JPS6341451A - エ−テル誘導体およびそれを有効成分とする殺ダニ、殺虫組成物 - Google Patents
エ−テル誘導体およびそれを有効成分とする殺ダニ、殺虫組成物Info
- Publication number
- JPS6341451A JPS6341451A JP61184677A JP18467786A JPS6341451A JP S6341451 A JPS6341451 A JP S6341451A JP 61184677 A JP61184677 A JP 61184677A JP 18467786 A JP18467786 A JP 18467786A JP S6341451 A JPS6341451 A JP S6341451A
- Authority
- JP
- Japan
- Prior art keywords
- group
- methyl
- compound
- formula
- water
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 230000000749 insecticidal effect Effects 0.000 title claims abstract description 12
- 239000000203 mixture Substances 0.000 title claims description 37
- 150000002170 ethers Chemical class 0.000 title claims description 9
- 230000003129 miticidal effect Effects 0.000 title abstract 2
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 17
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 14
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 13
- 125000000475 sulfinyl group Chemical group [*:2]S([*:1])=O 0.000 claims abstract description 13
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 12
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 9
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 7
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 4
- 229910052794 bromium Inorganic materials 0.000 claims abstract 3
- 229910052731 fluorine Inorganic materials 0.000 claims abstract 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract 3
- 239000004480 active ingredient Substances 0.000 claims description 16
- 239000011593 sulfur Substances 0.000 claims description 16
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 15
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 13
- 239000001301 oxygen Substances 0.000 claims description 13
- 125000001841 imino group Chemical group [H]N=* 0.000 claims description 12
- 230000000895 acaricidal effect Effects 0.000 claims description 11
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 11
- 239000001257 hydrogen Substances 0.000 claims description 10
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 9
- 239000000460 chlorine Substances 0.000 claims description 9
- 239000000126 substance Substances 0.000 claims description 9
- 125000004414 alkyl thio group Chemical group 0.000 claims description 8
- 150000002431 hydrogen Chemical class 0.000 claims description 8
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims 2
- 239000011737 fluorine Substances 0.000 claims 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 2
- 125000004455 (C1-C3) alkylthio group Chemical group 0.000 claims 1
- 150000001875 compounds Chemical class 0.000 abstract description 74
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- -1 alkali metal salt Chemical class 0.000 abstract description 28
- 239000003795 chemical substances by application Substances 0.000 abstract description 25
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- 239000002253 acid Substances 0.000 abstract description 8
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- 125000005905 mesyloxy group Chemical group 0.000 abstract description 6
- 238000002360 preparation method Methods 0.000 abstract description 3
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- 239000002516 radical scavenger Substances 0.000 abstract 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 119
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 40
- 238000003786 synthesis reaction Methods 0.000 description 32
- 230000015572 biosynthetic process Effects 0.000 description 30
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- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 24
- 239000000243 solution Substances 0.000 description 21
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
- 238000004519 manufacturing process Methods 0.000 description 17
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- 238000012360 testing method Methods 0.000 description 16
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 15
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 14
- 238000006243 chemical reaction Methods 0.000 description 13
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 12
- 238000009472 formulation Methods 0.000 description 12
- 241000238631 Hexapoda Species 0.000 description 10
- 239000013078 crystal Substances 0.000 description 10
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- 239000000843 powder Substances 0.000 description 9
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 8
- 239000000642 acaricide Substances 0.000 description 8
- 239000003814 drug Substances 0.000 description 8
- 229940079593 drug Drugs 0.000 description 8
- 239000000839 emulsion Substances 0.000 description 8
- 230000003647 oxidation Effects 0.000 description 8
