CH621045A5 - Pesticide containing, as active substance, an amidinophosphoric thioester, and the use of this composition. - Google Patents
Pesticide containing, as active substance, an amidinophosphoric thioester, and the use of this composition. Download PDFInfo
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- CH621045A5 CH621045A5 CH1647376A CH1647376A CH621045A5 CH 621045 A5 CH621045 A5 CH 621045A5 CH 1647376 A CH1647376 A CH 1647376A CH 1647376 A CH1647376 A CH 1647376A CH 621045 A5 CH621045 A5 CH 621045A5
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- Prior art keywords
- ethyl
- compounds
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- parts
- alkyl
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- 239000000203 mixture Substances 0.000 title claims abstract description 15
- 239000000575 pesticide Substances 0.000 title claims abstract description 6
- 239000013543 active substance Substances 0.000 title abstract description 6
- 150000007970 thio esters Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 27
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 11
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 11
- 241000244206 Nematoda Species 0.000 claims abstract description 10
- 239000001257 hydrogen Substances 0.000 claims abstract description 9
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 9
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims abstract description 6
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims abstract description 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 3
- 239000004480 active ingredient Substances 0.000 claims description 20
- -1 amidino-phosphoric acid thiolester Chemical class 0.000 claims description 14
- 239000002689 soil Substances 0.000 claims description 12
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 9
- 238000006243 chemical reaction Methods 0.000 claims description 9
- 239000003795 chemical substances by application Substances 0.000 claims description 9
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 7
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 claims description 6
- 230000001069 nematicidal effect Effects 0.000 claims description 6
- 241000607479 Yersinia pestis Species 0.000 claims description 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 239000007787 solid Substances 0.000 claims description 4
- OQLZINXFSUDMHM-UHFFFAOYSA-N Acetamidine Chemical compound CC(N)=N OQLZINXFSUDMHM-UHFFFAOYSA-N 0.000 claims description 3
- 239000011230 binding agent Substances 0.000 claims description 3
- 150000002431 hydrogen Chemical group 0.000 claims description 3
- 238000003756 stirring Methods 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- DMCAKSBKEPMBII-UHFFFAOYSA-N CCC[S+]=P(Cl)(Cl)[ClH]CC Chemical compound CCC[S+]=P(Cl)(Cl)[ClH]CC DMCAKSBKEPMBII-UHFFFAOYSA-N 0.000 claims description 2
- 239000004215 Carbon black (E152) Substances 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 239000004606 Fillers/Extenders Substances 0.000 claims description 2
- PNKUSGQVOMIXLU-UHFFFAOYSA-N Formamidine Chemical class NC=N PNKUSGQVOMIXLU-UHFFFAOYSA-N 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 239000002253 acid Substances 0.000 claims description 2
- 125000001931 aliphatic group Chemical group 0.000 claims description 2
- 229910052783 alkali metal Inorganic materials 0.000 claims description 2
- 150000001340 alkali metals Chemical group 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 230000029936 alkylation Effects 0.000 claims description 2
- 238000005804 alkylation reaction Methods 0.000 claims description 2
- 230000002862 amidating effect Effects 0.000 claims description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
- 229910052794 bromium Inorganic materials 0.000 claims description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 230000009089 cytolysis Effects 0.000 claims description 2
- 150000001983 dialkylethers Chemical class 0.000 claims description 2
- 239000003085 diluting agent Substances 0.000 claims description 2
- WCQOBLXWLRDEQA-UHFFFAOYSA-N ethanimidamide;hydrochloride Chemical compound Cl.CC(N)=N WCQOBLXWLRDEQA-UHFFFAOYSA-N 0.000 claims description 2
- 150000008282 halocarbons Chemical class 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical group 0.000 claims description 2
- 229930195733 hydrocarbon Natural products 0.000 claims description 2
- 150000002430 hydrocarbons Chemical class 0.000 claims description 2
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- PKNPHPOGCVNDFE-UHFFFAOYSA-N phosphono carbamimidate Chemical compound NC(=N)OP(O)(O)=O PKNPHPOGCVNDFE-UHFFFAOYSA-N 0.000 claims description 2
- 239000002798 polar solvent Substances 0.000 claims description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 2
- 150000003242 quaternary ammonium salts Chemical class 0.000 claims description 2
- 239000000376 reactant Substances 0.000 claims description 2
- 239000011541 reaction mixture Substances 0.000 claims description 2
- 229910052717 sulfur Chemical group 0.000 claims description 2
- 239000011593 sulfur Chemical group 0.000 claims description 2
- 150000003512 tertiary amines Chemical class 0.000 claims description 2
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 claims description 2
- 238000005809 transesterification reaction Methods 0.000 claims description 2
- 239000000243 solution Substances 0.000 description 9
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 241000196324 Embryophyta Species 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- 239000005995 Aluminium silicate Substances 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 235000012211 aluminium silicate Nutrition 0.000 description 6
- 239000008187 granular material Substances 0.000 description 6
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 6
- WSFSSNUMVMOOMR-UHFFFAOYSA-N formaldehyde Natural products O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- 206010061217 Infestation Diseases 0.000 description 4
- 235000019993 champagne Nutrition 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 244000046052 Phaseolus vulgaris Species 0.000 description 3
