CH575210A5 - O-(1-aryl-2-halovinyl) (di)thiophosphates - insecticides acaricides and nematocides - Google Patents
O-(1-aryl-2-halovinyl) (di)thiophosphates - insecticides acaricides and nematocidesInfo
- Publication number
- CH575210A5 CH575210A5 CH960972A CH960972A CH575210A5 CH 575210 A5 CH575210 A5 CH 575210A5 CH 960972 A CH960972 A CH 960972A CH 960972 A CH960972 A CH 960972A CH 575210 A5 CH575210 A5 CH 575210A5
- Authority
- CH
- Switzerland
- Prior art keywords
- sep
- larvae
- sec
- formula
- compound
- Prior art date
Links
- 230000000895 acaricidal effect Effects 0.000 title claims description 8
- 239000000642 acaricide Substances 0.000 title description 2
- 239000002917 insecticide Substances 0.000 title description 2
- 230000001069 nematicidal effect Effects 0.000 title 1
- 239000005645 nematicide Substances 0.000 title 1
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 15
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 11
- 229910052794 bromium Inorganic materials 0.000 claims abstract description 8
- 229910052760 oxygen Inorganic materials 0.000 claims abstract description 5
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims abstract description 3
- 229910052717 sulfur Inorganic materials 0.000 claims abstract description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims abstract 12
- 239000000460 chlorine Substances 0.000 claims description 130
- QUPDWYMUPZLYJZ-UHFFFAOYSA-N ethyl Chemical compound C[CH2] QUPDWYMUPZLYJZ-UHFFFAOYSA-N 0.000 claims description 105
- 150000001875 compounds Chemical class 0.000 claims description 25
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 20
- 238000012360 testing method Methods 0.000 claims description 18
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 17
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 12
- 239000004480 active ingredient Substances 0.000 claims description 10
- 239000001257 hydrogen Substances 0.000 claims description 9
- 230000000694 effects Effects 0.000 claims description 8
- 239000000839 emulsion Substances 0.000 claims description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 6
- 241000426497 Chilo suppressalis Species 0.000 claims description 6
- 241000258916 Leptinotarsa decemlineata Species 0.000 claims description 6
- 241000949016 Rhipicephalus bursa Species 0.000 claims description 6
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 6
- 238000002474 experimental method Methods 0.000 claims description 6
- 230000000749 insecticidal effect Effects 0.000 claims description 6
- 235000013601 eggs Nutrition 0.000 claims description 5
- 239000008187 granular material Substances 0.000 claims description 5
- 150000002431 hydrogen Chemical class 0.000 claims description 5
- 239000000203 mixture Substances 0.000 claims description 5
- 241000238876 Acari Species 0.000 claims description 4
- 241000196324 Embryophyta Species 0.000 claims description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 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
- 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
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 238000010790 dilution Methods 0.000 claims description 4
- 239000012895 dilution Substances 0.000 claims description 4
- 229910052736 halogen Inorganic materials 0.000 claims description 4
- 150000002367 halogens Chemical class 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 239000002574 poison Substances 0.000 claims description 4
- 231100000614 poison Toxicity 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 4
- 241000238631 Hexapoda Species 0.000 claims description 3
- 239000000575 pesticide Substances 0.000 claims description 3
- 239000007921 spray Substances 0.000 claims description 3
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 claims description 2
- 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
- 206010061217 Infestation Diseases 0.000 claims description 2
- 240000007594 Oryza sativa Species 0.000 claims description 2
- 235000010627 Phaseolus vulgaris Nutrition 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 239000013543 active substance Substances 0.000 claims description 2
- 239000003795 chemical substances by application 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
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
- 238000011156 evaluation Methods 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
- 239000011593 sulfur Substances 0.000 claims description 2
- 230000001419 dependent effect Effects 0.000 claims 4
- 239000002253 acid Substances 0.000 abstract description 7
- 125000000217 alkyl group Chemical group 0.000 abstract description 3
- 239000011230 binding agent Substances 0.000 abstract description 3
- 229910052783 alkali metal Inorganic materials 0.000 abstract description 2
- 150000001340 alkali metals Chemical class 0.000 abstract description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 abstract 1
- 238000010561 standard procedure Methods 0.000 abstract 1
- 125000005208 trialkylammonium group Chemical group 0.000 abstract 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 13
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- -1 methoxy, ethyl Chemical group 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 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
- 241000251730 Chondrichthyes Species 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-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
- 239000002904 solvent Substances 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 241000607479 Yersinia pestis Species 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 229910052799 carbon Inorganic materials 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
- 229910000104 sodium hydride Inorganic materials 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- VYWPPRLJNVHPEU-UHFFFAOYSA-N 2-chloro-1-(2,4-dichlorophenyl)ethanone Chemical compound ClCC(=O)C1=CC=C(Cl)C=C1Cl VYWPPRLJNVHPEU-UHFFFAOYSA-N 0.000 description 1
- WONYMNWUJVKVII-UHFFFAOYSA-N 3,5-diiodothyropropionic acid Chemical compound IC1=CC(CCC(=O)O)=CC(I)=C1OC1=CC=C(O)C=C1 WONYMNWUJVKVII-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 241001124076 Aphididae Species 0.000 description 1
- 241000238888 Argasidae 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
- 241001414835 Cimicidae 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
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 241000238816 Gryllidae 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
- 241001465754 Metazoa Species 0.000 description 1
- 241000257226 Muscidae Species 0.000 description 1
- 239000007832 Na2SO4 Substances 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 241001415279 Pseudococcidae Species 0.000 description 1
- 241000258921 Pulicidae Species 0.000 description 1
- 241001510071 Pyrrhocoridae Species 0.000 description 1
- 241001124072 Reduviidae Species 0.000 description 1
- 241000254062 Scarabaeidae Species 0.000 description 1
- KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 1
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 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
- 241000131339 Tipulidae Species 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
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 150000003857 carboxamides Chemical class 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 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
- 125000006606 n-butoxy group Chemical group 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
- 150000002825 nitriles Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 239000012053 oil suspension Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 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
- 239000012312 sodium hydride Substances 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 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
- 239000008096 xylene Substances 0.000 description 1
- 150000003738 xylenes Chemical class 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
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/113—Esters of phosphoric acids with unsaturated acyclic 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
- A01N57/14—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
-
- 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
- A01N57/16—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds containing heterocyclic 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
- C07F9/173—Esters of thiophosphoric acids with unsaturated acyclic alcohols
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Dentistry (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Title cpds. of formula (I): (where R1 is 1-3C alkyl (pref. Et); R2 is 3-5C alkyl (pref. n-Pr, s-Bu or i-Bu); each R3 is H, Cl, Br, Me or MeO; n = 1,2 or 3; X is O or S; Y is H or Cl; and Hal is Cl or Br) can be prepd. by standard methods, e.g. by reacting a cpd. (II): with R1O(R2S)P(X)Hal in the presence of an acid binder, or with R1OP(X)(Hal)2 followed by R2SM (where M is H, alkali metal, NH4 or trialkylammonium).
