CH578304A5 - S-(1-benzotriazolyl) dithiophosphates - with insecticidal, acaricidal, fungicidal and nematocidal activity - Google Patents
S-(1-benzotriazolyl) dithiophosphates - with insecticidal, acaricidal, fungicidal and nematocidal activityInfo
- Publication number
- CH578304A5 CH578304A5 CH1707672A CH1707672A CH578304A5 CH 578304 A5 CH578304 A5 CH 578304A5 CH 1707672 A CH1707672 A CH 1707672A CH 1707672 A CH1707672 A CH 1707672A CH 578304 A5 CH578304 A5 CH 578304A5
- Authority
- CH
- Switzerland
- Prior art keywords
- parts
- formula
- insecticidal
- acaricidal
- compound
- Prior art date
Links
- 230000000895 acaricidal effect Effects 0.000 title description 6
- 230000000749 insecticidal effect Effects 0.000 title description 6
- CTHWAVUCYKNDBS-UHFFFAOYSA-N benzotriazol-1-ylsulfanyl-dihydroxy-sulfanylidene-lambda5-phosphane Chemical class C1=CC=C2C(=C1)N=NN2SP(=S)(O)O CTHWAVUCYKNDBS-UHFFFAOYSA-N 0.000 title 1
- 230000000855 fungicidal effect Effects 0.000 title 1
- 230000001069 nematicidal effect Effects 0.000 title 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims abstract description 5
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims abstract description 3
- 229910052801 chlorine Inorganic materials 0.000 claims abstract description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims abstract description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims abstract description 3
- 150000001875 compounds Chemical class 0.000 claims description 15
- 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
- 241000238631 Hexapoda Species 0.000 claims description 3
- 241000607479 Yersinia pestis Species 0.000 claims description 3
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
- 241001465754 Metazoa Species 0.000 claims description 2
- 239000000460 chlorine Chemical group 0.000 claims description 2
- 239000001257 hydrogen Substances 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 125000002496 methyl group Chemical group [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
- 239000000575 pesticide Substances 0.000 claims description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 2
- 230000001419 dependent effect Effects 0.000 claims 3
- -1 n - pentyl Chemical group 0.000 abstract description 5
- 229910052783 alkali metal Inorganic materials 0.000 abstract description 2
- 150000001340 alkali metals Chemical group 0.000 abstract description 2
- 125000005210 alkyl ammonium group Chemical group 0.000 abstract description 2
- VSEROABGEVRIRY-UHFFFAOYSA-N 1-(chloromethyl)benzotriazole Chemical class C1=CC=C2N(CCl)N=NC2=C1 VSEROABGEVRIRY-UHFFFAOYSA-N 0.000 abstract 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical group N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 abstract 1
- 239000004480 active ingredient Substances 0.000 description 20
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- 239000008187 granular material Substances 0.000 description 9
- 239000000203 mixture Substances 0.000 description 8
- 238000012360 testing method Methods 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- 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
- 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
- 238000002360 preparation method Methods 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 239000013543 active substance Substances 0.000 description 4
- 239000000654 additive 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
- 239000007921 spray 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
- 241000196324 Embryophyta Species 0.000 description 3
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 241000258916 Leptinotarsa decemlineata Species 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
- 238000010790 dilution Methods 0.000 description 3
- 239000012895 dilution Substances 0.000 description 3
- 235000013601 eggs Nutrition 0.000 description 3
- 239000004495 emulsifiable concentrate Substances 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 241000238876 Acari Species 0.000 description 2
- 240000002024 Gossypium herbaceum Species 0.000 description 2
- 235000004341 Gossypium herbaceum Nutrition 0.000 description 2
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 2
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- 241000949016 Rhipicephalus bursa Species 0.000 description 2
- 241000238680 Rhipicephalus microplus Species 0.000 description 2
- 244000061456 Solanum tuberosum Species 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 241001454293 Tetranychus urticae Species 0.000 description 2
- 125000003354 benzotriazolyl group Chemical group N1N=NC2=C1C=CC=C2* 0.000 description 2
- QARVLSVVCXYDNA-UHFFFAOYSA-N bromobenzene Chemical compound BrC1=CC=CC=C1 QARVLSVVCXYDNA-UHFFFAOYSA-N 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 150000002191 fatty alcohols Chemical class 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 239000003921 oil Substances 0.000 description 2
