CH578305A5 - O-(Substd-propenyl) (thio) phosphates - insecticides and acaricides active against all growth stages - Google Patents
O-(Substd-propenyl) (thio) phosphates - insecticides and acaricides active against all growth stagesInfo
- Publication number
- CH578305A5 CH578305A5 CH1110373A CH1110373A CH578305A5 CH 578305 A5 CH578305 A5 CH 578305A5 CH 1110373 A CH1110373 A CH 1110373A CH 1110373 A CH1110373 A CH 1110373A CH 578305 A5 CH578305 A5 CH 578305A5
- Authority
- CH
- Switzerland
- Prior art keywords
- sep
- parts
- formula
- acaricides
- insecticides
- Prior art date
Links
- 230000000895 acaricidal effect Effects 0.000 title description 5
- 239000000642 acaricide Substances 0.000 title description 2
- 239000002917 insecticide Substances 0.000 title description 2
- ZPDKTVJZFVWAOC-UHFFFAOYSA-N 4-hydroxy-1,3,2,4lambda5-dioxathiaphosphetane 4-oxide Chemical class S1OP(O1)(O)=O ZPDKTVJZFVWAOC-UHFFFAOYSA-N 0.000 title 1
- -1 (alpha-methyl)benzyl Chemical group 0.000 claims abstract description 12
- 150000001875 compounds Chemical class 0.000 claims description 20
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 4
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 229910052760 oxygen Inorganic materials 0.000 claims description 4
- 239000001301 oxygen Substances 0.000 claims description 4
- 229910052717 sulfur Inorganic materials 0.000 claims description 4
- 239000011593 sulfur Substances 0.000 claims description 4
- 241000238631 Hexapoda Species 0.000 claims description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([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
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 2
- 239000000575 pesticide Substances 0.000 claims description 2
- 230000001419 dependent effect Effects 0.000 claims 2
- 239000002253 acid Substances 0.000 abstract description 4
- 125000000217 alkyl group Chemical group 0.000 abstract description 3
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 abstract 1
- TUCNEACPLKLKNU-UHFFFAOYSA-N acetyl Chemical compound C[C]=O TUCNEACPLKLKNU-UHFFFAOYSA-N 0.000 abstract 1
- 125000000304 alkynyl group Chemical group 0.000 abstract 1
- 239000004480 active ingredient Substances 0.000 description 20
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 239000008187 granular material Substances 0.000 description 9
- 239000000203 mixture Substances 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 239000002904 solvent Substances 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 239000005995 Aluminium silicate Substances 0.000 description 5
- 235000012211 aluminium silicate Nutrition 0.000 description 5
- 230000000749 insecticidal effect Effects 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
- 239000007921 spray Substances 0.000 description 5
- 239000000654 additive Substances 0.000 description 4
- 239000000839 emulsion Substances 0.000 description 4
- 229920000151 polyglycol Polymers 0.000 description 4
- 239000010695 polyglycol Substances 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 241000426497 Chilo suppressalis Species 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 3
- 241000196324 Embryophyta Species 0.000 description 3
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 235000019993 champagne Nutrition 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 235000013601 eggs Nutrition 0.000 description 3
- 239000004495 emulsifiable concentrate Substances 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 239000004563 wettable powder Substances 0.000 description 3
- 239000008096 xylene Substances 0.000 description 3
- 241001124076 Aphididae Species 0.000 description 2
- 241001425390 Aphis fabae Species 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 241000256244 Heliothis virescens Species 0.000 description 2
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 2
- 229920000663 Hydroxyethyl cellulose Polymers 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
- 241000256250 Spodoptera littoralis Species 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 241001454295 Tetranychidae Species 0.000 description 2
- 241001454293 Tetranychus urticae Species 0.000 description 2
- 240000006677 Vicia faba Species 0.000 description 2
- 235000010749 Vicia faba Nutrition 0.000 description 2
- 241000607479 Yersinia pestis Species 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 150000002191 fatty alcohols Chemical class 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 2
- 239000004615 ingredient Substances 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
- 239000002574 poison Substances 0.000 description 2
- 231100000614 poison Toxicity 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- 235000015112 vegetable and seed oil Nutrition 0.000 description 2
- 239000008158 vegetable oil Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- IQUPABOKLQSFBK-UHFFFAOYSA-N 2-nitrophenol Chemical class OC1=CC=CC=C1[N+]([O-])=O IQUPABOKLQSFBK-UHFFFAOYSA-N 0.000 description 1
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 1
- 241000238660 Blattidae Species 0.000 description 1
- 241000257161 Calliphoridae Species 0.000 description 1
- 241001414835 Cimicidae Species 0.000 description 1
- 241000255749 Coccinellidae Species 0.000 description 1
