IL32240A - Diesters of phosphonic and thionophosphonic acids and compositions for combating soil insects,nematodes and termites containing them - Google Patents
Diesters of phosphonic and thionophosphonic acids and compositions for combating soil insects,nematodes and termites containing themInfo
- Publication number
- IL32240A IL32240A IL32240A IL3224069A IL32240A IL 32240 A IL32240 A IL 32240A IL 32240 A IL32240 A IL 32240A IL 3224069 A IL3224069 A IL 3224069A IL 32240 A IL32240 A IL 32240A
- Authority
- IL
- Israel
- Prior art keywords
- soil
- compound
- nematodes
- preparation
- termites
- Prior art date
Links
- 239000002689 soil Substances 0.000 title claims description 21
- 241000256602 Isoptera Species 0.000 title claims description 5
- 241000244206 Nematoda Species 0.000 title claims description 4
- 241000238631 Hexapoda Species 0.000 title description 6
- 239000000203 mixture Substances 0.000 title description 5
- 239000002253 acid Substances 0.000 title description 4
- 150000007513 acids Chemical class 0.000 title description 2
- 150000005690 diesters Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims description 18
- 239000013543 active substance Substances 0.000 claims description 15
- 238000002360 preparation method Methods 0.000 claims description 9
- 239000003337 fertilizer Substances 0.000 claims description 3
- 238000000034 method Methods 0.000 claims description 3
- 239000000853 adhesive Substances 0.000 claims description 2
- 230000001070 adhesive effect Effects 0.000 claims description 2
- 230000000844 anti-bacterial effect Effects 0.000 claims description 2
- 230000000749 insecticidal effect Effects 0.000 claims description 2
- 239000000575 pesticide Substances 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims 3
- 239000000080 wetting agent Substances 0.000 claims 1
- 238000012360 testing method Methods 0.000 description 14
- 241000196324 Embryophyta Species 0.000 description 8
- 230000000694 effects Effects 0.000 description 5
- 239000008187 granular material Substances 0.000 description 5
- 241001136249 Agriotes lineatus Species 0.000 description 3
- 241000218473 Agrotis Species 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 229940125904 compound 1 Drugs 0.000 description 2
- 230000006378 damage Effects 0.000 description 2
- 238000010410 dusting Methods 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 229920000915 polyvinyl chloride Polymers 0.000 description 2
- 239000004800 polyvinyl chloride Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- DEXFNLNNUZKHNO-UHFFFAOYSA-N 6-[3-[4-[2-(2,3-dihydro-1H-inden-2-ylamino)pyrimidin-5-yl]piperidin-1-yl]-3-oxopropyl]-3H-1,3-benzoxazol-2-one Chemical group C1C(CC2=CC=CC=C12)NC1=NC=C(C=N1)C1CCN(CC1)C(CCC1=CC2=C(NC(O2)=O)C=C1)=O DEXFNLNNUZKHNO-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 241000902805 Aulacophora Species 0.000 description 1
- 241000258920 Chilopoda Species 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 241000289763 Dasygaster padockina Species 0.000 description 1
- 241001414892 Delia radicum Species 0.000 description 1
- 241000241125 Gryllotalpa gryllotalpa 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
- 240000008415 Lactuca sativa Species 0.000 description 1
- 241001143352 Meloidogyne Species 0.000 description 1
- 241000254071 Melolontha Species 0.000 description 1
- 241000254099 Melolontha melolontha Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000256259 Noctuidae Species 0.000 description 1
- 241000283973 Oryctolagus cuniculus Species 0.000 description 1
- 241000254044 Pachnoda marginata Species 0.000 description 1
- ABLZXFCXXLZCGV-UHFFFAOYSA-N Phosphorous acid Chemical class OP(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- 240000008042 Zea mays Species 0.000 description 1
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 description 1
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- KGNDCEVUMONOKF-UGPLYTSKSA-N benzyl n-[(2r)-1-[(2s,4r)-2-[[(2s)-6-amino-1-(1,3-benzoxazol-2-yl)-1,1-dihydroxyhexan-2-yl]carbamoyl]-4-[(4-methylphenyl)methoxy]pyrrolidin-1-yl]-1-oxo-4-phenylbutan-2-yl]carbamate Chemical compound C1=CC(C)=CC=C1CO[C@H]1CN(C(=O)[C@@H](CCC=2C=CC=CC=2)NC(=O)OCC=2C=CC=CC=2)[C@H](C(=O)N[C@@H](CCCCN)C(O)(O)C=2OC3=CC=CC=C3N=2)C1 KGNDCEVUMONOKF-UGPLYTSKSA-N 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 239000002361 compost Substances 0.000 description 1
- 229940125833 compound 23 Drugs 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 235000013601 eggs Nutrition 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- -1 gainst Species 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 239000003864 humus Substances 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002611 lead compounds Chemical class 0.000 description 1
- 235000009973 maize Nutrition 0.000 description 1
- 230000000361 pesticidal effect Effects 0.000 description 1
- 150000003008 phosphonic acid esters Chemical class 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 235000012045 salad Nutrition 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 210000002784 stomach Anatomy 0.000 description 1
- 230000002459 sustained effect Effects 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 238000009736 wetting Methods 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
- A01N57/18—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds
- A01N57/22—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds containing aromatic radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—Phosphorus compounds with one or more P—C bonds
- C07F9/38—Phosphonic acids [RP(=O)(OH)2]; Thiophosphonic acids ; [RP(=X1)(X2H)2(X1, X2 are each independently O, S or Se)]
- C07F9/40—Esters thereof
- C07F9/4071—Esters thereof the ester moiety containing a substituent or a structure which is considered as characteristic
- C07F9/4084—Esters with hydroxyaryl compounds
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)
Description
ot t acids and soil nematodes and termites containing This invention relates to pesticidal preparations containing them and their use as The present invention provides compounds of the formula in which represents an ethyl group and represents a or isobutyl group or in which represents a methyl group and represents an isopropyl or The present invention also provides a preparation for combating termites and which comprises a compound of the formula 1 and a The preparation may contain one or more of the following additives a a a wetting an adhesive a fertilizer or pesticides of bactericidal or insecticidal la The against which the compounds the instant case are are all insects at any one of their development or final live in the primarily harmful larvae of or wire worms eridae or larvae of Melolontha The order for the mole cricket and centipedes are also included in this for Meloidogyne and others are also effectively British Patent among compounds Of formula I above in which is lower alkyl and is methyl or It has surprisingly been found that the compounds of the present invention none of which has been specifically described in the above possess certain superior properties when compared with the above known as been shown in Example 9 A special problem arises in the destruction of soil because the active insecticide must act not only in the area actually but must also attack the harmful organism over a wider More the active substances lose their activity in the soil rapidly because of Nearly all phosphoric acid esters and phosphonic acid esters are wholly substantially destroyed by decomposition after a few days in an alkaline It unexpected that the compounds the formula Γ would possess such excellent stability in example the compound is stable for 2 months in the alkaline permanence test at pH In the form of an aqueous this active substance can be sprayed over a freshly whitewashed wall is to be Some other compounds of the formula I have proved to be equally The application technique as especially the formulation of the active substance into is in principle the same as is usually details will be found in Specification British Specification and Swiss Specification Typical examples of their use are given It has been found that in general granulates are the most suitable of the preparation for uniformly the active substances in the These granulates ensure the best sustained influence of the active substances on the surroundings without causing damage to plants by local or by killing off useful indirectly responsible for uniformly plant or are necessary to ensure such The phosphonates of the formula I can be manufactured by known inter alia by reacting a acid halide of the which and have the meanings given above and Y represents a halogen preferably a chlorine with a preferably the sodium of The reaction can be carried out either in the 8 Example 2 5 Parts of one of the active substances of the formula I are mixed with 95 parts of calcium carbonate and The product is used as a casting for bating soil insects nematodes or against insects that attack Example 5 Parts of of the active substances of the formula I are mixed with 95 parts of a pulverulent for sand or calcium and moistened with parte of water or and the mixture is then Before granulating the above or a mixture containing a greater amount of the active for 10 parts of active substance and 90 parts of calcium be admixed with a multiple for 100 to 900 a fertilizer if may be for ammonium These granulates are used to combat soil insects Example 4 20 Parts of one of the active substances of the formula I and parts of talcum are ground in a ball mill to extreme The resulting powder is used as a dusting agent to combat soil Example 50 Parts of one of the active substances of the formula I are mixed with 45 parts of parts 9 and parts of a mixture of the sodium salts of acid and a menatocidally active solution emulsifiable in water is which can be used at the same time to combat soil insects at E x m p 1 e Testing against white grubs of polyvinylchloride x 10 x 5 are filled with moist humus soil almost up to the 4 Grubs each of Fielolontha at the stage inserted around a notched potato stuck in the middle of the Even distribution of the larvae is An emulsion of an active substance prepared as described in I Example is sprayed with a chromatography atomizer over the surface of the humu3 soil in a concentration corresponding to 6 and 5 respectively of active substance per The polyvinylchloride container is covered with a perforated container acting as a During the testing period the soil must be kept uniformly Evaluation is carried out after 21 and 28 days and 20 grubs were used for each test a concentration of substance Testing against wire worms At Velesevac the soil of 3 plots of 25m2 each dusted on 25 April i 1968 with the active j stance formulated as described in Example and with broraophos formulated as dusting in each