CA1048047A - Esters - Google Patents
EstersInfo
- Publication number
- CA1048047A CA1048047A CA162,024A CA162024A CA1048047A CA 1048047 A CA1048047 A CA 1048047A CA 162024 A CA162024 A CA 162024A CA 1048047 A CA1048047 A CA 1048047A
- Authority
- CA
- Canada
- Prior art keywords
- formula
- group
- compound according
- carbon atoms
- parts
- Prior art date
- 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
Links
- 150000002148 esters Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 36
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 14
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 13
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims abstract description 9
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims abstract description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 5
- 239000001257 hydrogen Substances 0.000 claims abstract description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 4
- 125000005843 halogen group Chemical group 0.000 claims abstract description 4
- 241000238876 Acari Species 0.000 claims description 7
- 239000000460 chlorine Substances 0.000 claims description 7
- 238000000034 method Methods 0.000 claims description 7
- -1 sec.-butyl Chemical group 0.000 claims description 7
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 241000238631 Hexapoda Species 0.000 claims description 3
- 241000607479 Yersinia pestis Species 0.000 claims description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 2
- 241000500891 Insecta Species 0.000 claims description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 2
- 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 2
- 125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 claims 1
- 230000000895 acaricidal effect Effects 0.000 abstract description 5
- 230000000749 insecticidal effect Effects 0.000 abstract description 3
- 239000013543 active substance Substances 0.000 description 26
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 13
- 239000008187 granular material Substances 0.000 description 8
- 239000000203 mixture Substances 0.000 description 8
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-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
- 239000000839 emulsion Substances 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 239000005995 Aluminium silicate Substances 0.000 description 5
- 235000012211 aluminium silicate Nutrition 0.000 description 5
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 239000007921 spray Substances 0.000 description 5
- 241000196324 Embryophyta Species 0.000 description 4
- 239000002253 acid 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
- 239000003795 chemical substances by application Substances 0.000 description 4
- 229920000151 polyglycol Polymers 0.000 description 4
- 239000010695 polyglycol Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- 241000902805 Aulacophora Species 0.000 description 3
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 3
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-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
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 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
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 235000019993 champagne Nutrition 0.000 description 3
- 235000013601 eggs Nutrition 0.000 description 3
- 239000000843 powder 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
- 239000002689 soil Substances 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- 241000426497 Chilo suppressalis Species 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 2
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 2
- 241000258916 Leptinotarsa decemlineata Species 0.000 description 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- 244000061176 Nicotiana tabacum Species 0.000 description 2
- 235000002637 Nicotiana tabacum Nutrition 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 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
- 241000238680 Rhipicephalus microplus Species 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- 244000061456 Solanum tuberosum Species 0.000 description 2
- 241000256248 Spodoptera Species 0.000 description 2
- 241001454293 Tetranychus urticae Species 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000011575 calcium Substances 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
- 239000004495 emulsifiable concentrate Substances 0.000 description 2
- 238000011156 evaluation Methods 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
- 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
- 239000007787 solid Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000000725 suspension Substances 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
- QASBCTGZKABPKX-UHFFFAOYSA-N 4-(methylsulfanyl)phenol Chemical compound CSC1=CC=C(O)C=C1 QASBCTGZKABPKX-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 241001124076 Aphididae 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
- 241000283690 Bos taurus Species 0.000 description 1
- 241000907223 Bruchinae Species 0.000 description 1
- 241001260012 Bursa Species 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
- 241001414835 Cimicidae Species 0.000 description 1
- 241000255749 Coccinellidae Species 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 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
- 241001466044 Delphacidae 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
- QMMFVYPAHWMCMS-UHFFFAOYSA-N Dimethyl sulfide Chemical compound CSC QMMFVYPAHWMCMS-UHFFFAOYSA-N 0.000 description 1
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 206010061217 Infestation Diseases 0.000 description 1
- 241000238889 Ixodidae Species 0.000 description 1
- 241000257226 Muscidae Species 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
- 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
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- 241000256250 Spodoptera littoralis Species 0.000 description 1
- 241000254107 Tenebrionidae Species 0.000 description 1
- 241000255588 Tephritidae Species 0.000 description 1
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 1
- 241000130767 Tineidae 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
- 150000001298 alcohols Chemical class 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 229940115440 aluminum sodium silicate Drugs 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 229940077464 ammonium ion Drugs 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 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
- 238000006243 chemical reaction Methods 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
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper 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
- 239000003085 diluting agent Substances 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
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 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
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 150000004678 hydrides Chemical class 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
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 239000011630 iodine Substances 0.000 description 1
- 229910052740 iodine Inorganic materials 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 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
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 230000000361 pesticidal effect Effects 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
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 102220024375 rs201069984 Human genes 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000429 sodium aluminium silicate Substances 0.000 description 1
- 235000012217 sodium aluminium silicate Nutrition 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 125000005270 trialkylamine group Chemical group 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 150000003738 xylenes Chemical class 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N57/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds
- A01N57/10—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds
- A01N57/14—Biocides, pest repellants or attractants, or plant growth regulators containing organic phosphorus compounds having phosphorus-to-oxygen bonds or phosphorus-to-sulfur bonds containing aromatic radicals
-
- 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
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Molecular Biology (AREA)
- Agronomy & Crop Science (AREA)
- Biochemistry (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)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Abstract
ABSTRACT OF THE DISCLOSURE
Compounds of the formula (I)
Compounds of the formula (I)
Description
`^ -The present invention relates to thiophosphoric acid phenyl esters having pesticidal properties.
