NL8105228A - O-alkyl- en o-aryl-s-(tert.alkyl)alkylfosfonothioaten, werkwijze ter bereiding ervan, alsmede hun toepassing als insecticiden en nematociden. - Google Patents

O-alkyl- en o-aryl-s-(tert.alkyl)alkylfosfonothioaten, werkwijze ter bereiding ervan, alsmede hun toepassing als insecticiden en nematociden. Download PDF

Info

Publication number: NL8105228A
Authority: NL; Netherlands
Prior art keywords: carbon atoms; tert; alkyl; compounds according; group
Prior art date: 1980-11-21

Application number

NL8105228A

Other languages

English (en)

Dutch (nl)

Original Assignee

Rhone Poulenc Agrochimie

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.)

1980-11-21

Filing date

1981-11-18

Publication date

1982-06-16

1980-12-31 Priority claimed from US06/221,642 external-priority patent/US4391760A/en

1981-11-18 Application filed by Rhone Poulenc Agrochimie filed Critical Rhone Poulenc Agrochimie

1982-06-16 Publication of NL8105228A publication Critical patent/NL8105228A/nl

Links

238000000034 method Methods 0.000 title claims description 16
239000002917 insecticide Substances 0.000 title claims description 6
238000004519 manufacturing process Methods 0.000 title claims 2
239000005645 nematicide Substances 0.000 title description 2
125000004432 carbon atom Chemical group C* 0.000 claims description 46
150000001875 compounds Chemical class 0.000 claims description 42
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 claims description 27
125000000217 alkyl group Chemical group 0.000 claims description 25
239000004480 active ingredient Substances 0.000 claims description 23
238000002360 preparation method Methods 0.000 claims description 17
-1 tert-amyl Chemical group 0.000 claims description 17
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 claims description 15
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 15
238000006243 chemical reaction Methods 0.000 claims description 14
239000002904 solvent Substances 0.000 claims description 14
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 12
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 9
239000002253 acid Substances 0.000 claims description 8
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 8
239000003960 organic solvent Substances 0.000 claims description 8
241000238631 Hexapoda Species 0.000 claims description 7
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 7
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical group CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 claims description 6
125000003342 alkenyl group Chemical group 0.000 claims description 5
239000000460 chlorine Substances 0.000 claims description 5
229910052801 chlorine Inorganic materials 0.000 claims description 5
125000000262 haloalkenyl group Chemical group 0.000 claims description 5
230000001069 nematicidal effect Effects 0.000 claims description 5
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 5
150000003512 tertiary amines Chemical class 0.000 claims description 5
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
125000001188 haloalkyl group Chemical group 0.000 claims description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 claims description 3
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 claims description 3
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 3
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 claims description 3
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 claims description 3
125000000304 alkynyl group Chemical group 0.000 claims description 3
125000004429 atom Chemical group 0.000 claims description 3
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 3
GGSUCNLOZRCGPQ-UHFFFAOYSA-N diethylaniline Chemical compound CCN(CC)C1=CC=CC=C1 GGSUCNLOZRCGPQ-UHFFFAOYSA-N 0.000 claims description 3
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
229910052731 fluorine Inorganic materials 0.000 claims description 3
125000000232 haloalkynyl group Chemical group 0.000 claims description 3
229910052736 halogen Inorganic materials 0.000 claims description 3
150000002367 halogens Chemical group 0.000 claims description 3
150000007529 inorganic bases Chemical class 0.000 claims description 3
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 2
125000003545 alkoxy group Chemical group 0.000 claims description 2
125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 2
229910052794 bromium Inorganic materials 0.000 claims description 2
125000004093 cyano group Chemical group *C#N 0.000 claims description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims 2