- 235000019198 oils Nutrition 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
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 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
- 239000002244 precipitate 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
- 239000004563 wettable powder Substances 0.000 description 2
- 239000008096 xylene 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
- IFFHHNRFDNXJKI-UHFFFAOYSA-N 5-chloro-1-(chloromethyl)benzotriazole Chemical compound ClC1=CC=C2N(CCl)N=NC2=C1 IFFHHNRFDNXJKI-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
- 241000238660 Blattidae Species 0.000 description 1
- 241000907223 Bruchinae Species 0.000 description 1
- 241000257161 Calliphoridae Species 0.000 description 1
- 241001124134 Chrysomelidae Species 0.000 description 1
- 241001414835 Cimicidae Species 0.000 description 1
- 241000255749 Coccinellidae Species 0.000 description 1
- 229920000742 Cotton Polymers 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
- 235000009161 Espostoa lanata Nutrition 0.000 description 1
- 240000001624 Espostoa lanata Species 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
- 241000256257 Heliothis Species 0.000 description 1
- 241000256244 Heliothis virescens Species 0.000 description 1
- 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 1
- 206010061217 Infestation Diseases 0.000 description 1
- 241000238889 Ixodidae Species 0.000 description 1
- 241001124557 Lymantriidae Species 0.000 description 1
- 241000257226 Muscidae Species 0.000 description 1
- 241000256259 Noctuidae Species 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 244000046052 Phaseolus vulgaris Species 0.000 description 1
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 241001415279 Pseudococcidae Species 0.000 description 1
- 241000258921 Pulicidae Species 0.000 description 1
- 241000255893 Pyralidae Species 0.000 description 1
- 241001510071 Pyrrhocoridae Species 0.000 description 1
- 241001124072 Reduviidae Species 0.000 description 1
- 241000254062 Scarabaeidae Species 0.000 description 1
- 241000256248 Spodoptera Species 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
- 241001454295 Tetranychidae Species 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
- 150000001335 aliphatic alkanes 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
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 230000003115 biocidal effect Effects 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 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
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 238000011161 development 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
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- NAGJZTKCGNOGPW-UHFFFAOYSA-N dithiophosphoric acid Chemical compound OP(O)(S)=S NAGJZTKCGNOGPW-UHFFFAOYSA-N 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 235000013305 food Nutrition 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
- 239000005457 ice water Substances 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 230000001418 larval effect Effects 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 238000002156 mixing 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
- 239000012074 organic phase Substances 0.000 description 1
- 150000002903 organophosphorus compounds Chemical class 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 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
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 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
- 150000003672 ureas Chemical class 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/547—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom
- C07F9/6515—Heterocyclic compounds, e.g. containing phosphorus as a ring hetero atom having three nitrogen atoms as the only ring hetero atoms
- C07F9/6518—Five-membered rings
- C07F9/65188—Five-membered rings condensed with carbocyclic rings or carbocyclic ring systems
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
Cpds. of formula (I) (where R1 is Me or Et; R2 is n-Pr, i-Pr, n-Bu, n - pentyl, allyl or proparyl; R3 is H, Cl or CF3) are new cpds. pref. prepd. by reacting the corresp. 1-chloromethyl-benzotriazoles with MSP(O)(OR1)SR2 (M = alkali metal, NH4 or alkylammonium).
Description
Die vorliegende Erfindung betrifft ein Schädlingsbekämpfungsmittel, enthaltend als aktive Komponente ein Benztriazolyl-derivat, und seine Verwendung in der Schädlingsbekämpfung. Die Benztriazolyl-derivate haben die Formel (1)
EMI1.1
worin
R1 Methyl oder Äthyl,
R2 n-Propyl, Isopropyl, n-Butyl, n-Pentyl, Allyl oder Propargyl und
R3 Wasserstoff, Chlor oder Trifluormethyl bedeuten.