- 238000007254 oxidation reaction Methods 0.000 description 8
- 238000010898 silica gel chromatography Methods 0.000 description 8
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 239000012230 colorless oil Substances 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 7
- 238000005406 washing Methods 0.000 description 7
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 241000607479 Yersinia pestis Species 0.000 description 6
- 235000013601 eggs Nutrition 0.000 description 6
- 239000005457 ice water Substances 0.000 description 6
- 241000238876 Acari Species 0.000 description 5
- 241001454295 Tetranychidae Species 0.000 description 5
- 241001454293 Tetranychus urticae Species 0.000 description 5
- 239000000443 aerosol Substances 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 239000000284 extract Substances 0.000 description 5
- 239000008187 granular material Substances 0.000 description 5
- 125000005843 halogen group Chemical group 0.000 description 5
- 239000002917 insecticide Substances 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 235000019198 oils Nutrition 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- XGCNEPLXKDEVDP-UHFFFAOYSA-N 4-methyl-3-propylbenzenethiol Chemical compound CCCC1=CC(S)=CC=C1C XGCNEPLXKDEVDP-UHFFFAOYSA-N 0.000 description 4
- 241000254173 Coleoptera Species 0.000 description 4
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 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 4
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 4
- HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 4
- 239000011230 binding agent Substances 0.000 description 4
- 239000001294 propane Substances 0.000 description 4
- 229910052708 sodium Inorganic materials 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 125000005424 tosyloxy group Chemical group S(=O)(=O)(C1=CC=C(C)C=C1)O* 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
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- 241000258937 Hemiptera Species 0.000 description 3
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 3
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 3
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- 241000500437 Plutella xylostella Species 0.000 description 3
- 241001414989 Thysanoptera Species 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
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- 150000001340 alkali metals Chemical class 0.000 description 3
- 239000011575 calcium Substances 0.000 description 3
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- MWUXSHHQAYIFBG-UHFFFAOYSA-N nitrogen oxide Inorganic materials O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 3
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- IBODDUNKEPPBKW-UHFFFAOYSA-N 1,5-dibromopentane Chemical compound BrCCCCCBr IBODDUNKEPPBKW-UHFFFAOYSA-N 0.000 description 2
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/10—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C323/18—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
- C07C323/20—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and singly-bound oxygen atoms bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton with singly-bound oxygen atoms bound to carbon atoms of the same non-condensed six-membered aromatic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
-
- 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
- A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
- A01N31/08—Oxygen or sulfur directly attached to an aromatic ring system
- A01N31/16—Oxygen or sulfur directly attached to an aromatic ring system with two or more oxygen or sulfur atoms directly attached to the same aromatic ring system
-
- 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
- A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
- A01N33/02—Amines; Quaternary ammonium compounds
- A01N33/08—Amines; Quaternary ammonium compounds containing oxygen or sulfur
- A01N33/10—Amines; Quaternary ammonium compounds containing oxygen or sulfur having at least one oxygen or sulfur atom directly attached to an aromatic ring system
-
- 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
- A01N33/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds
- A01N33/16—Biocides, pest repellants or attractants, or plant growth regulators containing organic nitrogen compounds containing nitrogen-to-oxygen bonds
- A01N33/18—Nitro compounds
- A01N33/20—Nitro compounds containing oxygen or sulfur attached to the carbon skeleton containing the nitro group
-
- 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
- A01N39/00—Biocides, pest repellants or attractants, or plant growth regulators containing aryloxy- or arylthio-aliphatic or cycloaliphatic compounds, containing the group or, e.g. phenoxyethylamine, phenylthio-acetonitrile, phenoxyacetone