239000011737 fluorine Substances 0.000 claims 2
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims 1
125000001309 chloro group Chemical group Cl* 0.000 claims 1
125000001424 substituent group Chemical group 0.000 claims 1
239000000243 solution Substances 0.000 description 15
239000000203 mixture Substances 0.000 description 12
239000000047 product Substances 0.000 description 11
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
239000007788 liquid Substances 0.000 description 9
239000004094 surface-active agent Substances 0.000 description 9
239000000843 powder Substances 0.000 description 8
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
239000002585 base Substances 0.000 description 7
239000007921 spray Substances 0.000 description 7
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
230000000694 effects Effects 0.000 description 6
230000000749 insecticidal effect Effects 0.000 description 6
241001521235 Spodoptera eridania Species 0.000 description 5
239000007787 solid Substances 0.000 description 5
239000003381 stabilizer Substances 0.000 description 5
150000003573 thiols Chemical class 0.000 description 5
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
241000196324 Embryophyta Species 0.000 description 4
239000000654 additive Substances 0.000 description 4
239000000853 adhesive Substances 0.000 description 4
230000001070 adhesive effect Effects 0.000 description 4
239000003795 chemical substances by application Substances 0.000 description 4
239000004495 emulsifiable concentrate Substances 0.000 description 4
239000008187 granular material Substances 0.000 description 4
238000005507 spraying Methods 0.000 description 4
238000003756 stirring Methods 0.000 description 4
241000489975 Diabrotica Species 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
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
240000008042 Zea mays Species 0.000 description 3
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 3
235000002017 Zea mays subsp mays Nutrition 0.000 description 3
239000011149 active material Substances 0.000 description 3
229910052783 alkali metal Inorganic materials 0.000 description 3
150000001356 alkyl thiols Chemical class 0.000 description 3
150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
235000005822 corn Nutrition 0.000 description 3
230000007797 corrosion Effects 0.000 description 3
238000005260 corrosion Methods 0.000 description 3
239000002270 dispersing agent Substances 0.000 description 3
239000006185 dispersion Substances 0.000 description 3
239000000975 dye Substances 0.000 description 3
239000003995 emulsifying agent Substances 0.000 description 3
239000000839 emulsion Substances 0.000 description 3
150000002148 esters Chemical class 0.000 description 3
238000000227 grinding Methods 0.000 description 3
239000003112 inhibitor Substances 0.000 description 3
239000000543 intermediate Substances 0.000 description 3
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
239000011734 sodium Substances 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
239000000725 suspension Substances 0.000 description 3
238000005160 1H NMR spectroscopy Methods 0.000 description 2
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
229920001213 Polysorbate 20 Polymers 0.000 description 2
FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
150000001412 amines Chemical class 0.000 description 2
239000002518 antifoaming agent Substances 0.000 description 2
239000007798 antifreeze agent Substances 0.000 description 2
125000003118 aryl group Chemical group 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
239000003153 chemical reaction reagent Substances 0.000 description 2
239000000084 colloidal system Substances 0.000 description 2
235000014113 dietary fatty acids Nutrition 0.000 description 2
239000000194 fatty acid Substances 0.000 description 2
229930195729 fatty acid Natural products 0.000 description 2
150000004665 fatty acids Chemical class 0.000 description 2
230000000855 fungicidal effect Effects 0.000 description 2
239000000417 fungicide Substances 0.000 description 2
150000004820 halides Chemical class 0.000 description 2
238000010438 heat treatment Methods 0.000 description 2
239000004615 ingredient Substances 0.000 description 2
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 2
150000002576 ketones Chemical class 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
230000000361 pesticidal effect Effects 0.000 description 2
230000008635 plant growth Effects 0.000 description 2
239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 2
