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)
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 |
| DE2332162A DE2332162A1 (de) | 1972-06-27 | 1973-06-25 | Neue ester |
| SU731942144A SU677629A3 (ru) | 1972-06-27 | 1973-06-25 | Инсектоакарицидное средство |
| ZA734323*DA ZA734323B (en) | 1972-06-27 | 1973-06-26 | New esters |
| CS4596A CS172260B2 (OSRAM) | 1972-06-27 | 1973-06-26 | |
| US373825A US3879499A (en) | 1972-06-27 | 1973-06-26 | 0-1-phenyl-2 halovinyl-dithio phosphates |
| IT25864/73A IT998174B (it) | 1972-06-27 | 1973-06-26 | Esteri 0.1 fenil 2 alogeno vinilici dell acido tio oppure ditio fosfori co per l impiego come disinfestanti e procedimenti per la loro prepa razione |
| HUCI1388A HU167725B (OSRAM) | 1972-06-27 | 1973-06-26 | |
| AT560873A AT321033B (de) | 1972-06-27 | 1973-06-26 | Insektizides und akarizides Mittel |
| US373723A US3878268A (en) | 1972-06-27 | 1973-06-26 | Asymmetric o,s-dialkyl-o-{8 (phenyl)-vinyl{9 -thiophosphates |
| 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 |
| BE132712A BE801434A (fr) | 1972-06-27 | 1973-06-26 | Esters d'acides du phosphore et produits pesticides qui en renferment |
| GB3030373A GB1426187A (en) | 1972-06-27 | 1973-06-26 | Pesticidal vinyl esters of thiophosphoric acids |
| ES416271A ES416271A1 (es) | 1972-06-27 | 1973-06-26 | Procedimiento para la preparacion de esteres de acido o - 1- fenil - 2 -halongenvenil - tio- y ditio - fosforico. |
| DD171837A DD106255A5 (OSRAM) | 1972-06-27 | 1973-06-26 | |
| NL7308874A NL7308874A (OSRAM) | 1972-06-27 | 1973-06-26 | |
| FR7323246A FR2190831B1 (OSRAM) | 1972-06-27 | 1973-06-26 | |
| CA174,926A CA1048051A (en) | 1972-06-27 | 1973-06-26 | Esters |
| JP48072715A JPS4954539A (OSRAM) | 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 |
| US05/553,336 US3979484A (en) | 1972-06-27 | 1975-02-26 | O,S-Dialkyl-O-(1-methoxyphenyl-2-halovinyl)-dithiophosphates |
| US05/553,335 US3979483A (en) | 1972-06-27 | 1975-02-26 | Asymmetric OS-dialkyl-O-[(methoxyphenyl)-vinyl]-thiophosphates |
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 (OSRAM) |
| CH (1) | CH575210A5 (OSRAM) |
| CS (1) | CS172260B2 (OSRAM) |
| HU (1) | HU167725B (OSRAM) |
| SU (1) | SU677629A3 (OSRAM) |
| ZA (1) | ZA734323B (OSRAM) |
-
1972
- 1972-06-27 CH CH960972A patent/CH575210A5/de not_active IP Right Cessation
-
1973
- 1973-06-25 SU SU731942144A patent/SU677629A3/ru active
- 1973-06-26 ZA ZA734323*DA patent/ZA734323B/xx unknown
- 1973-06-26 BE BE132712A patent/BE801434A/xx unknown
- 1973-06-26 HU HUCI1388A patent/HU167725B/hu unknown
- 1973-06-26 CS CS4596A patent/CS172260B2/cs unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AU5700973A (en) | 1974-12-19 |
| SU677629A3 (ru) | 1979-07-30 |
| BE801434A (fr) | 1973-12-26 |
| ZA734323B (en) | 1974-02-27 |
| CS172260B2 (OSRAM) | 1976-12-29 |
| HU167725B (OSRAM) | 1975-12-25 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| GB1567692A (en) | Pesticidal cyclopropane carboxylicesters | |
| CH575210A5 (en) | O-(1-aryl-2-halovinyl) (di)thiophosphates - insecticides acaricides and nematocides | |
| DE2411809A1 (de) | Thiolphosphorsaeureester, verfahren zu ihrer herstellung und ihre verwendung | |
| CH592411A5 (en) | Phenoxymethyl- and phenylthiomethyl-pyridine derivs - with insecticidal, acaricidal and plant-growth regulating activity | |
| CA1048051A (en) | Esters | |
| DE2249462B2 (OSRAM) | ||
| DE2331594A1 (de) | Neue diphenylaether | |
| CH574215A5 (en) | 0-(2-Alkenylphenyl) O,S-dialkyl thiophosphates - with insecticidal, acaricidal, fungicidal and nematocidal activity | |
| CH572308A5 (en) | Pesticidal phosphorothiolates and-thiolothionates - O-(m)ethyl-5-propyl or butyl-O-substd phenyl-phosphorothiolates and-thiolothionates are insecticides, acaracides and fungicides | |
| CH608692A5 (en) | Pesticide comprising an N,N'-dicarbamic acid sulphide derivative as active ingredient | |
| CH574711A5 (en) | O-phenoxyphenyl-o-alkyl-s-alkyl thiophosphates - with insecticidal and acaricidal activity | |
| CH570765A5 (en) | Pyridyl (di)thiophosphates prepn - with biocidal activity | |
| CH602010A5 (en) | Alkynyloxy-benzyl-cyclopropane-carboxylates | |
| CH581435A5 (en) | Pesticidal 1,2,3-Triazol-4-yl-(thiono)phosph(on)ates - prepd. by reacting 4-hydroxy-1,2,4-triazoles with (thiono)phosphor(on)yl halides | |
| CH571815A5 (en) | Benztriazinonylmethyl organophosphorus esters - insecticides acaricides, fungicides, bactericides and nematocides | |
| CH574712A5 (en) | O-alkyl-s-alkyl-o-nitrophenyl thiophosphates - with pesticidal activity | |
| DE2356453A1 (de) | Alkylendithiophosphorsaeureester, verfahren zu ihrer herstellung und ihre verwendung | |
| CH573710A5 (en) | S-diphenylmethyl phosphorodithioates - with insecticidal, acaricidal, bactericidal, fungicidal and nematocidal activity | |
| CH575717A5 (en) | S-Arylthioalkyl-O,S-dialkyl dithiophosphates - with insecticidal, acaricidal, fungicidal, nematocidal activity, etc. | |
| CH583518A5 (en) | 0-(2-Alkenylphenyl) O,S-dialkyl thiophosphates - with insecticidal, acaricidal, fungicidal and nematocidal activity | |
| CH580387A5 (en) | Diphenylether phosphates as pesticides - from hydroxy diphenyl ethers and substd. phosphoric acid chlorides | |
| CH568013A5 (en) | Trifluoromethyl nitrophenyl-thio-and dithio-phosphates - - insecticides, acaricides, fungicides and herbicides | |
| CH575211A5 (en) | (di)thiophosphoric acid esters - with biocidal activity | |
| CH588807A5 (en) | N-Phenyl-N'-phenylthio-formamidine derivs - prepd. by reacting N-phenyl-formamidines with phenylsulphenyl halides | |
| CH612421A5 (en) | Pesticide comprising a (N-methyl- N'-phenylformamidino-mercapto)urea as active ingredient |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PL | Patent ceased | ||
| PL | Patent ceased |