CA1047522A - Esters d'acide thiolphosphorique - Google Patents

Esters d'acide thiolphosphorique

Info

Publication number: CA1047522A
Authority: CA; Canada
Prior art keywords: parts; active substance; acid esters; larvae; compounds
Prior art date: 1972-06-08
Legal status (The legal status 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 status listed.): Expired

Application number

CA248,140A

Other languages

English (en)

Inventor

Alexis A. Oswald

Paul L. Valint

Jozef Drabek

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Novartis AG

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.)

1972-06-08

Filing date

1976-03-18

Publication date

1979-01-30

1972-06-08 Priority claimed from CH859472A external-priority patent/CH572708A5/xx

1973-05-07 Priority claimed from CH642873A external-priority patent/CH581434A5/de

1973-06-07 Priority claimed from CA173,492A external-priority patent/CA1047521A/fr

1976-03-18 Application filed by Ciba Geigy AG filed Critical Ciba Geigy AG

1979-01-30 Application granted granted Critical

1979-01-30 Publication of CA1047522A publication Critical patent/CA1047522A/fr

Status Expired legal-status Critical Current

Links

239000002253 acid Substances 0.000 title description 5
150000002148 esters Chemical class 0.000 title description 3
150000001875 compounds Chemical class 0.000 claims abstract description 18
238000000034 method Methods 0.000 claims description 8
241000238876 Acari Species 0.000 claims description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
241000607479 Yersinia pestis Species 0.000 claims description 2
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
125000004093 cyano group Chemical group *C#N 0.000 claims 2
241000500891 Insecta Species 0.000 claims 1
230000000895 acaricidal effect Effects 0.000 abstract description 4
230000000749 insecticidal effect Effects 0.000 abstract description 4
-1 THIOL PHOSPHORIC ACID ESTERS Chemical class 0.000 abstract description 3
230000000361 pesticidal effect Effects 0.000 abstract 1
239000013543 active substance Substances 0.000 description 24
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
239000008187 granular material Substances 0.000 description 8
125000000134 2-(methylsulfanyl)ethyl group Chemical group [H]C([H])([H])SC([H])([H])C([H])([H])[*] 0.000 description 7
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 7
239000000839 emulsion Substances 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-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
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
239000000203 mixture Substances 0.000 description 5
239000007921 spray Substances 0.000 description 5
239000000126 substance Substances 0.000 description 5
239000005995 Aluminium silicate Substances 0.000 description 4
235000012211 aluminium silicate Nutrition 0.000 description 4
239000000969 carrier Substances 0.000 description 4
229920000151 polyglycol Polymers 0.000 description 4
239000010695 polyglycol Substances 0.000 description 4
239000000243 solution Substances 0.000 description 4
239000002904 solvent Substances 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
241000426497 Chilo suppressalis Species 0.000 description 3
241000196324 Embryophyta Species 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
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 3
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
241001454295 Tetranychidae Species 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
239000000654 additive Substances 0.000 description 3
JXLHNMVSKXFWAO-UHFFFAOYSA-N azane;7-fluoro-2,1,3-benzoxadiazole-4-sulfonic acid Chemical compound N.OS(=O)(=O)C1=CC=C(F)C2=NON=C12 JXLHNMVSKXFWAO-UHFFFAOYSA-N 0.000 description 3
235000019993 champagne Nutrition 0.000 description 3
239000003795 chemical substances by application Substances 0.000 description 3
239000004495 emulsifiable concentrate Substances 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 3
235000012239 silicon dioxide Nutrition 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
239000011734 sodium Substances 0.000 description 3
239000008096 xylene Substances 0.000 description 3
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
229920000742 Cotton Polymers 0.000 description 2
241000256244 Heliothis virescens Species 0.000 description 2
241000238631 Hexapoda Species 0.000 description 2
239000004354 Hydroxyethyl cellulose Substances 0.000 description 2
229920000663 Hydroxyethyl cellulose Polymers 0.000 description 2
244000046052 Phaseolus vulgaris Species 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
241000949016 Rhipicephalus bursa Species 0.000 description 2
244000061456 Solanum tuberosum Species 0.000 description 2
241000256250 Spodoptera littoralis Species 0.000 description 2
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
241001454293 Tetranychus urticae Species 0.000 description 2
239000000370 acceptor Substances 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
239000012141 concentrate Substances 0.000 description 2
239000000470 constituent Substances 0.000 description 2
239000003085 diluting agent Substances 0.000 description 2
238000010790 dilution Methods 0.000 description 2
239000012895 dilution Substances 0.000 description 2
239000002270 dispersing agent Substances 0.000 description 2
230000000694 effects Effects 0.000 description 2
235000013601 eggs Nutrition 0.000 description 2
238000011156 evaluation Methods 0.000 description 2
150000002191 fatty alcohols Chemical class 0.000 description 2
238000009472 formulation Methods 0.000 description 2
235000019447 hydroxyethyl cellulose Nutrition 0.000 description 2
229920005610 lignin Polymers 0.000 description 2
239000007788 liquid Substances 0.000 description 2