Description
Die vorliegende Erfindung betrifft Schädlingsbekämpfungs- mittel enthaltend als aktive Komponente einen O-l-Phenyl
2-halogen-vinyl-thio resp. -dithiophosphorsäureester und ihre Verwendung in der Schädlingsbekämpfung.
Die O-l-Phenyl-2-halogen-vinyl-thio resp. -dithiophosphorsäureester haben die Formel (I)
EMI1.1
R1 C1-C2-Alkyl, R1 C1-C2-Alkyl,
R3, R4 und R5 je Wasserstoffe, Halogen, C1-C6-Alkyl oder Cl-Cs-Alkoxy,
X Sauerstoff oder Schwefel,
Y Wasserstoff oder Chlor und
Hal Chlor oder Brom bedeuten.
Unter Halogen sind Fluor, Chlor, Brom oder Jod, insbesondere aber Chlor oder Brom zu verstehen.
Die bei R1 bis R5 stehenden Alkyl- und Alkoxygruppen können geradkettig oder verzweigt sein.
Beispiele solcher Gruppen sind u.a.: Methyl, Methoxy, Äthyl, Äthoxy, Propyl, Propoxy, Isopropyl, Isopropoxy, n-Butyl, n-Butoxy, i-, sek.-, tert.-Butyl, n-Pentyl und n-HexyL
Wegen ihrer Wirkung bevorzugt sind Verbindungen der
Formel I, worin
R1 Äthyl,
R2 n-Propyl,
R3, R4 und R5 je Wasserstoff, Chlor, Brom, Methyl oder Methoxy
X Sauerstoff,
Y Wasserstoff oder Chlor und
Hal Chlor bedeuten.
Die Verbindungen der Formel I werden nach folgenden an sich bekannten Methoden hergestellt:
EMI1.2
<tb> <SEP> i)
<tb> <SEP> x <SEP> Hai
<tb> <SEP> R1 <SEP> 0 <SEP> II <SEP> J <SEP> < <SEP> sälXrebindendes¯+
<tb> <SEP> R <SEP> + <SEP> H-C <SEP> \ <SEP> Mittel <SEP> # <SEP> i
<tb> <SEP> R2S <SEP> R
<tb> <SEP> (11) <SEP> Y <SEP> (iii)R54
<tb> <SEP> 2)
<tb> <SEP> x <SEP> X <SEP> Hal <SEP> R
<tb> <SEP> 3
<tb> <SEP> RlOPHal2 <SEP> + <SEP> H-C-C <SEP> 4 <SEP> dz <SEP> säurebindendes
<tb> <SEP> (IV) <SEP> y <SEP> (III <SEP> t <SEP> 4 <SEP> Mittel
<tb> <SEP> HiY <SEP> Y <SEP> 5 <SEP> .säurebindendes
<tb> <SEP> x <SEP> C <SEP> R <SEP> + <SEP> SH <SEP> Mittel
<tb> <SEP> 0 <SEP> II <SEP> 11R <SEP> (vi)
<tb> <SEP> 'JalsP <SEP> < <SEP> i <SEP> oder
<tb> <SEP> oder
<tb> <SEP> R4 <SEP> + <SEP> MeSR2 <SEP> -·
<tb> <SEP> R5
<tb> <SEP> (viI)
<tb> <SEP> I-Ial <SEP>
Y
<tb> <SEP> Ral <SEP> Y <SEP> Hai <SEP> X <SEP> R3
<tb> <SEP> 3) <SEP> \ <SEP> / <SEP> R3 <SEP> IilO <SEP> il <SEP> C
<tb> <SEP> II <SEP> II
<tb> <SEP> (K10)2Po-c-t-I <SEP> -oder
<tb> <SEP> 4 <SEP> R5 <SEP> R4 <SEP> --¹ <SEP> (v) <SEP> R5
<tb> <SEP> Pol
<tb> <SEP> 5
<tb> <SEP> Hal <SEP> Y <SEP> säurebindendes
<tb> X <SEP> C <SEP> R3 <SEP> + <SEP> R2SH <SEP> Mittel <SEP> 9 <SEP> I
<tb> püyyR34 <SEP> + <SEP> < <SEP> I
<tb> <SEP> (v) <SEP> R5 <SEP> (vii)
<tb>
EMI2.1
<tb> 4) <SEP> VIlI <SEP> + <SEP> SOCl <SEP> oder <SEP> Hal <SEP> Y
<tb> <SEP> POl5 <SEP> xi <SEP> + <SEP> + <SEP> wahlweise <SEP> nacheincmder
<tb> <SEP> 5 <SEP> R <SEP> OH <SEP> I <SEP> und <SEP> R2SH
<tb> <SEP> 012P00 <SEP> \ <SEP> 1 <SEP> 2
<tb> <SEP> (mix) <SEP> R5 <SEP> R4 <SEP> (x) <SEP> (xi)
<tb> <SEP> saurebindendes
<tb> <SEP> Mittel
<tb> <SEP> Mittel
<tb> <SEP> 5) <SEP> 0 <SEP> R3
<tb>
<SEP> Hai <SEP> Hal
<tb> <SEP> ii <SEP> 1 <SEP> säuYebindendes
<tb> <SEP> cl <SEP> P <SEP> + <SEP> HC <SEP> a <SEP> 9 <SEP> Mittel <SEP> ei
<tb> <SEP> 3
<tb> <SEP> Y <SEP> (XII) <SEP> R
<tb> <SEP> Hai <SEP> Y <SEP> 5
<tb> <SEP> X <SEP> C <SEP> R?
