IL44641A - Phenoxyphenyl dialkyl esters of thiophosphoric and dithiophosphoric acids,their preparation and insecticidal and acaricidal compositions containing them - Google Patents
Phenoxyphenyl dialkyl esters of thiophosphoric and dithiophosphoric acids,their preparation and insecticidal and acaricidal compositions containing themInfo
- Publication number
- IL44641A IL44641A IL44641A IL4464174A IL44641A IL 44641 A IL44641 A IL 44641A IL 44641 A IL44641 A IL 44641A IL 4464174 A IL4464174 A IL 4464174A IL 44641 A IL44641 A IL 44641A
- Authority
- IL
- Israel
- Prior art keywords
- formula
- compound according
- parts
- compound
- active substance
- Prior art date
Links
- 239000000203 mixture Substances 0.000 title claims description 12
- -1 Phenoxyphenyl Chemical group 0.000 title description 5
- 230000000895 acaricidal effect Effects 0.000 title description 5
- 239000002253 acid Substances 0.000 title description 4
- 230000000749 insecticidal effect Effects 0.000 title description 4
- 238000002360 preparation method Methods 0.000 title description 4
- 150000007513 acids Chemical class 0.000 title description 2
- 150000002148 esters Chemical class 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 34
- 238000000034 method Methods 0.000 claims description 8
- 239000007787 solid Substances 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 5
- 239000001257 hydrogen Substances 0.000 claims description 5
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 239000007788 liquid Substances 0.000 claims description 4
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 4
- 230000000361 pesticidal effect Effects 0.000 claims description 4
- 241000238876 Acari Species 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 3
- 241000607479 Yersinia pestis Species 0.000 claims description 3
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 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 3
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 229910052760 oxygen Inorganic materials 0.000 claims description 3
- 239000001301 oxygen Substances 0.000 claims description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
- 239000000460 chlorine Substances 0.000 claims description 2
- 229910052801 chlorine Inorganic materials 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims description 2
- 239000004480 active ingredient Substances 0.000 claims 3
- 239000004606 Fillers/Extenders Substances 0.000 claims 2
- 239000004094 surface-active agent Substances 0.000 claims 2
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims 1
- 241000500891 Insecta Species 0.000 claims 1
- 239000013543 active substance Substances 0.000 description 27
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 17
- 239000008187 granular material Substances 0.000 description 8
- 239000000839 emulsion Substances 0.000 description 7
- 239000000126 substance 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
- 239000005995 Aluminium silicate Substances 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 241000196324 Embryophyta Species 0.000 description 6
- 235000012211 aluminium silicate Nutrition 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 5
- 239000002904 solvent Substances 0.000 description 5
- 239000007921 spray Substances 0.000 description 5
- 239000000654 additive Substances 0.000 description 4
- 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 4
- 239000000969 carrier Substances 0.000 description 4
- 239000004495 emulsifiable concentrate Substances 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000002689 soil 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
- 229920000742 Cotton Polymers 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
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- 244000046052 Phaseolus vulgaris Species 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 244000061456 Solanum tuberosum Species 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 235000019993 champagne Nutrition 0.000 description 3
- 229920000151 polyglycol Polymers 0.000 description 3
- 239000010695 polyglycol Substances 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
- ZSBDGXGICLIJGD-UHFFFAOYSA-N 4-phenoxyphenol Chemical compound C1=CC(O)=CC=C1OC1=CC=CC=C1 ZSBDGXGICLIJGD-UHFFFAOYSA-N 0.000 description 2
- 241001124076 Aphididae Species 0.000 description 2
- 241001425390 Aphis fabae Species 0.000 description 2
- 241000902805 Aulacophora Species 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 206010061217 Infestation Diseases 0.000 description 2
- 241000258916 Leptinotarsa decemlineata 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
- 241000238680 Rhipicephalus microplus 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
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 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
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 235000013601 eggs Nutrition 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 2
- 229920005610 lignin Polymers 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
- 239000004033 plastic Substances 0.000 description 2
- 229920003023 plastic Polymers 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 2
- 235000012239 silicon dioxide Nutrition 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- 230000009885 systemic effect Effects 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
