CH571814A5 - 3-(Thiophosphorylthiomethyl)-oxazolo (4,5-b) pyridine-2(3H)-(thi)ones - with biocidal (esp insecticidal and acaricidal) activity - Google Patents

3-(Thiophosphorylthiomethyl)-oxazolo (4,5-b) pyridine-2(3H)-(thi)ones - with biocidal (esp insecticidal and acaricidal) activity

Info

Publication number: CH571814A5
Authority: CH; Switzerland
Prior art keywords: larvae; test; plants; formula; alkyl
Prior art date: 1972-10-06

Application number

CH1469672A

Other languages

German (de)

English (en)

Original Assignee

Ciba Geigy Ag

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1972-10-06

Filing date

1972-10-06

Publication date

1976-01-30

1972-10-06 Application filed by Ciba Geigy Ag filed Critical Ciba Geigy Ag

1972-10-06 Priority to CH1469672A priority Critical patent/CH571814A5/de

1973-09-10 Priority to IL43191A priority patent/IL43191A0/xx

1973-09-11 Priority to CA180,783A priority patent/CA1053233A/fr

1973-09-27 Priority to NL7313349A priority patent/NL7313349A/xx

1973-10-03 Priority to DE19732349746 priority patent/DE2349746A1/de

1973-10-04 Priority to TR17406A priority patent/TR17406A/xx

1973-10-04 Priority to DD173881A priority patent/DD108448A5/xx

1973-10-05 Priority to FR7335691A priority patent/FR2202101B1/fr

1973-10-05 Priority to JP48112211A priority patent/JPS4969841A/ja

1973-10-05 Priority to BE136377A priority patent/BE805709A/fr

1973-10-05 Priority to GB4666573A priority patent/GB1439067A/en

1973-10-05 Priority to IT29800/73A priority patent/IT1054145B/it

1976-01-30 Publication of CH571814A5 publication Critical patent/CH571814A5/de

Links

230000000749 insecticidal effect Effects 0.000 title claims abstract description 12
230000000895 acaricidal effect Effects 0.000 title claims abstract description 9
230000000694 effects Effects 0.000 title claims description 11
230000003115 biocidal effect Effects 0.000 title description 2
WJJMNDUMQPNECX-UHFFFAOYSA-N dipicolinic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=N1 WJJMNDUMQPNECX-UHFFFAOYSA-N 0.000 title 1
229910052760 oxygen Inorganic materials 0.000 claims abstract description 8
229910052736 halogen Inorganic materials 0.000 claims abstract description 5
150000002367 halogens Chemical class 0.000 claims abstract description 5
229910052717 sulfur Inorganic materials 0.000 claims abstract description 5
230000001069 nematicidal effect Effects 0.000 claims abstract description 3
239000004480 active ingredient Substances 0.000 claims description 36
238000012360 testing method Methods 0.000 claims description 28
150000001875 compounds Chemical class 0.000 claims description 25
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239000008187 granular material Substances 0.000 claims description 10
239000000839 emulsion Substances 0.000 claims description 9
239000000203 mixture Substances 0.000 claims description 9
239000002689 soil Substances 0.000 claims description 8
239000000126 substance Substances 0.000 claims description 8
125000006527 (C1-C5) alkyl group Chemical group 0.000 claims description 7
241000244206 Nematoda Species 0.000 claims description 7
239000007921 spray Substances 0.000 claims description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 7
241000426497 Chilo suppressalis Species 0.000 claims description 6
241000258916 Leptinotarsa decemlineata Species 0.000 claims description 6
239000003795 chemical substances by application Substances 0.000 claims description 6
239000004495 emulsifiable concentrate Substances 0.000 claims description 6
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
238000010790 dilution Methods 0.000 claims description 5
239000012895 dilution Substances 0.000 claims description 5
229910052739 hydrogen Inorganic materials 0.000 claims description 5
239000001257 hydrogen Substances 0.000 claims description 5
239000001301 oxygen Substances 0.000 claims description 5
239000000243 solution Substances 0.000 claims description 5
241000238876 Acari Species 0.000 claims description 4
241001425390 Aphis fabae Species 0.000 claims description 4
240000002024 Gossypium herbaceum Species 0.000 claims description 4
235000004341 Gossypium herbaceum Nutrition 0.000 claims description 4
235000007688 Lycopersicon esculentum Nutrition 0.000 claims description 4
241000243784 Meloidogyne arenaria Species 0.000 claims description 4
241001465754 Metazoa Species 0.000 claims description 4
244000046052 Phaseolus vulgaris Species 0.000 claims description 4
241000238680 Rhipicephalus microplus Species 0.000 claims description 4
240000003768 Solanum lycopersicum Species 0.000 claims description 4
244000061456 Solanum tuberosum Species 0.000 claims description 4
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
238000002474 experimental method Methods 0.000 claims description 4
150000002431 hydrogen Chemical class 0.000 claims description 4
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
239000002574 poison Substances 0.000 claims description 4
231100000614 poison Toxicity 0.000 claims description 4
