CH574711A5 - O-phenoxyphenyl-o-alkyl-s-alkyl thiophosphates - with insecticidal and acaricidal activity - Google Patents
O-phenoxyphenyl-o-alkyl-s-alkyl thiophosphates - with insecticidal and acaricidal activityInfo
- Publication number
- CH574711A5 CH574711A5 CH952972A CH952972A CH574711A5 CH 574711 A5 CH574711 A5 CH 574711A5 CH 952972 A CH952972 A CH 952972A CH 952972 A CH952972 A CH 952972A CH 574711 A5 CH574711 A5 CH 574711A5
- Authority
- CH
- Switzerland
- Prior art keywords
- larvae
- formula
- compound
- alkyl
- hydrogen
- Prior art date
Links
- 230000000895 acaricidal effect Effects 0.000 title claims description 7
- 230000000749 insecticidal effect Effects 0.000 title claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 15
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 5
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 4
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 4
- 150000002367 halogens Chemical class 0.000 claims abstract description 4
- 150000001875 compounds Chemical class 0.000 claims description 23
- 238000012360 testing method Methods 0.000 claims description 16
- 239000001257 hydrogen Substances 0.000 claims description 13
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 10
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 10
- 239000004480 active ingredient Substances 0.000 claims description 9
- 239000000839 emulsion Substances 0.000 claims description 7
- 241000426497 Chilo suppressalis Species 0.000 claims description 6
- 241000258916 Leptinotarsa decemlineata Species 0.000 claims description 6
- 230000000694 effects Effects 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 5
- 239000008187 granular material Substances 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- 241000238876 Acari Species 0.000 claims description 4
- 241000196324 Embryophyta Species 0.000 claims description 4
- 244000061176 Nicotiana tabacum Species 0.000 claims description 4
- 235000002637 Nicotiana tabacum Nutrition 0.000 claims description 4
- 244000046052 Phaseolus vulgaris Species 0.000 claims description 4
- 241000949016 Rhipicephalus bursa Species 0.000 claims description 4
- 241000238680 Rhipicephalus microplus Species 0.000 claims description 4
- 244000061456 Solanum tuberosum Species 0.000 claims description 4
- 241000256250 Spodoptera littoralis Species 0.000 claims description 4
- 241001454293 Tetranychus urticae Species 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 230000001419 dependent effect Effects 0.000 claims description 4
- 238000010790 dilution Methods 0.000 claims description 4
- 239000012895 dilution Substances 0.000 claims description 4
- 235000013601 eggs Nutrition 0.000 claims description 4
- 238000011156 evaluation Methods 0.000 claims description 4
- 238000002474 experimental method Methods 0.000 claims description 4
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 239000002574 poison Substances 0.000 claims description 4
- 231100000614 poison Toxicity 0.000 claims description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
- 241000607479 Yersinia pestis Species 0.000 claims description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 3
- 239000000460 chlorine Substances 0.000 claims description 3
- 150000002431 hydrogen Chemical class 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 239000000575 pesticide Substances 0.000 claims description 3
- 239000007921 spray Substances 0.000 claims description 3
- 229920000742 Cotton Polymers 0.000 claims description 2
- 235000009161 Espostoa lanata Nutrition 0.000 claims description 2
- 240000001624 Espostoa lanata Species 0.000 claims description 2
- 241000238631 Hexapoda Species 0.000 claims description 2
- 206010061217 Infestation Diseases 0.000 claims description 2
- 241001465754 Metazoa Species 0.000 claims description 2
- 240000007594 Oryza sativa Species 0.000 claims description 2
- 235000010627 Phaseolus vulgaris Nutrition 0.000 claims description 2
- 239000013543 active substance Substances 0.000 claims description 2
- 238000004587 chromatography analysis Methods 0.000 claims description 2
