或(C 1-C 6)-烷基, m為0至2之整數]。
- 如請求項6之化合物或其鹽,其中,在式(IA)表示之化合物或其鹽,R 1A為鹵素、(C 1-C 6)-烷基、(C 1-C 6)-鹵烷基、(C 2-C 6)-烯基、(C 2-C 6)-炔基、(C 3-C 6)-環烷基、(C 1-C 6)-烷氧基或(C 1-C 6)-鹵烷氧基。
- 如請求項6之化合物或其鹽,其中,在式(IA)表示之化合物或其鹽,R 2A及R 3A分別為(C 1-C 3)-烷基。
- 如請求項6之化合物或其鹽,其中,在式(IA)表示之化合物或其鹽,R 4A為鹵素、(C 1-C 6)-鹵烷基、(C 1-C 6)-烷基亞磺醯基、(C 1-C 6)-烷基磺醯基、硝基或氰基。
- 如請求項7之化合物或其鹽,其中,在式(IB)表示之化合物或其鹽,R 2A及R 3A分別為(C 1-C 3)-烷基。
- 如請求項7之化合物或其鹽,其中,在式(IB)表示之化合物或其鹽,R 4A為鹵素、(C 1-C 6)-鹵烷基、(C 1-C 6)-烷基亞磺醯基、(C 1-C 6)-烷基磺醯基、硝基或氰基。
- 一種線蟲之防除方法,其係將有效量含有如請求項6或7之化合物或其鹽之殺線蟲組成物施用在土壤、線蟲或植物體。
- 一種農園藝用殺線蟲劑,其係將如請求項6或7之化合物或其鹽作為有效成分含有。
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