- 230000000895 acaricidal effect Effects 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 239000004495 emulsifiable concentrate Substances 0.000 description 3
- 229920000151 polyglycol Polymers 0.000 description 3
- 239000010695 polyglycol Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 230000009885 systemic effect Effects 0.000 description 3
- 235000015112 vegetable and seed oil Nutrition 0.000 description 3
- 239000008158 vegetable oil Substances 0.000 description 3
- 241001124076 Aphididae Species 0.000 description 2
- 241001425390 Aphis fabae Species 0.000 description 2
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 2
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 2
- 241000243786 Meloidogyne incognita Species 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- 241001454293 Tetranychus urticae Species 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 2
- 230000000749 insecticidal effect Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- 244000291564 Allium cepa Species 0.000 description 1
- 235000002732 Allium cepa var. cepa Nutrition 0.000 description 1
- 241000399934 Ditylenchus Species 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 241001480224 Heterodera Species 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- 241001220360 Longidorus Species 0.000 description 1
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 1
- 241001143352 Meloidogyne Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 244000061176 Nicotiana tabacum Species 0.000 description 1
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 241001148650 Paratylenchus Species 0.000 description 1
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
- 241000193943 Pratylenchus Species 0.000 description 1
- 241000201377 Radopholus Species 0.000 description 1
- 240000000111 Saccharum officinarum Species 0.000 description 1
- 235000007201 Saccharum officinarum Nutrition 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
- 240000003768 Solanum lycopersicum Species 0.000 description 1
- 241001220308 Trichodorus Species 0.000 description 1
- 240000006677 Vicia faba Species 0.000 description 1
- 235000010749 Vicia faba Nutrition 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
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- DNEHKUCSURWDGO-UHFFFAOYSA-N aluminum sodium Chemical compound [Na].[Al] DNEHKUCSURWDGO-UHFFFAOYSA-N 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- RYAGRZNBULDMBW-UHFFFAOYSA-L calcium;3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Ca+2].COC1=CC=CC(CC(CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O RYAGRZNBULDMBW-UHFFFAOYSA-L 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- YDEXUEFDPVHGHE-GGMCWBHBSA-L disodium;(2r)-3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Na+].[Na+].COC1=CC=CC(C[C@H](CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O YDEXUEFDPVHGHE-GGMCWBHBSA-L 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 230000001984 ectoparasiticidal effect Effects 0.000 description 1
- 235000013601 eggs Nutrition 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 230000000855 fungicidal effect Effects 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000004009 herbicide Substances 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 208000015181 infectious disease Diseases 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000003750 molluscacide Substances 0.000 description 1
- 230000002013 molluscicidal effect Effects 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- 231100000208 phytotoxic Toxicity 0.000 description 1
- 230000000885 phytotoxic effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000003128 rodenticide Substances 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 235000021003 saturated fats Nutrition 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- KZOJQMWTKJDSQJ-UHFFFAOYSA-M sodium;2,3-dibutylnaphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S([O-])(=O)=O)=C(CCCC)C(CCCC)=CC2=C1 KZOJQMWTKJDSQJ-UHFFFAOYSA-M 0.000 description 1
- SRAWNDFHGTVUNZ-UHFFFAOYSA-M sodium;3,6-dibutylnaphthalene-1-sulfonate Chemical compound [Na+].[O-]S(=O)(=O)C1=CC(CCCC)=CC2=CC(CCCC)=CC=C21 SRAWNDFHGTVUNZ-UHFFFAOYSA-M 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 238000009827 uniform distribution Methods 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000008096 xylene Substances 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
- A01N57/26—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-nitrogen bonds
- A01N57/28—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-nitrogen bonds containing acyclic or cycloaliphatic 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
- C07F9/22—Amides of acids of phosphorus
- C07F9/24—Esteramides
- C07F9/2454—Esteramides the amide moiety containing a substituent or a structure which is considered as characteristic
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
Novel pesticides are described which contain, as active substance, a compound of the formula I <IMAGE> in which R1 denotes hydrogen, C1-C4-alkyl or cyclopropyl, R2 denotes C3-C5-alkyl and R3 denotes methyl or ethyl These compositions are particularly suitable for controlling nematodes.
Description
**WARNUNG** Anfang DESC Feld konnte Ende CLMS uberlappen **.
PATENTANSPRÜCHE
1. Schädlingsbekämpfungsmittel enthaltend als mindestens eine aktive Komponente eine Verbindung der Formel I
EMI1.1
R1 Wasserstoff, ,-C4-Alkyl oder Cyclopropyl, R2 C3-Cs-Alkyl und
R3 Methyl oder Äthyl bedeuten, zusammen mit geeigneten Streckmitteln und/oder Verteilungsmitteln.
2. Mittel gemäss Anspruch 1, wobei in der Formel I R1 Wasserstoff oder Methyl, R2 n-Propyl und R3 Äthyl bedeuten.
3. Mittel gemäss Anspruch 1 enthaltend als Wirkstoff N-(O-Äthyl-S -n-propylthiophosphoryl) -acetamidin.
4. Verwendung des Mittels gemäss Anspruch 1 zur Bekämpfung von Nematoden und zur Verhütung von Nematodenbefall.
Die vorliegende Erfindung betrifft Schädlingsbekämpfungsmittel mit Amidino-phosphorsäurethiolester als Wirkstoffe, sowie die Verwendung dieser Mittel zur Bekämpfung von Nematoden.