- FHIVAFMUCKRCQO-UHFFFAOYSA-N diazinon Chemical compound CCOP(=S)(OCC)OC1=CC(C)=NC(C(C)C)=N1 FHIVAFMUCKRCQO-UHFFFAOYSA-N 0.000 claims description 2
- 235000005489 dwarf bean Nutrition 0.000 claims description 2
- 239000004495 emulsifiable concentrate Substances 0.000 claims description 2
- 235000013305 food Nutrition 0.000 claims description 2
- 239000011521 glass Substances 0.000 claims description 2
- 230000001418 larval effect Effects 0.000 claims description 2
- 239000004033 plastic Substances 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 abstract description 3
- 229910052783 alkali metal Inorganic materials 0.000 abstract description 2
- 150000001340 alkali metals Chemical group 0.000 abstract description 2
- 150000003839 salts Chemical class 0.000 abstract 2
- KDTZBYPBMTXCSO-UHFFFAOYSA-N 2-phenoxyphenol Chemical compound OC1=CC=CC=C1OC1=CC=CC=C1 KDTZBYPBMTXCSO-UHFFFAOYSA-N 0.000 abstract 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical group N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 1
- 125000005210 alkyl ammonium group Chemical group 0.000 abstract 1
- RLOWWWKZYUNIDI-UHFFFAOYSA-N phosphinic chloride Chemical compound ClP=O RLOWWWKZYUNIDI-UHFFFAOYSA-N 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
- 239000002904 solvent Substances 0.000 description 5
- 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
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 241001415279 Pseudococcidae Species 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 150000002903 organophosphorus compounds Chemical class 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 125000006701 (C1-C7) alkyl group Chemical group 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
- 241001124076 Aphididae Species 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- 241000238660 Blattidae Species 0.000 description 1
- 241000257161 Calliphoridae Species 0.000 description 1
- 241001414835 Cimicidae Species 0.000 description 1
- 241000256113 Culicidae Species 0.000 description 1
- 241001466044 Delphacidae Species 0.000 description 1
- 241001481702 Dermanyssidae Species 0.000 description 1
- 241001414830 Diaspididae Species 0.000 description 1
- 241001243087 Gryllotalpidae Species 0.000 description 1
- 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 1
- 241001124557 Lymantriidae Species 0.000 description 1
- 241000257226 Muscidae Species 0.000 description 1
- 241000256259 Noctuidae Species 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 241000258921 Pulicidae Species 0.000 description 1
- 241000255893 Pyralidae Species 0.000 description 1
- 241001510071 Pyrrhocoridae Species 0.000 description 1
- 241001124072 Reduviidae Species 0.000 description 1
- 241000254107 Tenebrionidae Species 0.000 description 1
- 241000255588 Tephritidae Species 0.000 description 1
- 241001454295 Tetranychidae Species 0.000 description 1
- 241000896028 Tettigoniidae Species 0.000 description 1
- 241000130767 Tineidae Species 0.000 description 1
- 241000131339 Tipulidae Species 0.000 description 1
- 239000000642 acaricide Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000003857 carboxamides Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 239000005457 ice water Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 238000010626 work up procedure Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
Classifications
-
- 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
- C07F9/18—Esters of thiophosphoric acids with hydroxyaryl compounds
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Molecular Biology (AREA)
- Agronomy & Crop Science (AREA)
- Biochemistry (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
Cpds. of formula (I): (where R1 is 1-4C alkyl; R2 is Me or Et; R3-R6 are H, Cl or Br; R7 is H, Cl or NO2) are pref. prepd. by (a) reacting the corresp. 2-hydroxydiphenyl ether (or its salt) with R2O (R1S)POCl; (b) reacting the corresp. 2-(R2O)(Cl)P(O)O-substd. cpd. with R1SH (or its salt); or (c) reacting the corresp. 2-(R1O)2P(S)O-substd. cpd. with (R')3N, R'OCSSM, MSR' or MS followed by R2Hal (where R' is alkyl; M is alkali metal, NH4 or alkylammonium; Hal is halogen).