According to the present invention there are provided Compounds of the formula (I) R 0\10 ~ R2 (I) wherein R represents a~me~hyl or ethyl group, Rl represents a C3-C5-alkyl group, R2 represents an alkylthiomethyl, alkylsulfinylmethyl or alkylsulfonylmethyl group having at most 5 carbon atoms in toto or a group of the formula -S(CH2)mCN~ -SO(CH2)mCN~ -S(CH2)mCl~ -SO(CH2)mCl, SCC13, SOCC13, S(CH2)mCOOR3, -SO(CH2)mCOOR3, ~S(CH2)mCON(R4)R5 or -SO(CH2)mCON~R4)R5 wherein R3 represents an alkyl group having at most 4 carbon atoms, R4 and R5 independently of one another represent~a hydrogen atom or an alkyl group having at most 4 carbon atoms and m represents the integer 1 or 2; and Xl ~nd X2 independently of one another represent a hydrogen or halogen atom or an alkyl group having at most 4 carbon atoms.
By halogen is meant fluorine, chlorine, bromine or iodine, in particular chlorine or bromine.
The alkyl groups and moieties within the definitions of Rl to R5 may be straight-chain or branched. Examples of such groups or moieties are as appropriate to the definitions: methyl, ethyl, propyl, isopropyl and n-~
i-, sec. and tert. butyl.
Rl in the compounds of formula I preferably represents an n-propyl, i-propyl, i-butyl, sec.-butyl, or n-pentyl group. Most preferably R repre-sents an ethyl group and ~ represents an n-propyl group.
Preferably R2 represents a group of the formula -SCH2CN3 -SOCH2C~ -SCH2Cl, SOCH2Cl, -SCC13, -SOCC13, -SCH2COOR3, -SOCH2COOR3, -SCH2CON \ or -SOCH2CON \ (wherein R3 represents a methyl or ethyl group and R4 and ~5 independently of one another represent a hydrogen atom or methyl group); especially a group of the formula -SC}l2CN, -SCH2Cl, -scH2cooc2Hs~ or -ScH2co 2 R2 may also suitably represent an alkylthiomethyl, alkylsulphinyl-methyl or alkylsulphonylmethyl group containing at most 4 carbon atoms in the said alkyl moiety; preferably a methylthiometh~l, methylsulphinylmethyl or methylsulphonyl~et~yl group.
Preferably X, and X2 each represents a chlorine or bromine atom or a methyl group.
The compounds of formula I can be manufactured by the following processes which are analogous to those known in the art;
la) RO O R
> p _ Cl + HO ~ 2 acid binding 1 ~ ~1 agent (II) X2 (III) lb) R ~ O ~ ~eO ~ 1 -D
RlS X
(II~ (IV) ~8~7
According to the present invention there are provided Compounds of the formula (I) R 0\10 ~ R2 (I) wherein R represents a~me~hyl or ethyl group, Rl represents a C3-C5-alkyl group, R2 represents an alkylthiomethyl, alkylsulfinylmethyl or alkylsulfonylmethyl group having at most 5 carbon atoms in toto or a group of the formula -S(CH2)mCN~ -SO(CH2)mCN~ -S(CH2)mCl~ -SO(CH2)mCl, SCC13, SOCC13, S(CH2)mCOOR3, -SO(CH2)mCOOR3, ~S(CH2)mCON(R4)R5 or -SO(CH2)mCON~R4)R5 wherein R3 represents an alkyl group having at most 4 carbon atoms, R4 and R5 independently of one another represent~a hydrogen atom or an alkyl group having at most 4 carbon atoms and m represents the integer 1 or 2; and Xl ~nd X2 independently of one another represent a hydrogen or halogen atom or an alkyl group having at most 4 carbon atoms.
By halogen is meant fluorine, chlorine, bromine or iodine, in particular chlorine or bromine.
The alkyl groups and moieties within the definitions of Rl to R5 may be straight-chain or branched. Examples of such groups or moieties are as appropriate to the definitions: methyl, ethyl, propyl, isopropyl and n-~
i-, sec. and tert. butyl.
Rl in the compounds of formula I preferably represents an n-propyl, i-propyl, i-butyl, sec.-butyl, or n-pentyl group. Most preferably R repre-sents an ethyl group and ~ represents an n-propyl group.
Preferably R2 represents a group of the formula -SCH2CN3 -SOCH2C~ -SCH2Cl, SOCH2Cl, -SCC13, -SOCC13, -SCH2COOR3, -SOCH2COOR3, -SCH2CON \ or -SOCH2CON \ (wherein R3 represents a methyl or ethyl group and R4 and ~5 independently of one another represent a hydrogen atom or methyl group); especially a group of the formula -SC}l2CN, -SCH2Cl, -scH2cooc2Hs~ or -ScH2co 2 R2 may also suitably represent an alkylthiomethyl, alkylsulphinyl-methyl or alkylsulphonylmethyl group containing at most 4 carbon atoms in the said alkyl moiety; preferably a methylthiometh~l, methylsulphinylmethyl or methylsulphonyl~et~yl group.