Die neuen Mittel enthaltend Amidino-phosphorsäurethiolester stellen eine eng begrenzte Gruppe hochwirksamer Verbindungen dar und entsprechen der Formel I
EMI1.2
worin
R1 Wasserstoff, C1-C4 Alkyl oder Cyclopropyl,
R2 C3-Cs Alkyl und
R3 Methyl oder Äthyl bedeuten und wobei solche Verbindungen bevorzugt sind, bei denen R1 Wasserstoff oder Methyl,
R2 n-Propyl und
R3 Äthyl sind.
Unter den angegebenen Alkylresten sind, abhängig von der für R1 und R2 angegebenen Definition, Methyl, Äthyl, Propyl, Isopropyl sowie die isomeren Butyl- und Amylgruppen zu verstehen. Aus der DE-OS 2 312 738 und der DE-OS 2 451 911 und der US-PS 3 734 980 sind bereits phosphorylierte Formamidine bekanntgeworden. Ihre nematizide Wirkung ist jedoch sehr unbefriedigend. Darüber hinaus besitzen sie keine genügende Erdboden-Stabilität, wie sie für den Einsatz gegen Bodenschädlinge unerlässlich ist.
Es hat sich nun gezeigt, dass die Verbindungen der Formel I beide Forderungen in hohem Masse erfüllen. Dies ist besonders überraschend, weil unmittelbar homologe Verbindungen diese Eigenschaften nur in wenig ausgeprägter Form zeigen, also für die Praxis unbrauchbar sind.
Die Verbindungen der Formel I werden beispielsweise nach einem der folgenden Verfahren hergestellt:
EMI1.3
wobei X Halogen, bevorzugt Chlor, Brom oder Jod, oder aber einen Sulfatrest darstellt, Me = Alkalimetall oder NH4 und Y Sauerstoff oder Schwefel bedeuten.
Beim 1. Verfahren der Amidierung eines Thiophosphorsäureesterchlorids werden Reaktionstemperaturen von 0 bis 100 C, bevorzugt 10-45 C, angewendet.
Die Umsetzungen werden in gegenüber den Reaktionsteilnehmern inerten Lösungs- oder Verdünnungsmitteln durchgeführt. Es kommen beispielsweise folgende in Frage:
Aliphatische oder aromatische oder halogenierte Kohlenwasserstoffe und ätherartige Verbindungen wie Dialkyläther.
Die Reaktion verläuft in Gegenwart eines säurebindenden Mittels bzw. Kondensationsmittels. Als solche kommen z. B.
tertiäre Amine in Frage (vgl. DE-OS 2451 911).
Das 2. Verfahren der Umesterung eines Amidino-phosphorsäurethionoesters wird im Temperaturbereich von 20 bis 100" C in Wasser als notwendigem Lösungsmittel der Hydro
Thiol-Salz lysestufe durchgeführt. Es kommen aber auch Gemische aus Wasser und einem nichtmischbaren Lösungsmittel wie Kohlenwasserstoff in Frage. Hierbei ist der gleichzeitige Einsatz von quatemären Ammoniumsalzen wie Tetrabutylammoniumbromid vorteilhaft.
Im 2. Reaktionsschritt der Alkylierung des gebildeten Thiol-Salzes werden nichtwässrige polare Lösungsmittel wie Acetonitril oder Dimethylformamid verwendet (vgl. US-PS 3 896 193).
Herstellungsvorschrift
20 g (0,21 Mole) Acetamidinhydrochlorid werden in 100 ml Wasser gelöst. Portionenweise wird unter starkem Rühren eine Lösung von 40 g (0,2 Mole) O-Äthyl-S-n-propyl-thiophosphorsäurechlorid in 400 ml Methylenchlorid zugefügt. Danach versetzt man das Reaktionsgemisch tropfenweise mit einer 0,4molaren NaOH-Lösung, die 16 g festem
NaOH entspricht. Die Temperatur steigt dabei auf ca. 30".
Nach beendeter Reaktion rührt man noch ca. 4 Std. bei Raumtemperatur nach, trennt die Methylenchlorid-Schicht ab, trocknet sie über Natriumsulfat und dampft sie ein. Man erhält 38 g N-(O-Äthyl-S-n-propyl-thiophosphoryl)-acetamidin als zähes Öl, das nach kurzer Zeit zu farblosen Kristallen er starr, Smp. 48-50 [Verb. Nr. 2]. Die Umkristallisation liefert ein farbloses Produkt, Smp. 55-57".
Auf diese Art oder nach einer oben angegebenen Methode werden auch folgende Verbindungen hergestellt:
EMI2.1
EMI2.2
Verbindungen der Formel I wirken vor allem gegen Nematoden des pflanzenpathogenen Bereichs, unter denen die Gattungen Meloidogyne, Radopholus, Pratylenchus, Ditylenchus, Heterodera, Paratylenchus, Belonolaismus, Trichodorus, Longidorus zu nennen sind. Der besondere Vorteil dieser Verbindungen ist ihre systemische Wirkung, die es erlaubt, die Schädlinge nicht nur durch Erdobenbehandlung, sondern auch durch Blattapplikation über die zu schützende Pflanze zu bekämpfen (Basipetaler Transport).