Description
Die vorliegende Erfindung betrifft Schädlingsbekämpfungsmittel, enthaltend als aktive Komponente eine organische Phosphorverbindung und ihre Venvendung in der Schädlingsbekämpfung.
Die organischen Phosphorverbindungen haben die Formel (I)
EMI1.1
worin RI C1-C7-Alkyl,
R2 Methyl oder Äthyl
R7 Wasserstoff oder Nitro und R5, R6, R8, R9 und Rlo je Wasserstoff oder Halogen bedeuten.
Die bei R1 stehenden Alkylgruppen können geradkettig oder verzweigt sein. Beispiele solcher Gruppen sind u.a.: Methyl, Äthyl, Propyl, n-Butyl, i-, sek.,- tert.-Butyl, n-Pentyl, n-Hexyl und n-Heptyl.
Wegen ihrer Wirkung bevorzugt sind Verbindungen der Formel 1, worin
R1 Methyl, Äthyl, Propyl, Isopropyl, n-Butyl oder tert. Butyl,
R2 Methyl oder Äthyl,
R5, R6, R8, R9 und Rlo je Wasserstoff, Chlor oder Brom und
R7 Wasserstoff oder Nitro, bedeuten.
Die Verbindungen der Formel I können nach folgenden, an sich bekannten Methoden hergestellt werden:
EMI1.2
EMI1.3
<tb> säurebindendes
<tb> Mittel
<tb>
EMI1.4
In den Formeln II, III und IV haben R1 bis Rlo die für die Formel I angegebene Bedeutung und Me steht für ein Alkalimetall, insbesondere Natrium oder Kalium, oder eine 0+ Ammoniumgruppe, wie z. B. die Gruppe (R)3-NH, worin R Wasserstoff oder C14-Alkyl bedeutet.
Als säurebindende Mittel kommen in Frage: tertiäre Amine, z. B. Trialkylamine, Pyridin, Dialkylaniline; anorganische Basen, wie Hydride, Hydroxide; Karbonate und Bikarbonate von Alkali- und Erdalkalimetallen. Bei den Umsetzungen ist es machmal zweckmässig, Katalysatoren, wie z. B.
Kupfer oder Kupferchlorid, zu venvenden. Die Verfahren 1 und 2 werden bei einer Reaktionstemperatur zwischen -2 bis 130" C, bei normalem Druck und in Lösungs- oder Verdünnungsmitteln durchgeführt.
Als Lösungs- oder Verdünnungsmittel eignen sich z. B.
Äther und ätherartige Verbindungen, wie Diäthyläther, Dipropyläther, Dioxan, Tetrahydrofuran; Amide, wie N,Ndialkylierte Carbonsäureamide; aliphatische, aromatische sowie halogenierte Kohlenwasserstoffe, insbesondere Benzol, Toluol, Xylole, Chloroform, Chlorbenzol; Nitrile wie Acetonitrile; DMSO, Ketone wie Aceton, Methyläthylketon, Wasser.
Die Ausgangsstoffe der Formeln II, III und IV lassen sich analog bekannten Methoden herstellen.
Die Verbindungen der Formel I können zur Bekämpfung verschiedenartiger tierischer und pflanzlicher Schädlinge eingesetzt werden.
Insbesondere eignen sie sich zur Bekämpfung aller Entwicklungsstadien, wie z. B. Eier, Larven, Puppen, Nymphen und Adulte von Insekten der Familien: Tettigoniidae, Cryllidae, Gryllotalpidae, Blattidae, Reduviidae, Pyrrhocoridae, Cimicidae, Delphacidae, Aphididae, Diaspididae, Pseudococcidae, Scarabaeidae, Dermestidae, Coccinellidae, Tenebrionidae, Chrysomelidae, Bruchidae, Tineidae, Noctuidae, Lymantriidae, Pyralidae, Culicidae, Tipulidae, Stomoxydae, Trypetidae, Muscidae, Calliphoridae und Pulicidae, sowie Akariden der Familien Isodidae, Tetranychidae und Dermanyssidae.
