JPH09503764A - 有害生物防除剤としてのチオリン酸エステル - Google Patents
有害生物防除剤としてのチオリン酸エステルInfo
- Publication number
- JPH09503764A JPH09503764A JP7510588A JP51058895A JPH09503764A JP H09503764 A JPH09503764 A JP H09503764A JP 7510588 A JP7510588 A JP 7510588A JP 51058895 A JP51058895 A JP 51058895A JP H09503764 A JPH09503764 A JP H09503764A
- Authority
- JP
- Japan
- Prior art keywords
- alkyl
- alkoxy
- optionally substituted
- halogen
- substituted
- 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.)
- Withdrawn
Links
- 241000607479 Yersinia pestis Species 0.000 title claims abstract description 12
- RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 73
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 10
- 125000000547 substituted alkyl group Chemical group 0.000 claims abstract description 10
- 125000003107 substituted aryl group Chemical group 0.000 claims abstract description 3
- 150000003580 thiophosphoric acid esters Chemical class 0.000 claims abstract description 3
- 229910052736 halogen Inorganic materials 0.000 claims description 41
- 150000002367 halogens Chemical class 0.000 claims description 41
- 239000000460 chlorine Substances 0.000 claims description 37
- 229910052801 chlorine Inorganic materials 0.000 claims description 37
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 35
- 125000000217 alkyl group Chemical group 0.000 claims description 31
- 125000003545 alkoxy group Chemical group 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 18
- 239000002253 acid Substances 0.000 claims description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 11
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 9
- 239000000370 acceptor Substances 0.000 claims description 8
- 238000004519 manufacturing process Methods 0.000 claims description 8
- XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 claims description 7
- 238000006243 chemical reaction Methods 0.000 claims description 7
- 125000001424 substituent group Chemical group 0.000 claims description 7
- RYYWUUFWQRZTIU-UHFFFAOYSA-N Thiophosphoric acid Chemical class OP(O)(S)=O RYYWUUFWQRZTIU-UHFFFAOYSA-N 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- 239000003085 diluting agent Substances 0.000 claims description 6
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 2
- HPFKOFNYNQMWEF-UHFFFAOYSA-N chloro-dihydroxy-sulfanylidene-$l^{5}-phosphane Chemical class OP(O)(Cl)=S HPFKOFNYNQMWEF-UHFFFAOYSA-N 0.000 claims description 2
- 238000002955 isolation Methods 0.000 claims description 2
- 239000004094 surface-active agent Substances 0.000 claims description 2
- 239000000945 filler Substances 0.000 claims 1
- 230000000361 pesticidal effect Effects 0.000 claims 1
- 125000005346 substituted cycloalkyl group Chemical group 0.000 abstract 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 33
- 229910052731 fluorine Inorganic materials 0.000 description 33
- 239000011737 fluorine Substances 0.000 description 33
- 239000000203 mixture Substances 0.000 description 23
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 19
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical class CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 19
- -1 benzimidoylthio Chemical class 0.000 description 18
- 238000002360 preparation method Methods 0.000 description 18
- 239000002904 solvent Substances 0.000 description 16
- 239000003995 emulsifying agent Substances 0.000 description 15
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 125000004432 carbon atom Chemical group C* 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