Preferably X, and X2 each represents a chlorine or bromine atom or a methyl group.
The compounds of formula I can be manufactured by the following processes which are analogous to those known in the art;
la) RO O R
> p _ Cl + HO ~ 2 acid binding 1 ~ ~1 agent (II) X2 (III) lb) R ~ O ~ ~eO ~ 1 -D
RlS X
(II~ (IV) ~8~7
2) \ P-Cl -~ H0 ~ acid binding \ ~ ~ R2 (V) x2 (VI) (X)n R0 0 acid binding \!1_o /9~R2 -~ HSR
/ ~\ ~ (VII) agent Cl ~
(VI) X2 (VIII) 10R0 > S ~ ( 3)3 (X) R30C~--SMe S (XI) ~ ~Hal or >
MeSR3 ~(XII) (XIV) or Me2S l(XIII) In the formulae II to XIV, R, Rl, R2, Xl and ~2 have the meanings given for the formula I, Me represents an alkali metal ( in particular sodium or potassium~ or ammonium or alkyl-ammoniumion~ R3 represents hydrogen or alkyl with 1 to 4 carbon atoms and Hal represents a halogen atom, such as chlorine, bromine or iodine.
Suitable acid binding agents are: tertiary amines, e.g.
trialkylamines, pyridine, dialkylanilines; inorganic bases, such as hydrides, hydroxides; carbonates and bicarbonates of alkali and alkaline earth metals.
During the reactions it is sometimes necessary to use a catalyst~ for example copper or copper chloride. Processes 1~ 2, and 3 can be carried out at normal pressure and in solvents or diluentsO
~4~ L7 EXamples of suitable solvents or diluents are: ether and ethereal compounds, such as diethyl ether, dipropyl ether, dioxan, tetra~
hydrofuran; amides, such as N,N-dialkylated carboxylic acid amides; aliphaticg aromatic and halogenated hydrocarbons, in particular benæene, toluene, xylenes, chloroform, chlorobenzene3 nitriles, such as acetonitrile; dimethyl sulphoxide; alcohols, such as ethanol and ketones~ such as acetone, ethyl methyl ketone, water.
The starting materials of the formulae, II~ III, IV, V and IX
are known or may be manufactured in analogous manner to known methods, e.g.
those described in German Auslegeschriften 1051863, 1063177, 1088980 or i298990.
The active substances of the formula I are suitable for combatting pests of the class Insecta or of the order Acarina. Thus the compounds of formula I surprisingly have markedly better action against all development stages, e.gO eggs~ larvae, pupae, nymphs and adults, of insects and repre-sentatives of the order Acarina, such as mites andticks than e.g. analogous compounds of German patent 1138041. Thus the compounds of the formula I can be used against insects of the families:
Tetti~oniidae Tenebrionidae 5~ Chrysomel_ ae E~ Bruchidae BIattidae Tineidae Reduviidae Noctindae Pyrrhocoridae Lymatriida Cimicidae Pyralidae Delphacidae Culicidae Aphididae ~
Diaspididae Stomoxydae PseudocQccidae Trypetidae Scarabaeldae Muscidae Dermestidae Calliphoridae and Coccinellidae Pulicidae Acarida of the families:
Ixodidae Argasidae and Dermanyssidae.
The insecticidal a~d/or acaricidal action can be substantially broadened and adapted to suit the particular circumstances by the addition of other insecticides and/or acaricides.
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 convention-ally used in formulation technique~such, for example, as 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 inîthe conventional formulation which is commonly employed in application technology. Mention may also be made of cattle dips and spray races, in which aqueous preparations are used.
The agents according to the invention are manufactured 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 may take, and be used in the following forms:
Solid forms:
Dusts, tracking agents, granules~ coated granules, impregnated granules and homogeneous granules.
Liquid forms:
a) active substances which are dispersible in water: wettable 8~
powders, pastes, emulsions;
b) solutions.
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 parts of taleum 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,
/ ~\ ~ (VII) agent Cl ~
(VI) X2 (VIII) 10R0 > S ~ ( 3)3 (X) R30C~--SMe S (XI) ~ ~Hal or >
MeSR3 ~(XII) (XIV) or Me2S l(XIII) In the formulae II to XIV, R, Rl, R2, Xl and ~2 have the meanings given for the formula I, Me represents an alkali metal ( in particular sodium or potassium~ or ammonium or alkyl-ammoniumion~ R3 represents hydrogen or alkyl with 1 to 4 carbon atoms and Hal represents a halogen atom, such as chlorine, bromine or iodine.
Suitable acid binding agents are: tertiary amines, e.g.
trialkylamines, pyridine, dialkylanilines; inorganic bases, such as hydrides, hydroxides; carbonates and bicarbonates of alkali and alkaline earth metals.
During the reactions it is sometimes necessary to use a catalyst~ for example copper or copper chloride. Processes 1~ 2, and 3 can be carried out at normal pressure and in solvents or diluentsO
~4~ L7 EXamples of suitable solvents or diluents are: ether and ethereal compounds, such as diethyl ether, dipropyl ether, dioxan, tetra~
hydrofuran; amides, such as N,N-dialkylated carboxylic acid amides; aliphaticg aromatic and halogenated hydrocarbons, in particular benæene, toluene, xylenes, chloroform, chlorobenzene3 nitriles, such as acetonitrile; dimethyl sulphoxide; alcohols, such as ethanol and ketones~ such as acetone, ethyl methyl ketone, water.