Die insektizide oder akarizide Wirkung lässt sich durch Zusatz von anderen Insektiziden und/oder Akariziden wesentlich verbreitern und an gegebene Umstände anpassen.
Die Verbindungen der Formel I können für sich allein oder zusammen mit geeigneten Trägern und/oder Zuschlagstoffen eingesetzt werden. Geeignete Träger und Zuschlagstoffe können fest oder flüssig sein und entsprechen den in der Formulierungstechnik üblichen Stoffen, wie z. B.
natürlichen oder regenerierten Stoffen, Lösungs-, Dispergier-, Netz-, Haft-, Verdickungs-, Binde- und/oder Düngemitteln.
Zur Applikation können die Verbindungen der Formel I zu Stäubemitteln, Emulsionskonzentraten, Granulaten, Dispersionen, Sprays, zu Lösungen oder Aufschlämmungen in üblicher Formulierung, die in der Applikationstechnik zum Allgemeinwissen gehört, verarbeitet werden.
Die Herstellung erfindungsgemässer Mittel erfolgt in an sich bekannter Weise durch inniges Vermischen und/oder Vermahlen von Wirkstoffen der Formel I mit den geeigneten Trägerstoffen, gegebenenfalls unter Zusatz von gegenüber den Wirkstoffen inerten Dispergier- oder Lösungsmitteln. Die Wirkstoffe können z. B. in den in der deutschen Offenlegungsschrift 2 248 307 auf den Seiten 12 bis 18 beschriebenen Aufarbeitungsformen vorliegen und angewendet werden.
Beispiel 1
Zu einer auf 10 C abgekühlten Lösung von 58 g 4,2',4' Trichlor-2-hydroxy-diphenyläther und 22 g Triäthylamin in 500 ml absolutem Diäthyläther werden unter Rühren 41 g O-Äthyl-S-n-propylthiolphosphorsäurechlorid in 60 ml Di äthyläther so schnell zugetropft, dass die Temperatur 30 C nicht übersteigt. Man rührt noch zwei Stunden bei 20-25 C und versetzt das Gemisch unter weiterem Rühren mit 300 ml Eiswasser. Die organische Phase wird abgetrennt, einmal mit Wasser und zweimal mit eiskalter 2 %iger Natronlauge geschüttelt und dann mit Wasser neutral gewaschen. Nun behandelt man die Ätherphase mit Aktivkohle, filtriert, trocknet und dampft das Lösungsmittel ab. Der obige Rückstand wird drei Stunden bei 70" C und 0,1 Torr getrocknet.
Man erhält die Verbindung der Formel
EMI2.1
als gelbstichiges, nicht destillierbares, viskoses Öl: nD20 = 1,5737.
Auf analoge Weise werden auch folgende Verbindungen hergestellt:
EMI2.2
EMI3.1
Beispiel 2
Insektizide Frassgift-Wirkung
Tabak- und Kartoffelstauden wurden mit einer 0,05 %igen wässrigen Wirkstoffemulsion (erhalten aus einem 10%gen emulgierbaren Konzentrat) besprüht.
Nach dem Antrocknen des Belages wurden die Tabakpflanzen mit Eulenraupen (Spodoptera littoralis) und die Kartoffelstauden mit Kartoffelkäfer-Larven (Leptinotarsa decemlineata) besetzt. Der Versuch wird bei 24 C und 60% relativer Luftfeuchtigkeit durchgeführt.
Die Verbindungen gemäss Beispiel 1 zeigten im obigen Test Frassgift-Wirkung gegen Spodoptera littoralis und Leptinotarsa decemlineata.