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- 125000002877 alkyl aryl group Chemical group 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 230000008029 eradication Effects 0.000 description 7
- 229920000151 polyglycol Polymers 0.000 description 7
- 239000010695 polyglycol Substances 0.000 description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
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- 241001414720 Cicadellidae Species 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
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- 125000003118 aryl group Chemical group 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 239000008187 granular material Substances 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
- 239000002689 soil Substances 0.000 description 5
- 239000007858 starting material Substances 0.000 description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 4
- 241000196324 Embryophyta Species 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 241000238631 Hexapoda Species 0.000 description 4
- 241001674048 Phthiraptera Species 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 229910052794 bromium Inorganic materials 0.000 description 4
- 229910052500 inorganic mineral Inorganic materials 0.000 description 4
- 239000002917 insecticide Substances 0.000 description 4
- 235000010755 mineral Nutrition 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- KNCHDRLWPAKSII-UHFFFAOYSA-N 4-ethyl-2-methylpyridine Chemical group CCC1=CC=NC(C)=C1 KNCHDRLWPAKSII-UHFFFAOYSA-N 0.000 description 3
- 241001143309 Acanthoscelides obtectus Species 0.000 description 3
- 206010004194 Bed bug infestation Diseases 0.000 description 3
- 235000003899 Brassica oleracea var acephala Nutrition 0.000 description 3
- 235000011301 Brassica oleracea var capitata Nutrition 0.000 description 3
- 235000001169 Brassica oleracea var oleracea Nutrition 0.000 description 3
- 241001327638 Cimex lectularius Species 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000004606 Fillers/Extenders Substances 0.000 description 3
- 241000257303 Hymenoptera Species 0.000 description 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 3
- 241000500437 Plutella xylostella Species 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 241000125167 Rhopalosiphum padi Species 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
- 235000019441 ethanol Nutrition 0.000 description 3
- 238000003958 fumigation Methods 0.000 description 3
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- 239000002480 mineral oil Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000005645 nematicide Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- FOMXNJDIEWJLCN-UHFFFAOYSA-N 2-[chloro(ethoxy)phosphoryl]sulfanylbutane Chemical compound CCOP(Cl)(=O)SC(C)CC FOMXNJDIEWJLCN-UHFFFAOYSA-N 0.000 description 2
- SYBYTAAJFKOIEJ-UHFFFAOYSA-N 3-Methylbutan-2-one Chemical compound CC(C)C(C)=O SYBYTAAJFKOIEJ-UHFFFAOYSA-N 0.000 description 2
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- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
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- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
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- 235000011181 potassium carbonates Nutrition 0.000 description 1
- NTTOTNSKUYCDAV-UHFFFAOYSA-N potassium hydride Chemical compound [KH] NTTOTNSKUYCDAV-UHFFFAOYSA-N 0.000 description 1