The starting materials of the formulae, II~ III, IV, V and IX
are known or may be manufactured in analogous manner to known methods, e.g.
those described in German Auslegeschriften 1051863, 1063177, 1088980 or i298990.
The active substances of the formula I are suitable for combatting pests of the class Insecta or of the order Acarina. Thus the compounds of formula I surprisingly have markedly better action against all development stages, e.gO eggs~ larvae, pupae, nymphs and adults, of insects and repre-sentatives of the order Acarina, such as mites andticks than e.g. analogous compounds of German patent 1138041. Thus the compounds of the formula I can be used against insects of the families:
Tetti~oniidae Tenebrionidae 5~ Chrysomel_ ae E~ Bruchidae BIattidae Tineidae Reduviidae Noctindae Pyrrhocoridae Lymatriida Cimicidae Pyralidae Delphacidae Culicidae Aphididae ~
Diaspididae Stomoxydae PseudocQccidae Trypetidae Scarabaeldae Muscidae Dermestidae Calliphoridae and Coccinellidae Pulicidae Acarida of the families:
Ixodidae Argasidae and Dermanyssidae.
The insecticidal a~d/or acaricidal action can be substantially broadened and adapted to suit the particular circumstances by the addition of other insecticides and/or acaricides.
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 convention-ally used in formulation technique~such, for example, as 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 inîthe conventional formulation which is commonly employed in application technology. Mention may also be made of cattle dips and spray races, in which aqueous preparations are used.
The agents according to the invention are manufactured 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 may take, and be used in the following forms:
Solid forms:
Dusts, tracking agents, granules~ coated granules, impregnated granules and homogeneous granules.
Liquid forms:
a) active substances which are dispersible in water: wettable 8~
powders, pastes, emulsions;
b) solutions.
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 parts of taleum 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.~0 parts of polyethylene glycol, 91 parts of kaolin (particle si~e 0.3 - 0.8 mm).
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 thus obtained solution is sprayed on kaolin, and the acetone subsequently evaporated in vacuo.
~ettable powder:
The following constituents are used for the preparation of a) a 40%, b) and c) a 25%, and d3 a 10% wettable powder:
a) 40 parts of active substance, 5 parts of sodium lignin sulphonate, ~4~ 7 1 part of sodium dibutyl~naphthalene sulphonate, 54 parts of silicic acid.
b) 25 parts of active substance,
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 thus obtained solution is sprayed on kaolin, and the acetone subsequently evaporated in vacuo.
~ettable powder:
The following constituents are used for the preparation of a) a 40%, b) and c) a 25%, and d3 a 10% wettable powder:
a) 40 parts of active substance, 5 parts of sodium lignin sulphonate, ~4~ 7 1 part of sodium dibutyl~naphthalene 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 mix~ure (1:1), 1.5 parts of sodium dibutyl naphthalene sulphonate, 19.5 parts of silicic acid, 19.5 parts of Champagne chalkg 28.1 parts of kaolin.
c) 25 parts of active substance, 2.5 parts of isooctylphenoxy-polyoxyethylene-ethanol, 1.7 parts of Champagne chalk/hydroxyethyl cellulose mixture (1:1), 8.3 parts of sodium aluminium silicate, 16.5 parts of kieselguhr, 46 parts of kaolin.
d) 10 parts of active substance, 3 parts of a mixture of the sodi~ salts of saturated fatty alcohol sulphates,
c) 25 parts of active substance, 2.5 parts of isooctylphenoxy-polyoxyethylene-ethanol, 1.7 parts of Champagne chalk/hydroxyethyl cellulose mixture (1:1), 8.3 parts of sodium aluminium silicate, 16.5 parts of kieselguhr, 46 parts of kaolin.
d) 10 parts of active substance, 3 parts of a mixture of the sodi~ salts of saturated fatty alcohol sulphates,
5 ~cparts of naphthalenesulphonic acid/formaldehyde condensate, 82 parts o~ kaolin.
The active substances are intimately mixed, in suitable mixers, with the additives, the mixture being then ground in the appropriate mills and rollers. Wettable powders are obtained which can be diluted with water to give suspensions of an~ desired concentration.
~sifiable concentrates^
The following substances are used to produce a) a 10% and b) a 25% emulsifiable concentrate:
a) 10 parts of active substance, 3.4 parts of epoxidised vegetable oil, ~L~4~7 3.4 parts of a combination emulsifier consisting of fatty alcohol polyglycol ether and alkylarylsulphonate calcium saltg parts of dimethylformamide, 43~2 parts of xylene.
b) 25 parts of active substance, 2.5 parts of epoxidised vegetable oil, parts of an alkylarylsulphonate/fatty alcohol-polyglycol ether mixture, parts of dimethylformamide, 5?~5 parts of xylene.
From these concentrates it is possible to produce, by dilution with water, emulsions of any desired concentration.
Spray:
~
The following constituents are used to prepare a 5% spray:
5 parts of active substance, 1 part of epichlorohydrin~
94 parts of benzine (boiling limits 160 - l90 C).