238000002360 preparation method Methods 0.000 claims description 4
239000011593 sulfur Substances 0.000 claims description 4
230000009885 systemic effect Effects 0.000 claims description 4
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239000000575 pesticide Substances 0.000 claims description 3
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240000001624 Espostoa lanata Species 0.000 claims description 2
241000256257 Heliothis Species 0.000 claims description 2
241000256244 Heliothis virescens Species 0.000 claims description 2
206010061217 Infestation Diseases 0.000 claims description 2
235000010627 Phaseolus vulgaris Nutrition 0.000 claims description 2
241001481703 Rhipicephalus <genus> Species 0.000 claims description 2
241000949016 Rhipicephalus bursa Species 0.000 claims description 2
241000256248 Spodoptera Species 0.000 claims description 2
241000256250 Spodoptera littoralis Species 0.000 claims description 2
241001454294 Tetranychus Species 0.000 claims description 2
241001454293 Tetranychus urticae Species 0.000 claims description 2
240000006677 Vicia faba Species 0.000 claims description 2
235000010749 Vicia faba Nutrition 0.000 claims description 2
241000607479 Yersinia pestis Species 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
235000013601 eggs Nutrition 0.000 claims description 2
238000011156 evaluation Methods 0.000 claims description 2
235000013305 food Nutrition 0.000 claims description 2
239000007789 gas Substances 0.000 claims description 2
239000011521 glass Substances 0.000 claims description 2
239000004033 plastic Substances 0.000 claims description 2
229920003023 plastic Polymers 0.000 claims description 2
238000009331 sowing Methods 0.000 claims description 2
230000000855 fungicidal effect Effects 0.000 abstract description 2
229910052751 metal Inorganic materials 0.000 abstract description 2
239000002184 metal Substances 0.000 abstract description 2
125000000217 alkyl group Chemical group 0.000 abstract 4
125000003342 alkenyl group Chemical group 0.000 abstract 1
125000000304 alkynyl group Chemical group 0.000 abstract 1
239000000460 chlorine Substances 0.000 description 28
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
-1 methoxy, methoxymethyl ethyl Chemical group 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
239000005995 Aluminium silicate Substances 0.000 description 5
241000233866 Fungi Species 0.000 description 5
235000012211 aluminium silicate Nutrition 0.000 description 5
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 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
239000002904 solvent Substances 0.000 description 5
239000000654 additive Substances 0.000 description 4
229920000151 polyglycol Polymers 0.000 description 4
239000010695 polyglycol Substances 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 3
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
239000002253 acid Substances 0.000 description 3
239000000969 carrier Substances 0.000 description 3
235000019993 champagne Nutrition 0.000 description 3
229910052801 chlorine Inorganic materials 0.000 description 3
239000012141 concentrate Substances 0.000 description 3
235000013399 edible fruits Nutrition 0.000 description 3
238000004452 microanalysis Methods 0.000 description 3
239000000377 silicon dioxide Substances 0.000 description 3
239000008096 xylene Substances 0.000 description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
239000004354 Hydroxyethyl cellulose Substances 0.000 description 2
229920000663 Hydroxyethyl cellulose Polymers 0.000 description 2
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
239000002202 Polyethylene glycol Substances 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
241000254107 Tenebrionidae Species 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
241000221561 Ustilaginales Species 0.000 description 2
239000013543 active substance Substances 0.000 description 2
229910052784 alkaline earth metal Inorganic materials 0.000 description 2
239000011230 binding agent Substances 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
229910052794 bromium Inorganic materials 0.000 description 2
235000013339 cereals Nutrition 0.000 description 2
238000006243 chemical reaction Methods 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
239000003085 diluting agent Substances 0.000 description 2
239000002270 dispersing agent Substances 0.000 description 2
239000000428 dust Substances 0.000 description 2
150000002170 ethers Chemical class 0.000 description 2
125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
150000002191 fatty alcohols Chemical class 0.000 description 2
238000009472 formulation Methods 0.000 description 2
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239000004615 ingredient Substances 0.000 description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
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238000000034 method Methods 0.000 description 2
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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