- 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
- 241000132121 Acaridae Species 0.000 description 1
- 241000254032 Acrididae Species 0.000 description 1
- 241000238888 Argasidae 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
- 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
- KXDHJXZQYSOELW-UHFFFAOYSA-N Carbamic acid Chemical class NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 241001414835 Cimicidae Species 0.000 description 1
- 241000255749 Coccinellidae Species 0.000 description 1
- 240000001980 Cucurbita pepo Species 0.000 description 1
- 235000009804 Cucurbita pepo subsp pepo Nutrition 0.000 description 1
- 241000256113 Culicidae Species 0.000 description 1
- 241001481702 Dermanyssidae Species 0.000 description 1
- 241000131287 Dermestidae Species 0.000 description 1
- 241001414830 Diaspididae Species 0.000 description 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
- PNKUSGQVOMIXLU-UHFFFAOYSA-N Formamidine Chemical class NC=N PNKUSGQVOMIXLU-UHFFFAOYSA-N 0.000 description 1
- 241000219146 Gossypium Species 0.000 description 1
- 240000002024 Gossypium herbaceum Species 0.000 description 1
- 235000004341 Gossypium herbaceum Nutrition 0.000 description 1
- 241000238816 Gryllidae Species 0.000 description 1
- 241001243087 Gryllotalpidae Species 0.000 description 1
- 241000256257 Heliothis Species 0.000 description 1
- 241000256244 Heliothis virescens Species 0.000 description 1
- 241000238631 Hexapoda Species 0.000 description 1
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 1
- 241000238889 Ixodidae Species 0.000 description 1
- 241001124557 Lymantriidae Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 241000257226 Muscidae Species 0.000 description 1
- 241000256259 Noctuidae Species 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 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
- 241001124072 Reduviidae 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
- 239000005864 Sulphur Chemical group 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
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 1
- 241000219873 Vicia Species 0.000 description 1
- 239000000642 acaricide Substances 0.000 description 1
- 239000000370 acceptor Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 150000001338 aliphatic hydrocarbons 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
- PZZYQPZGQPZBDN-UHFFFAOYSA-N aluminium silicate Chemical compound O=[Al]O[Si](=O)O[Al]=O PZZYQPZGQPZBDN-UHFFFAOYSA-N 0.000 description 1
- 229910000323 aluminium silicate Inorganic materials 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 235000013877 carbamide Nutrition 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 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
- 239000002361 compost Substances 0.000 description 1
- ORTQZVOHEJQUHG-UHFFFAOYSA-L copper(II) chloride Chemical compound Cl[Cu]Cl ORTQZVOHEJQUHG-UHFFFAOYSA-L 0.000 description 1
- 238000000151 deposition Methods 0.000 description 1
- FHIVAFMUCKRCQO-UHFFFAOYSA-N diazinon Chemical compound CCOP(=S)(OCC)OC1=CC(C)=NC(C(C)C)=N1 FHIVAFMUCKRCQO-UHFFFAOYSA-N 0.000 description 1
- 229960001760 dimethyl sulfoxide Drugs 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
- 239000000428 dust Substances 0.000 description 1
- 235000005489 dwarf bean Nutrition 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
- 150000007529 inorganic bases Chemical class 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
- 150000002576 ketones Chemical class 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
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 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
- 230000007935 neutral effect Effects 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- RBXVOQPAMPBADW-UHFFFAOYSA-N nitrous acid;phenol Chemical class ON=O.OC1=CC=CC=C1 RBXVOQPAMPBADW-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 239000012074 organic phase Substances 0.000 description 1
- 150000002903 organophosphorus compounds Chemical class 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000012071 phase Substances 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
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007858 starting material Substances 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
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000000080 wetting agent Substances 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
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/12—Esters of phosphoric acids with hydroxyaryl compounds
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/16—Esters of thiophosphoric acids or thiophosphorous acids
- C07F9/165—Esters of thiophosphoric acids
- C07F9/18—Esters of thiophosphoric acids with hydroxyaryl compounds
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth 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)
Description
AJ' The present invention provides phenoxyphenyl dialkyl esters of thiophosphoric and dithiophosphoric acids, processes for their manufacture, pesticidal compositions containing them and a method of using them in pest control.
The compounds of the present invention have the formula wherein R1 represents an alkyl group having from 3 to 7 carbon atoms , R2 represents an ethyl group ^3* ^4» ^5 anc ^ independently of one another represent a hydrogen or halogen atom or a nitro group and X represents an oxygen or sulphur atom.