Beispiel 3
Wirkung gegen Chilo suppressalis
Je 6 Reispflanzen der Sorte Caloro wurden in Plastiktöpfe, die einen oberen Durchmesser von 17 cm aufwiesen, ver pflanzt und zu einer Höhe von ca. 60 cm aufgezogen. Die
Infestation mit Chilo-suppressalis-Larven (L1; 3-4 mm lang) erfolgte 2 Tage nach der Wirkstoffzugabe in Granulatform (Aufwandmenge 8 kg Aktivsubstanz pro Hektare) in das
Paddy-Wasser. Die Auswertung auf insektizide Wirkung er folgte 10 Tage nach der Zugabe des Granulates.
Die Verbindungen gemäss Beispiel 1 wirkten im obigen Test gegen Chilo suppressalis.
Beispiel 4
Wirkung gegen Zecken
A. Rhipicephalus bursa
Je 5 adulte Zecken bzw. 50 Zeckenlarven wurden in ein
Glasröhrchen gezählt und für 1 bis 2 Minuten in 2 ml einer wässrigen Emulsion aus einer Verdünnungsreihe mit je 100,
10, 1 und 0,1 ppm Testsubstanz getaucht. Das Röhrchen wurde dann mit einem genormten Wattebausch verschlossen und auf den Kopf gestellt, damit die Wirkstoffemulsion von der Watte aufgenommen werden konnte.
Die Auswertung erfolgte bei den Adulten nach 2 Wochen und bei den Larven nach 2 Tagen. Für jeden Versuch liefen 2 Wiederholungen.
B. Boophilus microplus (Larven)
Mit einer analogen Verdünnungsreihe wie beim Test A wurden mit je 20 sensiblen resp. OP-resistenten Larven Versuche durchgeführt. (Die Resistenz bezieht sich auf die Verträglichkeit von Diazinon).
Die Verbindungen gemäss Beispiel 1 wirkten in diesen Tests gegen Adulte und Larven von Rhipicephalus bursa und sensible resp. OP-resistente Larven von Boophilus microplus.
Beispiel 5
Akarizide Wirkung
Phaseolus vulgaris (Buschbohnen) wurden 12 Stunden vor dem Test auf akarizide Wirkung mit einem infestierten
Blattstück aus einer Massenzucht von Tetranychus urticae belegt. Die übergelaufenen beweglichen Stadien wurden aus einem Chromatographiezerstäuber mit den emulgierten Test präparaten bestäubt, dass kein Ablaufen der Spritzbrühe eintrat. Nach zwei bis 7 Tagen wurden Larven, Adulte und
Eier unter dem Binokular auf lebende und tote Individuen ausgewertet und das Ergebnis in Prozenten ausgedrückt.
Während der Haltezeit standen die behandelten Pflanzen in Gewächshauskabinen bei 25" C.
Die Verbindungen gemäss Beispiel 1 wirkten im obigen
Test gegen Adulte, Larven und Eier von Tetranychus urticae.
PATENTANSPRUCH 1
Schädlingsbekämpfungsmittel, enthaltend als aktive Kom ponente eine Verbindung der Formel (I)
EMI3.2
worin
R1 C1--Alkyl,
R2 Methyl oder Äthyl, R7 Wasserstoff oder Nitro und R5, R6, R8, R9 und R1o je Wasserstoff oder Halogen bedeuten.
UNTERANSPRÜCHE
1. Mittel gemäss Patentanspruch I, enthaltend eine Ver bindung der Formel (I), worin
R1 Methyl, Äthyl, Propyl, Isopropyl, n-Butyl oder tert.
Butyl,
R2 Methyl oder Äthyl, 5 Rss R6, R8, R9 und R1o je Wasserstoff, Chlor oder Brom und
R7 Wasserstoff oder Nitro bedeuten.
2. Mittel gemäss Unteranspruch 1, enthaltend eine Ver bindung der Formel
**WARNUNG** Ende DESC Feld konnte Anfang CLMS uberlappen**.
The present invention relates to pesticides containing an organic phosphorus compound as active component and their use in pest control.