Vorteilhaft sind solche Mittel, die eine gleichmässige Verteilung des Wirkstoffes über eine 10-20 cm tief reichende Bodenschicht gewährleisten. Die Applikationsweise und die Applikationsform sind insbesondere vom Pflanzentyp, dem Klima und den Bodenverhältnissen abhängig. Da die neuen Wirkstoffe nicht phytotoxisch sind und die Keimfähigkeit nicht beeinträchtigen, können sie auch ohne Beachtung einer sogenannten Karenzzeit unmittelbar vor oder nach der Einsaat der Pflanzen angewendet werden. Ebenso können schon bestehende Pflanzenkulturen mit den neuen Mitteln behandelt werden. Ausserdem lassen sich auch zur Vermehrung bestimmte Pflanzenteile wie Saatgut, Stengelstücke (Zuckerrohr) oder Zwiebeln sowie Wurzeln oder Jungpflanzen mit Dispersionen oder Lösungen der Wirkstoffe beizen.
Die Verbindungen der Formel I besitzen neben hervorragender nematizider Wirkung auch deutliche insektizide, akarizide, ektoparasitizide und zum Teil auch fungizide und bakterizide Wirkung.
Sie können für sich allein oder zusammen mit geeigneten Trägern und/oder anderen Zuschlagstoffen verwendet werden.
Geeignete Träger und Zuschlagstoffe können fest oder flüssig sein und entsprechen den in der Formulierungstechnik üblichen Stoffen wie z. B. natürlichen oder regenerierten mineralischen Stoffen, Lösungs-, Dispergier-, Netz-, Haft-, Verdikkungs-, Binde- oder Düngemitteln. Die Verbindungen der Formel I können zur Verbreiterung des Wirkungsspektrums auch mit weiteren bekannten Insektiziden, Akariziden, Nematiziden sowie auch mit Fungiziden, Herbiziden, Molluskiziden bzw. Rodentiziden kombiniert werden.
Der Gehalt an Wirkstoff in handelsfähigen Mitteln liegt zwischen 0,1-90%.
Zur Applikation können die Verbindungen der Formel I in den folgenden Aufarbeitungformen vorliegen (wobei die Gewichts-Prozentangaben in Klammern vorteilhafte Mengen an Wirkstoff darstellen): Feste Aufarbeitungsformen:
Stäubemittel und Streumittel (bis zu 10%)
Granulate, Umhüllungsgranulate, Imprägnierungsgranulate und Homogengranulate (1-80%); Flüssige Aufarbeitungsformen: a) in Wasser dispergierbare Wirkstoffkonzentrate:
Spritzpulver (wettable powders) und Pasten (25-90% in der Handelspackung, 0,01-15% in gebrauchsfertiger Lö sung);
Emulsions- und Lösungskonzentrate (10-50%; 0,01-15 % in gebrauchsfertiger Lösung); b) Lösungen (0,1-20%).
Die Wirkstoffe der Formel I vorliegender Erfindung können beispielsweise wie folgt formuliert werden: Stäubemittel:
Zur Herstellung eines a) 5 %igen und b) 2 %igen Stäubemit tels werden die folgenden Stoffe verwendet: a) 5 Teile Wirkstoff,
95 Teile Talkum; b) 2 Teile Wirkstoff,
1 Teil hochdisperse Kieselsäure,
97 Teile Talkum.
Die Wirkstoffe werden mit den Trägerstoffen vermischt und vermahlen und können in dieser Form zur Anwendung verstäubt werden.
Granulat:
Zur Herstellung eines 5 %igen Granulates werden die fol genden Stoffe verwendet:
5 Teile Wirkstoff,
0,25 Teile epoxidierbares Pflanzenöl,
0,25 Teile Cetylpolyglykoläther,
3,50 Teile Polyäthylenglykol,
91 Teile Kaolin (Korngrösse 0,3-0,8 mm).
Die Aktivsubstanz wird mit epoxidierbarem Pflanzenöl vermischt und mit 6 Teilen Aceton gelöst, hierauf wird Poly äthylenglykol und Cetylpolyglykoläther zugesetzt. Die so erhaltene Lösung wird auf Kaolin aufgesprüht, und anschliessend wird das Aceton im Vakuum verdampft. Ein derartiges Mikrogranulat wird vorteilhaft zur Bekämpfung von Bodenschädlingen verwendet.
Spritzpulver:
Zur Herstellung eines a) 70%igen, b) 40%igen, c) und d) 25 %igen, e) 10 %igen Spritzpulvers werden folgende Be standteile verwendet: a) 70 Teile Wirkstoff,