Example 1 0-ethyl-5-n-propyl-0-(4-methylmerca~to-phenyl~-thiophosph_te 12.2 g of triethylamine are added to a solution of 16.8 g of 4-methyl-mercapto-phenol in 150 ml of benzene. While stirring constantly, 24.4 g of thiophosphoric-0-ethyl-S-n-propyl-ester chloride are added drop-wise at 10 - 15 C0 Stirring is then continued for 12 hours at room temper-ature. The mixture is washed with water, 3% sodium carbonate solution, and again with waterg then dried over anhydrous sodium sulphate. The benzene is distilled off and the residu0 is purified by molecular distillation, to give 27 g of the compound of the formula ~48(~7 2 5\ ~
(n~c3H7s s~3 with a melting point of 125 C/O.OOl Torr; n D = 1.5501. The following compounds are also manufactured in analogous manner:
R S >
The active substances are intimately mixed, in suitable mixers, with the additives, the mixture being then ground in the appropriate mills and rollers. Wettable powders are obtained which can be diluted with water to give suspensions of an~ desired concentration.
~sifiable concentrates^
The following substances are used to produce a) a 10% and b) a 25% emulsifiable concentrate:
a) 10 parts of active substance, 3.4 parts of epoxidised vegetable oil, ~L~4~7 3.4 parts of a combination emulsifier consisting of fatty alcohol polyglycol ether and alkylarylsulphonate calcium saltg parts of dimethylformamide, 43~2 parts of xylene.
b) 25 parts of active substance, 2.5 parts of epoxidised vegetable oil, parts of an alkylarylsulphonate/fatty alcohol-polyglycol ether mixture, parts of dimethylformamide, 5?~5 parts of xylene.
From these concentrates it is possible to produce, by dilution with water, emulsions of any desired concentration.
Spray:
~
The following constituents are used to prepare a 5% spray:
5 parts of active substance, 1 part of epichlorohydrin~
94 parts of benzine (boiling limits 160 - l90 C).
Example 1 0-ethyl-5-n-propyl-0-(4-methylmerca~to-phenyl~-thiophosph_te 12.2 g of triethylamine are added to a solution of 16.8 g of 4-methyl-mercapto-phenol in 150 ml of benzene. While stirring constantly, 24.4 g of thiophosphoric-0-ethyl-S-n-propyl-ester chloride are added drop-wise at 10 - 15 C0 Stirring is then continued for 12 hours at room temper-ature. The mixture is washed with water, 3% sodium carbonate solution, and again with waterg then dried over anhydrous sodium sulphate. The benzene is distilled off and the residu0 is purified by molecular distillation, to give 27 g of the compound of the formula ~48(~7 2 5\ ~
(n~c3H7s s~3 with a melting point of 125 C/O.OOl Torr; n D = 1.5501. The following compounds are also manufactured in analogous manner:
R S >
6 5 ~9L8~D~7 _ . .
~d u~
~1 ~1 ~1 ~ 11 11 11 R c~
D p~ X ~
..
n . . , _ ~t V ~ ~
~ I ~ X
. _ r~
.
V ~Q V
~ C~ ~ C`~ ~`;i ., ,~
r~
~:~ 3 .
U~
0:;
_ _ _ ~_ -~4~3~47 . ~ _ .. = .. ,..... ...
.
,~ o u~
U~
R C~f~ C`15 fl C`
. __ . _ _ ~D ~
. ., . . , _ I
U~ ~ X ~ C
_ I
~ ~ 0 ~ ~
V
.
~ ~ ~T~ V ~ ~ ~
. . _ ..
C~ ~ ~ X ~q X P~
.
~; ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~
~ V ~
,,,, ,.,,,,,, . ~ . . _ _ . . ..
X :: ~ X
~; ~ ,~ V~ y~ V~ ,~ V~ y~ y~
3~41~47 ., ___ R
. .__ ~ . . . . _ ,.
~9 ~ X ~: X
U~ ~ C X
. .. ... . , _____ .
~ c~ c~ c~ ~1 ~ C`l C~ ~ ~
I X ~ ~ ~ O
~ ~ a a ~ ~ ~
~ .
~ O
. . . . ... ..
~ I d _I ~ ~ ~ ~ ~ ``~
~; ~ X ~ ~ !r ~ C ~ X~ ~-2z ~ ~ ~ ol~ ~ o Example 2 Insecticidal ingest ~oison action Tobacco and potato plants were sprayed with a 0.05% aqueous emwl-sion (obtained from a 10% emulsifiable concentrate).
A~ter the coating had dried, the tobacco plants were populated with Egyptian cotton leaf worms (Spodoptera literalis) and the potato plants with Colorado potatO beetle larvae (~eptinotarsa decemlineata). The test was carried out at 24 C and 60% relative humidity. In the above test, the ` compounds according tocExample I displayed ingest poison action against Spodoptera literalis and Leptinotarsa decemlineata.
Example 3 Six rice plants at a time of the variety Caloro were transplanted into plastic pots (diameter at the top = 17 cm) and reared to a height of about 60 cm~ I~nfestation with Chilo suppressalis larvae (Ll: 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 active substance per hectare). Evaluation of the insectieidal action took plaee 10 days after application of the granules.
The eompo~ds aceording to Example I were active in the above test against Chilo suppressalis.
ExamF~e 4 Aetion a~ st Aulacophora femoralis, Paehmoda and Chortophila larvae Sterilised eompost earth was homogeneously mixed with a wettable powder containing 25% of aetive substance so that there resulted a rate of application of ~ kg of active substance per hectar~.