235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
239000003755 preservative agent Substances 0.000 description 2
230000001681 protective effect Effects 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
238000007086 side reaction Methods 0.000 description 2
239000000377 silicon dioxide Substances 0.000 description 2
239000002689 soil Substances 0.000 description 2
239000011550 stock solution Substances 0.000 description 2
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
239000013008 thixotropic agent Substances 0.000 description 2
239000000080 wetting agent Substances 0.000 description 2
ABJSOROVZZKJGI-OCYUSGCXSA-N (1r,2r,4r)-2-(4-bromophenyl)-n-[(4-chlorophenyl)-(2-fluoropyridin-4-yl)methyl]-4-morpholin-4-ylcyclohexane-1-carboxamide Chemical compound C1=NC(F)=CC(C(NC(=O)[C@H]2[C@@H](C[C@@H](CC2)N2CCOCC2)C=2C=CC(Br)=CC=2)C=2C=CC(Cl)=CC=2)=C1 ABJSOROVZZKJGI-OCYUSGCXSA-N 0.000 description 1
OWGJXSYVHQEVHS-UHFFFAOYSA-N 1-dichlorophosphorylethane Chemical compound CCP(Cl)(Cl)=O OWGJXSYVHQEVHS-UHFFFAOYSA-N 0.000 description 1
125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 1
FOGYNLXERPKEGN-UHFFFAOYSA-N 3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfopropyl)phenoxy]propane-1-sulfonic acid Chemical class COC1=CC=CC(CC(CS(O)(=O)=O)OC=2C(=CC(CCCS(O)(=O)=O)=CC=2)OC)=C1O FOGYNLXERPKEGN-UHFFFAOYSA-N 0.000 description 1
BCFOOQRXUXKJCL-UHFFFAOYSA-N 4-amino-4-oxo-2-sulfobutanoic acid Chemical class NC(=O)CC(C(O)=O)S(O)(=O)=O BCFOOQRXUXKJCL-UHFFFAOYSA-N 0.000 description 1
239000005995 Aluminium silicate Substances 0.000 description 1
MKDWKCOAGBJQKP-UHFFFAOYSA-N CC(C)(C)[S+]=P(C)(Cl)Cl Chemical compound CC(C)(C)[S+]=P(C)(Cl)Cl MKDWKCOAGBJQKP-UHFFFAOYSA-N 0.000 description 1
XCZIGEQKFCRATM-UHFFFAOYSA-N CCP(Cl)(Cl)=[S+]C(C)(C)C Chemical compound CCP(Cl)(Cl)=[S+]C(C)(C)C XCZIGEQKFCRATM-UHFFFAOYSA-N 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
244000045232 Canavalia ensiformis Species 0.000 description 1
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 1
241000254173 Coleoptera Species 0.000 description 1
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
239000001692 EU approved anti-caking agent Substances 0.000 description 1
239000005909 Kieselgur Substances 0.000 description 1
241000255777 Lepidoptera Species 0.000 description 1
IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 1
235000010617 Phaseolus lunatus Nutrition 0.000 description 1
231100000674 Phytotoxicity Toxicity 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
238000010521 absorption reaction Methods 0.000 description 1
150000001242 acetic acid derivatives Chemical class 0.000 description 1
239000000443 aerosol Substances 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
150000003973 alkyl amines Chemical class 0.000 description 1
125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
125000004414 alkyl thio group Chemical group 0.000 description 1
235000012211 aluminium silicate Nutrition 0.000 description 1
150000003862 amino acid derivatives Chemical class 0.000 description 1
150000001449 anionic compounds Chemical class 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
229910000020 calcium bicarbonate Inorganic materials 0.000 description 1
229920005551 calcium lignosulfonate Polymers 0.000 description 1
235000011132 calcium sulphate Nutrition 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
VNWKTOKETHGBQD-AKLPVKDBSA-N carbane Chemical group [15CH4] VNWKTOKETHGBQD-AKLPVKDBSA-N 0.000 description 1
239000000969 carrier Substances 0.000 description 1
150000001767 cationic compounds Chemical class 0.000 description 1
239000007810 chemical reaction solvent Substances 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
239000004927 clay Substances 0.000 description 1
239000012141 concentrate Substances 0.000 description 1
239000007859 condensation product Substances 0.000 description 1
238000001816 cooling Methods 0.000 description 1
239000006184 cosolvent Substances 0.000 description 1
238000007865 diluting Methods 0.000 description 1
235000019329 dioctyl sodium sulphosuccinate Nutrition 0.000 description 1
YHAIUSTWZPMYGG-UHFFFAOYSA-L disodium;2,2-dioctyl-3-sulfobutanedioate Chemical compound [Na+].[Na+].CCCCCCCCC(C([O-])=O)(C(C([O-])=O)S(O)(=O)=O)CCCCCCCC YHAIUSTWZPMYGG-UHFFFAOYSA-L 0.000 description 1
229940071161 dodecylbenzenesulfonate Drugs 0.000 description 1
239000012259 ether extract Substances 0.000 description 1
150000002170 ethers Chemical class 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
238000001125 extrusion Methods 0.000 description 1