5 Teile Natriumdibutylnaphthylsulfon at,
3 Teile Naphthalinsulfonsäure-Phenolsulfonsäuren-
Formaldehyd-Kondensat 3:2:1,
10 Teile Kaolin,
12 Teile Champagne-Kreide; b) 40 Teile Wirkstoff,
5 Teile Ligninsulfonsäure-Natriumsalz,
1 Teil Dibutylnaphthalinsulfonsäure-Natriumsalz,
54 Teile Kieselsäure;
c) 25 Teile Wirkstoff,
4,5 Teile Calcium-Ligninsulfonat,
1,9 Teile Champagne-Kreide/Hydroxyäthylcellulose
Gemisch (1 :1),
1,5 Teile Natrium-dibutyl-naphthalinsulfonat,
19,5 Teile Kieselsäure,
19,5 Teile Champagne-Kreide,
28,1 Teile Kaolin; d) 25 Teile Wirkstoff,
2,5 Teile Isooctylphenoxy-polyoxyäthylen-äthanol,
1,7 Teile Champagne-Kreide/Hydroxyäthylcellulose
Gemisch (1:1),
8,3 Teile Natriumaluminiumsilikat,
16,5 Teile Kieselgur,
46 Teile Kaolin; e) 10 Teile Wirkstoff,
3 Teile Gemisch der Natriumsalze von gesättigten Fett alkoholsulfaten,
5 Teile Naphthalinsulfonsäure/Formaldehyd-Kon densat,
82 Teile Kaolin.
Die Wirkstoffe werden in geeigneten Mischern mit den Zuschlagstoffen innig vermischt und auf entsprechenden Mühlen und Walzen vermahlen. Man erhält Spritzpulver von vorzüglicher Benetzbarkeit und Schwebefähigkeit, die sich mit Wasser zu Suspensionen jeder gewünschten Konzentration verdünnen und zur Boden- und Blattapplikation verwenden lassen.
Emulgierbare Konzentrate:
Zur Herstellung eines 25 %igen emulgierbaren Konzentra tes werden folgende Stoffe verwendet:
25 Teile Wirkstoff,
2,5 Teile epoxydiertes Pflanzenöl,
10 Teile eines Alkylarylsulfonat/Fettalkoholpolyglykol äther-Gemisches,
5 Teile Dimethylformamid,
57,5 Teile Xylol.
Aus solchen Konzentraten können durch Verdünnen mit Wasser Emulsionen jeder gewünschten Konzentration hergestellt werden.
Beispiel 1
Prüfung der nematiziden Wirkung
Zur Prüfung gegen Bodennematoden wird die Wirksubstanz in einer Konzentration von 10 und 2,5 ppm in durch Wurzelgallen-Nematoden (Meloidogyne incognita) infizierte Erde bzw. Sand gegeben und innig vermischt. In die so vorbereiteten Böden werden unmittelbar danach einerseits Tomatensetzlinge und anderseits Tabaksetzlinge gepflanzt.
Zur Beurteilung der nematiziden Wirkung werden 28 Tage nach dem Pflanzen die an den Wurzeln vorhandenen Gallen ausgezählt.
Verbindungen der Formel I zeigten im obigen Versuch eine gute Wirkung gegen Meloidogyne incognita, wie aus den Mittelwerten dreier Parallelversuche hervorgeht. Dabei wurde folgender Notenschlüssel zugrundegelegt:
0 = 0- 5% Befall
1 = 5-25% Befall
2 = 25-80% Befall
3 = über 80% Befall (unwirksam)
Die Verbindungen der Formel I zeigten bei einer Wirk stoflkonzentration von 10 ppm durchweg volle Wirkung (Note 0), bei 2,5 ppm fast vollständige Wirkung mit einer Befallsminderung auf 0-25% (Noten 0 oder 1). Neben anderen erwiesen sich insbesondere die Verbindungen Nr. 1, 2, 4, 8,
12, 13 und 14 auch in dieser Konzentration als voll wirksam (Note 0).
Unmittelbar strukturhomologe Verbindungen wie
EMI4.1
Smp. 130-135 C (bekannt aus US-PS 3 734 980) semikristallin zeigten selbst bei hohen Dosierungen von 25 und 50 ppm keinerlei nematizide Wirksamkeit.
Beispiel 2
Akarizide Wirkung
Bohnenpflanzen (Phaseolus vulgaris) wurden 12 Stunden vor dem Test mit einem infestierten Blattstück aus einer Massenzucht von Tetranychus urticae belegt. Die übergelaufenen beweglichen Stadien wurden aus einem Chromatographiezerstäuber mit den emulgierten Testpräparaten so besprüht, dass kein Ablaufen der Spritzbrühe eintrat. Nach 2 bis 7 Tagen bei 250 C im Gewächshaus wurden Larven, Adulte und Eier unter dem Binokular auf lebende und tote Individuen ausgewertet.
Verbindungen der Formel I zeigten einen hohen Wirkungsgrad gegen Adulte und Larven von Tetranychus urticae.
Beispiel 3
Systemisch-insektizide Wirkung: Aphis fabae
Zur Feststellung der systemischen Wirkung wurden bewurzelte Bohnenpflanzen (Vicia faba) in eine 0,01 %ige wässrige Wirkstofflösung (erhalten aus einem 10%igen emulgierbaren Konzentrat) eingestellt. Nach 24 Stunden wurden auf die oberirdischen Pflanzenteile Blattläuse (Aphis fabae) gesetzt.
Durch eine spezielle Einrichtung waren die Tiere vor der Kontakt- und Gaswirkung geschützt. Der Versuch wurde bei 24 C und 70% relativer Luftfeuchtigkeit durchgeführt.
Die im Saftstrom der Pflanze transportierten Verbindungen Nr. 2, 3 und 8 bewirkten vollständige Abtötung der Blattläuse.
** WARNING ** beginning of DESC field could overlap end of CLMS **.
PATENT CLAIMS
1. Pesticides containing a compound of the formula I as at least one active component
EMI1.1
R1 is hydrogen,, -C4-alkyl or cyclopropyl, R2 C3-Cs-alkyl and
R3 is methyl or ethyl, together with suitable extenders and / or distributing agents.