The organic phosphorus compounds have the formula (I)
EMI1.1
where RI is C1-C7-alkyl,
R2 methyl or ethyl
R7 is hydrogen or nitro and R5, R6, R8, R9 and Rlo are each hydrogen or halogen.
The alkyl groups at R1 can be straight-chain or branched. Examples of such groups include: methyl, ethyl, propyl, n-butyl, i-, sec., - tert-butyl, n-pentyl, n-hexyl and n-heptyl.
Because of their action, compounds of the formula 1 are preferred in which
R1 methyl, ethyl, propyl, isopropyl, n-butyl or tert. Butyl,
R2 methyl or ethyl,
R5, R6, R8, R9 and Rlo each hydrogen, chlorine or bromine and
R7 is hydrogen or nitro.
The compounds of the formula I can be prepared by the following methods known per se:
EMI1.2
EMI1.3
<tb> acid-binding
<tb> means
<tb>
EMI1.4
In the formulas II, III and IV, R1 to Rlo have the meaning given for the formula I and Me stands for an alkali metal, in particular sodium or potassium, or a 0+ ammonium group, such as. B. the group (R) 3-NH, in which R is hydrogen or C14-alkyl.
Suitable acid-binding agents are: tertiary amines, e.g. B. trialkylamines, pyridine, dialkylanilines; inorganic bases such as hydrides, hydroxides; Carbonates and bicarbonates of alkali and alkaline earth metals. In the reactions, it is sometimes useful to use catalysts such. B.
Copper or copper chloride to be used. Processes 1 and 2 are carried out at a reaction temperature between -2 to 130 ° C., under normal pressure and in solvents or diluents.
Suitable solvents or diluents are, for. B.
Ethers and ethereal compounds such as diethyl ether, dipropyl ether, dioxane, tetrahydrofuran; Amides, such as N, N-dialkylated carboxamides; aliphatic, aromatic and halogenated hydrocarbons, in particular benzene, toluene, xylenes, chloroform, chlorobenzene; Nitriles such as acetonitrile; DMSO, ketones such as acetone, methyl ethyl ketone, water.
The starting materials of the formulas II, III and IV can be prepared analogously to known methods.
The compounds of the formula I can be used for combating various animal and plant pests.
In particular, they are suitable for combating all stages of development, such. B. Eggs, larvae, pupae, nymphs and adults of insects belonging to the families: Tettigoniidae, Cryllidae, Gryllotalpidae, Blattidae, Reduviidae, Pyrrhocoridae, Cimicidae, Delphacidae, Aphididae, Diaspididae, Pseudococcidae, Chrysomermelidae, Pseudococcidae, Scarcinellestidae, Tenebrionidae, Chrcinomelestidae. Tineidae, Noctuidae, Lymantriidae, Pyralidae, Culicidae, Tipulidae, Stomoxydae, Trypetidae, Muscidae, Calliphoridae and Pulicidae, as well as acarids of the families Isodidae, Tetranychidae and Dermanyssidae.
The insecticidal or acaricidal effect can be significantly broadened by adding other insecticides and / or acaricides and adapted to given circumstances.
The compounds of the formula I can be used alone or together with suitable carriers and / or additives. Suitable carriers and additives can be solid or liquid and correspond to the substances customary in formulation technology, such as. B.
natural or regenerated substances, solvents, dispersants, wetting agents, adhesives, thickeners, binders and / or fertilizers.
For application, the compounds of the formula I can be processed into dusts, emulsion concentrates, granules, dispersions, sprays, into solutions or slurries in a customary formulation which is part of general knowledge in application technology.