case in a concentration corresponding to kg of active substance per and prepared for the of maize which t was carried out on i On 29 the plants not infested by wire worms j were In comparison with 100 sound plants control plot that had not been treated there sound plants from a field treated with compound 23 98 sound plants from a field treated with Example j Testing against cutworms and Agrotis On Canton plots measuring which were Ί with planted with salad Λ dilute aqueous spray broth was prepared from an cmulaion the compound prepared desoribed in Example and applied in an amount of 2 litres per 2 kg ctive substance per Evaluation after weeks revealed the following i To the effect as stomach 12 Petri dishes were filled with moist fermented compost soil a layer 5 cm and 1 cutworm each of the to stage together with J bait granulates was placed on top of the The granulate consisted of j compressed dry fodder for rabbits and of the compound After 28 hours the following effects were Agrotis Agrotis excla ationis Living Dead Living Lead Compound 1 1 11 Untreated control 0 12 0 Example 9 Comparative testa with compounds known from Patent Sneci The activity of the compound of the present inven with that of the knovm compound Aulacophora Test Kethod young Zuchetti plants each were planted in pots soil had been previously treated with the equivalent of 8 of active Each pot was then infested with larvae 18 of the test The number of dead larvae is recorded after 20 days and in the event that mortality is at 10 days the soil is Test Pachnoda marginata Test Pots are filled with soil treated with the equivalent of 8 of active substance and infested with 5 larvae 30 Small pieces of apple are lightly buried into the soil and serve as the being maintained slightly The number of dead larvae is recorded after lOarxi 20 days and la the event that mortality is achieved at 10 days the soil is 15 Test Results Similarly the activity of compound 1 of the present was compared with that of the known compound Test Chortophila brassicae plants were 1 in pots whose been previously treated with the equivalent of 8 hectare of active Each pot was then infested with 15 eggs of the test animal which within 2 The number of dead is recorded after 10 Test insufficientOCRQuality
Claims (1)
1. in which and R have the meanin s specified in claim 9 A process as claimed in 8 substantially as cribed in Example 1 A preparation for destroying soil termites and which comprises as active ingredient a compound as claimed in Claim 1 together with a suitable A preparation as claimed in Claim 10 wherein there is present one or more than one of the following a a a a a wetting agent and adhesive a fertilizer or other pesticides of a bactericidal or insecticidal A preparation as claimed in claim 10 or claim 11 wherein the active ingredient is the compound claimed in pf claims 2 to A preparation as in claim 10 claim wherein the active ingredient is the compound claimed in claim 6 or 7 A preparation as claimed in claim 10 substantially as described in anyone of Examples 2 to A method of combatting soil nematodes and termites which comprises applying to the soil as active substance a pound of the formula 1 as defined claim 1 A as 1 wherein the a in a m wherein active sub compound or PARTNER insufficientOCRQuality
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH790468A CH497844A (en) | 1968-05-28 | 1968-05-28 | Pesticidal organophosphorus cpds. |
CH528769A CH526915A (en) | 1969-04-08 | 1969-04-08 | Pesticidal organophosphorus cpds. |
Publications (2)
Publication Number | Publication Date |
---|---|
IL32240A0 IL32240A0 (en) | 1969-07-30 |
IL32240A true IL32240A (en) | 1973-08-29 |
Family
ID=25697384
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
IL32240A IL32240A (en) | 1968-05-28 | 1969-05-19 | Diesters of phosphonic and thionophosphonic acids and compositions for combating soil insects,nematodes and termites containing them |
Country Status (11)
Country | Link |
---|---|
AT (1) | AT303453B (en) |
BE (1) | BE733613A (en) |
DE (1) | DE1925653A1 (en) |
DK (1) | DK127002B (en) |
ES (1) | ES367711A1 (en) |
FR (1) | FR2009484A1 (en) |
GB (1) | GB1275796A (en) |
IE (1) | IE32828B1 (en) |
IL (1) | IL32240A (en) |
NL (1) | NL6908046A (en) |
SU (1) | SU383240A3 (en) |
-
1969
- 1969-05-19 IL IL32240A patent/IL32240A/en unknown
- 1969-05-20 DE DE19691925653 patent/DE1925653A1/en active Pending
- 1969-05-21 GB GB25854/69A patent/GB1275796A/en not_active Expired
- 1969-05-26 IE IE716/69A patent/IE32828B1/en unknown
- 1969-05-27 NL NL6908046A patent/NL6908046A/xx unknown
- 1969-05-27 FR FR6917249A patent/FR2009484A1/fr active Pending
- 1969-05-27 ES ES367711A patent/ES367711A1/en not_active Expired
- 1969-05-27 BE BE733613D patent/BE733613A/xx unknown
- 1969-05-27 AT AT891670A patent/AT303453B/en not_active IP Right Cessation
- 1969-05-28 DK DK286669AA patent/DK127002B/en unknown
- 1969-05-28 SU SU1334729A patent/SU383240A3/ru active
Also Published As
Publication number | Publication date |
---|---|
DK127002B (en) | 1973-09-10 |
IL32240A0 (en) | 1969-07-30 |
NL6908046A (en) | 1969-12-02 |
BE733613A (en) | 1969-11-27 |
IE32828B1 (en) | 1973-12-12 |
DE1925653A1 (en) | 1969-12-04 |
ES367711A1 (en) | 1971-04-16 |
IE32828L (en) | 1969-11-28 |
AT303453B (en) | 1972-11-27 |
FR2009484A1 (en) | 1970-02-06 |
GB1275796A (en) | 1972-05-24 |
SU383240A3 (en) | 1973-05-25 |
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