Wegen ihrer Wirkung von besonderer Bedeutung sind Verbindungen der Formel I, worin
R1 Äthyl und
R2 n-Propyl bedeuten.
Die Verbindungen der Formel I können nach folgendem an sich bekanntem Verfahren hergestellt werden:
EMI1.2
In den Formeln II und III haben R1 bis R3 die für die Formel I angegebene Bedeutung und Me steht für ein Alkalimetall, insbesondere Natrium oder Kalium, Ammonium oder Alkylammonium.
Die Umsetzung wird bei normalem Druck, bei einer Tem- peratur von -10-120" C, insbesondere bei + 20-70" C und in gegenüber den Reaktionsteilnehmern inerten Lösungsoder Verdünnungsmitteln durchgeführt. Als Lösungs- oder Verdünnungsmittel sind z. B. folgende geeignet: aromatische Kohlenwasserstoffe, wie Benzol, Toluol, Halogenkohlenwasserstoffe, Chlorbenzol, Polychlorbenzole, Brombenzol, chlorierte Alkane mit 1 bis 3 Kohlenstoffatomen, Äther, wie Dioxan, Tetrahydrofuran; Ester, wie Essigsäureäthylester; Ketone, wie Aceton, Methyläthylketon, Diäthylketon, Nitrile, z. B. Acetonitril.
Ausgangsstoffe der Formln II sind bekannt oder können analog bekannter 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. Sie 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:
Tettignoiidae, 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 Ixodidae, Argasidae, 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/oder 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-, Verdickungs-, Binde- und/oder Düngemitteln.
Zur Applikation können die Verbindungen der Formeln I und Ia 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 Formeln I mit den geeigneten Trägerstoffen, gegebenenfalls unter Zusatz von gegenüber den Wirkstoffen inerten Dispergier- oder Löungsmitteln.
Die Wirkstoffe können in den folgenden Aufarbeitungsformen vorliegen und angewendet werden: Feste Ausfarbeitungsformen:
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 nischen 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 % oder sogar reiner Wirkstoff eingesetzt werden können.
Die Wirkstoffe der Formeln 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 %igen, 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) 25eigen 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).
Herstellungsbeispiel
Herstellung von O-Äthyl-S-(n)-propyl-S-[(5-chlor benztriazol- 1 -yl)-methyl] -dithiophosphat
20,2 g 1-Chlormethyl-5-chlorbenztriazol und 23,5 Kaliumsalz des Dithiophosphorsäure-O-äthyl-S-(n)-propylesters werden in 200 ml absolutem Aceton unter Rühren gelöst. Anschliessend wird auf 50 C erwärmt und 15 Stunden bei dieser Temperatur gerührt, wobei ein feiner weisser Niederschlag ausfällt. Die Aceton-Lösung wird nach dem Abfiltrieren dieses Niederschlages bei Raumtemperatur zur Trockene eingedampft. Das zurückbleibende, hellbraune Ö1 wird in 300 ml Äther gelöst. Nach dem Waschen der Ätherlösung mit 100 ml Eiswasser wird die organische Phase mit Magnesiumsulfat getrocknet und der Äther abgedampft.
Man erhält die Verbindung der Formel
EMI2.1
als hellbraunes Öl, mit einer Refraktion von nD40 = 1,6685.
Auf analoge Weise werden auch folgende Verbindungen hergestellt:
EMI2.2
EMI3.1
Beispiel 1
Insektizide Frassgift-Wirkung Baumwollpflanzen und Kartoffelstauden wurden mit einer 0,05 %igen wässrigen Wirkstoffemulsion (erhalten aus einem 10%igen emulgierbaren Konzentrat) besprüht.
Nach dem Antrockenen des Belages wurden die Baumwollpflanzen je mit Spodoptera littoralis- bzw. Heliothis virescens-Larven L3 und die Kartoffelstauden mit Kartoffelkäfer-Larven (Leptinotarsa decemlineata) besetzt. Der Versuch wurde bei 24 C und 60 % relativer Luftfeuchtigkeit durchgeführt.