2. Composition according to claim 1, wherein in the formula I R1 is hydrogen or methyl, R2 is n-propyl and R3 is ethyl.
3. Composition according to claim 1 containing as active ingredient N- (O-ethyl-S-n-propylthiophosphoryl) acetamidine.
4. Use of the agent according to claim 1 for combating nematodes and for preventing nematode attack.
The present invention relates to pesticides with amidino-phosphoric acid thiolester as active ingredients, and to the use of these compositions for controlling nematodes.
The new agents containing amidino-phosphoric acid thiol esters represent a narrowly limited group of highly effective compounds and correspond to the formula I.
EMI1.2
wherein
R1 is hydrogen, C1-C4 alkyl or cyclopropyl,
R2 C3-Cs alkyl and
R3 is methyl or ethyl and preferred compounds are those in which R1 is hydrogen or methyl,
R2 n-propyl and
R3 are ethyl.
The alkyl radicals indicated are, depending on the definition given for R1 and R2, methyl, ethyl, propyl, isopropyl and the isomeric butyl and amyl groups. Phosphorylated formamidines have already become known from DE-OS 2 312 738 and DE-OS 2 451 911 and US Pat. No. 3,734,980. However, their nematicidal activity is very unsatisfactory. In addition, they do not have sufficient soil stability, which is essential for use against soil pests.
It has now been shown that the compounds of the formula I meet both of these requirements to a high degree. This is particularly surprising because directly homologous compounds show these properties only in a slightly pronounced form, ie they are unusable in practice.
The compounds of the formula I are prepared, for example, by one of the following processes:
EMI1.3
where X is halogen, preferably chlorine, bromine or iodine, or else a sulfate radical, Me = alkali metal or NH4 and Y is oxygen or sulfur.
In the first method of amidating a thiophosphoric acid ester chloride, reaction temperatures of 0 to 100 C, preferably 10-45 C, are used.
The reactions are carried out in solvents or diluents which are inert to the reactants. For example, the following are possible:
Aliphatic or aromatic or halogenated hydrocarbons and ethereal compounds such as dialkyl ethers.
The reaction proceeds in the presence of an acid-binding agent or condensing agent. As such, e.g. B.
tertiary amines in question (see. DE-OS 2451 911).
The second process of transesterification of an amidino-phosphoric acid urethionoester in the temperature range from 20 to 100 ° C. in water is the necessary solvent for the hydro
Thiol salt lysis stage performed. Mixtures of water and an immiscible solvent such as hydrocarbon are also suitable. The simultaneous use of quaternary ammonium salts such as tetrabutylammonium bromide is advantageous here.
In the second reaction step of the alkylation of the thiol salt formed, non-aqueous polar solvents such as acetonitrile or dimethylformamide are used (cf. US Pat. No. 3,896,193).
Manufacturing instructions
20 g (0.21 mole) of acetamidine hydrochloride are dissolved in 100 ml of water. A solution of 40 g (0.2 mole) of O-ethyl-S-n-propyl-thiophosphoric acid chloride in 400 ml of methylene chloride is added in portions with vigorous stirring. Then the reaction mixture is added dropwise with a 0.4 molar NaOH solution which contains 16 g of solid
Corresponds to NaOH. The temperature rises to about 30 ".
After the reaction has ended, stirring is continued for about 4 hours at room temperature, the methylene chloride layer is separated off, dried over sodium sulfate and evaporated. 38 g of N- (O-ethyl-S-n-propyl-thiophosphoryl) acetamidine are obtained as a viscous oil which after a short time becomes rigid to colorless crystals, mp. 48-50 [verb. No. 2]. The recrystallization gives a colorless product, mp 55-57 ".
The following connections are also produced in this way or according to a method specified above:
EMI2.1
EMI2.2
Compounds of the formula I act especially against nematodes of the plant pathogenic region, among which the genera Meloidogyne, Radopholus, Pratylenchus, Ditylenchus, Heterodera, Paratylenchus, Belonolaismus, Trichodorus, Longidorus are to be mentioned. The special advantage of these compounds is their systemic effect, which allows the pests to be controlled not only by soil treatment, but also by foliar application via the plant to be protected (basipetal transport).
Means are advantageous which ensure a uniform distribution of the active substance over a 10-20 cm deep layer of soil. The method of application and the form of application depend in particular on the type of plant, the climate and the soil conditions. Since the new active ingredients are not phytotoxic and do not impair the ability to germinate, they can be used immediately before or after planting, even without observing a so-called grace period. Existing crops can also be treated with the new agents. In addition, certain plant parts such as seeds, stem pieces (sugar cane) or onions as well as roots or young plants can be treated with dispersions or solutions of the active compounds for propagation.
In addition to excellent nematicidal activity, the compounds of the formula I also have significant insecticidal, acaricidal, ectoparasiticidal and in some cases also fungicidal and bactericidal activity.
They can be used alone or together with suitable carriers and / or other additives.
Suitable carriers and additives can be solid or liquid and correspond to the substances commonly used in formulation technology, e.g. B. natural or regenerated mineral substances, solvents, dispersants, wetting agents, adhesives, thickeners, binders or fertilizers. To broaden the spectrum of action, the compounds of the formula I can also be combined with other known insecticides, acaricides, nematicides and also with fungicides, herbicides, molluscicides or rodenticides.
The content of active ingredient in commercial products is between 0.1-90%.