<tb> <SEP> II <SEP> II <SEP> < <SEP> + <SEP> wahlwei.se <SEP> nacheinander
<tb> <SEP> 2
<tb> <SEP> C12P-dP <SEP> R <SEP> R1OH <SEP> und <SEP> R2
<tb> <SEP> Rq <SEP> (X) <SEP> (xi
<tb> <SEP> (Ix) <SEP> R5 <SEP> (X) <SEP> (XI)
<tb> <SEP> säurebindendes
<tb> <SEP> Mittel
<tb> <SEP> I
<tb>
In den Formeln II bis XII haben R1, R2, R3, R4, R5, X, Y, und Hal die für die Formel I angegebene Bedeutung und Me steht für ein Alkalimetall, insbesondere für Natrium oder Kalium, Ammonium oder (C1-C4-Alkyl)3- ammonium.
Als säurebindende Mittel kommen in Frage: tertiäre Amine, z. B. Trialkylamine, Pyridin, Dialkylaniline; anorganische Basen, wie Hydroxide; Karbonate und Bikarbonate von Alkali-, Erdalkalimetallen.
Die Verfahren 1 bis 5 werden bei einer Reaktionstemperatur zwischen -10-100 C, insbesondere zwischen 20-80 C, bei normalem oder erhöhtem Druck und in Lösungs- oder
Verdünnungsmitteln durchgeführt.
Als Lösungs- oder Verdünnungsmittel eignen sich z. B.
Äther und ätherartige Verbindungen, wie Diäthyläther, Dipro pyläther, Dioxan, Dimethoxyäthan, Tetrahydrofuran; Amide wie N,N-di-alkylierte Carbonsäureamide; aliphatische, aroma tische sowie halogenierte Kohlenwasserstoffe, insbesondere
Benzol, Toluol, Xylole, Chloroform, Chlorbenzol; Nitrile wie
Acetonitrile; DMSO, Ketone wie Aceton, Methyläthylketon.
Die Ausgangsstoffe der Formeln II, III, IV, VIII, IX und
XII sind teilweise bekannt oder können analog bekannten
Methoden hergestellt werden.
Die Verbindungen der Formel I weisen eine breite biozide
Wirkung auf und eignen sich daher zur Bekämpfung von ver schiedenartigen pflanzlichen und tierischen Schädlingen und als Pflanzenregulatoren.
Insbesondere besitzen die Verbindungen der Formel I insektizide und akarizide Eigenschaften und können gegen alle Entwicklungsstadien wie z. B. Eier, Larven, Puppen, Nymphen und Adulte von Insekten und Vertretern der Ordnung Akarina eingesetzt werden, wie z. B. gegen Insekten der Familien: Tettigoniidae, Gryllidae, Gryllotalpidae, Blattidae, Reduviidae, Pyrrhocoridae, Cimicidae, Delphacidae, Aphididae, Diaspididae, Pseudococcidae, Scarabaeidae, Dermestidae, Coccinellidae, Tenebrionidae, Chrysomelidae, Bruchidae, Tineidae, Noctuidae, Lymantriidae, Pyralidae, Culicidae, Tipulidae, Stomoxydae, Trypetidae, Muscidae, Calliphoriade und Pulicidae, sowie Akariden der Familien Ixodiae, Arga sidae, Tetranychidae und Dermanyssidae.
Die insektizide oder akarizide Wirkung lässt sich durch
Zusatz von anderen Insektiziden und/oder Akariziden wesent lich verbreitern und an gegebene Umstände anpassen.
Die Verbindungen der Formel I können für sich allein oder zusammen mit geeigneten Trägern und/oder Zuschlag stoffen eingesetzt werden. Geeignete Träger und Zuschlag stoffe 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, Di spersionen, 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 Nr. 2248 307 anf den Seiten 12 bis 18 beschriebenen Aufarbeitungsformen vorliegen und angewendet werden:
Beispiel 1
Unter Rühren wird in eine Suspension von 6,25 g NaH (50 %ige Öl Suspension) in 150 ml Tetrahydrofuran 30,0 g 0-Äthyl-5-propylchlordithiophosphat zugetropft. Danach werden unter Rühren während 11/2 Stunden bei 25-30 C 30,7 g 2-Chlor-2',4'-dichloracetophenon zugetropft. Das Reaktionsgemisch wird 3 Stunden bei Raumtemperatur und 1 Stunde bei 40-45 C gerührt.
Nach der vorsichtigen Zerstörung des überschüssigen Natriumhydrids mit 20 ml abs.