150000002191 fatty alcohols Chemical class 0.000 description 1
150000002193 fatty amides Chemical class 0.000 description 1
239000003337 fertilizer Substances 0.000 description 1
230000009969 flowable effect Effects 0.000 description 1
125000001153 fluoro group Chemical group F* 0.000 description 1
238000009472 formulation Methods 0.000 description 1
239000007789 gas Substances 0.000 description 1
239000000499 gel Substances 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
230000002363 herbicidal effect Effects 0.000 description 1
239000004009 herbicide Substances 0.000 description 1
239000003906 humectant Substances 0.000 description 1
MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 description 1
229910052622 kaolinite Inorganic materials 0.000 description 1
RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 1
QWDJLDTYWNBUKE-UHFFFAOYSA-L magnesium bicarbonate Chemical compound [Mg+2].OC([O-])=O.OC([O-])=O QWDJLDTYWNBUKE-UHFFFAOYSA-L 0.000 description 1
239000002370 magnesium bicarbonate Substances 0.000 description 1
229910000022 magnesium bicarbonate Inorganic materials 0.000 description 1
235000014824 magnesium bicarbonate Nutrition 0.000 description 1
239000000463 material Substances 0.000 description 1
239000008268 mayonnaise Substances 0.000 description 1
235000010746 mayonnaise Nutrition 0.000 description 1
229940100630 metacresol Drugs 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
235000010981 methylcellulose Nutrition 0.000 description 1
239000002480 mineral oil Substances 0.000 description 1
235000010446 mineral oil Nutrition 0.000 description 1
238000002156 mixing Methods 0.000 description 1
239000003607 modifier Substances 0.000 description 1
SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 1
239000003921 oil Substances 0.000 description 1
239000002245 particle Substances 0.000 description 1
230000035515 penetration Effects 0.000 description 1
239000000575 pesticide Substances 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
229940031826 phenolate Drugs 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
230000002265 prevention Effects 0.000 description 1
230000001737 promoting effect Effects 0.000 description 1
238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
238000004062 sedimentation Methods 0.000 description 1
239000003352 sequestering agent Substances 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
229910052814 silicon oxide Inorganic materials 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
229920005552 sodium lignosulfonate Polymers 0.000 description 1
FGDMJJQHQDFUCP-UHFFFAOYSA-M sodium;2-propan-2-ylnaphthalene-1-sulfonate Chemical compound [Na+].C1=CC=CC2=C(S([O-])(=O)=O)C(C(C)C)=CC=C21 FGDMJJQHQDFUCP-UHFFFAOYSA-M 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
238000010183 spectrum analysis Methods 0.000 description 1
210000002784 stomach Anatomy 0.000 description 1
150000003445 sucroses Chemical class 0.000 description 1
239000004546 suspension concentrate Substances 0.000 description 1
229920002994 synthetic fiber Polymers 0.000 description 1
WMXCDAVJEZZYLT-UHFFFAOYSA-N tert-butylthiol Chemical compound CC(C)(C)S WMXCDAVJEZZYLT-UHFFFAOYSA-N 0.000 description 1
CZDYPVPMEAXLPK-UHFFFAOYSA-N tetramethylsilane Chemical compound C[Si](C)(C)C CZDYPVPMEAXLPK-UHFFFAOYSA-N 0.000 description 1
239000002562 thickening agent Substances 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
239000008158 vegetable oil Substances 0.000 description 1
239000004563 wettable powder Substances 0.000 description 1
238000009736 wetting Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/28—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)]
- C07F9/42—Halides thereof
- C07F9/425—Acid or estermonohalides thereof, e.g. RP(=X)(YR)(Hal) (X, Y = O, S; R = H, or hydrocarbon group)
- 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
- A01N57/20—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-carbon bonds containing acyclic or cycloaliphatic radicals
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/18—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
- C07F9/4075—Esters with hydroxyalkyl compounds
- 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)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
General Health & Medical Sciences (AREA)
Biochemistry (AREA)
Molecular Biology (AREA)
Pest Control & Pesticides (AREA)
Agronomy & Crop Science (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)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Lubrication Details And Ventilation Of Internal Combustion Engines (AREA)