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229920001223 polyethylene glycol Polymers 0.000 description 2
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125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
239000007787 solid Substances 0.000 description 2
239000000454 talc Substances 0.000 description 2
229910052623 talc Inorganic materials 0.000 description 2
235000015112 vegetable and seed oil Nutrition 0.000 description 2
239000008158 vegetable oil Substances 0.000 description 2
239000004563 wettable powder Substances 0.000 description 2
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
IQUPABOKLQSFBK-UHFFFAOYSA-N 2-nitrophenol Chemical class OC1=CC=CC=C1[N+]([O-])=O IQUPABOKLQSFBK-UHFFFAOYSA-N 0.000 description 1
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
TUWOEDOQOKTAAA-UHFFFAOYSA-N 6-chloro-3-(chloromethyl)-[1,3]oxazolo[4,5-b]pyridin-2-one Chemical compound C1=C(Cl)C=C2OC(=O)N(CCl)C2=N1 TUWOEDOQOKTAAA-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
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241000894006 Bacteria Species 0.000 description 1
241000221198 Basidiomycota Species 0.000 description 1
241000539677 Berant virus 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
241000283690 Bos taurus Species 0.000 description 1
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XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
PNKUSGQVOMIXLU-UHFFFAOYSA-N Formamidine Chemical compound NC=N PNKUSGQVOMIXLU-UHFFFAOYSA-N 0.000 description 1
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UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 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
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208000031888 Mycoses Diseases 0.000 description 1
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ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
241001415279 Pseudococcidae Species 0.000 description 1
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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
239000000642 acaricide Substances 0.000 description 1
239000000853 adhesive Substances 0.000 description 1
230000001070 adhesive effect Effects 0.000 description 1
239000003513 alkali Substances 0.000 description 1
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
150000001342 alkaline earth metals Chemical class 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
150000001408 amides Chemical class 0.000 description 1
238000009835 boiling Methods 0.000 description 1
229920005551 calcium lignosulfonate Polymers 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
150000004657 carbamic acid derivatives Chemical class 0.000 description 1
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150000003857 carboxamides Chemical class 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
239000007931 coated granule Substances 0.000 description 1
238000011161 development Methods 0.000 description 1
POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
238000000605 extraction Methods 0.000 description 1
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244000037666 field crops Species 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
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150000008282 halocarbons Chemical class 0.000 description 1
150000004679 hydroxides Chemical class 0.000 description 1
238000005470 impregnation Methods 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
239000002917 insecticide Substances 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
239000011630 iodine 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
125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
229920005610 lignin Polymers 0.000 description 1
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125000005394 methallyl group Chemical group 0.000 description 1
238000002156 mixing Methods 0.000 description 1
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 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
150000002825 nitriles Chemical class 0.000 description 1
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229910052700 potassium Inorganic materials 0.000 description 1
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 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
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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
239000007858 starting material Substances 0.000 description 1
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125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
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239000002562 thickening agent Substances 0.000 description 1
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235000013311 vegetables Nutrition 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1
150000003738 xylenes Chemical class 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds
- A01N57/14—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds containing aromatic radicals