- 241001466044 Delphacidae Species 0.000 description 1
- 241001481702 Dermanyssidae Species 0.000 description 1
- 241001414830 Diaspididae Species 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- PNKUSGQVOMIXLU-UHFFFAOYSA-N Formamidine Chemical compound NC=N PNKUSGQVOMIXLU-UHFFFAOYSA-N 0.000 description 1
- 241000238816 Gryllidae Species 0.000 description 1
- 241001243087 Gryllotalpidae Species 0.000 description 1
- 206010061217 Infestation Diseases 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- WRQNANDWMGAFTP-UHFFFAOYSA-N Methylacetoacetic acid Chemical compound COC(=O)CC(C)=O WRQNANDWMGAFTP-UHFFFAOYSA-N 0.000 description 1
- 241000257226 Muscidae Species 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
- 241001674048 Phthiraptera Species 0.000 description 1
- 241001415279 Pseudococcidae Species 0.000 description 1
- 241000258921 Pulicidae Species 0.000 description 1
- 241001510071 Pyrrhocoridae Species 0.000 description 1
- 241001124072 Reduviidae Species 0.000 description 1
- 241000254062 Scarabaeidae Species 0.000 description 1
- 241000255588 Tephritidae Species 0.000 description 1
- 241000896028 Tettigoniidae Species 0.000 description 1
- 235000002098 Vicia faba var. major Nutrition 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
- 239000003513 alkali Substances 0.000 description 1
- 150000001342 alkaline earth metals Chemical class 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- DNEHKUCSURWDGO-UHFFFAOYSA-N aluminum sodium Chemical compound [Na].[Al] DNEHKUCSURWDGO-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 229920005551 calcium lignosulfonate Polymers 0.000 description 1
- RYAGRZNBULDMBW-UHFFFAOYSA-L calcium;3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Ca+2].COC1=CC=CC(CC(CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O RYAGRZNBULDMBW-UHFFFAOYSA-L 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 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
- 150000003857 carboxamides Chemical class 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- IOBDNVXNQYTKEO-UHFFFAOYSA-N chloro-hydroxy-propoxy-sulfanylidene-$l^{5}-phosphane Chemical compound CCCOP(O)(Cl)=S IOBDNVXNQYTKEO-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 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
- NAGJZTKCGNOGPW-UHFFFAOYSA-N dithiophosphoric acid Chemical class OP(O)(S)=S NAGJZTKCGNOGPW-UHFFFAOYSA-N 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 235000005489 dwarf bean Nutrition 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000002474 experimental method Methods 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 238000004519 manufacturing process Methods 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
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000002903 organophosphorus compounds Chemical class 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- LPNYRYFBWFDTMA-UHFFFAOYSA-N potassium tert-butoxide Chemical compound [K+].CC(C)(C)[O-] LPNYRYFBWFDTMA-UHFFFAOYSA-N 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 102200012974 rs121918641 Human genes 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- KZOJQMWTKJDSQJ-UHFFFAOYSA-M sodium;2,3-dibutylnaphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S([O-])(=O)=O)=C(CCCC)C(CCCC)=CC2=C1 KZOJQMWTKJDSQJ-UHFFFAOYSA-M 0.000 description 1
- SRAWNDFHGTVUNZ-UHFFFAOYSA-M sodium;3,6-dibutylnaphthalene-1-sulfonate Chemical compound [Na+].[O-]S(=O)(=O)C1=CC(CCCC)=CC2=CC(CCCC)=CC=C21 SRAWNDFHGTVUNZ-UHFFFAOYSA-M 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 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
- 239000000080 wetting agent Substances 0.000 description 1
- 150000003738 xylenes Chemical class 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
- C07F9/16—Esters of thiophosphoric acids or thiophosphorous acids
- C07F9/165—Esters of thiophosphoric acids
- C07F9/173—Esters of thiophosphoric acids with unsaturated acyclic alcohols
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Biochemistry (AREA)
- General Health & Medical Sciences (AREA)
- Molecular Biology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
New title cpds. are of formula: (R1 = Me or Et; R2 = 3-5C alkyl; R3 = 1-3C alkyl, allyl, 3-6C alkynyl, (alpha-methyl)benzyl MeOCH2.CH2, Me(O.CH2.CH2)2 or 1-methyl-2-methoxyethyl). They are prepd. by (a) reacting R1O.R2S.P(X)Cl with CH3CO.CH2.CO2R3 in presence of acid accepted or (b) by reacting Cl2.P(X).O.C(CH3)=CHCO2R3 with R1OH and R2SH in any order.
Description
Die vorliegende Erfindung betrifft Schädlingsbekämpfungsmittel, enthaltend als aktive Komponente einen Thiobzw. Dithiophosphorsäureester, und ihre Verwendung in der Schädlingsbekämpfung. Die Thio- und Dithiophosphorsäureester haben die Formel (I)
EMI1.1
worin
R1 Methyl oder Äthyl,
R2 C3-C5-Alkyl,
R3 Methoxyäthyl, Methoxyäthoxyäthyl oder 1-Methyl2-methoxy-äthyl und
X Sauerstoff oder Schwefel bedeuten.
Die bei R2 stehenden Alkylgruppen können geradkettig oder verzweigt sein. Beispiele solcher Gruppen sind u. a.: n-Propyl; Isopropyl; n-, i-, sek.- und tert.-Butyl; sowie n-Pentyl.
Wegen ihrer Wirkung bevorzugt sind Verbindungen der Formel (I), worin
R1 Äthyl,
R2 n-Propyl, Isobutyl oder sek.-Butyl,
R3 1-Methyl-2-methoxyäthyl und
X Sauerstoff oder Schwefel bedeuten.