Die Verbindungen gemäss Herstellungsbeispiel zeigten im obigen Test eine gute insektizide Frassgift-Wirkung gegen Spodoptera-, Heliothis- und Leptinotarsa decemlineata-Larven.
Beispiel 2
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 Aktivusbstanz pro Hektare) in das Paddy-Wasser. Die Auswertung auf insektizide Wirkung erfolgte 10 Tage nach der Zugabe des Granulates.
Die Verbindungen gemäss Herstellungsbeispiel wirkten im obigen Test gegen Chilo suppressalis.
Beispiel 3
Wirkung gegen Zecken A. Rhipicephalus bursa
Je 5 adulte Zecken bzw. 50 Zeckenlarven wurden in ein Glasröhrchen gezählt und für 1 bis 2 Minuten in 2 ml einer wässrigen Emulsion aus einer Verdünnungsreihe mit je 100, 10, 1 oder 0,I ppm Testsubstanz getaucht. Das Röhrchen wurde dann mit einem genormten Wattebausch verschlossen und auf den Kopf gestellt, damit die Wirkstoffemulsion von der Watte aufgenommen werden konnte.
Die Auswertung erfolgte bei den Adulten nach 2 Wochen und bei den Larven nach 2 Tagen. Für jeden Versuch liefen 2 Wiederholungen.
B. Boophilus microplus (Larven)
Mit einer analogen Verdünnungsreihe wie beim Test A wurden mit je 20 sensiblen resp. OP-resistenten Larven Versuche durchgeführt. (Die Resistenz bezieht sich auf die Verträglichkeit von Diazinon.)
Die Verbindungen gemäss Herstellungsbeispiel wirkten in diesen Tests gegen Adulte von Larven von Rhipicephalus bursa und sensible resp. OP-resistente Larven von Boophilus microplus.
Beispiel 4
Akarizide Wirkung
Phaseolus vulgaris (Pflanzen) 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 gemäss Herstellungsbeispiel wirkten im obigen Test gegen Adulte, Larven und Eier von Tetranychus urticae.
The present invention relates to a pesticide containing a benzotriazolyl derivative as the active component and its use in pest control. The benzotriazolyl derivatives have the formula (1)
EMI1.1
wherein
R1 methyl or ethyl,
R2 n-propyl, isopropyl, n-butyl, n-pentyl, allyl or propargyl and
R3 is hydrogen, chlorine or trifluoromethyl.
Because of their action of particular importance are compounds of the formula I in which
R1 ethyl and
R2 mean n-propyl.
The compounds of the formula I can be prepared by the following process known per se:
EMI1.2
In the formulas II and III, R1 to R3 have the meaning given for the formula I and Me represents an alkali metal, in particular sodium or potassium, ammonium or alkylammonium.
The reaction is carried out at normal pressure, at a temperature of -10-120 ° C., in particular at + 20-70 ° C., and in solvents or diluents which are inert towards the reactants. As a solvent or diluent, for. B. the following are suitable: aromatic hydrocarbons, such as benzene, toluene, halogenated hydrocarbons, chlorobenzene, polychlorobenzenes, bromobenzene, chlorinated alkanes with 1 to 3 carbon atoms, ethers, such as dioxane, tetrahydrofuran; Esters, such as ethyl acetate; Ketones such as acetone, methyl ethyl ketone, diethyl ketone, nitriles, e.g. B. acetonitrile.
Starting materials of the formula II are known or 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. But they have in particular insecticidal and acaricidal properties and can be used against all stages of development, such. B. eggs, larvae, pupae, nymphs and adults, are used by insects and representatives of the order Akarina, such as. B. against family insects:
Tettignoiidae, 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 and Pulicidae, as well as acarids of the families Ixodidae, Argasidae, 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. B.
organic phosphorus compounds,
Derivatives of nitrophenols,
Formamidine,
Ureas,
Carbamates and / or 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 formulas I and Ia can be processed into dusts, emulsion concentrates, granules, dispersions, sprays, into solutions or slurries in customary formulations, which are common knowledge in application technology.