Landscapes

Life Sciences & Earth Sciences (AREA)
Agronomy & Crop Science (AREA)
Pest Control & Pesticides (AREA)
Plant Pathology (AREA)
Health & Medical Sciences (AREA)
Engineering & Computer Science (AREA)
Dentistry (AREA)
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CH1469672A 1972-10-06 1972-10-06 3-(Thiophosphorylthiomethyl)-oxazolo (4,5-b) pyridine-2(3H)-(thi)ones - with biocidal (esp insecticidal and acaricidal) activity CH571814A5 (en)

Priority Applications (12)

Application Number	Priority Date	Filing Date	Title
CH1469672A CH571814A5 (en)	1972-10-06	1972-10-06	3-(Thiophosphorylthiomethyl)-oxazolo (4,5-b) pyridine-2(3H)-(thi)ones - with biocidal (esp insecticidal and acaricidal) activity
IL43191A IL43191A0 (en)	1972-10-06	1973-09-10	Novel esters of dithiophosphoric acid,their preparation and their use in pest control
CA180,783A CA1053233A (fr)	1972-10-06	1973-09-11	Esters dithiophosphates de carbamates ou de thiocarbamates cycliques de pyridine
NL7313349A NL7313349A (fr)	1972-10-06	1973-09-27
DE19732349746 DE2349746A1 (de)	1972-10-06	1973-10-03	Thiophosphorsaeureester von oxazolopyridinverbindungen und diese enthaltende schaedlingsbekaempfungsmittel
TR17406A TR17406A (tr)	1972-10-06	1973-10-04	Yeni heterosiller
DD173881A DD108448A5 (fr)	1972-10-06	1973-10-04
FR7335691A FR2202101B1 (fr)	1972-10-06	1973-10-05
JP48112211A JPS4969841A (fr)	1972-10-06	1973-10-05
BE136377A BE805709A (fr)	1972-10-06	1973-10-05	Esters phosphoriques renfermant un heterocycle et produits pesticides qui en contiennent
GB4666573A GB1439067A (en)	1972-10-06	1973-10-05	Dithiophosphate esters having pesticidal properties
IT29800/73A IT1054145B (it)	1972-10-06	1973-10-05	Ditiofosfati loro preparazione e loro impiego quali disinfestanti

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
CH1469672A CH571814A5 (en)	1972-10-06	1972-10-06	3-(Thiophosphorylthiomethyl)-oxazolo (4,5-b) pyridine-2(3H)-(thi)ones - with biocidal (esp insecticidal and acaricidal) activity

Publications (1)

Publication Number	Publication Date
CH571814A5 true CH571814A5 (en)	1976-01-30

Family

ID=4403090

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH1469672A CH571814A5 (en)	1972-10-06	1972-10-06	3-(Thiophosphorylthiomethyl)-oxazolo (4,5-b) pyridine-2(3H)-(thi)ones - with biocidal (esp insecticidal and acaricidal) activity

Country Status (3)

Country	Link
BE (1)	BE805709A (fr)
CH (1)	CH571814A5 (fr)
TR (1)	TR17406A (fr)

1972
- 1972-10-06 CH CH1469672A patent/CH571814A5/de not_active IP Right Cessation
1973
- 1973-10-04 TR TR17406A patent/TR17406A/xx unknown
- 1973-10-05 BE BE136377A patent/BE805709A/fr unknown

Also Published As

Publication number	Publication date
BE805709A (fr)	1974-04-05
TR17406A (tr)	1975-03-24