Die Verbindungen der Formel I werden nach folgenden an sich bekannten Methoden hergestellt:
EMI1.2
<tb> <SEP> x
<tb> R, <SEP> R1Oüi <SEP> X <SEP> II
<tb> <SEP> R2S <SEP> (11) <SEP> + <SEP> + <SEP> Mittel <SEP> > <SEP> I(iii)
<tb> 1) <SEP> Mittl
<tb> 2) <SEP> PXC13 <SEP> + <SEP> CH3COCH2COOR3 <SEP> säurebindendes
<tb> <SEP> Mittel'\
<tb> <SEP> (iv) <SEP> ( <SEP> III)
<tb> <SEP> X <SEP> CH
<tb> <SEP> ri <SEP> 1 <SEP> /
<tb> <SEP> (C1) <SEP> I"O-C=CH-COOR, <SEP> + <SEP> 1. <SEP> R1OH <SEP> (VI) <SEP> säurebindendes <SEP> 1
<tb> <SEP> (v) <SEP> 2. <SEP> R2SH <SEP> (via) <SEP> Mittel
<tb> <SEP> oder
<tb> <SEP> 1. <SEP> R28H <SEP> (vii)
<tb> <SEP> 2. <SEP> R1OH <SEP> (VI)
<tb>
Als säurebindende Mittel kommen in Frage: tertiäre Amine, z. B.
Trialkylamine, Pyridin und Dialkylaniline; und anorganische Basen, wie Hydroxide; Karbonate und Bikarbonate von Alkali- oder Erdalkalimetallen.
Die Verfahren 1 und 2 werden bei einer Reaktionstemperatur zwischen -10-100" C, insbesondere zwischen 20 bis 80" C, bei normalem oder erhöhtem Druck und in Lösungsoder Verdünnungsmitteln durchgeführt.
Als Lösungs- oder Verdünnungsmittel eignen sich z. B.
Äther und ätherartige Verbindungen, wie Diäthyläther, Dipropyläther, Dioxan, Dimethoxyäthan, Tetrahydrofuran; Amide wie N,N-di-alkylierte Carbonsäureamide; aliphatische, aromatische sowie halogenierte Kohlenwasserstoffe, insbesondere Benzol, Toluol, Xylole, Chloroform, Chlorbenzol; Nitrile wie Acetonitrile; DMSO, Ketone wie Aceton, Methyl äthylketon.
Die Ausgangsstoffe der Formeln II, III und IV sind teilweise bekannt und können analog bekannten Methoden hergestellt werden.
Die Verbindungen der Formel I weisen eine breite biozide Wirkung auf und eignen sich daher zur Bekämpfung von verschiedenartigen pflanzlichen und tierischen Schädlingen.
Die Verbindungen der Formel I besitzen aber insbesondere insektizide und akarizide Eigenschaften und können gegen alle Entwicklungsstadien, wie z. B. Eier, Larven, Puppen, Nymphen und Adulte, von Insekten und Vertretern der Ordnung Akarina eingesetzt werden, wie z. B. gegen Insekten der Familien Tettigoniidae, Gryllidae, Gryllotalpidae, Blattidae, Reduviidae, Pyrrhocoridae, Cimicidae, Delphacidae, Aphididae, Diaspididae, Pseudococcidae, Scarabaeidae, Dermestidae, Coccinellidae, Tenebrionidae, Chrysomelidae, Bruchidae, Tineidae, Noctuidae, Lymantriidae, Pyralidae, Culicidae, Tripulidae, Stomoxydae, Trypetidae, Muscidae, Calliphoridae und Pulicidae, sowie Akariden der Familien Tetranychidae und Dermanyssidae.
Die insektizide oder akarizide Wirkung lässt sich durch Zusatz von anderen Insektiziden und/oder Akariziden wesentlich verbreitern und an gegebene Umstände anpassen.
Als Zusätze eignen sich z. B.: organische Phosphorverbindungen,
Derivate von Nitrophenolen,
Formamidine,
Harnstoffe,
Carbamate und chlorierte Kohlenwasserstoffe.
Die Verbindungen der Formel I können zusammen mit geeigneten Trägern und/oder Zuschlagstoffen eingesetzt werden. Geeignete Träger und Zuschlagstoffe können fest oder flüssig sein und entsprechen den in der Formulierungstechnik üblichen Stoffen, wie z. B. natürlichen oder regenerierten Stoffen, Lösungs-, Dispergier-, Netz-, Haft-, Verdikkungs-, Binde- und/oder Düngemitteln.
Zur Applikation können die Verbindungen der Formel I zu Stäubemitteln, Emulsionskonzentraten, Granulaten, Dispersionen, Sprays, zu Lösungen oder Aufschlämmungen in üblicher Formulierung, die in der Applikationstechnik zum Allgemeinwissen gehören, verarbeitet werden.
Die Herstellung erfindungsgemässer Mittel erfolgt in an sich bekannter Weise durch inniges Vermischen und/oder Vermahlen von Wirkstoffen der Formel I mit den geeigneten Trägerstoffen, gegebenenfalls unter Zusatz von gegenüber den Wirkstoffen inerten Dispergier- oder Lösungsmitteln.
Die Wirkstoffe können in den folgenden Aufarbeitungsformen vorliegen und angewendet werden: Feste Aufarbeitungsformen:
Stäubemittel, Streumittel, Granulate (Umhüllungs granulate, Imprägnierungsgranulate und Homogen granulate); flüssige Aufarbeitungsformen: a) in Wasser dispergierbare Wirkstoffkonzentrate:
Spritzpulver (wettable powders), Pasten, Emulsionen; b) Lösungen.