For application, the compounds of the formula I can be present in the following working-up forms (the percentages by weight in brackets representing advantageous amounts of active ingredient): Solid working-up forms:
Dusts and grit (up to 10%)
Granules, coating granules, impregnation granules and homogeneous granules (1-80%); Liquid processing forms: a) active ingredient concentrates dispersible in water:
Wettable powders and pastes (25-90% in retail packaging, 0.01-15% in ready-to-use solution);
Emulsion and solution concentrates (10-50%; 0.01-15% in ready-to-use solution); b) Solutions (0.1-20%).
The active compounds of the formula I of the present invention can be formulated, for example, as follows:
The following substances are used to produce a) 5% and b) 2% dusts: a) 5 parts of active ingredient,
95 parts talc; b) 2 parts of active ingredient,
1 part of highly disperse silica,
97 parts of talc.
The active ingredients are mixed and ground with the carriers and can be dusted in this form for use.
Granules:
The following substances are used to produce a 5% granulate:
5 parts of active ingredient,
0.25 parts of epoxidizable vegetable oil,
0.25 parts of cetyl polyglycol ether,
3.50 parts of polyethylene glycol,
91 parts of kaolin (grain size 0.3-0.8 mm).
The active substance is mixed with epoxidizable vegetable oil and dissolved with 6 parts of acetone, then poly ethylene glycol and cetyl polyglycol ether are added. The solution thus obtained is sprayed onto kaolin, and the acetone is then evaporated off in vacuo. Such microgranules are advantageously used to control soil pests.
Spray powder:
The following constituents are used to prepare a) 70%, b) 40%, c) and d) 25%, e) 10% wettable powder: a) 70 parts of active ingredient,
5 parts of sodium dibutylnaphthyl sulfone at,
3 parts of naphthalenesulfonic acid-phenolsulfonic acids-
Formaldehyde condensate 3: 2: 1,
10 parts of kaolin,
12 parts of champagne chalk; b) 40 parts of active ingredient,
5 parts of sodium lignosulfonic acid,
1 part of dibutylnaphthalenesulfonic acid sodium salt,
54 parts of silica;
c) 25 parts of active ingredient,
4.5 parts of calcium lignin sulfonate,
1.9 parts champagne chalk / hydroxyethyl cellulose
Mixture (1: 1),
1.5 parts of sodium dibutyl naphthalenesulfonate,
19.5 parts of silica,
19.5 parts of champagne chalk,
28.1 parts kaolin; d) 25 parts of active ingredient,
2.5 parts of isooctylphenoxy-polyoxyethylene-ethanol,
1.7 parts champagne chalk / hydroxyethyl cellulose
Mixture (1: 1),
8.3 parts of sodium aluminum silicate,
16.5 parts of diatomaceous earth,
46 parts of kaolin; e) 10 parts of active ingredient,
3 parts mixture of the sodium salts of saturated fat alcohol sulfates,
5 parts of naphthalenesulfonic acid / formaldehyde condensate,
82 parts of kaolin.
The active ingredients are intimately mixed with the additives in suitable mixers and ground on appropriate mills and rollers. This gives wettable powders of excellent wettability and suspension, which can be diluted with water to form suspensions of any desired concentration and used for soil and leaf application.
Emulsifiable concentrates:
The following substances are used to produce a 25% emulsifiable concentrate:
25 parts of active ingredient,
2.5 parts of epoxidized vegetable oil,
10 parts of an alkylarylsulfonate / fatty alcohol polyglycol ether mixture,
5 parts of dimethylformamide,
57.5 parts xylene.
Emulsions of any desired concentration can be prepared from such concentrates by dilution with water.
example 1
Testing the nematicidal activity
For testing against soil nematodes, the active substance is given in a concentration of 10 and 2.5 ppm in soil or sand infected by root-gall nematodes (Meloidogyne incognita) and mixed intimately. Immediately afterwards, tomato seedlings and tobacco seedlings are planted in the so prepared soil.
To assess the nematicidal activity, the galls present at the roots are counted 28 days after planting.
Compounds of formula I showed a good activity against Meloidogyne incognita in the above test, as can be seen from the mean values of three parallel tests. The following clef was used:
0 = 0- 5% infestation
1 = 5-25% infestation
2 = 25-80% infestation
3 = over 80% infestation (ineffective)
The compounds of the formula I showed consistently full activity (grade 0) at an active substance concentration of 10 ppm, almost complete activity at 2.5 ppm with an infection reduction to 0-25% (grades 0 or 1). Among others, compounds No. 1, 2, 4, 8,
12, 13 and 14 are also fully effective in this concentration (grade 0).
Immediately structural homologous connections such as
EMI4.1
130-135 C (known from US Pat. No. 3,734,980) semicrystalline showed no nematicidal activity even at high dosages of 25 and 50 ppm.
Example 2
Acaricidal effects
Bean plants (Phaseolus vulgaris) were covered with an infested leaf piece from a mass cultivation of Tetranychus urticae 12 hours before the test. The overflowed moving stages were sprayed with the emulsified test preparations from a chromatography atomizer so that the spray liquor did not run off. After 2 to 7 days at 250 C in the greenhouse, larvae, adults and eggs were evaluated under the binocular for living and dead individuals.
Compounds of formula I showed a high efficiency against adults and larvae of Tetranychus urticae.