The agents according to the invention are prepared in a manner known per se by intimately mixing and / or grinding active ingredients of the formula I with the suitable carriers, optionally with the addition of dispersants or solvents which are inert towards the active ingredients. The active ingredients can, for. B. in the work-up forms described in the German Offenlegungsschrift 2 248 307 on pages 12 to 18 are available and used.
example 1
To a solution, cooled to 10 ° C., of 58 g of 4.2 ', 4' trichloro-2-hydroxy-diphenyl ether and 22 g of triethylamine in 500 ml of absolute diethyl ether, 41 g of O-ethyl-Sn-propylthiolphosphoric acid chloride in 60 ml of diethyl ether are added while stirring added dropwise so quickly that the temperature does not exceed 30 C. The mixture is stirred for a further two hours at 20-25 ° C. and 300 ml of ice water are added to the mixture while stirring. The organic phase is separated off, shaken once with water and twice with ice-cold 2% sodium hydroxide solution and then washed neutral with water. The ether phase is now treated with activated charcoal, filtered, dried and the solvent is evaporated. The above residue is dried for three hours at 70 ° C. and 0.1 torr.
The compound of the formula is obtained
EMI2.1
as a yellowish, non-distillable, viscous oil: nD20 = 1.5737.
The following connections are also established in the same way:
EMI2.2
EMI3.1
Example 2
Insecticidal feed poison effect
Tobacco and potato plants were sprayed with a 0.05% aqueous active substance emulsion (obtained from a 10% emulsifiable concentrate).
After the covering had dried on, the tobacco plants were populated with owl caterpillars (Spodoptera littoralis) and the potato plants with Colorado beetle larvae (Leptinotarsa decemlineata). The experiment is carried out at 24 C and 60% relative humidity.
In the above test, the compounds according to Example 1 showed a food poison action against Spodoptera littoralis and Leptinotarsa decemlineata.
Example 3
Effect against Chilo suppressalis
In each case 6 rice plants of the Caloro variety were planted in plastic pots which had an upper diameter of 17 cm and raised to a height of about 60 cm. The
Infestation with Chilo suppressalis larvae (L1; 3-4 mm long) took place 2 days after the addition of the active ingredient in granulate form (application rate 8 kg active ingredient per hectare) into the
Paddy water. The evaluation of the insecticidal effect he followed 10 days after the addition of the granules.
The compounds according to Example 1 were effective against Chilo suppressalis in the above test.
Example 4
Effect against ticks
A. Rhipicephalus bursa
5 adult ticks and 50 tick larvae were each in one
Glass tubes counted and for 1 to 2 minutes in 2 ml of an aqueous emulsion from a dilution series with 100,
10, 1 and 0.1 ppm test substance immersed. The tube was then closed with a standardized cotton ball and turned upside down so that the active ingredient emulsion could be absorbed by the cotton wool.
The evaluation was carried out after 2 weeks for the adults and after 2 days for the larvae. Two repetitions were run for each attempt.
B. Boophilus microplus (larvae)
With an analogous dilution series as in test A, 20 sensitive resp. OP-resistant larval experiments were carried out. (The resistance relates to the tolerance of Diazinon).
The compounds according to Example 1 were active in these tests against adults and larvae of Rhipicephalus bursa and sensitive, respectively. OP-resistant larvae of Boophilus microplus.
Example 5
Acaricidal effect
Phaseolus vulgaris (French beans) were infested with a 12 hours prior to testing for acaricidal activity
Piece of leaf from a mass cultivation of Tetranychus urticae occupied. The overflowing mobile stages were dusted with the emulsified test preparations from a chromatography atomizer, so that the spray mixture did not run off. After two to 7 days, larvae, adults and
Eggs evaluated under the dissecting microscope for living and dead individuals and the result expressed as a percentage.
During the holding time, the treated plants stood in greenhouse cabins at 25 "C.
The compounds according to Example 1 worked in the above
Test against adults, larvae and eggs of Tetranychus urticae.
PATENT CLAIM 1
Pesticides containing a compound of the formula (I) as the active component
EMI3.2
wherein
R1 C1 - alkyl,
R2 is methyl or ethyl, R7 is hydrogen or nitro and R5, R6, R8, R9 and R1o are each hydrogen or halogen.