Der Gehalt an Wirkstoff in den oben beschriebenen Mitteln liegt zwischen 0,1 bis 95 %, dabei ist zu erwähnen, dass bei der Applikation aus dem Flugzeug oder mittels anderer geeigneter Applikationsgeräte Konzentrationen bis zu 99,5 Wo eingesetzt werden können.
Die Wirkstoffe der Formel I können beispielsweise wie folgt formuliert werden: Stäubemittel:
Zur Herstellung eines a) 5 %igen und b) 2 %igen Stäubemittels werden die folgenden Stoffe verwendet: a) 5 Teile Wirkstoff,
95 Teile Talkum; b) 2 Teile Wirkstoff,
1 Teil hochdisperse Kieselsäure,
97 Teile Talkum.
Die Wirkstoffe werden mit den Trägerstoffen vermischt und vermahlen.
Granulat:
Zur Herstellung eines 5 %igen Granulates werden die folgenden Stoffe verwendet:
5 Teile Wirkstoff,
0,25 Teile Epichlorhydrin,
0,25 Teile Cetylpolyglykoläther,
3,50 Teile Polyäthylenglykol,
91 Teile Kaolin (Korngrösse 0,3-0,8 mm).
Die Aktivsubstanz wird mit Epichlorhydrin vermischt und mit 6 Teilen Aceton gelöst, hierauf wird Polyäthylenglykol und Cetylpolyglykoläther zugesetzt. Die so erhaltene Lösung wird auf Kaolin aufgesprüht und anschliessend das Aceton im Vakuum verdampft.
Spritzpulver:
Zur Herstellung eines a) 40 wiegen, b) und c) 25 %igen, d) 10%igen Spritzpulvers werden folgende Bestandteile verwendet: a) 40 Teile Wirkstoff,
5 Teile Ligninsulfonsäure-Natriumsalz,
1 Teil Dibutylnaphthalinsulfonsäure-Natriumsalz,
54 Teile Kieselsäure; b) 25 Teile Wirkstoff,
4,5 Teile Calcium-Ligninsulfonat,
1,9 Teile Champagne-Kreide/Hydroxyäthylcellulose
Gemisch (1:1),
1,5 Teile Natrium-dibutyl-naphthalinsulfonat,
19,5 Teile Kieselsäure,
19,5 Teile Champagne-Kreide,
28,1 Teile Kaolin; c) 25 Teile Wirkstoff,
2,5 Teile Isooctylphenoxy-polyoxyäthylen-äthanol,
1,7 Teile Champagne-Kreide/Hydroxyäthylcellulose
Gemisch (1 :1),
8,3 Teile Natriumaluminiumsilikat,
16,5 Teile Kieselgur,
46 Teile Kaolin;
d) 10 Teile Wirkstoff,
3 Teile Gemisch der Natriumsalze von gesättigten
Fettalkoholsulfaten,
5 Teile Naphthalinsulfonsäure/Formaldehyd
Kondensat,
82 Teile Kaolin.
Die Wirkstoffe werden in geeigneten Mischern mit den Zuschlagstoffen innig vermischt und auf entsprechenden Mühlen und Walzen vermahlen. Man erhält Spritzpulver, die sich mit Wasser zu Suspensionen jeder gewünschten Konzentration verdünnen lassen.
Emulgierbare Konzentrate:
Zur Herstellung eines a) 10%igen und b) 25 %igen emulgierbaren Konzentrates werden folgende Stoffe verwendet: a) 10 Teile Wirkstoff,
3,4 Teile epoxydiertes Pflanzenöl,
3,4 Teile eines Kombinationsemulgators, bestehend aus Fettalkoholpolyglykoläther und Alkylaryl sulfonat-Calcium-Salz,
40 Teile Dimethylformamid,
43,2 Teile Xylol; b) 25 Teile Wirkstoff,
2,5 Teile epoxydiertes Pflanzenöl,
10 Teile eines Alkylarylsulfonat/Fettalkoholpoly glykoläther-Gemisches,
5 Teile Dimethylformamid,
57,5 Teile Xylol.
Aus solchen Konzentraten können durch Verdünnen mit Wasser Emulsionen jeder gewünschten Konzentration hergestellt werden.
Sprühmittel:
Zur Herstellung eines 5 %igen Sprühmittels werden die folgenden Bestandteile verwendet:
5 Teile Wirkstoff,
1 Teil Epichlorhydrin,
94 ¯ Teile Benzin (Siedegrenzen 160-190 C).
Beispiel 1
Herstellung von O-Äthyl-S-(n)propyl- 1 -carbomethoxy 1 -propen-2-yl-thiolphosphat
22,4 g Kalium-t-butylat und 23,2 g Acetessigsäuremethylester werden in 100 ml Dimethylformamid vorgelegt.
Man lässt bei 20-30 C 40 g O-Äthyl-S-(n)propyl-thiochlorphosphat zutropfen und rührt die Reaktionsmischung noch während 16 Stunden bei Raumtemperatur. Anschliessend entfernt man das Lösungsmittel im Vakuum bei 60 C Badtemperatur, nimmt den Rückstand in 100 ml Methylenchlorid auf und wäscht ihn zweimal mit je 30 ml 1n Natronlauge aus.
Nach dem Abdampfen des Lösungsmittels im Vakuum erhält man als Rückstand die Verbindung der Formel
EMI2.1
mit einem Siedepunkt von 90" C/0,001 Torr und einer Refraktion von nD25 = 1,4818.