NL8105228A 1980-11-21 1981-11-18 O-alkyl- en o-aryl-s-(tert.alkyl)alkylfosfonothioaten, werkwijze ter bereiding ervan, alsmede hun toepassing als insecticiden en nematociden. NL8105228A (nl)

Applications Claiming Priority (6)

Application Number	Priority Date	Filing Date	Title
US20909380A	1980-11-21	1980-11-21
US20909480A	1980-11-21	1980-11-21
US20909480		1980-11-21
US20909380		1980-11-21
US22164280		1980-12-31
US06/221,642 US4391760A (en)	1980-12-31	1980-12-31	S-(Tertiary alkyl) alkylphosphonothioic halides

Publications (1)

Publication Number	Publication Date
NL8105228A true NL8105228A (nl)	1982-06-16

Family

ID=27395322

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NL8105228A NL8105228A (nl)	1980-11-21	1981-11-18	O-alkyl- en o-aryl-s-(tert.alkyl)alkylfosfonothioaten, werkwijze ter bereiding ervan, alsmede hun toepassing als insecticiden en nematociden.

Country Status (19)

Country	Link
AT (1)	AT380885B (da)
AU (1)	AU553581B2 (da)
BG (1)	BG36349A3 (da)
BR (1)	BR8107581A (da)
CA (1)	CA1224474A (da)
CH (2)	CH650002A5 (da)
DD (1)	DD202167A5 (da)
DE (1)	DE3146056A1 (da)
DK (1)	DK515181A (da)
ES (2)	ES507318A0 (da)
GB (2)	GB2087891B (da)
IL (1)	IL64186A0 (da)
IT (1)	IT1140285B (da)
LU (1)	LU83780A1 (da)
MA (1)	MA19336A1 (da)
NL (1)	NL8105228A (da)
OA (1)	OA06955A (da)
PH (2)	PH18262A (da)
RO (3)	RO85049B (da)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4472391A (en) *	1980-11-21	1984-09-18	Rhone-Poulenc Agrochimie	O-Aryl-s-(tertiary alkyl) alkylphosphonothioate insecticides and nematocides

1981
- 1981-11-02 IL IL64186A patent/IL64186A0/xx unknown
- 1981-11-18 NL NL8105228A patent/NL8105228A/nl not_active Application Discontinuation
- 1981-11-18 RO RO105809A patent/RO85049B/ro unknown
- 1981-11-18 RO RO114687A patent/RO90683B/ro unknown
- 1981-11-18 RO RO81114686A patent/RO87258A/ro unknown
- 1981-11-19 AU AU77631/81A patent/AU553581B2/en not_active Ceased
- 1981-11-19 GB GB8134877A patent/GB2087891B/en not_active Expired
- 1981-11-19 PH PH26514A patent/PH18262A/en unknown
- 1981-11-19 BG BG054210A patent/BG36349A3/xx unknown
- 1981-11-19 CA CA000390415A patent/CA1224474A/en not_active Expired
- 1981-11-20 CH CH7469/81A patent/CH650002A5/fr not_active IP Right Cessation
- 1981-11-20 AT AT0501181A patent/AT380885B/de not_active IP Right Cessation
- 1981-11-20 CH CH5245/84A patent/CH651575A5/fr not_active IP Right Cessation
- 1981-11-20 DE DE19813146056 patent/DE3146056A1/de not_active Withdrawn
- 1981-11-20 DK DK515181A patent/DK515181A/da not_active Application Discontinuation
- 1981-11-20 LU LU83780A patent/LU83780A1/fr unknown
- 1981-11-20 BR BR8107581A patent/BR8107581A/pt unknown
- 1981-11-20 ES ES507318A patent/ES507318A0/es active Granted
- 1981-11-20 DD DD81235018A patent/DD202167A5/de unknown
- 1981-11-20 MA MA19540A patent/MA19336A1/fr unknown
- 1981-11-20 IT IT25205/81A patent/IT1140285B/it active
- 1981-11-21 OA OA57551A patent/OA06955A/xx unknown
1982
- 1982-10-13 ES ES516464A patent/ES8400751A1/es not_active Expired
1983
- 1983-09-26 PH PH29595A patent/PH19084A/en unknown
- 1983-12-05 GB GB08332398A patent/GB2140808B/en not_active Expired