Young zucchetti plants (Cucumis pepo) were put into plastic pots with the treated soil ~3 plants per pot; diameter of pot = 7 cm). Each pot was infeeted immediately after~ards with 5 Aulacophora femoralis and Pachmoda i9iV47 or Chortophila larvae. The control was carried out 4, 8, 16 and 32 days after depositing the larvae.
At 80 - 100% kill after the first control, a fresh infestation with 5 larvae each was carried out in the same soil sample with 3 new zucchetti plants. If the activity was less than 80%, the remaining larvae remained in the soil sample until the control immediately following. If an active sub-stance at a rate of application of 8 kg/ha~still effected a 100% kill7 a further control with 4 and 2 kg of active substance per hectare was carried out.
In the above test, the compounds according to Example I displayed action against Aulacophora femoralis, Pachmoda and Chortophila larvae.
Exam~e_5 ction ag_ nst ticks -~) Rhlcephalus burs Five adult ticks and 50 tick larvae were counted into a glass tube and immersed for l to 2 minutes in 2 ml of an aqueous emulsion from an emulsion series each containing lOO~ lO, l and~O.l ppm of test substance.
The tube was then sealed with a standardised cotton wool plug and placed on its head, so that the active substance emulsion could be adsorbed by the cotton wool.
In the oase 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 case with 20 OP-sensitive larvae using an an~logous dilution series as in the case of test A. (The resistance refers to the tolerability of Diazinon).
The compounds according to Example I acted in these tests against adults and larvae of Rhicephalus bursa and sensitive and OP-resistant larvae of Boophilus microplus.
Example 6 Acaracidal action Phaseolus vulgaris (dwarf beans) have an infested piece of leaf from a mass culture of Tetranychus urticae placed onthem 12 hours before the test for the acaricidal action. The mobile stages which have migrated are sprayed with the e~ulsified tes~ preparations from a chromatography a~omiser so that the spray broth does not run offO The number of living and dead larvae, adults and eggs are evaluated after 2 to 7 days under a stereoscopic microscope and the res~lt expressed in percentages. During the "interim", the treated plants are kept in gr0enhouse compartments at 25 C.
The compounds according to ~xample 1 were ac~ive in the above test against eggs, larvae and adults of Tetranychus urticae.
~d u~
~1 ~1 ~1 ~ 11 11 11 R c~
D p~ X ~
..
n . . , _ ~t V ~ ~
~ I ~ X
. _ r~
.
V ~Q V
~ C~ ~ C`~ ~`;i ., ,~
r~
~:~ 3 .
U~
0:;
_ _ _ ~_ -~4~3~47 . ~ _ .. = .. ,..... ...
.
,~ o u~
U~
R C~f~ C`15 fl C`
. __ . _ _ ~D ~
. ., . . , _ I
U~ ~ X ~ C
_ I
~ ~ 0 ~ ~
V
.
~ ~ ~T~ V ~ ~ ~
. . _ ..
C~ ~ ~ X ~q X P~
.
~; ~ ~ ~ ~ ~ ~ ~ ~ ~ ~ ~
~ V ~
,,,, ,.,,,,,, . ~ . . _ _ . . ..
X :: ~ X
~; ~ ,~ V~ y~ V~ ,~ V~ y~ y~
3~41~47 ., ___ R
. .__ ~ . . . . _ ,.
~9 ~ X ~: X
U~ ~ C X
. .. ... . , _____ .
~ c~ c~ c~ ~1 ~ C`l C~ ~ ~
I X ~ ~ ~ O
~ ~ a a ~ ~ ~
~ .
~ O
. . . . ... ..
~ I d _I ~ ~ ~ ~ ~ ``~
~; ~ X ~ ~ !r ~ C ~ X~ ~-2z ~ ~ ~ ol~ ~ o Example 2 Insecticidal ingest ~oison action Tobacco and potato plants were sprayed with a 0.05% aqueous emwl-sion (obtained from a 10% emulsifiable concentrate).
A~ter the coating had dried, the tobacco plants were populated with Egyptian cotton leaf worms (Spodoptera literalis) and the potato plants with Colorado potatO beetle larvae (~eptinotarsa decemlineata). The test was carried out at 24 C and 60% relative humidity. In the above test, the ` compounds according tocExample I displayed ingest poison action against Spodoptera literalis and Leptinotarsa decemlineata.
Example 3 Six rice plants at a time of the variety Caloro were transplanted into plastic pots (diameter at the top = 17 cm) and reared to a height of about 60 cm~ I~nfestation with Chilo suppressalis larvae (Ll: 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 active substance per hectare). Evaluation of the insectieidal action took plaee 10 days after application of the granules.
The eompo~ds aceording to Example I were active in the above test against Chilo suppressalis.
ExamF~e 4 Aetion a~ st Aulacophora femoralis, Paehmoda and Chortophila larvae Sterilised eompost earth was homogeneously mixed with a wettable powder containing 25% of aetive substance so that there resulted a rate of application of ~ kg of active substance per hectar~.
Young zucchetti plants (Cucumis pepo) were put into plastic pots with the treated soil ~3 plants per pot; diameter of pot = 7 cm). Each pot was infeeted immediately after~ards with 5 Aulacophora femoralis and Pachmoda i9iV47 or Chortophila larvae. The control was carried out 4, 8, 16 and 32 days after depositing the larvae.