Auf analoge Weise werden die folgenden Verbindungen hergestellt: Verbindung Nr. 1
EMI3.1
Verbindung Nr. 2
EMI3.2
Verbindung Nr. 3
EMI3.3
Verbindung Nr. 4
EMI3.4
Beispiel 2 A. Insektizide Frassgift-Wirkung
Tabakpflanzen wurden mit einer 0,05 %igen wässrigen Wirkstoffemulsion (erhalten aus einem 10%igen emulgierbaren Konzentrat) besprüht.
Nach dem Antrocknen des Belages wurden die Tabakpflanzen mit Raupen von Spodoptera littoralis im L3-Stadium bzw. von Heliothis virescens im L3-Stadium besetzt.
Der Versuch wurde bei 24 C und 60% relativer Luftfeuchtigkeit durchgeführt.
Die Verbindungen Nrn. 1 bis 4 gemäss Beispiel 1 zeigten im obigen Test gute Frassgift-Wirkung gegen Spodoptera littoralis und Heliothis virescens.
B. Insektizide Kontakt-Wirkung
Einen Tag vor der Applikation wurden in Töpfen angezogene Puffbohnen (Vicia faba) mit ca. 200 Blattläusen (Aphis fabae) pro Pflanze infiziert. Die Applikation erfolgte mittels Druckluitspntze auf die mit Läusen besetzten Blätter mit einer Spritzbrühe in einer Konzentration von 1000 ppm (hergestellt aus einem 25 %igen wettable powder).
Die Bonitierung erfolgte 24 Stunden nach der Applikation.
Die Verbindungen Nrn. 1 bis 4 gemäss Beispiel 1 zeigten im obigen Test gute Kontakt-Wirkung gegen Aphis fabae.
Beispiel 3
Wirkung gegen Chilo suppressalis
Je 6 Reispflanzen der Sorte Caloro wurden in Plastiktöpfen, die einen oberen Durchmesser von 17 cm aufwiesen, verpflanzt und zu einer Höhe von ca. 60 cm aufgezogen. Die Infestation mit Chilo suppressalis-Larven (L1; 3-4 mm lang) erfolgte 2 Tage nach der Wirkstoffzugabe in Granulatform (Aufwandmenge 8 kg Aktivsubstanz pro Hektare) in das Paddy-Wasser. Die Auswertung auf insektizide Wirkung erfolgte 10 Tage nach der Zugabe des Granulates.
Die Verbindungen Nrn. 1 bis 4 gemäss Beispiel 1 zeigten im obigen Test gute Wirkung gegen Chilo suppressalis.
Beispiel 4
Wirkung gegen Spinnmilben
Phaseolus vulgaris (Buschbohnen) wurden 12 Stunden vor dem Test auf akarizide Wirkung mit einem infestierten Blattstück aus einer Massenzucht von Tetranychus urticae belegt. Die übergelaufenen beweglichen Stadien wurden aus einem Chromatographiezerstäuber mit den emulgierten Testpräparaten bestäubt, dass kein Ablaufen der Spritzbrühe eintrat. Nach zwei bis 7 Tagen wurden Larven, Adulte und Eier unter dem Binokular auf lebende und tote Individuen ausgewertet und das Ergebnis in Prozenten ausgedrückt.
Während der Haltezeit standen die behandelten Pflanzen in Gewächshauskabinen bei 25 C.
Die Verbindungen Nrn. 1 bis 4 gemäss Beispiel 1 zeigten gute Wirkung im obigen Test gegen Eier, Larven und Adulte von Tetranychus urticae.
The present invention relates to pesticides containing as active component a Thiobzw. Phosphoric dithiophosphate, and their use in pest control. The thio and dithiophosphoric acid esters have the formula (I)
EMI1.1
wherein
R1 methyl or ethyl,
R2 C3-C5-alkyl,
R3 methoxyethyl, methoxyethoxyethyl or 1-methyl2-methoxyethyl and
X represent oxygen or sulfur.
The alkyl groups at R2 can be straight-chain or branched. Examples of such groups include: a .: n-propyl; Isopropyl; n-, i-, sec- and tert-butyl; and n-pentyl.
Because of their action, compounds of the formula (I) in which
R1 ethyl,
R2 n-propyl, isobutyl or sec-butyl,
R3 1-methyl-2-methoxyethyl and
X represent oxygen or sulfur.
The compounds of the formula I are prepared by the following methods known per se:
EMI1.2
<tb> <SEP> x
<tb> R, <SEP> R1Oüi <SEP> X <SEP> II
<tb> <SEP> R2S <SEP> (11) <SEP> + <SEP> + <SEP> medium <SEP>> <SEP> I (iii)
<tb> 1) <SEP> Avg
<tb> 2) <SEP> PXC13 <SEP> + <SEP> CH3COCH2COOR3 <SEP> acid-binding
<tb> <SEP> Medium '\
<tb> <SEP> (iv) <SEP> (<SEP> III)
<tb> <SEP> X <SEP> CH
<tb> <SEP> ri <SEP> 1 <SEP> /
<tb> <SEP> (C1) <SEP> I "O-C = CH-COOR, <SEP> + <SEP> 1. <SEP> R1OH <SEP> (VI) <SEP> acid-binding <SEP> 1
<tb> <SEP> (v) <SEP> 2. <SEP> R2SH <SEP> (via) <SEP> means
<tb> <SEP> or
<tb> <SEP> 1. <SEP> R28H <SEP> (vii)
<tb> <SEP> 2. <SEP> R1OH <SEP> (VI)
<tb>
Suitable acid-binding agents are: tertiary amines, e.g. B.