SUBCLAIMS
1. Agent according to claim I, containing a compound of the formula (I), in which
R1 methyl, ethyl, propyl, isopropyl, n-butyl or tert.
Butyl,
R2 is methyl or ethyl, 5 Rss R6, R8, R9 and R1o are each hydrogen, chlorine or bromine and
R7 mean hydrogen or nitro.
2. Means according to dependent claim 1, containing a compound of the formula Ver
** WARNING ** End of DESC field could overlap beginning of CLMS **.
Claims (1)
Priority Applications (16)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH952972A CH574711A5 (en) | 1972-06-23 | 1972-06-23 | O-phenoxyphenyl-o-alkyl-s-alkyl thiophosphates - with insecticidal and acaricidal activity |
| IL42475A IL42475A0 (en) | 1972-06-23 | 1973-06-11 | Diphenyl ether derivatives containing phsophorus their manufacture and their use as pesticides |
| CA173,880A CA1009247A (en) | 1972-06-23 | 1973-06-12 | Diphenyl ethers |
| NL7308580A NL7308580A (en) | 1972-06-23 | 1973-06-20 | |
| US00371905A US3833691A (en) | 1972-06-23 | 1973-06-20 | 2-(o,s-dilower alkyl-thiolphosphoryl)diphenyl ethers |
| DE2331594A DE2331594A1 (en) | 1972-06-23 | 1973-06-20 | NEW DIPHENYL ETHERS |
| EG237/73A EG11418A (en) | 1972-06-23 | 1973-06-21 | New diphenyl ethers used as insecticides |
| IT25750/73A IT989407B (en) | 1972-06-23 | 1973-06-22 | DIPHENYLETERS |
| ZA734236A ZA734236B (en) | 1972-06-23 | 1973-06-22 | New diphenyl ethers |
| BE132585A BE801290A (en) | 1972-06-23 | 1973-06-22 | PHENOXYPHENYL PHOSPHOROTHIOLATES AND PESTICIDE PRODUCTS CONTAINING THEM |
| JP48070690A JPS4954542A (en) | 1972-06-23 | 1973-06-22 | |
| GB2988673A GB1424397A (en) | 1972-06-23 | 1973-06-22 | Pesticidal phosphorus containing diphenyl ethers |
| ES416145A ES416145A1 (en) | 1972-06-23 | 1973-06-22 | 2-(o,s-dilower alkyl-thiolphosphoryl)diphenyl ethers |
| DD171767A DD106258A5 (en) | 1972-06-23 | 1973-06-22 | |
| AT551573A AT321645B (en) | 1972-06-23 | 1973-06-22 | Insecticidal and acaricidal agents |
| FR7322868A FR2423496A1 (en) | 1972-06-23 | 1973-06-22 | PHENOXYPHENYL PHOSPHOROTHIOLATES AND PESTICIDE PRODUCTS CONTAINING THEM |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH952972A CH574711A5 (en) | 1972-06-23 | 1972-06-23 | O-phenoxyphenyl-o-alkyl-s-alkyl thiophosphates - with insecticidal and acaricidal activity |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CH574711A5 true CH574711A5 (en) | 1976-04-30 |
Family
ID=4352949
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CH952972A CH574711A5 (en) | 1972-06-23 | 1972-06-23 | O-phenoxyphenyl-o-alkyl-s-alkyl thiophosphates - with insecticidal and acaricidal activity |
Country Status (3)
| Country | Link |
|---|---|
| BE (1) | BE801290A (en) |
| CH (1) | CH574711A5 (en) |
| ZA (1) | ZA734236B (en) |
-
1972
- 1972-06-23 CH CH952972A patent/CH574711A5/en not_active IP Right Cessation
-
1973
- 1973-06-22 BE BE132585A patent/BE801290A/en unknown
- 1973-06-22 ZA ZA734236A patent/ZA734236B/en unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BE801290A (en) | 1973-12-26 |
| ZA734236B (en) | 1974-03-27 |
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| PL | Patent ceased |