- 229910000105 potassium hydride Inorganic materials 0.000 description 1
- TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
- 229940086066 potassium hydrogencarbonate Drugs 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
- 229960003351 prussian blue Drugs 0.000 description 1
- 239000013225 prussian blue Substances 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 239000011435 rock Substances 0.000 description 1
- 229910052624 sepiolite Inorganic materials 0.000 description 1
- 235000019355 sepiolite Nutrition 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 238000003307 slaughter Methods 0.000 description 1
- 238000002791 soaking Methods 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 235000017550 sodium carbonate Nutrition 0.000 description 1
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910000104 sodium hydride Inorganic materials 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000003206 sterilizing agent Substances 0.000 description 1
- HXJUTPCZVOIRIF-UHFFFAOYSA-N sulfolane Chemical compound O=S1(=O)CCCC1 HXJUTPCZVOIRIF-UHFFFAOYSA-N 0.000 description 1
- 150000003462 sulfoxides Chemical class 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229920001059 synthetic polymer Polymers 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/16—Esters of thiophosphoric acids or thiophosphorous acids
- C07F9/165—Esters of thiophosphoric acids
- C07F9/177—Esters of thiophosphoric acids with cycloaliphatic alcohols
-
- 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
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds
- A01N57/12—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds containing acyclic or cycloaliphatic radicals
-
- 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
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds
- A01N57/14—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds containing aromatic radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/16—Esters of thiophosphoric acids or thiophosphorous acids
- C07F9/165—Esters of thiophosphoric acids
- C07F9/1651—Esters of thiophosphoric acids with hydroxyalkyl compounds with further substituents on alkyl
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/16—Esters of thiophosphoric acids or thiophosphorous acids
- C07F9/165—Esters of thiophosphoric acids
- C07F9/1653—Esters of thiophosphoric acids with arylalkanols
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
Description
Claims (1)
- 【特許請求の範囲】 1.一般式(I) 式中、Rは随時置換されていてもよいアルキルを表わし、 R1は随時置換されていてもよいアルキルを表わし、 R2は随時置換されていてもよいアルキルを表わし、そして R3は随時置換されていてもよいアルキル、随時置換されていてもよいシク ロアルキルまたは随時置換されていてもよいアリールを表わす、 の置換されたチオリン酸エステル。 2.Rが随時ハロゲン及び/またはC1〜C4−アルコキシで置換されていても よいC1〜C6−アルキルを表わし、R1が随時ハロゲン及び/またはC1〜C4− アルコキシで置換されていてもよいC1〜C6−アルキルを表わし、R2が随時ハ ロゲン及び/またはC1〜C4−アルコキシで置換されていてもよいC1〜C6−ア ルキルを表わし、そしてR3が随時ハロゲン及び/またはC1〜C4−アルコキシ で置換されていてもよいC1〜C6−アルキルを表わすか、随時ハロゲン及び/ま たはC1〜C4−アルキル及び/またはC1〜C4−アルコキシで置換されていても よいC3〜C7−シクロアルキルを表わし、ここにC1〜C4−アルキル及びC1〜 C4−アルコキシ基はハロゲンで置換されることができるか;或いはハロゲン; C1〜C4−アルキル及び/またはC1〜C4−アルコキシからの 1個またはそれ以上の同一もしくは相異なる置換基を有し得るフェニルを表わし 、ここにC1〜C4−アルキル及びC1〜C4−アルコキシ基がハロゲン;ニトロ及 び/またはシアノ(CN)で置換されることができる、請求の範囲第1項記載の 化合物。 3.Rが随時ハロゲン及び/またはC1〜C4−アルコキシで置換されていても よいC1〜C4−アルキルを表わし、R1が随時ハロゲン及び/またはC1〜C4− アルコキシで置換されていてもよいC1〜C4−アルキルを表わし、R2が随時ハ ロゲン及び/またはC1〜C4−アルコキシで置換されていてもよいC1〜C4−ア ルキルを表わし、そしてR3が随時ハロゲン及び/またはC1〜C4−アルコキシ で置換されていてもよいC1〜C5−アルキルを表わすか、随時ハロゲン及び/ま たはC1〜C4−アルキル及び/またはC1〜C4−アルコキシで置換されていても よいC3〜C6−シクロアルキルを表わし、ここにC1〜C4−アルキル及びC1〜 C4−アルコキシ基はハロゲンで置換されることができるか;或いはハロゲン; C1〜C4−アルキル及び/またはC1〜C4−アルコキシからの1個またはそれ以 上の同一もしくは相異なる置換基を有し得るフェニルを表わし、ここにC1〜C4 −アルキル及びC1〜C4−アルコキシ基がハロゲン;ニトロ及び/またはシアノ (CN)で置換されることができる、請求の範囲第1項記載の化合物。 