238000004519 manufacturing process Methods 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
239000000843 powder Substances 0.000 description 2
239000007787 solid Substances 0.000 description 2
238000003756 stirring Methods 0.000 description 2
239000000725 suspension Substances 0.000 description 2
239000000454 talc Substances 0.000 description 2
235000012222 talc Nutrition 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
QFBDCSDDHUBEGG-UHFFFAOYSA-N 1,2-dibutylnaphthalene;sodium Chemical compound [Na].C1=CC=CC2=C(CCCC)C(CCCC)=CC=C21 QFBDCSDDHUBEGG-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
SGHBRHKBCLLVCI-UHFFFAOYSA-N 3-hydroxybenzonitrile Chemical compound OC1=CC=CC(C#N)=C1 SGHBRHKBCLLVCI-UHFFFAOYSA-N 0.000 description 1
241001124076 Aphididae Species 0.000 description 1
241000238888 Argasidae Species 0.000 description 1
241000238660 Blattidae Species 0.000 description 1
241000283690 Bos taurus Species 0.000 description 1
241000907223 Bruchinae Species 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
241000257161 Calliphoridae Species 0.000 description 1
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
241001124134 Chrysomelidae Species 0.000 description 1
241001414835 Cimicidae Species 0.000 description 1
241000255749 Coccinellidae Species 0.000 description 1
241000256113 Culicidae Species 0.000 description 1
241001466044 Delphacidae Species 0.000 description 1
241000131287 Dermestidae Species 0.000 description 1
241001414830 Diaspididae Species 0.000 description 1
LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
241000238816 Gryllidae Species 0.000 description 1
241001243087 Gryllotalpidae Species 0.000 description 1
241000238889 Ixodidae Species 0.000 description 1
241000258915 Leptinotarsa Species 0.000 description 1
241000258916 Leptinotarsa decemlineata Species 0.000 description 1
241001435619 Lile Species 0.000 description 1
241001465754 Metazoa Species 0.000 description 1
241000403354 Microplus Species 0.000 description 1
241000257226 Muscidae Species 0.000 description 1
244000061176 Nicotiana tabacum Species 0.000 description 1
235000002637 Nicotiana tabacum Nutrition 0.000 description 1
241000256259 Noctuidae Species 0.000 description 1
BPQQTUXANYXVAA-UHFFFAOYSA-N Orthosilicate Chemical compound [O-][Si]([O-])([O-])[O-] BPQQTUXANYXVAA-UHFFFAOYSA-N 0.000 description 1
240000007594 Oryza sativa Species 0.000 description 1
235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
241001415279 Pseudococcidae Species 0.000 description 1
241000258921 Pulicidae Species 0.000 description 1
241000255893 Pyralidae Species 0.000 description 1
241001510071 Pyrrhocoridae Species 0.000 description 1
241001124072 Reduviidae Species 0.000 description 1
241001481703 Rhipicephalus <genus> Species 0.000 description 1
241000254062 Scarabaeidae Species 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
235000002595 Solanum tuberosum Nutrition 0.000 description 1
QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
241000254107 Tenebrionidae Species 0.000 description 1
241000255588 Tephritidae Species 0.000 description 1
241000896028 Tettigoniidae Species 0.000 description 1
241000130767 Tineidae Species 0.000 description 1
241000131339 Tipulidae Species 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
229910052783 alkali metal Inorganic materials 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
125000000217 alkyl group Chemical group 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
150000001448 anilines Chemical class 0.000 description 1
125000003118 aryl group Chemical group 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
238000009835 boiling Methods 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
239000011575 calcium Substances 0.000 description 1
159000000007 calcium salts Chemical class 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
239000007931 coated granule Substances 0.000 description 1
239000011248 coating agent Substances 0.000 description 1
238000000576 coating method Methods 0.000 description 1
ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 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
238000001035 drying Methods 0.000 description 1
239000000428 dust Substances 0.000 description 1
235000005489 dwarf bean Nutrition 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
239000011521 glass Substances 0.000 description 1
238000000227 grinding Methods 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
150000004678 hydrides Chemical class 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
150000004679 hydroxides Chemical class 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
239000002917 insecticide Substances 0.000 description 1
150000002500 ions Chemical class 0.000 description 1
239000000463 material Substances 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
238000002156 mixing Methods 0.000 description 1
238000000199 molecular distillation Methods 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
239000002245 particle Substances 0.000 description 1
239000006072 paste Substances 0.000 description 1
239000004033 plastic Substances 0.000 description 1
229920003023 plastic Polymers 0.000 description 1
239000002574 poison Substances 0.000 description 1
231100000614 poison Toxicity 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
239000011591 potassium Substances 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
229920006395 saturated elastomer Polymers 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
229910021653 sulphate ion Inorganic materials 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 description 1
125000005270 trialkylamine group Chemical group 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Landscapes