The alkyl groups represented by R1 can be straight-chain or branched. Examples of such groups include: n-butyl, iso-butyl, sec. butyl and tert. butyl, n-pentyl, n-hexyl, n-heptyl and isomers thereof.
Preferred compounds on account of their action are those of the formula I wherein R1 represents n-propyl, sec. butyl, n-pentyl or n-heptyl, represents ethyl, R-j, R^, R^ and R^ each represents hydrogen, chlorine, bromine and/or nitro, and X represents oxygen or sulphur.
The compounds of the formula I can be manufactured by the following methods which are known per se: K ' (Illb) the formulae II to IV, the symbols R. to R,. and X 1 b have the same meanings as for the formula I and Me re- i^' presents an alkali metal, in particular sodium or potassium, or represents the group (R)<-jJlH, wherein R represents hydrogen or alkyl with 1 to 4 carbon atoms.
Suitable acid acceptors are: tertiary amines, e.g. trialkyl- amines, pyridine, dialkyl anilines; inorganic bases, e.g. hydrides, hydroxides, carbonates and bicarbonates of alkali metals and alkaline earth metals.. It is sometimes necessary to use catalysts in the reactions, e.g. copper or copper chloride.
Processes la, lb and 2 are carried out at a reaction temperature between -2°C and +130°C, at normal pressure, and in solvents or diluents.
Examples suitable solvents or diluents are: ethers and ethereal compounds, e.g. diethyl ether, dipropyl ether, dioxan, tetra- hydrofuran; amides, e.g. Ν,Ν-dialkylated carboxy amides; aliphatic, aromatic and halogenated hydrocarbons, in particular benzene, toluene, xylene, chloroform, chlorobenzene ; nitriles, e.g. acetonitrile ; dimethyl sulphoxide, ketones, e.g. acetone, methyl ethyl ketone; water.
The starting materials of the formulae II, III, IV and V are known and can be manufactured in analogous manner to known methods.
\. The compounds of the formula I exhibit a broad biocidal activity and can be used for the control of a variety of plant and animal pests.
In particular they are suitable for combating insects of the families: Acrididae, Blattidae, Gryllidae, Gry llotalpidae , Tettigoni- idae, Cimicidae, P^fyrrhocoridae , Reduviidae, Aphididae, Delphacddae, Diaspididae, Pseudococc idae , Chrysomelisae , Coccinellidae , Bruchidae, Scarabaeidae , Dermestidae, Tene-brionidae, Curulionidae , Tineidae, Noctuidae, Lymantriidae , Pyralidae, Galleridae, Culicidae, Tipulidae, Stomoxydae, Muscidae, Calliphoridae , Trypetidae, Pulicidae as well as Acaridae of the families: Ixodidae, Argasidae, Tetranchidae , Dermany ssidae .
By addition of other, indecticides and/or acaricides it is possible to improve substantially the insecticidal or acaricidal action and to adapt it to given circumstances.
Examples of suitable additives are: organic phosphorus compounds, nitrophenols and derivatives thereof; formamidines ; ureas; carbamates and chlorinated hydrocarbons.- - The compounds of the formula I may be used as pure active substance or together with suitable carriers and/or additives. Suitable carriers and additives can be solid or liquid and correspond to the substances conventionally used in formulation technology, for example natural or regenerated substances, solvents, dispersants, wetting agents adhesives, thickeners, binders and/or fertilisers.
For application, the compounds of the formula I may be processed to dusts, emulsion concentrates, granules,. dispersions, sprays, to solutions or suspensions, in the conventional formulation which is commonly employed in application technology. Mention is also to be made of cattle dips and spray races, in which aqueous preparations are used .
The agents according to the invention are manufactur in known manner by intimately mixing and/or grinding active substances of the formula I .with the suitable carriers, optionally with the addition of dispersants or solvents which are. inert towards the active substances. The active . substances can take, and be used in, the following forms: Solid forms: , ''. dusts, tracking agents, granules, coated granules, impregnated granules and homogeneous granules. 1 Liquid forms: a) active substances which are dispersible in water: v?ettable powders, pasts, emulsions: b) solutions .
The content of active substance in the above described agents is between 0.1% to 95%, in which connection it should be mentioned that, in the case of application from aircraft or some. other suitable means of application, it is possible to use concentrations of up to 99.5% or even pure active substance.