Trialkylamines, pyridine and dialkylanilines; and inorganic bases such as hydroxides; Carbonates and bicarbonates of alkali or alkaline earth metals.
Processes 1 and 2 are carried out at a reaction temperature between -10-100 "C, in particular between 20 to 80" C, under normal or elevated pressure and in solvents or diluents.
Suitable solvents or diluents are, for. B.
Ethers and ethereal compounds such as diethyl ether, dipropyl ether, dioxane, dimethoxyethane, tetrahydrofuran; Amides such as N, N-di-alkylated carboxamides; aliphatic, aromatic and halogenated hydrocarbons, in particular benzene, toluene, xylenes, chloroform, chlorobenzene; Nitriles such as acetonitrile; DMSO, ketones such as acetone, methyl ethyl ketone.
Some of the starting materials of the formulas II, III and IV are known and can be prepared analogously to known methods.
The compounds of the formula I have a broad biocidal action and are therefore suitable for combating various types of plant and animal pests.
However, the compounds of formula I have in particular insecticidal and acaricidal properties and can be used against all stages of development, such as. B. eggs, larvae, pupae, nymphs and adults, are used by insects and representatives of the order Akarina, such as. B. against insects of the families Tettigoniidae, Gryllidae, Gryllotalpidae, Blattidae, Reduviidae, Pyrrhocoridae, Cimicidae, Delphacidae, Aphididae, Diaspididae, Pseudococcidae, Scarabaeidae, Dermestymaline Tile, Cincinellidae, Chrysidae, Chrysulidae, Crysulidae, Lysidae, Chrysulidae, Coccinellidae, Tenebromionelidae Tripulidae, Stomoxydae, Trypetidae, Muscidae, Calliphoridae and Pulicidae, as well as acarids of the families Tetranychidae and Dermanyssidae.
The insecticidal or acaricidal effect can be significantly broadened by adding other insecticides and / or acaricides and adapted to given circumstances.
Suitable additives are, for. E.g .: organic phosphorus compounds,
Derivatives of nitrophenols,
Formamidine,
Ureas,
Carbamates and chlorinated hydrocarbons.
The compounds of the formula I can be used together with suitable carriers and / or additives. Suitable carriers and additives can be solid or liquid and correspond to the substances customary in formulation technology, such as. B. natural or regenerated substances, solvents, dispersants, wetting agents, adhesives, thickeners, binders and / or fertilizers.
For application, the compounds of the formula I can be processed into dusts, emulsion concentrates, granules, dispersions, sprays, into solutions or slurries in the customary formulation, which are part of general knowledge in application technology.
The agents according to the invention are prepared in a manner known per se by intimately mixing and / or grinding active ingredients of the formula I with the suitable carriers, optionally with the addition of dispersants or solvents which are inert towards the active ingredients.
The active ingredients can be present and used in the following working-up forms: Solid working-up forms:
Dusts, grit, granules (coating granules, impregnation granules and homogeneous granules); Liquid processing forms: a) Active substance concentrates dispersible in water:
Wettable powders, pastes, emulsions; b) Solutions.
The content of active ingredient in the agents described above is between 0.1 and 95%; it should be mentioned here that concentrations of up to 99.5 weeks can be used for application from an aircraft or other suitable application devices.
The active ingredients of the formula I can be formulated as follows, for example: Dusts:
The following substances are used to produce a) 5% and b) 2% dust: a) 5 parts of active ingredient,
95 parts of talc; b) 2 parts of active ingredient,
1 part of highly dispersed silica,
97 parts of talc.
The active ingredients are mixed and ground with the carrier substances.
Granules:
The following substances are used to produce 5% granules:
5 parts active ingredient,
0.25 parts epichlorohydrin,
0.25 part of cetyl polyglycol ether,
3.50 parts of polyethylene glycol,
91 parts of kaolin (grain size 0.3-0.8 mm).
The active substance is mixed with epichlorohydrin and dissolved with 6 parts of acetone, then polyethylene glycol and cetyl polyglycol ether are added. The solution obtained in this way is sprayed onto kaolin and the acetone is then evaporated in vacuo.
Wettable powder:
The following ingredients are used to produce a) weigh 40, b) and c) 25%, d) 10% wettable powder: a) 40 parts of active ingredient,
5 parts of lignin sulfonic acid sodium salt,
1 part dibutylnaphthalenesulfonic acid sodium salt,
54 parts of silica; b) 25 parts of active ingredient,
4.5 parts calcium lignosulfonate,
1.9 parts of champagne chalk / hydroxyethyl cellulose
Mixture (1: 1),
1.5 parts of sodium dibutyl naphthalene sulfonate,
19.5 parts of silica,
19.5 parts of champagne chalk,
28.1 parts of kaolin; c) 25 parts of active ingredient,
2.5 parts of isooctylphenoxy-polyoxyethylene-ethanol,
1.7 parts of champagne chalk / hydroxyethyl cellulose
Mixture (1: 1),
8.3 parts sodium aluminum silicate,
16.5 parts kieselguhr,
46 parts of kaolin;
d) 10 parts of active ingredient,
3 parts mixture of the sodium salts of saturated
Fatty alcohol sulfates,
5 parts of naphthalenesulfonic acid / formaldehyde
Condensate,
82 parts of kaolin.