4.RがC1〜C4−アルキルを表わし、R1がC1〜C4−アルキルを表わし、 R2がC1〜C4−アルキルを表わし、そしてR3が随時塩素及び/またはC1〜C2 −アルコキシで置換されていてもよいC1〜C5−アルキルを表わすか、C5〜C6 −シクロアルキルを表わすか、或いは随時塩素で置換されていてもよいフェニル を表わす、請求の範囲第1項記載の 化合物。 5.a)一般式(II) 式中、R及びR1は上記の意味を有する、 のクロロチオリン酸エステルを適当ならば酸受容体の存在下及び適当ならば希釈 剤の存在下で一般式(III) 式中、R2及びR3は上記の意味を有する、 の化合物と反応させるか、或いは b)一般式(IV) 式中、R1は上記の意味を有する、 のチオリン酸二塩化物を最初の反応工程において適当ならば酸受容体の存在下及 び適当ならば希釈剤の存在下で一般式(V) R−OH (V) 式中、Rは上記の意味を有する、 のアルコールと反応させ、そして生じる一般式(II) 式中、R及びR1は上記の意味を有する、 の生成物を適当ならば単離した後に適当ならば酸受容体の存在下及び適当ならば 希釈剤の存在下で一般式(III) 式中、R2及びR3は上記の意味を有する、 の化合物と反応させることを特徴とする、請求の範囲第1項記載の一般式(I) の置換されたチオリン酸エステルの製造方法。 6.少なくとも1つの請求の範囲第1項記載の式(I)の化合物からなること を特徴とする、有害生物防除剤。 7.有害生物を防除する際の請求の範囲第1項記載の式(I)の化合物の使用 。 8.請求の範囲第1項記載の式(I)の化合物を有害生物及び/またはその環 境上に作用させることを特徴とする、有害生物の防除方法。 9.請求の範囲第1項記載の式(I)の化合物を増量剤及び/または表面活性 剤と混合することを特徴とする、有害生物防除剤の製造方法。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE4334196.9 | 1993-10-07 | ||
DE19934334196 DE4334196A1 (de) | 1993-10-07 | 1993-10-07 | Phosphorsäure-Derivate |
PCT/EP1994/003203 WO1995009860A1 (de) | 1993-10-07 | 1994-09-26 | Thiophosphorsäureester als schädlingsbekämpfungsmittel |
Publications (1)
Publication Number | Publication Date |
---|---|
JPH09503764A true JPH09503764A (ja) | 1997-04-15 |
Family
ID=6499618
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP7510588A Withdrawn JPH09503764A (ja) | 1993-10-07 | 1994-09-26 | 有害生物防除剤としてのチオリン酸エステル |
Country Status (6)
Country | Link |
---|---|
EP (1) | EP0722450A1 (ja) |
JP (1) | JPH09503764A (ja) |
CN (1) | CN1133046A (ja) |
AU (1) | AU7809994A (ja) |
DE (1) | DE4334196A1 (ja) |
WO (1) | WO1995009860A1 (ja) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH08231566A (ja) * | 1994-12-28 | 1996-09-10 | Nippon Bayeragrochem Kk | 有機燐酸エステル誘導体及び殺虫殺センチュウ剤 |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS58222123A (ja) * | 1982-06-18 | 1983-12-23 | Yoshino Kogyosho Co Ltd | 合成樹脂製シ−ト状体 |
JPS61133236A (ja) * | 1984-12-03 | 1986-06-20 | Showa Denko Kk | キヤツプラベル |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE2545392A1 (de) * | 1975-10-10 | 1977-04-21 | Bayer Ag | Benzimidoylthionothiolphosphorsaeureester, verfahren zu ihrer herstellung und ihre verwendung als insektizide und akarizide |
US4473562A (en) * | 1982-08-26 | 1984-09-25 | Chevron Research Company | Pesticidal O-(N-alkoxy-aliphatic hydroxamate)-phosphorus esters and thioesters |
JPH08183495A (ja) * | 1994-12-29 | 1996-07-16 | Toshiyuki Fujiwara | 水上浮体構造物の海抜高さ制御方法 |
-
1993
- 1993-10-07 DE DE19934334196 patent/DE4334196A1/de not_active Withdrawn
-
1994
- 1994-09-26 AU AU78099/94A patent/AU7809994A/en not_active Abandoned
- 1994-09-26 WO PCT/EP1994/003203 patent/WO1995009860A1/de not_active Application Discontinuation
- 1994-09-26 CN CN 94193706 patent/CN1133046A/zh active Pending
- 1994-09-26 EP EP94928815A patent/EP0722450A1/de not_active Withdrawn
- 1994-09-26 JP JP7510588A patent/JPH09503764A/ja not_active Withdrawn
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS58222123A (ja) * | 1982-06-18 | 1983-12-23 | Yoshino Kogyosho Co Ltd | 合成樹脂製シ−ト状体 |
JPS61133236A (ja) * | 1984-12-03 | 1986-06-20 | Showa Denko Kk | キヤツプラベル |
Also Published As
Publication number | Publication date |
---|---|
WO1995009860A1 (de) | 1995-04-13 |
CN1133046A (zh) | 1996-10-09 |
EP0722450A1 (de) | 1996-07-24 |
AU7809994A (en) | 1995-05-01 |
DE4334196A1 (de) | 1995-04-13 |
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