The active substances of the formula I can, for example, be formulated as follows: Dusts The following substances are used to manufacture a) a 5% and b) a 2% dust: '" · a) 5 parts of active substance . 95 parts of talcum b) 2 parts of active substance 1 part of highly disperse silicic acid 97 parts of talcum.
The active substances are mixed with the carriers and ground.
Granules - The following substances are used to produce 5% granules : 5 parts of active substance, 0.25 parts of epichlorohydrin, . 0.25 parts of cetyl polyglycol ether, 3.50 parts of polyethylene glycol, 91 parts of kaolin (particle size 0.3-0.8 ram).
The active substance is mixed with epichlorohydrin and dissolved with 6 parts of acetone; the polyethylene glycol and cetyl polyglycol ether are then added. The resulting solution is sprayed on kaolin, . and the acetone is subsequently evaporated in vacuo. lettable powder: The following constituents are used for the preparation of a) a 40%, b) and c) a 25%, and d) a 10% vettable powder: a) 40 parts of active substance, 5 . parts of sodium lignin sulphonate, 1 part of sodium dibutylrnaphthalene sulphonate, 54.. parts of silicic . acid . b) 25 parts of active substance, 4.5 parts of calcium lignin sulphonate, 1.9 parts of Champagne chalk/hydroxyethyl cellulose mixture (1:1), 1.5 parts of sodium dibutyl naphthalene . sulphonate, 19.5 parts of silicic acid, 19.5 parts of Champagne chalk, 28.1 parts of kaolin. c) 25 parts of active substance, 2.5 parts of isooctylphenoxy-polyoxye thylene ethanol, 1.7 parts of Champagne chalk/hydroxyeth l cellulose mixture (1:1), 8.3 parts of sodiurn aluminium silicate, 16.6 parts of kieselguhr, 46 parts of kaolin. d) 10 parts of active substance, 3 parts of a mixture of the sodium salts of saturated fatt alcohol sulphates, 5 parts of naphthalenesulphonic acid/. formaldehyde condensate , 82 parts of kaolin.
The active substances are intimately mixed, in suitable mixers, with the additives, the mixture being then ground in the appropriate mills and rollers. ettable powders are obtained -which can be diluted with water to give. suspensions of any desired concentration.
Emulsifiable concentrates: The following substances are used to produce a) a 10% and b) a 25% emulsifiable concentrate: 10 parts of active substance, 3.4 parts of epoxidised vegetable oil, 13. parts of a combination emulsifier consistin of fatty alcohol polyglycol ether and alkyl aryl sulphonate calcium salt, 40 parts of dime hyIformamide , 43.2 parts of xylene, 25 parts of active substance, 2.5 parts of epoxidised vegetable oil, 10 parts of an alk larylsulphonate/fatty alcoholglycol ether mixture, . 5 par s of dimethylformamide , 57.5 parts of xylene.
From these concentrates it is possible to produce, by dilution with water, emulsions of any desired concentra tion..
Spray: ■ The following constituents are used to prepared a 57o spray: 5 parts of active substance, 1 part of epichlorohydrin, 94 parts of benzene (boiling limits 160°C-190°C) .
E X AM P L E 1 With stirring, 41 g of O-ethyl-S-n-propylthiolphosphoric chloride in 60 ml of diethyl ether is added dropwise so rapidl to a solution, cooled to 10°C, of 37 g of 4-hydroxydiphenyl ether and 22 g of trie hylamine in 500 ml of absolute diethyl ether that the temperature does not rise above 30°C. The reaction mixture is stirred for a further 2 hours at 20°-30°G and treated, with continued stirring, with 300 ml of ice wate ; The organic phase is isolated, shaken once with water and twice with ice cold 570 sodium hydroxide solution and then washed neutral with water.
The ethereal phase is treated with activated charcoal, filtered, dried, and the solvent is evaporated off. The oily residue is dried for 3 hours at 70°C and 0.1 Torr to yield the compound of the formula as a yellowish, non-distillable , viscous oil with a refraction 20° of η υ = 1.5524.
The following compounds are also manufactured in analogous manner: Example 2 A) Insecticidal ingest poison, action Cotton and potato plants were sprayed with a 0.05% aqueous emuls ion (obtained from a 10% emulsifiable concentrate).