At 80 - 100% kill after the first control, a fresh infestation with 5 larvae each was carried out in the same soil sample with 3 new zucchetti plants. If the activity was less than 80%, the remaining larvae remained in the soil sample until the control immediately following. If an active sub-stance at a rate of application of 8 kg/ha~still effected a 100% kill7 a further control with 4 and 2 kg of active substance per hectare was carried out.
In the above test, the compounds according to Example I displayed action against Aulacophora femoralis, Pachmoda and Chortophila larvae.
Exam~e_5 ction ag_ nst ticks -~) Rhlcephalus burs Five adult ticks and 50 tick larvae were counted into a glass tube and immersed for l to 2 minutes in 2 ml of an aqueous emulsion from an emulsion series each containing lOO~ lO, l and~O.l ppm of test substance.
The tube was then sealed with a standardised cotton wool plug and placed on its head, so that the active substance emulsion could be adsorbed by the cotton wool.
In the oase 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 case with 20 OP-sensitive larvae using an an~logous dilution series as in the case of test A. (The resistance refers to the tolerability of Diazinon).
The compounds according to Example I acted in these tests against adults and larvae of Rhicephalus bursa and sensitive and OP-resistant larvae of Boophilus microplus.
Example 6 Acaracidal action Phaseolus vulgaris (dwarf beans) have an infested piece of leaf from a mass culture of Tetranychus urticae placed onthem 12 hours before the test for the acaricidal action. The mobile stages which have migrated are sprayed with the e~ulsified tes~ preparations from a chromatography a~omiser so that the spray broth does not run offO The number of living and dead larvae, adults and eggs are evaluated after 2 to 7 days under a stereoscopic microscope and the res~lt expressed in percentages. During the "interim", the treated plants are kept in gr0enhouse compartments at 25 C.
The compounds according to ~xample 1 were ac~ive in the above test against eggs, larvae and adults of Tetranychus urticae.
Claims (22)
PROPERTY OR PRIVILEGE IS CLAIMED ARE DEFINED AS FOLLOWS:
1. Compounds of the formula (I) wherein R represents a methyl or ethyl group, R1 represents a C3-C5 alkyl group, R2 represents an alkylthiomethyl, alkylsulfinylmethyl or alkylsulfonylmethyl group having at most 5 carbon atoms in toto or a group of the formula -S(CH2)mCN, -SO(CH2)mCN, -S(CH2)mCl, -SO(CH2)mCl, SCC13, SOCC13, -S(CH2)mCOOR3, -SO(CH2)mCOOR3, -S(CH2)mCON(R4)R5 or --SO(CH2)mCON(R4)R5 wherein R3 represents an alkyl group having at most 4 carbon atoms, R4 and R5 independently of one another represent a hydrogen atom or an alkyl group having at most 4 carbon atoms and m represents the integer 1 or 2; and X1 and X2 indepently of one another represent a hydrogen or halogen atom or an alkyl group having at most 4 carbon atoms.
2. Compounds according to claim 1 wherein R1 represents an n-propyl, i-propyl, i-butyl, sec.-butyl, or n-pentyl group.
3. Compounds according to claim 2 wherein R represents an ethyl group and R1 represents an n-propyl group.
4. Compounds according to claim 1 wherein X1 and X2 independently of one another represent hydrogen, chlorine or bromine atom or a methyl group.
5. Compounds according to any one of claims 2 to 4 wherein R2 repre-sents a group of the formula -SCH2CN, -SOCH2CN, -SCH2Cl, SOCH2Cl, -SCC13, -SOCC13, -SCH2COOR3, -SOCH2COOR3, -SCH2CON(R4)R5, or -SOCH2CON(R4)R5 wherein R3 represents a methyl or ethyl group and R4 and R5 independently of one another represent a hydrogen atom or methyl group.
6. Compounds according to any one of claims 2 to 4 wherein R2 represents a group of the formula -SCH2Cl, -SCH2CN, -SCH2COOC2H5 or -S-CH2CONH2.
7. Compounds according to any one of claims 2 to 4 wherein R2 represents an alkylthiomethyl, alkylsulfinylmethyl or akylsulfonylmethyl group.
8. Compounds according to any one of claims 2 to 4 wherein R2 represents a methylthiomethyl, methylsulfinylmethyl or methylsulfonylmethyl group.
9. The compound according to claim 1 of the formula
10. The compound according to claim 1 of the formula
11. The compound according to claim 1 of the formula
12. The compound according to claim 1 of the formula
13. The compound according to claim 1 of the formula
14. The compound according to claim 1 of the formula
15. The compound according to claim 1 of the formula
16. The compound according to claim 1 of the formula
17. The compound according to claim 1 of the formula
18. The compound according to claim 1 of the formula
19. The compound according to claim 1 of the formula
20. A method of combatting pests of the class Insecta or Acarina at a locus, which comprises applying to said locus a compound as claimed in claim 1.