Example 3
Systemic insecticidal activity: Aphis fabae
In order to determine the systemic effect, rooted bean plants (Vicia faba) were placed in a 0.01% strength aqueous active ingredient solution (obtained from a 10% strength emulsifiable concentrate). After 24 hours, aphids (Aphis fabae) were placed on the aerial plant parts.
The animals were protected from contact and gas effects by a special device. The test was carried out at 24 C and 70% relative humidity.
Compounds Nos. 2, 3 and 8 transported in the sap flow of the plant completely killed the aphids.
Claims (4)
Priority Applications (22)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH1647376A CH621045A5 (en) | 1976-12-30 | 1976-12-30 | Pesticide containing, as active substance, an amidinophosphoric thioester, and the use of this composition. |
SU772556351A SU745350A1 (en) | 1976-12-30 | 1977-12-22 | Nematocidic agent |
AU31992/77A AU517698B2 (en) | 1976-12-30 | 1977-12-23 | Amidino-phosphoric acid thiol esters for combating pests |
NL7714370A NL7714370A (en) | 1976-12-30 | 1977-12-23 | PROCEDURE FOR PREPARING AMIDINO-PHOSPHORIC ACID THIOL ESTERS AND THEIR USE FOR CONTROL OF HARMFUL ORGANISMS. |
FR7738988A FR2376154A1 (en) | 1976-12-30 | 1977-12-23 | AMIDINOPHOSPHORIC ACID THIOLESTERS, THEIR PREPARATION AND THEIR APPLICATION FOR THE CONTROL OF PARASITES |
EG714/77A EG12832A (en) | 1976-12-30 | 1977-12-26 | Amidino-phosphoric acid thiol esters for combating pests |
PT67460A PT67460B (en) | 1976-12-30 | 1977-12-27 | Process for preparing amidino-phosphoric acid thiol estersfor combating pests |
DE19772758173 DE2758173A1 (en) | 1976-12-30 | 1977-12-27 | AMIDINO-PHOSPHORIC ACID ETHIOLESTERS FOR THE CONTROL OF SCHAEDLINGS |
CS778935A CS194828B2 (en) | 1976-12-30 | 1977-12-28 | Insecticide,acaricide and nematocide and process for preparing effective component |
PL1977203431A PL107331B1 (en) | 1976-12-30 | 1977-12-28 | MEASURE FOR COMBATING PESTS |
IL53707A IL53707A (en) | 1976-12-30 | 1977-12-28 | Amidino-phosphoric acid thiol esters,their production and their use for combating pests |
CA293,989A CA1093573A (en) | 1976-12-30 | 1977-12-28 | Amidino-phosphoric acid thiol esters for combating pests |
TR19912A TR19912A (en) | 1976-12-30 | 1977-12-29 | pesticides |
GB54180/77A GB1595809A (en) | 1976-12-30 | 1977-12-29 | Amidino phorsporic acid thiol esters and their use for combating pests |
BR7708734A BR7708734A (en) | 1976-12-30 | 1977-12-29 | ORGANIC COMPOUNDS, PROCESS FOR THE PREPARATION OF THESE, PRAGUICIDE COMPOSITION AND ITS USE |
AT940577A AT355874B (en) | 1976-12-30 | 1977-12-29 | INSECTICIDAL, ACARICIDAL AND NEMATICIDAL AGENTS |
BE183954A BE862456A (en) | 1976-12-30 | 1977-12-29 | AMIDINOPHOSPHORIC ACID THIOLESTERS, THEIR PREPARATION AND THEIR APPLICATION FOR THE CONTROL OF PARASITES |
ZA00777727A ZA777727B (en) | 1976-12-30 | 1977-12-29 | Amidino-phosphoric acid thiol esters for combating pests |
ES465545A ES465545A1 (en) | 1976-12-30 | 1977-12-29 | Amidino phorsporic acid thiol esters and their use for combating pests |
JP15860877A JPS5384921A (en) | 1976-12-30 | 1977-12-29 | Amidino phosphoric thiol esters process for preparing same and harmful organism controlling agent containing same as effective component |
OA56359A OA05841A (en) | 1976-12-30 | 1977-12-30 | Amidinophosphoric acid thiolesters their preparation and application to the control of parasites. |
US05/919,335 US4203978A (en) | 1976-12-30 | 1978-06-26 | Amidino-phosphoric acid thiol esters for combating pests |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH1647376A CH621045A5 (en) | 1976-12-30 | 1976-12-30 | Pesticide containing, as active substance, an amidinophosphoric thioester, and the use of this composition. |
Publications (1)
Publication Number | Publication Date |
---|---|
CH621045A5 true CH621045A5 (en) | 1981-01-15 |
Family
ID=4417688
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH1647376A CH621045A5 (en) | 1976-12-30 | 1976-12-30 | Pesticide containing, as active substance, an amidinophosphoric thioester, and the use of this composition. |
Country Status (3)
Country | Link |
---|---|
BE (1) | BE862456A (en) |
CH (1) | CH621045A5 (en) |
ZA (1) | ZA777727B (en) |
-
1976
- 1976-12-30 CH CH1647376A patent/CH621045A5/en not_active IP Right Cessation
-
1977
- 1977-12-29 BE BE183954A patent/BE862456A/en unknown
- 1977-12-29 ZA ZA00777727A patent/ZA777727B/en unknown
Also Published As
Publication number | Publication date |
---|---|
ZA777727B (en) | 1978-10-25 |
BE862456A (en) | 1978-06-29 |
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