After the coating had dried, the cotton plants, were popu- . lated with Spodoptera littoralis or Heliothis virescens larvae and the potato plants with Colorado potato bettle larvae (Leptinotarsa decemlineata) . The test was carried out at 24°C and 60% relative humidity. In the above test, the compounds according to Example 1 displayed good ingest poiso action against Spodoptera littoralis, Heliothis and Leptinotarsa decemlineata larvae.', B) System insecticide! action To determine the systemic action, rooted bean plants (Vicia . fabae) were put into a 0.01% aqueous active substance solution (obtained from a 10% emulsifiable concentrate) . After 24 hours, aphide (Aphis fabae) were placed on the parts of the plant above the soil. The aphids were protected from contact and gas action by means of a special device. The test was carried out at 24°C and 70°C relative humidity. In the above test, the compounds according to Example 1 have systemic action against Aphis fabae.
. Example 3 '■; Action against Chilo suppressalis Six rice plants at a time of the. variety Caloro were transplanted into plastic pots (diameter at the top = 17 cm) arid reared to a height of about 60 cm. Infestation with Chilo suppressalis larvae (L, : 3-4 mm long) took place 2 days after the active substance had been applied in granule form to the paddy water (rate of application: 8 kg of actiive substance per hectare) . Evaluation of the insecticidal action took place 10 days afte application of the granules The compounds according to Example 1 v?ere active in the above test against Chilo suppressalis.
EXAMPLE 4 Sterilised compost earth was homogeneously mixed v/ith a wettable powder containing 25^ of active substance so that there resulted a rate of application of 8 kg of active substance per hectare. ' ; Young zucchetti plants .(Cucumis pepo) were put into plastic pots with the treated soil (3 plants per potj diameter of pot = 7 cm). Each pot was infected immediately afterwards with 5 Aulacophora femoralis and Pachmoda or Chortophila larvae. The control was carried out. 8, 16 and 32 days after depositing the larvae.
At 80-lOOfc kill after the first control, a fresh infestation with 5 larvae each was carried out in the same soil sample with new zucchetti plants. If the activity v/as less than' 8o$ , the remaining larvae remained in the soil sample until the control immediately following. If on active substance at a rate of application of 8 kg/ha still effected a lOO^ kill, a further control with h and 2 kg of active substance per hectare was carried out.
In. the above test, the compounds according to Example ί displayed action .against Aulacophora femoralis, Pachmoda and Chortophila larvae.
EXAMPLE 5 Action against ticks A) Rhipicephalus bursa Five adult ticks and 50 tick larvae were counted into a glass tube and immersed for 1 to 2 minutes in 2 ml of a aqueous emulsion from an emulsion series each containing 100, 10, 1 or 0.1 ppm of test subs ance. The tube was then sealed with a standardised cotton wool', plug and placed on its head, so that the active substance emulsion could be absorbed b the cotton wool.
In the case of the adults evaluation took place after 2 weeks, and in that of the larvae after 2 days. Each test-was repeated twice.
B) Boophilus microplus (larvae) Tests were carried out in each ca^e with 20 OP-sensitive larvae using a dilution series analogous to that of test A. (The resistance refers to the tolerability of Diazinon) . The compounds according to Example 1 acted in these tests against adults and larvae of Rhipicephalus bursa and sensitive and OP-resistant larvae of Boophilus microplus.
EXAMPLE 6 Acaricidal action Phaseolus vulgaris (dwarf beans) have an infested piece of leaf from a mass culture of Tetranychus urticae placed on them 12 hours before the test for the acaricidal action. The mobile stages which have migrated are sprayed v?ith the emulsified test preparations front a chromatography atomiser so that the spray broth does not run off. The number of liv5.ng and dead larvae, adults and eggs are evaluated after 2 to 7 days under a stereoscopic microscope and the result expressed in percentages. During the "interim", the treated plants are kept in greenhouse compartments at 25°C.
The compounds according to Example 1.were active in the above test against eggs, larvae and adults of Tetranychus urticae.
Claims (3)
1. 44641-2 We claim: 1. A compound of the formula I wherein R-^ represents an alkyl group having from 3 to 7 carbon atoms , R-2 represents an ethyl group R^, R^, R^ and R^ independently of one another represent a hydrogen or halogen atom or a nitro group and X represents an oxygen or sulphur atom.