Äthylalkohol wird mit 400 ml Wasser verdünnt, der Wirkstoff mit Benzol extrahiert und die Benzollösung mit Wasser gewaschen. Das Benzol wird nach dem Trocknen mit Na2SO4 abdestilliert.
Man erhält die Verbindung der Formel
EMI3.1
mit einem Siedepunkt von 152 C/0,06 Torr als hellgelbes Öl.
Auf analoge Weise werden auch folgende Verbindungen hergestellt:
EMI3.2
R1 R2 R3 R4 R5 X Y Hal Physikalische Daten CiH5 (n)C3H7 2-Cl 4-Cl 5-Cl O Cl Cl Sdp. 1300 C/0,001 Torr CiH5 (n)C3H7 2-Cl 4-Cl H O Cl Cl nD25: 1,5505 C2H5 (n)C3H7 2-Cl 5-Cl H O H Cl Sdp. 1500 C/0,02 Torr C2H5 (n)C3H7 2-Cl 4-Cl 5-Cl S Cl Cl Sdp. 140 C/0,001 Torr C2H6 (n)C3H7 2-Cl 4-Cl 5-Cl O H Cl nD22: 1,5400 C2H5 (n)C3H7 2-Cl 4-Cl 5-Cl S H Cl nD22:) 1,5767 C2H5 (n)C3H7 2-OCH3 5-Cl H O Cl Cl nD24: 1,5073 C2H5 (n)C3H7 2-OCH3 5-Cl H S Cl Cl nD25: 1,5130 C2H5 (n)C3H7 2-CH3 4-Cl H O Cl Cl nD25; 1,5278 C2H5 (n)C3H7 3-CH3 4-Cl H O Cl Cl nD25: 1,5317 C2H5 (n)C3H7 3-Cl 4-OCH3 H O Cl Cl nD25: 1,5446 C2H5 (n)C3H7 2-Cl 4-OCH3 H O Cl Cl nD25:
1,5332 CiH5 (n)C3H7 2-Cl 4-OCH3 H S Cl Cl nD25: 1,5330 C2H5 (n)C3H7 2-Cl 4-OCH3 5-Cl S Cl Cl nD25: 1,5162 C2H5 (n)C3H7 2-OCH3 5-Br H O Cl Cl nD24: 1,5281 C2H5 (n)C3H7 2-OCH3 5-Br H S Cl Cl nD24: 1,5520 C2H5 (n)C3H7 2-OCH3 5-Cl H O H Cl nD20: 1,5500 C2H5 (n)C3H7 2-OCH3 5-Cl H S H Cl nD20: 1,5545 c2H5 (n)C3H7 2-Cl 4-OCH3 H O H Cl nD20: 1,4687 C2H5 (n)C3H7 2-Cl 4-OCH3 H S H Cl nD20: 1,5588 C2H5 (n)C3H7 2-OCH3 5-Br H O H Cl nD25: 1,5651 C2H5 (n)C3H7 2-OCH3 5-Br H S H Cl nD25: 1,5668 QH5 (n)C3H7 2-Cl 4-OCH3 5-Cl O H Cl nD25: 1,5529 C2H5 (n)C3H7 2-Cl 4-OCH3 5-Cl S H Cl nD25: 1,5718 C2H5 (n)C3H7 H H H O H Cl Sdp.155 C/0,005 Torr C2H5 (n)C3H7 4-Cl H H O H Cl Sdp. 150 C/0,001 Torr C2H5 (n)C4H9 2-Cl 4-Cl 5-Cl S H Cl nD23:
1,5642 (n)C3H7 (n)C3H7 2-Cl 4-Cl 5-Cl O H Cl nD23: 1,5438 C2H5 (n)C3H7 2-Cl 4-Cl H O H Cl Sdp. 1500 C/0,02 Torr C2H5 (n)C3H7 2-Cl 4-Cl 5-Cl O H Br nD23: 1,5482 CH3 (n)C3H7 2-Cl 4-Cl 5-Cl S H Cl C2H5 (n)C5H11 2-Cl 4-Cl 5-Cl S H Cl C2H5 (n)C3H7 H- H H O Cl Cl C2H5 (n)C3H7 4-Cl H H O Cl Cl Hs (n)C3H7 4-Br H H O Cl Cl C2H5 (n)C3H7 3-Cl H H O Cl Cl C2H5 (n)C3H7 2-Cl H H O Cl Cl CiH5 (n)C3H7 4-Br H H O H Cl C2H5 (n)C3H7 3-Cl H H O H Cl C2H5 (n)C3H7 2-Cl H H O H Cl R1 R2 R3 R4 R5 X Y Hal Physikalische Daten CH3 (n)C3H7 H H H O H Cl CH3 (n)C3H7 4-Cl H H O H Cl CH3 (n)C3H7 2-Cl 4-Cl H O H Cl CH3 (n)C3H7 H H H O Cl Cl CH3 (n)C3H7 4-Cl H H O Cl Cl CH3 (n)C3H7 2-Cl 4-Cl H O Cl Cl CH3 (n)C3H7 2-Cl 4-Cl 5-Cl O H Cl <RTI
ID=4.4> C2H5 (sek)C4H9 H H H O H Cl CiH5 (sek)C4Hg H 4-Cl H O H Cl C2H5 (sek)C4H9 2-Cl 4-Cl H O H Cl C2H5 (sek)C4H9 2-Cl 4-Cl 5-Cl O H Cl C2H5 (sek)C4H9 H H H O Cl Cl C2H5 (sek)C4Hg 4-Cl H H O Cl Cl C2H5 (sek)C4Hg 2-Cl 4-Cl H O Cl Cl C2H5 (i)C4H9 H H H O H Cl C2H5 (i)C4H9 4-Cl H H O H Cl C2H5 (i)C4H9 2-Cl 4-Cl H O H Cl C2H5 (i)C4H9 2-Cl 4-Cl 5-Cl O H Cl C2H5 (i)C4H9 H H H O Cl Cl C2H5 (i)C4H9 4-Cl H H O Cl Cl C,H5 (i)C4H9 2-Cl 4-Cl H O Cl Cl
Beispiel 2
A. Insektizide Frassgift-Wirkung
Tabak- und Kartoffelstauden wurden mit einer 0,05 %igen wässrigen Wirkstoffemulsion (erhalten aus einem 10 %igen 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, verpflanzt 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 erfolgte 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 wurden 2 Wiederholungen durchgeführt.