The active ingredients are intimately mixed with the additives in suitable mixers and ground on appropriate mills and rollers. Wettable powders are obtained which can be diluted with water to form suspensions of any desired concentration.
Emulsifiable concentrates:
The following substances are used to produce a) 10% and b) 25% emulsifiable concentrate: a) 10 parts of active ingredient,
3.4 parts epoxidized vegetable oil,
3.4 parts of a combination emulsifier, consisting of fatty alcohol polyglycol ether and alkylaryl sulfonate calcium salt,
40 parts of dimethylformamide,
43.2 parts of xylene; b) 25 parts of active ingredient,
2.5 parts epoxidized vegetable oil,
10 parts of an alkylarylsulfonate / fatty alcohol poly glycol ether mixture,
5 parts of dimethylformamide,
57.5 parts of xylene.
Emulsions of any desired concentration can be prepared from such concentrates by dilution with water.
Spray:
The following ingredients are used to make a 5% spray:
5 parts active ingredient,
1 part epichlorohydrin,
94 ¯ parts gasoline (boiling limit 160-190 C).
example 1
Production of O-ethyl-S- (n) propyl-1-carbomethoxy 1-propen-2-yl-thiol phosphate
22.4 g of potassium t-butoxide and 23.2 g of methyl acetoacetate are placed in 100 ml of dimethylformamide.
40 g of O-ethyl-S- (n) propyl-thiochlorophosphate are added dropwise at 20-30 ° C. and the reaction mixture is stirred for a further 16 hours at room temperature. The solvent is then removed in vacuo at a bath temperature of 60 ° C., the residue is taken up in 100 ml of methylene chloride and washed twice with 30 ml of 1N sodium hydroxide solution each time.
After the solvent has been evaporated off in vacuo, the compound of the formula is obtained as the residue
EMI2.1
with a boiling point of 90 "C / 0.001 Torr and a refraction of nD25 = 1.4818.
The following compounds are prepared in an analogous manner: Compound No. 1
EMI3.1
Connection No. 2
EMI3.2
Compound No. 3
EMI3.3
Compound No. 4
EMI3.4
Example 2 A. Insecticidal feed poison effect
Tobacco plants were sprayed with a 0.05% aqueous active ingredient emulsion (obtained from a 10% emulsifiable concentrate).
After the coating had dried on, the tobacco plants were populated with caterpillars of Spodoptera littoralis in the L3 stage or by Heliothis virescens in the L3 stage.
The experiment was carried out at 24 C and 60% relative humidity.
In the above test, compounds Nos. 1 to 4 according to Example 1 showed a good feed poison action against Spodoptera littoralis and Heliothis virescens.
B. Insecticidal contact effect
One day before application, broad beans (Vicia faba) grown in pots were infected with about 200 aphids (Aphis fabae) per plant. The application was carried out by means of a Druckluitspntze on the leaves infected with lice with a spray mixture in a concentration of 1000 ppm (made from a 25% wettable powder).
The rating took place 24 hours after the application.
The compounds Nos. 1 to 4 according to Example 1 showed good contact action against Aphis fabae in the above test.
Example 3
Effect against Chilo suppressalis
6 rice plants of the Caloro variety were transplanted into plastic pots with an upper diameter of 17 cm and raised to a height of about 60 cm. The infestation with Chilo suppressalis larvae (L1; 3-4 mm long) took place 2 days after the addition of the active ingredient in granulate form (application rate 8 kg active ingredient per hectare) in the paddy water. The insecticidal activity was evaluated 10 days after the granules had been added.
Compounds nos. 1 to 4 according to Example 1 showed good activity against Chilo suppressalis in the above test.
Example 4
Effect against spider mites
Phaseolus vulgaris (French beans) were coated with an infected piece of leaf from a mass cultivation of Tetranychus urticae 12 hours before the test for acaricidal activity. The overflowing mobile stages were dusted with the emulsified test preparations from a chromatography atomizer so that the spray mixture did not run off. After two to 7 days, larvae, adults and eggs were evaluated under the binocular for living and dead individuals and the result was expressed as a percentage.
During the holding time, the treated plants stood in greenhouse cabins at 25 C.
The compounds nos. 1 to 4 according to Example 1 showed good activity in the above test against eggs, larvae and adults of Tetranychus urticae.