Legal Events

Date	Code	Title	Description
1981-06-30	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
DE2360631A1 (de)	1974-06-12	1,2,4-triazolylphosphorsaeure- bzw. phosphonsaeureester, verfahren zu ihrer herstellung und ihre verwendung
DE2303185C2 (de)	1986-01-09	Thiophosphorsäurephenylester, Verfahren zu ihrer Herstellung sowie diese enthaltende Schädlingsbekämpfungsmittel
DE2412564A1 (de)	1974-10-17	N,n-dimethylcarbamoyl-1,2,4-triazolyl(3)-ester, verfahren zu ihrer herstellung und ihre verwendung
DE2411809A1 (de)	1974-09-26	Thiolphosphorsaeureester, verfahren zu ihrer herstellung und ihre verwendung
DE2429747A1 (de)	1975-01-23	1,3,5-triazapenta-1,4-diene, verfahren zu ihrer herstellung und ihre verwendung
DE2304128C2 (de)	1982-05-06	Thiolphosphorsäureester, Verfahren zu ihrer Herstellung und ihre Verwendung in der Schädlingsbekämpfung
CH580910A5 (fr)	1976-10-29
CH571814A5 (en)	1976-01-30	3-(Thiophosphorylthiomethyl)-oxazolo (4,5-b) pyridine-2(3H)-(thi)ones - with biocidal (esp insecticidal and acaricidal) activity
DE2350696A1 (de)	1974-04-18	Neue ester
DE2422324C2 (de)	1984-05-03	Diphenyläther-phosphorverbindungen, Verfahren zu ihrer Herstellung und diese enthaltende Schädlingsbekämpfungsmittel
DE2349755A1 (de)	1974-04-11	Thiophosphorsaeureester von thiadiazdverbindungen und diese enthaltende schaedlingsbekaempfungsmittel
DE2350695A1 (de)	1974-04-18	Neue ester
DE2349746A1 (de)	1974-04-11	Thiophosphorsaeureester von oxazolopyridinverbindungen und diese enthaltende schaedlingsbekaempfungsmittel
DE2439663A1 (de)	1975-03-06	Diphenylaetherphosphate, verfahren zu ihrer herstellung und ihre verwendung
AT328795B (de)	1976-04-12	Schadlingsbekampfungsmittel
CH573206A5 (en)	1976-03-15	Pesticidal 5-halo-1,2,4-triazol-3-yl carbamates - e.g. 1-isopropyl-5-chloro-1,2,4-triazol-3-yl dimethylcarbamate
DE2430758A1 (de)	1975-01-23	Oxadiazolylverbindungen, verfahren zu ihrer herstellung und ihre verwendung zur schaedlingsbekaempfung
CH570766A5 (en)	1975-12-31	Biocidal triazolyl dithio phosphates - prepd from dithiophosphoric acid halides and 3-hydroxy triazoles
CH575211A5 (en)	1976-05-14	(di)thiophosphoric acid esters - with biocidal activity
CH571308A5 (en)	1976-01-15	Biocidal triazolyl dithio phosphates - prepd from dithio phosphoric acid halides and 3-hydroxy triazoles
CH571817A5 (en)	1976-01-30	Pesticidal 1,2,4-triazol-3-yl phosph(on)ates - e.g. O,O-diethyl-O-(1-methyl-5-(alpha-carbethoxybenzyl)-1,2,4-triazol-- 3-yl)-phosphate
CH579873A5 (en)	1976-09-30	Oxadiazolyls from hydroxydiazoles and phosphoric acid halides - with wide biocidal activity
CH571816A5 (en)	1976-01-30	O-Triazolyl O-alkyl (thio)phosph(on)ates - with biocidal (esp insecticidal) activity
CH571307A5 (en)	1976-01-15	Biocidal triazolyl dithio phosphates - prepd from dithiophosphoric acid halides and 1-(chloro) phenyl-3-hydroxy triazoles
DE2401957A1 (de)	1974-07-25	Phosphorverbindungen, verfahren zu ihrer herstellung und ihre verwendung