Die Verbindungen gemäss Beispiel 1 wirkten im obigen Test gegen Adulte und Larven von Rhipicephalus bursa.
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 Testpräparaten 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 Komponente eine Verbindung der Formel (I)
EMI4.1
worin
R1 C1-C5-Alkyl, R2 Ct-C6-Alkyl,
R3, R4 und R5 je Wasserstoff, Halogen, C-Cs-Alkyl oder C1-C5-Alkoxy,
**WARNUNG** Ende DESC Feld konnte Anfang CLMS uberlappen**.
The present invention relates to pesticides containing an O-1-phenyl as the active component
2-halogen-vinyl-thio resp. -dithiophosphoric acid esters and their use in pest control.
The O-l-phenyl-2-halogen-vinyl-thio resp. -dithiophosphoric acid esters have the formula (I)
EMI1.1
R1 C1-C2-alkyl, R1 C1-C2-alkyl,
R3, R4 and R5 each hydrogen, halogen, C1-C6-alkyl or Cl-Cs-alkoxy,
X oxygen or sulfur,
Y hydrogen or chlorine and
Hal mean chlorine or bromine.
Halogen is to be understood as meaning fluorine, chlorine, bromine or iodine, but especially chlorine or bromine.
The alkyl and alkoxy groups at R1 to R5 can be straight-chain or branched.
Examples of such groups include: methyl, methoxy, ethyl, ethoxy, propyl, propoxy, isopropyl, isopropoxy, n-butyl, n-butoxy, i-, sec-, tert-butyl, n-pentyl and n-hexyl
Because of their effect, compounds of the
Formula I, wherein
R1 ethyl,
R2 n-propyl,
R3, R4 and R5 are each hydrogen, chlorine, bromine, methyl or methoxy
X oxygen,
Y hydrogen or chlorine and
Hal mean chlorine.
The compounds of the formula I are prepared by the following methods known per se:
EMI1.2
<tb> <SEP> i)
<tb> <SEP> x <SEP> shark
<tb> <SEP> R1 <SEP> 0 <SEP> II <SEP> J <SEP> <<SEP> sälXrebindendes¯ +
<tb> <SEP> R <SEP> + <SEP> H-C <SEP> \ <SEP> Medium <SEP> # <SEP> i
<tb> <SEP> R2S <SEP> R
<tb> <SEP> (11) <SEP> Y <SEP> (iii) R54
<tb> <SEP> 2)
<tb> <SEP> x <SEP> X <SEP> Hal <SEP> R
<tb> <SEP> 3
<tb> <SEP> RlOPHal2 <SEP> + <SEP> H-C-C <SEP> 4 <SEP> dz <SEP> acid-binding
<tb> <SEP> (IV) <SEP> y <SEP> (III <SEP> t <SEP> 4 <SEP> medium
<tb> <SEP> HiY <SEP> Y <SEP> 5 <SEP>. acid-binding
<tb> <SEP> x <SEP> C <SEP> R <SEP> + <SEP> SH <SEP> medium
<tb> <SEP> 0 <SEP> II <SEP> 11R <SEP> (vi)
<tb> <SEP> 'JalsP <SEP> <<SEP> i <SEP> or
<tb> <SEP> or
<tb> <SEP> R4 <SEP> + <SEP> MeSR2 <SEP> - ·
<tb> <SEP> R5
<tb> <SEP> (viI)
<tb> <SEP> I-Ial <SEP>
Y
<tb> <SEP> Ral <SEP> Y <SEP> Hai <SEP> X <SEP> R3
<tb> <SEP> 3) <SEP> \ <SEP> / <SEP> R3 <SEP> IilO <SEP> il <SEP> C
<tb> <SEP> II <SEP> II
<tb> <SEP> (K10) 2Po-c-t-I <SEP> -or
<tb> <SEP> 4 <SEP> R5 <SEP> R4 <SEP> --¹ <SEP> (v) <SEP> R5
<tb> <SEP> Pol
<tb> <SEP> 5
<tb> <SEP> Hal <SEP> Y <SEP> acid-binding
<tb> X <SEP> C <SEP> R3 <SEP> + <SEP> R2SH <SEP> Medium <SEP> 9 <SEP> I
<tb> püyyR34 <SEP> + <SEP> <<SEP> I
<tb> <SEP> (v) <SEP> R5 <SEP> (vii)
<tb>
EMI2.1
<tb> 4) <SEP> VIlI <SEP> + <SEP> SOCl <SEP> or <SEP> Hal <SEP> Y
<tb> <SEP> POl5 <SEP> xi <SEP> + <SEP> + <SEP> alternatively <SEP> one after the other
<tb> <SEP> 5 <SEP> R <SEP> OH <SEP> I <SEP> and <SEP> R2SH
<tb> <SEP> 012P00 <SEP> \ <SEP> 1 <SEP> 2
<tb> <SEP> (mix) <SEP> R5 <SEP> R4 <SEP> (x) <SEP> (xi)
<tb> <SEP> acid-binding
<tb> <SEP> means
<tb> <SEP> means
<tb> <SEP> 5) <SEP> 0 <SEP> R3
<tb>
<SEP> shark <SEP> Hal
<tb> <SEP> ii <SEP> 1 <SEP> säuYebindingendes
<tb> <SEP> cl <SEP> P <SEP> + <SEP> HC <SEP> a <SEP> 9 <SEP> medium <SEP> ei
<tb> <SEP> 3
<tb> <SEP> Y <SEP> (XII) <SEP> R
<tb> <SEP> Shark <SEP> Y <SEP> 5
<tb> <SEP> X <SEP> C <SEP> R?