-
- 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
- A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
- A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
- A01N41/10—Sulfones; Sulfoxides
-
- 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
- A01N49/00—Biocides, pest repellants or attractants, or plant growth regulators, containing compounds containing the group, wherein m+n>=1, both X together may also mean —Y— or a direct carbon-to-carbon bond, and the carbon atoms marked with an asterisk are not part of any ring system other than that which may be formed by the atoms X, the carbon atoms in square brackets being part of any acyclic or cyclic structure, or the group, wherein A means a carbon atom or Y, n>=0, and not more than one of these carbon atoms being a member of the same ring system, e.g. juvenile insect hormones or mimics thereof
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C317/00—Sulfones; Sulfoxides
- C07C317/16—Sulfones; Sulfoxides having sulfone or sulfoxide groups and singly-bound oxygen atoms bound to the same carbon skeleton
- C07C317/22—Sulfones; Sulfoxides having sulfone or sulfoxide groups and singly-bound oxygen atoms bound to the same carbon skeleton with sulfone or sulfoxide groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C323/00—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups
- C07C323/23—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton
- C07C323/31—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton
- C07C323/32—Thiols, sulfides, hydropolysulfides or polysulfides substituted by halogen, oxygen or nitrogen atoms, or by sulfur atoms not being part of thio groups containing thio groups and nitrogen atoms, not being part of nitro or nitroso groups, bound to the same carbon skeleton having the sulfur atom of at least one of the thio groups bound to a carbon atom of a six-membered aromatic ring of the carbon skeleton having at least one of the nitrogen atoms bound to an acyclic carbon atom of the carbon skeleton
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Insects & Arthropods (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP61184677A JPS6341451A (ja) | 1986-08-06 | 1986-08-06 | エ−テル誘導体およびそれを有効成分とする殺ダニ、殺虫組成物 |
US07/078,151 US4931474A (en) | 1986-08-06 | 1987-07-27 | Ether derivative and an acaricidal or insecticidal composition comprising said derivative |
EP87111243A EP0255935A1 (en) | 1986-08-06 | 1987-08-04 | An ether derivative and an acaricidal or insecticidal composition comprising said derivative |
KR1019870008625A KR880002820A (ko) | 1986-08-06 | 1987-08-06 | 에테르 유도체와 이들 유도체로 구성된 살비제 또는 살충제 조성물 |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
JP61184677A JPS6341451A (ja) | 1986-08-06 | 1986-08-06 | エ−テル誘導体およびそれを有効成分とする殺ダニ、殺虫組成物 |
Publications (2)
Publication Number | Publication Date |
---|---|
JPS6341451A true JPS6341451A (ja) | 1988-02-22 |
JPH0434989B2 JPH0434989B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1992-06-09 |
Family
ID=16157428
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP61184677A Granted JPS6341451A (ja) | 1986-08-06 | 1986-08-06 | エ−テル誘導体およびそれを有効成分とする殺ダニ、殺虫組成物 |
Country Status (4)
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2013157229A1 (ja) | 2012-04-20 | 2013-10-24 | クミアイ化学工業株式会社 | アルキルフェニルスルフィド誘導体及び有害生物防除剤 |
JP5616519B1 (ja) * | 2013-08-21 | 2014-10-29 | 北興化学工業株式会社 | 置換フェニルエーテル化合物および有害生物防除剤 |
WO2015025826A1 (ja) * | 2013-08-21 | 2015-02-26 | 北興化学工業株式会社 | 置換フェニルエーテル化合物および有害生物防除剤 |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0388682A1 (de) * | 1989-03-15 | 1990-09-26 | Bayer Ag | Substituierte Heteroarylphenylether, Verfahren zu ihrer Herstellung und ihre Verwendung als Insektizide |
AU643121B2 (en) * | 1991-03-19 | 1993-11-04 | Sumitomo Chemical Company, Limited | Aromatic compounds, their production processes and their compositions for the control of insect pests |
US5262441A (en) * | 1991-03-19 | 1993-11-16 | Sumitomo Chemical Company Limited | Aromatic compounds, their production processes and their compositions for the control of insect pests |
DE102006016641A1 (de) * | 2006-04-08 | 2007-10-11 | Bayer Cropscience Ag | Verwendung von 3-(2,4,6-Trimethylphenyl)-4-neopentylcarbonyloxy-5,5-tetramethylen-Δ3-dihydrofuran-2-on zur Bekämpfung von Dipteren aus der Familie der Cecidomyiidae |
Family Cites Families (28)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3154581A (en) * | 1961-10-18 | 1964-10-27 | Parke Davis & Co | Substituted amines |
NL6504268A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1965-04-03 | 1966-10-04 | ||