21. A method according to claim 20 wherein the locus comprises agri-cultural or horticultural crops or plants.
22. A method according to claim 20 or 21, wherein the pests are insects.
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH122672A CH569415A5 (en) | 1972-01-26 | 1972-01-26 | Thiophosphate esters - insecticides,acaricides,fungistats and bacteriostats |
CH1460072A CH576232A5 (en) | 1972-10-05 | 1972-10-05 | Thiophosphate esters - insecticides,acaricides,fungistats and bacteriostats |
CH1852872 | 1972-12-20 |
Publications (1)
Publication Number | Publication Date |
---|---|
CA1048047A true CA1048047A (en) | 1979-02-06 |
Family
ID=27172806
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CA162,024A Expired CA1048047A (en) | 1972-01-26 | 1973-01-25 | Esters |
Country Status (13)
Country | Link |
---|---|
JP (1) | JPS6036403B2 (en) |
AT (1) | AT319662B (en) |
BE (1) | BE794503A (en) |
CA (1) | CA1048047A (en) |
DD (1) | DD103142A5 (en) |
DE (1) | DE2303185C2 (en) |
ES (1) | ES410937A1 (en) |
FR (1) | FR2169223B1 (en) |
GB (2) | GB1421562A (en) |
HU (1) | HU167104B (en) |
IL (2) | IL41306A (en) |
IT (1) | IT978469B (en) |
NL (1) | NL7301018A (en) |
Families Citing this family (7)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS5727081B2 (en) * | 1974-04-05 | 1982-06-08 | ||
JPS5635166B2 (en) * | 1973-07-31 | 1981-08-15 | ||
DE2357526C2 (en) * | 1973-11-17 | 1982-04-22 | Bayer Ag, 5090 Leverkusen | O-phenylthionothiolphosphoric acid esters, process for their preparation and their use as insecticides and acaricides |
DE2625764A1 (en) * | 1976-06-09 | 1977-12-29 | Bayer Ag | TRIFLUOROMETHYLTHIO-PHENYL (DI) -THIO -PHOSPHORIC ACID ESTER, METHOD FOR THEIR PRODUCTION AND USE AS INSECTICIDE AND ACARICIDE |
DE2709932A1 (en) * | 1977-03-08 | 1978-09-14 | Bayer Ag | TRIFLUORMETHYLSULFINYLPHENYLTHIONO (THIOL) PHOSPHORIC ACID ESTER, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS INSECTICIDES, ACARICIDES AND NEMATICIDES |
DE2714038A1 (en) * | 1977-03-30 | 1978-10-19 | Bayer Ag | TRIFLUORMETHYLSULFONYLPHENYLTHIONO (THIOL) PHOSPHORIC ACID ESTERS OR. -ESTERAMIDES, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE AS INSECTICIDES AND ACARICIDES |
JPS55133389A (en) * | 1979-04-03 | 1980-10-17 | Takeda Chem Ind Ltd | Organic phosphoric ester and insecticide comprising it |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CH459657A (en) * | 1964-07-10 | 1968-07-15 | Bayer Ag | Fungitoxic agent |
US3839511A (en) * | 1970-12-26 | 1974-10-01 | Bayer Ag | O-ethyl-s-n-propyl-o-(substituted phenyl)-phosphorothiolates |
-
0
- BE BE794503D patent/BE794503A/en not_active IP Right Cessation
-
1973
- 1973-01-17 IL IL41306A patent/IL41306A/en unknown
- 1973-01-22 DD DD168378A patent/DD103142A5/xx unknown
- 1973-01-23 DE DE2303185A patent/DE2303185C2/en not_active Expired
- 1973-01-24 NL NL7301018A patent/NL7301018A/xx not_active Application Discontinuation
- 1973-01-25 HU HUCI1332A patent/HU167104B/hu unknown
- 1973-01-25 CA CA162,024A patent/CA1048047A/en not_active Expired
- 1973-01-25 JP JP48010658A patent/JPS6036403B2/en not_active Expired
- 1973-01-25 ES ES410937A patent/ES410937A1/en not_active Expired
- 1973-01-25 GB GB3482775A patent/GB1421562A/en not_active Expired
- 1973-01-25 AT AT61873A patent/AT319662B/en not_active IP Right Cessation
- 1973-01-25 FR FR7302564A patent/FR2169223B1/fr not_active Expired
- 1973-01-25 GB GB379973A patent/GB1421561A/en not_active Expired
- 1973-01-25 IT IT19605/73A patent/IT978469B/en active
-
1975
- 1975-10-22 IL IL48344A patent/IL48344A0/en unknown
Also Published As
Publication number | Publication date |
---|---|
FR2169223A1 (en) | 1973-09-07 |
IL41306A (en) | 1976-11-30 |
IT978469B (en) | 1974-09-20 |
DE2303185A1 (en) | 1973-08-09 |
HU167104B (en) | 1975-08-28 |
BE794503A (en) | 1973-07-25 |
ES410937A1 (en) | 1976-05-16 |
GB1421561A (en) | 1976-01-21 |
DD103142A5 (en) | 1974-01-12 |
IL48344A0 (en) | 1975-12-31 |
IL41306A0 (en) | 1973-03-30 |
GB1421562A (en) | 1976-01-21 |
JPS6036403B2 (en) | 1985-08-20 |
NL7301018A (en) | 1973-07-30 |
JPS4882042A (en) | 1973-11-02 |
DE2303185C2 (en) | 1986-01-09 |
FR2169223B1 (en) | 1979-01-19 |
AT319662B (en) | 1975-01-10 |
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