<tb> <SEP> II <SEP> II <SEP> <<SEP> + <SEP> alternatively <SEP> one after the other
<tb> <SEP> 2
<tb> <SEP> C12P-dP <SEP> R <SEP> R1OH <SEP> and <SEP> R2
<tb> <SEP> Rq <SEP> (X) <SEP> (xi
<tb> <SEP> (Ix) <SEP> R5 <SEP> (X) <SEP> (XI)
<tb> <SEP> acid binding
<tb> <SEP> means
<tb> <SEP> I
<tb>
In the formulas II to XII, R1, R2, R3, R4, R5, X, Y, and Hal have the meaning given for the formula I and Me stands for an alkali metal, in particular for sodium or potassium, ammonium or (C1-C4- Alkyl) 3-ammonium.
Suitable acid-binding agents are: tertiary amines, e.g. B. trialkylamines, pyridine, dialkylanilines; inorganic bases such as hydroxides; Carbonates and bicarbonates of alkali, alkaline earth metals.
The method 1 to 5 are at a reaction temperature between -10-100 C, in particular between 20-80 C, at normal or elevated pressure and in solution or
Diluents carried out.
Suitable solvents or diluents are, for. B.
Ether and ethereal compounds such as diethyl ether, Dipro pyläther, dioxane, dimethoxyethane, tetrahydrofuran; Amides such as N, N-di-alkylated carboxamides; aliphatic, aromatic and halogenated hydrocarbons, in particular
Benzene, toluene, xylenes, chloroform, chlorobenzene; Nitriles like
Acetonitrile; DMSO, ketones such as acetone, methyl ethyl ketone.
The starting materials of the formulas II, III, IV, VIII, IX and
XII are known in some cases or can be known analogously
Methods are produced.
The compounds of formula I have a broad biocidal range
Effect on and are therefore suitable for controlling various types of plant and animal pests and as plant regulators.
In particular, the compounds of formula I have insecticidal and acaricidal properties and can be used against all stages of development such. B. eggs, larvae, pupae, nymphs and adults of insects and representatives of the order Akarina are used, such. B. against insects of the families: Tettigoniidae, Gryllidae, Gryllotalpidae, Blattidae, Reduviidae, Pyrrhocoridae, Cimicidae, Delphacidae, Aphididae, Diaspididae, Pseudococcidae, Scarabaeidae, Dermestymaline, Termalymaline T, Crysulidae, Crysulidae, Chrysulidae, Crysulidae, Crysulidae , Tipulidae, Stomoxydae, Trypetidae, Muscidae, Calliphoriade and Pulicidae, as well as acarids of the families Ixodiae, Arga sidae, Tetranychidae and Dermanyssidae.
The insecticidal or acaricidal effect can be through
Substantially broaden the addition of other insecticides and / or acaricides and adapt to the 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 those in the
Formulation technology usual substances such. B. natural or regenerated substances, solvents, dispersants, wetting agents,
Adhesives, thickeners, binders and / or fertilizers.
For application, the compounds of formula I can be used to form dusts, emulsion concentrates, granules, dispersions, sprays, solutions or slurries in the customary formulation used in application technology for
General knowledge is heard, processed.
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 processing forms described in the German Offenlegungsschrift No. 2248 307 on pages 12 to 18 are available and used:
example 1
While stirring, 30.0 g of 0-ethyl-5-propylchlorodithiophosphate are added dropwise to a suspension of 6.25 g of NaH (50% strength oil suspension) in 150 ml of tetrahydrofuran. Then 30.7 g of 2-chloro-2 ', 4'-dichloroacetophenone are added dropwise at 25-30 ° C. over a period of 11/2 hours with stirring. The reaction mixture is stirred at room temperature for 3 hours and at 40-45 ° C. for 1 hour.
After carefully destroying the excess sodium hydride with 20 ml of abs.
Ethyl alcohol is diluted with 400 ml of water, the active ingredient is extracted with benzene and the benzene solution is washed with water. The benzene is distilled off after drying with Na2SO4.
The compound of the formula is obtained
EMI3.1
with a boiling point of 152 ° C / 0.06 Torr as a light yellow oil.