CH480012A (de) * | 1966-11-11 | 1969-10-31 | Ciba Geigy | Schädlingsbekämpfungsmittel |
CH481571A (de) * | 1967-01-20 | 1969-11-30 | Ciba Geigy | Schädlingsbekämpfungsmittel |
DE1957706C3 (de) * | 1968-11-18 | 1978-06-29 | Pfizer Corp., Colon (Panama) | Kernsubstituierte 3-Phenoxy-l-phenoxyalkylamino-propan-2-ole und Arzneimittel auf deren Basis |
GB1308191A (en) * | 1970-04-06 | 1973-02-21 | Science Union & Cie | Thiochroman derivatives and a process for preparing them |
CA956974A (en) * | 1970-06-22 | 1974-10-29 | Yasunori Abe | Compounds having the herbicidal effect and the process for the manufacture thereof |
BE795355A (fr) * | 1972-02-14 | 1973-05-29 | Nippon Kayaku Kk | Procedes de preparation d'ethers diphenyliques et acaricides les renfermant |
US3798276A (en) * | 1972-03-14 | 1974-03-19 | H Bayer | Herbicidal 4-trifluoromethyl-4'-nitrodiphenyl ethers |
DE2225873A1 (de) * | 1972-05-27 | 1973-12-13 | Bayer Ag | Isocyandiphenylaether |
CH589408A5 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1973-04-18 | 1977-07-15 | Ciba Geigy Ag | |
EG11593A (en) * | 1973-07-03 | 1980-07-31 | Bayer Ag | Halogenated 4-trifluiromethyl-4-cyano-diphenyl-ethers process for their preparation and their use as herbicides |
JPS5735162B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) * | 1973-07-19 | 1982-07-27 | ||
NL7505165A (nl) * | 1974-05-09 | 1975-11-11 | Ciba Geigy | Werkwijze voor het bereiden van nieuwe ethers. |
US3998972A (en) * | 1974-10-14 | 1976-12-21 | Ciba-Geigy Corporation | Diphenyl derivatives |
ZA754241B (en) * | 1974-11-01 | 1976-06-30 | Haessle Ab | New amines |
JPS5179723A (en) * | 1974-12-27 | 1976-07-12 | Nippon Kayaku Kk | Satsudanizai |
DE2616755A1 (de) * | 1975-04-18 | 1976-10-28 | Ciba Geigy Ag | Diaether, verfahren zu ihrer herstellung und ihre verwendung |
US4243681A (en) * | 1977-10-11 | 1981-01-06 | Mead Johnson & Company | Alkylthiophenoxypropanolamines and pharmaceutical compositions and uses thereof |
SE7807408L (sv) * | 1978-06-30 | 1979-12-31 | Haessle Ab | Hjertaktiva foreningar |
US4147805A (en) * | 1978-07-28 | 1979-04-03 | Mead Johnson & Company | Alkylthiophenoxyalkylamines and the pharmaceutical use thereof |
IT7949841A0 (it) * | 1978-08-07 | 1979-07-24 | Sandoz Ag | Derivati dell'1,4-bis-fenossi-buta no,loro preparazione e loro impiegocome erbicidi(caso 130-6794) |
DD150456A5 (de) * | 1979-03-01 | 1981-09-02 | Ciba Geigy Ag | Verfahren zur herstellung von derivaten des 3-amino-1,2-propandiols |
DE2935292A1 (de) * | 1979-08-31 | 1981-03-19 | Siemens AG, 1000 Berlin und 8000 München | Integrierte gleichrichterschaltung |
US4410548A (en) * | 1980-07-09 | 1983-10-18 | Reckitt & Colman Products Limited | Propanolamine derivatives |
AU7140481A (en) * | 1980-07-17 | 1982-01-21 | J.T. Baker Chemicals B.V. | Benzyl phenylethers as plant growth regulant |
DE3128117A1 (de) * | 1980-07-29 | 1982-03-11 | Yamanouchi Pharmaceutical Co., Ltd., Tokyo | Neue phenyl-aethylaminderivate, verfahren zu ihrer herstellung |
DE3461796D1 (en) * | 1983-02-23 | 1987-02-05 | Bayer Ag | Agent for regulating the growth of plants |
-
1986
- 1986-08-06 JP JP61184677A patent/JPS6341451A/ja active Granted
-
1987
- 1987-07-27 US US07/078,151 patent/US4931474A/en not_active Expired - Fee Related
- 1987-08-04 EP EP87111243A patent/EP0255935A1/en not_active Ceased
- 1987-08-06 KR KR1019870008625A patent/KR880002820A/ko not_active Withdrawn
Cited By (9)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2013157229A1 (ja) | 2012-04-20 | 2013-10-24 | クミアイ化学工業株式会社 | アルキルフェニルスルフィド誘導体及び有害生物防除剤 |
KR20150013487A (ko) | 2012-04-20 | 2015-02-05 | 구미아이 가가쿠 고교 가부시키가이샤 | 알킬페닐설파이드 유도체 및 유해생물 방제제 |
JPWO2013157229A1 (ja) * | 2012-04-20 | 2015-12-21 | クミアイ化学工業株式会社 | アルキルフェニルスルフィド誘導体及び有害生物防除剤 |
US9332754B2 (en) | 2012-04-20 | 2016-05-10 | Kumiai Chemical Industry Co., Ltd. | Alkyl phenyl sulfide derivative and pest control agent |
AP3772A (en) * | 2012-04-20 | 2016-08-31 | Kumiai Chemical Industry Co | Alkylphenylsulphide derivative and pest control agent |
AU2013250690B2 (en) * | 2012-04-20 | 2017-01-19 | Ihara Chemical Industry Co., Ltd. | Alkylphenylsulphide derivative and pest control agent |
US10023532B2 (en) | 2012-04-20 | 2018-07-17 | Kumiai Chemical Industry Co., Ltd. | Alkyl phenyl sulfide derivative and pest control agent |
JP5616519B1 (ja) * | 2013-08-21 | 2014-10-29 | 北興化学工業株式会社 | 置換フェニルエーテル化合物および有害生物防除剤 |
WO2015025826A1 (ja) * | 2013-08-21 | 2015-02-26 | 北興化学工業株式会社 | 置換フェニルエーテル化合物および有害生物防除剤 |
Also Published As
Publication number | Publication date |
---|---|
US4931474A (en) | 1990-06-05 |
EP0255935A1 (en) | 1988-02-17 |
KR880002820A (ko) | 1988-05-11 |
JPH0434989B2 (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) | 1992-06-09 |
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