2. A compound according to claim 1 wherein represents an n-propyl, sec. butyl, n-pentyl or n-heptyl group .
3. A compound according to claim 2 wherein R, represents an n-propyl group. A compound according to any one of claims 1 to 3 wherein , R^ and R^ independently of one another represent a hydrogen, chlorine or bromine atom or a nitro group. The compound according to claim 4t of the formula 0 44641- The. compound according to claim 4 of the formula 0 The compound according to claim 4 of the formula 0 (n) The compound according to claim 4 of the formula ) The compound according to claim 4 of the formula (n) The compound according to claim . 4 of the formula ,(n)X The compound according to claim ,4 of the formula The compound according to claim 4 of the formula The compound according to claim ;4 of the formula The compound according to claim 4 of the formula The compound according to claim 4 of the formula O c,0 -O- SC5U\Hn) 44641-2 . ' solid pesticidal composition which comprises a compound as claimed in any one of claims 1 to 9 as active ingredient, a solid extender and optionally a surface active agent. A liquid pesticidal composition which · comprises a compound as claimed in any one of claims 1 -to 9 as active ingredient, a liquid diluent and a surface ac ive agent. A method of combatting pests of the class Insecta or of the order Acarina at a locus, which method comprises applying to the locus a compound as claimed in any one o claims 1 to 9. A method .according to claim 18 wherein the locus comprises growing crops or plants. 20. A solid pesticidal composition which comprises a compound as claimed in any one of claims IQ to 15 as active ingredient, a solid extender and optionally a surface active agent. 21
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH672173A CH575719A5 (en) | 1973-05-11 | 1973-05-11 | |
CH388474 | 1974-03-20 |
Publications (2)
Publication Number | Publication Date |
---|---|
IL44641A0 IL44641A0 (en) | 1974-06-30 |
IL44641A true IL44641A (en) | 1977-01-31 |
Family
ID=25694091
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
IL44641A IL44641A (en) | 1973-05-11 | 1974-04-15 | Phenoxyphenyl dialkyl esters of thiophosphoric and dithiophosphoric acids,their preparation and insecticidal and acaricidal compositions containing them |
Country Status (9)
Country | Link |
---|---|
JP (1) | JPS5013537A (en) |
AT (1) | AT326415B (en) |
CA (1) | CA1045149A (en) |
DD (1) | DD117802A5 (en) |
DE (1) | DE2422324C2 (en) |
FR (1) | FR2228784B1 (en) |
GB (1) | GB1451278A (en) |
IL (1) | IL44641A (en) |
NL (1) | NL179907C (en) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPH0737707U (en) * | 1993-10-19 | 1995-07-11 | 稔 竹内 | Tire slipper |
-
1974
- 1974-04-15 IL IL44641A patent/IL44641A/en unknown
- 1974-04-16 CA CA197,594A patent/CA1045149A/en not_active Expired
- 1974-04-26 NL NLAANVRAGE7405687,A patent/NL179907C/en not_active IP Right Cessation
- 1974-05-07 FR FR7415702A patent/FR2228784B1/fr not_active Expired
- 1974-05-08 DE DE2422324A patent/DE2422324C2/en not_active Expired
- 1974-05-09 DD DD178390A patent/DD117802A5/xx unknown
- 1974-05-10 JP JP49052133A patent/JPS5013537A/ja active Pending
- 1974-05-10 GB GB2084574A patent/GB1451278A/en not_active Expired
- 1974-05-10 AT AT389474A patent/AT326415B/en not_active IP Right Cessation
Also Published As
Publication number | Publication date |
---|---|
NL179907C (en) | 1986-12-01 |
DE2422324A1 (en) | 1974-11-21 |
FR2228784A1 (en) | 1974-12-06 |
DE2422324C2 (en) | 1984-05-03 |
DD117802A5 (en) | 1976-02-05 |
AT326415B (en) | 1975-12-10 |
FR2228784B1 (en) | 1976-12-17 |
IL44641A0 (en) | 1974-06-30 |
NL7405687A (en) | 1974-11-13 |
NL179907B (en) | 1986-07-01 |
GB1451278A (en) | 1976-09-29 |
CA1045149A (en) | 1978-12-26 |
ATA389474A (en) | 1975-02-15 |
JPS5013537A (en) | 1975-02-13 |
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