The following connections are also established in the same way:
EMI3.2
R1 R2 R3 R4 R5 XY Hal Physical data CiH5 (n) C3H7 2-Cl 4-Cl 5-Cl O Cl Cl bp. 1300 C / 0.001 Torr CiH5 (n) C3H7 2-Cl 4-Cl HO Cl Cl nD25: 1 , 5505 C2H5 (n) C3H7 2-Cl 5-Cl HOH Cl b.p. 1500 C / 0.02 Torr C2H5 (n) C3H7 2-Cl 4-Cl 5-Cl S Cl Cl b.p. 140 C / 0.001 Torr C2H6 ( n) C3H7 2-Cl 4-Cl 5-Cl OH Cl nD22: 1.5400 C2H5 (n) C3H7 2-Cl 4-Cl 5-Cl SH Cl nD22 :) 1.5767 C2H5 (n) C3H7 2-OCH3 5 -Cl HO Cl Cl nD24: 1.5073 C2H5 (n) C3H7 2-OCH3 5-Cl HS Cl Cl nD25: 1.5130 C2H5 (n) C3H7 2-CH3 4-Cl HO Cl Cl nD25; 1.5278 C2H5 (n) C3H7 3-CH3 4-Cl HO Cl Cl nD25: 1.5317 C2H5 (n) C3H7 3-Cl 4-OCH3 HO Cl Cl nD25: 1.5446 C2H5 (n) C3H7 2-Cl 4 -OCH3 HO Cl Cl nD25:
1.5332 CiH5 (n) C3H7 2-Cl 4-OCH3 HS Cl Cl nD25: 1.5330 C2H5 (n) C3H7 2-Cl 4-OCH3 5-Cl S Cl Cl nD25: 1.5162 C2H5 (n) C3H7 2 -OCH3 5-Br HO Cl Cl nD24: 1.5281 C2H5 (n) C3H7 2-OCH3 5-Br HS Cl Cl nD24: 1.5520 C2H5 (n) C3H7 2-OCH3 5-Cl HOH Cl nD20: 1.5500 C2H5 (n) C3H7 2-OCH3 5-Cl HSH Cl nD20: 1.5545 c2H5 (n) C3H7 2-Cl 4-OCH3 HOH Cl nD20: 1.4687 C2H5 (n) C3H7 2-Cl 4-OCH3 HSH Cl nD20 : 1.5588 C2H5 (n) C3H7 2-OCH3 5-Br HOH Cl nD25: 1.5651 C2H5 (n) C3H7 2-OCH3 5-Br HSH Cl nD25: 1.5668 QH5 (n) C3H7 2-Cl 4- OCH3 5-Cl OH Cl nD25: 1.5529 C2H5 (n) C3H7 2-Cl 4-OCH3 5-Cl SH Cl nD25: 1.5718 C2H5 (n) C3H7 HHHOH Cl b.p. 155 C / 0.005 Torr C2H5 (n) C3H7 4-Cl HHOH Cl b.p. 150 C / 0.001 Torr C2H5 (n) C4H9 2-Cl 4-Cl 5-Cl SH Cl nD23:
1.5642 (n) C3H7 (n) C3H7 2-Cl 4-Cl 5-Cl OH Cl nD23: 1.5438 C2H5 (n) C3H7 2-Cl 4-Cl HOH Cl bp 1500 C / 0.02 torr C2H5 (n) C3H7 2-Cl 4-Cl 5-Cl OH Br nD23: 1.5482 CH3 (n) C3H7 2-Cl 4-Cl 5-Cl SH Cl C2H5 (n) C5H11 2-Cl 4-Cl 5-Cl SH Cl C2H5 (n) C3H7 H- HHO Cl Cl C2H5 (n) C3H7 4-Cl HHO Cl Cl Hs (n) C3H7 4-Br HHO Cl Cl C2H5 (n) C3H7 3-Cl HHO Cl Cl C2H5 (n) C3H7 2-Cl HHO Cl Cl CiH5 (n) C3H7 4-Br HHOH Cl C2H5 (n) C3H7 3-Cl HHOH Cl C2H5 (n) C3H7 2-Cl HHOH Cl R1 R2 R3 R4 R5 XY Hal Physical data CH3 (n) C3H7 HHHOH Cl CH3 (n) C3H7 4-Cl HHOH Cl CH3 (n) C3H7 2-Cl 4-Cl HOH Cl CH3 (n) C3H7 HHHO Cl Cl CH3 (n) C3H7 4-Cl HHO Cl Cl CH3 (n) C3H7 2 -Cl 4-Cl HO Cl Cl CH3 (n) C3H7 2-Cl 4-Cl 5-Cl OH Cl <RTI
ID = 4.4> C2H5 (sec) C4H9 HHHOH Cl CiH5 (sec) C4Hg H 4-Cl HOH Cl C2H5 (sec) C4H9 2-Cl 4-Cl HOH Cl C2H5 (sec) C4H9 2-Cl 4-Cl 5-Cl OH Cl C2H5 (sec) C4H9 HHHO Cl Cl C2H5 (sec) C4Hg 4-Cl HHO Cl Cl C2H5 (sec) C4Hg 2-Cl 4-Cl HO Cl Cl C2H5 (i) C4H9 HHHOH Cl C2H5 (i) C4H9 4-Cl HHOH Cl C2H5 (i) C4H9 2-Cl 4-Cl HOH Cl C2H5 (i) C4H9 2-Cl 4-Cl 5-Cl OH Cl C2H5 (i) C4H9 HHHO Cl Cl C2H5 (i) C4H9 4-Cl HHO Cl Cl C , H5 (i) C4H9 2-Cl 4-Cl HO Cl Cl
Example 2
A. 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
6 rice plants of the Caloro variety were transplanted into plastic pots with 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) in the paddy water. The insecticidal activity was evaluated 10 days after the granules had been added.
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 or 50 tick larvae were counted in a glass tube and immersed 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 each. 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 performed for each experiment.
In the above test, the compounds according to Example 1 were effective against adults and larvae of Rhipicephalus bursa.
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 coated with an infected piece of leaf from a mass cultivation of Tetranychus urticae 12 hours before the test for acaricidal activity. 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 were evaluated under the binocular for living and dead individuals and the result was expressed as a percentage.
During the # holding time #, the treated plants stood in greenhouse cabins at 25 C.
In the above test, the compounds according to Example 1 were effective against adults, larvae and eggs of Tetranychus urticae.