Claims (1)
Priority Applications (11)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH1110373A CH578305A5 (en) | 1973-07-30 | 1973-07-30 | O-(Substd-propenyl) (thio) phosphates - insecticides and acaricides active against all growth stages |
IL43068A IL43068A (en) | 1972-09-08 | 1973-08-24 | Thio-and dithiophosphoric acid esters,their manufacture and their use in pest control |
NL7312077A NL7312077A (en) | 1972-09-08 | 1973-08-31 | |
DE19732344762 DE2344762A1 (en) | 1972-09-08 | 1973-09-05 | NEW ESTERS |
US394694A US3883618A (en) | 1972-09-08 | 1973-09-06 | O-alkyl-s-alkyl-o-(1-hydrocarbyloxy carbonyl-1-propen-2-yl)dithiophosphates |
JP48100735A JPS4969835A (en) | 1972-09-08 | 1973-09-06 | |
ES73418550A ES418550A1 (en) | 1972-09-08 | 1973-09-07 | O-alkyl-s-alkyl-o-(1-hydrocarbyloxy carbonyl-1-propen-2-yl)dithiophosphates |
GB4224273A GB1436404A (en) | 1972-09-08 | 1973-09-07 | Phosphorus-containing unsaturated carboxylic acid esters |
DD173359A DD108891A5 (en) | 1972-09-08 | 1973-09-07 | |
FR7332330A FR2198952B1 (en) | 1972-09-08 | 1973-09-07 | |
AT777873A AT322912B (en) | 1972-09-08 | 1973-09-07 | INSECTICIDAL AND ACARICIDAL AGENT |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH1110373A CH578305A5 (en) | 1973-07-30 | 1973-07-30 | O-(Substd-propenyl) (thio) phosphates - insecticides and acaricides active against all growth stages |
Publications (1)
Publication Number | Publication Date |
---|---|
CH578305A5 true CH578305A5 (en) | 1976-08-13 |
Family
ID=4370078
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH1110373A CH578305A5 (en) | 1972-09-08 | 1973-07-30 | O-(Substd-propenyl) (thio) phosphates - insecticides and acaricides active against all growth stages |
Country Status (1)
Country | Link |
---|---|
CH (1) | CH578305A5 (en) |
-
1973
- 1973-07-30 CH CH1110373A patent/CH578305A5/en not_active IP Right Cessation
Similar Documents
Publication | Publication Date | Title |
---|---|---|
CH592411A5 (en) | Phenoxymethyl- and phenylthiomethyl-pyridine derivs - with insecticidal, acaricidal and plant-growth regulating activity | |
DE2457147A1 (en) | 1,2,4-TRIAZOLE DERIVATIVES, PROCESS FOR THEIR PRODUCTION AND USE | |
DE2411809A1 (en) | THIOLPHOSPHORIC ACID ESTERS, PROCESS FOR THEIR MANUFACTURING AND USE | |
CH578305A5 (en) | O-(Substd-propenyl) (thio) phosphates - insecticides and acaricides active against all growth stages | |
DE2751028C2 (en) | Thio-substituted carbamic acid derivatives, processes for their preparation and pesticides | |
DE2150074C3 (en) | New phenyl esters, processes for their manufacture and pesticides | |
DE2344762A1 (en) | NEW ESTERS | |
CH575717A5 (en) | S-Arylthioalkyl-O,S-dialkyl dithiophosphates - with insecticidal, acaricidal, fungicidal, nematocidal activity, etc. | |
CH604522A5 (en) | (4,5)-Benzospiro-(2,4)-heptane-(1)-carboxylate esters | |
DE2418363A1 (en) | 1,2,4-THIADIAZOLYL PHOSPHORUS COMPOUNDS, METHOD FOR THEIR MANUFACTURING AND USE | |
DE2350886A1 (en) | NEW ESTERS | |
CH627621A5 (en) | Pesticide containing thio-substituted carbamic acid derivatives | |
DE2354586A1 (en) | Pesticidal phenyl (di) thiophosphates - useful as insecticides, acarimide-imides and nematocides | |
CH593012A5 (en) | 1-Methyl-2-(esterified carboxy)-1-alkenyl (di) thiophosphate derivs - prepd. e.g. by reacting alpha-substd. acetoacetates with (di)thiophosphoryl halides (BE190376) | |
CH569417A5 (en) | O-(Substd-propenyl) (thio) phosphates - insecticides and acaricides active against all growth stages | |
CH574713A5 (en) | s-Picolyl phosphoridithioates - useful as insecticides, acaricides and plant-growth regulators | |
CH583516A5 (en) | O,S-dialkyl-S-(oxadiazolyl-methyl)-dithiophosphates - used as pesticides, prepd. from chloro-methyl-oxadiazole and dithiophosphate salt | |
DE2457146A1 (en) | 1-(2-Cyanoethyl)-1,2,4-triazol-3-yl dimethylcarbamates - prepd. by reacting 3-hydroxy cpds. with dimethylcarbamoyl chloride | |
CH583518A5 (en) | 0-(2-Alkenylphenyl) O,S-dialkyl thiophosphates - with insecticidal, acaricidal, fungicidal and nematocidal activity | |
CH590007A5 (en) | 1-(2-Cyanoethyl)-1,2,4-triazol-3-yl (thio)phosph(on)ates - prepd. by reacting 3-hydroxy cpds. with (thio)phosphor(on)yl halides | |
DE2440761A1 (en) | Biocidal phosphonates esp. active against cotton pests, flies and aphi - prepd. by reaction of substd. phosphorohalide with substd. phenol and acid-binding agent | |
DE2415747A1 (en) | THIOLPHOSPHORIC ACID ESTERS, PROCESS FOR THEIR MANUFACTURING AND USE | |
DE2430758A1 (en) | Oxadiazolyls from hydroxydiazoles and phosphoric acid halides - with wide biocidal activity | |
CH564909A5 (en) | 1-Phosphoryl-5-amino-1,2,4-triazoles - as insecticides and acaricides from 5-aminotriazoles and bis-dimethylaminophosphoryl-chloride | |
CH578304A5 (en) | S-(1-benzotriazolyl) dithiophosphates - with insecticidal, acaricidal, fungicidal and nematocidal activity |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PL | Patent ceased |