Also Published As

Publication number	Publication date
RO85049B (ro)	1984-09-30
PH19084A (en)	1985-12-19
RO87258B (ro)	1985-08-31
IL64186A0 (en)	1982-02-28
CH650002A5 (fr)	1985-06-28
ES8307831A1 (es)	1983-02-16
OA06955A (fr)	1983-07-31
RO87258A (ro)	1985-08-31
CA1224474A (en)	1987-07-21
ES516464A0 (es)	1983-11-01
AT380885B (de)	1986-07-25
GB2087891A (en)	1982-06-03
LU83780A1 (fr)	1983-09-01
GB2140808A (en)	1984-12-05
GB2087891B (en)	1985-02-06
IT1140285B (it)	1986-09-24
PH18262A (en)	1985-05-14
RO90683A (ro)	1987-01-30
ES8400751A1 (es)	1983-11-01
ES507318A0 (es)	1983-02-16
GB8332398D0 (en)	1984-01-11
DE3146056A1 (de)	1982-06-16
MA19336A1 (fr)	1982-07-01
GB2140808B (en)	1985-06-19
DD202167A5 (de)	1983-08-31
RO85049A (ro)	1984-08-17
IT8125205A0 (it)	1981-11-20
BG36349A3 (en)	1984-10-15
BR8107581A (pt)	1982-08-17
DK515181A (da)	1982-05-22
ATA501181A (de)	1985-12-15
RO90683B (ro)	1987-01-31
AU7763181A (en)	1982-05-27
CH651575A5 (fr)	1985-09-30
AU553581B2 (en)	1986-07-24

Legal Events

Date	Code	Title	Description
1985-01-01	A85	Still pending on 85-01-01
1989-01-02	BV	The patent application has lapsed

Publication	Publication Date	Title
JPH0623164B2 (ja)	1994-03-30	殺害虫剤としての作用を有するベンゾイル尿素化合物
JPH0676394B2 (ja)	1994-09-28	１、３―チアゾール誘導体、それらの製造方法および殺虫組成物
US3819755A (en)	1974-06-25	O,o-dialkyl-o-(4-trifluoromethylphenyl)-thionophosphoric acid esters
US2615037A (en)	1952-10-21	O,o-di(4-chlorophenyl) n-alkylamidothiophosphates
NL8105228A (nl)	1982-06-16	O-alkyl- en o-aryl-s-(tert.alkyl)alkylfosfonothioaten, werkwijze ter bereiding ervan, alsmede hun toepassing als insecticiden en nematociden.
CA1100991A (en)	1981-05-12	Esters
US3741968A (en)	1973-06-26	Certain o-(2-pyrimidyl) phosphates and their use as insecticides
US3992533A (en)	1976-11-16	O-ethyl-S-N-propyl-O-(2-chloro-4-bromophenyl)-thiophosphate
KR840001888B1 (ko)	1984-10-24	N-포스포닐카보닐-카바메이트의 제조방법
US4000314A (en)	1976-12-28	Pesticidal N-(2,2-dicyanovinyl)-N-benzyl-anilines
US3823235A (en)	1974-07-09	Certain o-(2-pyrimidyl)phosphates and their use as insecticides
FR2516517A1 (fr)	1983-05-20	Derives o-alcoyl et o-aryl s-(tertioalcoyle) alcoylphosphonothioates, leur preparation et leur application
GB1594261A (en)	1981-07-30	Benzyloxime ethers
EP0031689B1 (en)	1983-09-28	O-aryl-s-tertiary alkyl alkylphosphonodithioate insecticides and nematocides
US3982015A (en)	1976-09-21	N-propargyl-anilinomethylenemalodinitrile derivatives
IL45284A (en)	1977-01-31	Pyrazolinyl thiophosphates processes for the preparation thereof and insecticidal acaricidal and nematicidal compositions containing the same
US3114673A (en)	1963-12-17	Novel 2, 5-dimethyl-6-(dialkylaminoalkyl) phenyl methylcarbamates and compositions and method for controlling insects
DE2249462C3 (da)	1976-05-20
IL43144A (en)	1977-02-28	Thiophosphoric acid amide esters their preparation and their use in insecticidal acaricidal and nematicidal compositions
KR840000742B1 (ko)	1984-05-31	0-아릴-s-3차 알킬 알킬포스포노디티오에이트의제조 방법
HU191059B (en)	1986-12-28	Insecticide and ovicide compositions containing benzoyl-carbamide derivatives as active substances further process for preparing the active substances
US4428945A (en)	1984-01-31	O-Alkyl S-(tertiary alkyl) alkylphosphonothioate insecticides and nematocides
US3879412A (en)	1975-04-22	1-(4-Chlorophenyl)-5-methyl-3-(0,0-diethylthiono phosphoryl)-1,2,4-triazole
DE2249462B2 (da)	1975-10-16
HU185007B (en)	1984-11-28	Herbicide composition and process for preparing the active substances, n-trifluoro-acetyl-n-phospono-methyl-glycine esters