PATENT CLAIM 1
Pesticides containing as active component a compound of the formula (I)
EMI4.1
wherein
R1 C1-C5-alkyl, R2 Ct-C6-alkyl,
R3, R4 and R5 each hydrogen, halogen, C-Cs-alkyl or C1-C5-alkoxy,
** WARNING ** End of DESC field could overlap beginning of CLMS **.
Claims (1)
Priority Applications (24)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH960972A CH575210A5 (en) | 1972-06-27 | 1972-06-27 | O-(1-aryl-2-halovinyl) (di)thiophosphates - insecticides acaricides and nematocides |
IL42474A IL42474A (en) | 1972-06-27 | 1973-06-11 | Esters of o-1-phenyl-2-halovinyl-thio-and dithio-phosphoric acids,processes for their manufacture and pesticidal compositions containing them |
AU57009/73A AU477349B2 (en) | 1972-06-27 | 1973-06-18 | 1-phenyl-2-halovinyl-thio (dithio) phosphoric acid esters |
SU731942144A SU677629A3 (en) | 1972-06-27 | 1973-06-25 | Insecticide-acaricide |
DE2332162A DE2332162A1 (en) | 1972-06-27 | 1973-06-25 | NEW ESTERS |
ES416271A ES416271A1 (en) | 1972-06-27 | 1973-06-26 | Asymmetric o,s-dialkyl-o-{8 (phenyl)-vinyl{9 -thiophosphates |
DD171837A DD106255A5 (en) | 1972-06-27 | 1973-06-26 | |
BE132712A BE801434A (en) | 1972-06-27 | 1973-06-26 | PHOSPHORUS ACID ESTERS AND PESTICIDE PRODUCTS THAT CONTAIN IT |
HUCI1388A HU167725B (en) | 1972-06-27 | 1973-06-26 | |
EG244/73A EG11445A (en) | 1972-06-27 | 1973-06-26 | 0-1-phenyl-2-halovinyl-thio and dithiophosphoric acid esters,processes for their manufacture and to their use in pest control |
US373825A US3879499A (en) | 1972-06-27 | 1973-06-26 | 0-1-phenyl-2 halovinyl-dithio phosphates |
ZA734323*DA ZA734323B (en) | 1972-06-27 | 1973-06-26 | New esters |
CA174,926A CA1048051A (en) | 1972-06-27 | 1973-06-26 | Esters |
US373723A US3878268A (en) | 1972-06-27 | 1973-06-26 | Asymmetric o,s-dialkyl-o-{8 (phenyl)-vinyl{9 -thiophosphates |
CS4596A CS172260B2 (en) | 1972-06-27 | 1973-06-26 | |
FR7323246A FR2190831B1 (en) | 1972-06-27 | 1973-06-26 | |
IT25864/73A IT998174B (en) | 1972-06-27 | 1973-06-26 | ESTERS 0.1 PHENYL 2 HALOGEN VINYL ACID THIUM OR DITHIUM PHOSPHORUS CO FOR USE AS DISINFESTANT AND PROCEDURES FOR THEIR PREPA RATION |
NL7308874A NL7308874A (en) | 1972-06-27 | 1973-06-26 | |
AT560873A AT321033B (en) | 1972-06-27 | 1973-06-26 | Insecticidal and acaricidal agents |
GB3030373A GB1426187A (en) | 1972-06-27 | 1973-06-26 | Pesticidal vinyl esters of thiophosphoric acids |
JP48072715A JPS4954539A (en) | 1972-06-27 | 1973-06-27 | |
US05/553,334 US3950520A (en) | 1972-06-27 | 1975-02-26 | Asymmetric O,S-dialkyll-O-[(phenyl)-vinyl]-thlophosphates as insecticides |
US05/553,335 US3979483A (en) | 1972-06-27 | 1975-02-26 | Asymmetric OS-dialkyl-O-[(methoxyphenyl)-vinyl]-thiophosphates |
US05/553,336 US3979484A (en) | 1972-06-27 | 1975-02-26 | O,S-Dialkyl-O-(1-methoxyphenyl-2-halovinyl)-dithiophosphates |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH960972A CH575210A5 (en) | 1972-06-27 | 1972-06-27 | O-(1-aryl-2-halovinyl) (di)thiophosphates - insecticides acaricides and nematocides |
Publications (1)
Publication Number | Publication Date |
---|---|
CH575210A5 true CH575210A5 (en) | 1976-05-14 |
Family
ID=4353766
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH960972A CH575210A5 (en) | 1972-06-27 | 1972-06-27 | O-(1-aryl-2-halovinyl) (di)thiophosphates - insecticides acaricides and nematocides |
Country Status (6)
Country | Link |
---|---|
BE (1) | BE801434A (en) |
CH (1) | CH575210A5 (en) |
CS (1) | CS172260B2 (en) |
HU (1) | HU167725B (en) |
SU (1) | SU677629A3 (en) |
ZA (1) | ZA734323B (en) |
-
1972
- 1972-06-27 CH CH960972A patent/CH575210A5/en not_active IP Right Cessation
-
1973
- 1973-06-25 SU SU731942144A patent/SU677629A3/en active
- 1973-06-26 BE BE132712A patent/BE801434A/en unknown
- 1973-06-26 CS CS4596A patent/CS172260B2/cs unknown
- 1973-06-26 HU HUCI1388A patent/HU167725B/hu unknown
- 1973-06-26 ZA ZA734323*DA patent/ZA734323B/en unknown
Also Published As
Publication number | Publication date |
---|---|
HU167725B (en) | 1975-12-25 |
SU677629A3 (en) | 1979-07-30 |
CS172260B2 (en) | 1976-12-29 |
ZA734323B (en) | 1974-02-27 |
BE801434A (en) | 1973-12-26 |
AU5700973A (en) | 1974-12-19 |
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