Agricultural Chemicals And Associated Chemicals (AREA)

CA248,140A 1972-06-08 1976-03-18 Esters d'acide thiolphosphorique Expired CA1047522A (fr)

Applications Claiming Priority (3)

Application Number	Priority Date	Filing Date	Title
CH859472A CH572708A5 (en)	1972-06-08	1972-06-08	Cyanophenyl-thiolphosphates - insecticides and acaricides
CH642873A CH581434A5 (en)	1973-05-07	1973-05-07	Cyanophenyl-thiolphosphates - insecticides and acaricides
CA173,492A CA1047521A (fr)	1972-06-08	1973-06-07	Esters d'acide thiolphosphorique

Publications (1)

Publication Number	Publication Date
CA1047522A true CA1047522A (fr)	1979-01-30

Family

ID=27162846

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA248,140A Expired CA1047522A (fr)	1972-06-08	1976-03-18	Esters d'acide thiolphosphorique

Country Status (1)

Country	Link
CA (1)	CA1047522A (fr)

1976
- 1976-03-18 CA CA248,140A patent/CA1047522A/fr not_active Expired

Publication	Publication Date	Title
CA1100991A (fr)	1981-05-12	Traduction non-disponible
CA1058192A (fr)	1979-07-10	Ethers
GB1570928A (en)	1980-07-09	Pesticidal cyclopropane carboxylic acid esters
CA1048524A (fr)	1979-02-13	Esters
CA1048047A (fr)	1979-02-06	Esters
US4028377A (en)	1977-06-07	O,S-dialkyl- and O-alkyl-S-alkoxyalkyl-S-1,2,4-oxa-diazolyl-3-methylene dithiophosphates
US3898306A (en)	1975-08-05	O-(2-vinyl phenyl) thiolphosphates
CA1047522A (fr)	1979-01-30	Esters d'acide thiolphosphorique
CA1042461A (fr)	1978-11-14	Triaza-1,3,5 penta-1,4 dienes utilises comme pesticides
US3968222A (en)	1976-07-06	Insecticidal O,S-dialkyl esters of pyridylthio-and-pyridyldithio-phosphoric acids
CA1047521A (fr)	1979-01-30	Esters d'acide thiolphosphorique
CA1048048A (fr)	1979-02-06	Esters
US4044124A (en)	1977-08-23	Triazolylphosphorus compounds
US4002768A (en)	1977-01-11	Phenylalkinyl ethers
US3927149A (en)	1975-12-16	O-(methyl or ethyl)-O(S) lower alkyl-O-(4-phenoxyphenyl)phosphates
US3991141A (en)	1976-11-09	O-methyl/ethyl-S-propyl/butyl-O-phenyl thiphosphates and dithiophosphates having a thioether group on the phenyl ring
IL43144A (en)	1977-02-28	Thiophosphoric acid amide esters their preparation and their use in insecticidal acaricidal and nematicidal compositions
US3925517A (en)	1975-12-09	Phosphorylformamidines
US3957801A (en)	1976-05-18	O,s-dialkyl esters of pyridylthio- and pyridyldithiophosphoric acid
US3883618A (en)	1975-05-13	O-alkyl-s-alkyl-o-(1-hydrocarbyloxy carbonyl-1-propen-2-yl)dithiophosphates
US3896191A (en)	1975-07-22	O-ethyl-s-m-propyl-o-(2,6-dichloro-4-bromophenyl)phosphorothiolate
US4064263A (en)	1977-12-20	4,5-Benzospiro(2,4)-heptane (and hepta-4,6-diene)-1-carboxylic acid esters and compositions containing same
US3969442A (en)	1976-07-13	O-(2-Vinylphenyl)-thiolphosphates
CA1045149A (fr)	1978-12-26	Esthers
US3943202A (en)	1976-03-09	O-methyl/ethyl-s-propyl/butyl-o-phenyl thiophosphates and dithiophosphates having an ether group or the phenyl ring