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 niche 0.1 to 95%, it should be mentioned that concentrations of up to 99.5% or even pure active ingredient can be used for application from the 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) 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 of gasoline (boiling point 160-190 C).
Manufacturing example
Production of O-ethyl-S- (n) -propyl-S - [(5-chlorobenztriazol-1 -yl) -methyl] -dithiophosphate
20.2 g of 1-chloromethyl-5-chlorobenzotriazole and 23.5 g of potassium salt of dithiophosphoric acid O-ethyl-S- (n) -propyl ester are dissolved in 200 ml of absolute acetone with stirring. The mixture is then heated to 50 ° C. and stirred for 15 hours at this temperature, a fine white precipitate separating out. After this precipitate has been filtered off, the acetone solution is evaporated to dryness at room temperature. The remaining, light brown oil is dissolved in 300 ml of ether. After washing the ethereal solution with 100 ml of ice water, the organic phase is dried with magnesium sulfate and the ether is evaporated.
The compound of the formula is obtained
EMI2.1
as a light brown oil, with a refraction of nD40 = 1.6685.
The following connections are also established in the same way:
EMI2.2
EMI3.1
example 1
Insecticidal food poison effect Cotton plants and potato plants were sprayed with a 0.05% aqueous active substance emulsion (obtained from a 10% emulsifiable concentrate).
After the covering had dried on, the cotton plants were each populated with Spodoptera littoralis or Heliothis virescens larvae L3 and the potato plants with Colorado beetle larvae (Leptinotarsa decemlineata). The experiment was carried out at 24 C and 60% relative humidity.
In the above test, the compounds according to the preparation example showed a good insecticidal feed poison action against Spodoptera, Heliothis and Leptinotarsa decemlineata larvae.
Example 2
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 of active substance per hectare) in the paddy water. The insecticidal activity was evaluated 10 days after the granules had been added.
The compounds according to the preparation example acted against Chilo suppressalis in the above test.
Example 3
Action against ticks A. Rhipicephalus bursa
5 adult ticks or 50 tick larvae were counted in a glass tube and immersed for 1 to 2 minutes in 2 ml of an aqueous emulsion from a dilution series with 100, 10, 1 or 0.1 ppm test substance each. The tube was then closed with a standardized cotton ball and turned upside down so that the active ingredient emulsion could be absorbed by the cotton wool.
The evaluation was carried out after 2 weeks for the adults and after 2 days for the larvae. Two repetitions were run for each attempt.
B. Boophilus microplus (larvae)
With an analogous dilution series as in test A, 20 sensitive resp. OP-resistant larval experiments were carried out. (The resistance refers to the tolerance of Diazinon.)
The compounds according to the preparation example worked in these tests against adults of larvae of Rhipicephalus bursa and sensitive resp. OP-resistant larvae of Boophilus microplus.
Example 4
Acaricidal effect
Phaseolus vulgaris (plants) were covered 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.
In the above test, the compounds according to the preparation example acted against adults, larvae and eggs of Tetranychus urticae.
Claims (1)
Priority Applications (7)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH1707672A CH578304A5 (en) | 1972-11-23 | 1972-11-23 | S-(1-benzotriazolyl) dithiophosphates - with insecticidal, acaricidal, fungicidal and nematocidal activity |
NL7315882A NL7315882A (en) | 1972-11-23 | 1973-11-20 | |
DE19732357910 DE2357910A1 (en) | 1972-11-23 | 1973-11-20 | BENZTRIAZOLYL DERIVATIVES, THE PROCESS FOR THEIR MANUFACTURING AND THEIR USE |
JP13158473A JPS49133530A (en) | 1972-11-23 | 1973-11-21 | |
FR7341618A FR2207928B1 (en) | 1972-11-23 | 1973-11-22 | |
GB5427873A GB1440796A (en) | 1972-11-23 | 1973-11-22 | Phosphorus-containing benztriazolyl derivatives having pesticidal properties |
BE138016A BE807636A (en) | 1972-11-23 | 1973-11-22 | PHOSPHORUS ACID ESTERS AND PESTICIDE PRODUCTS CONTAINING THEM |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH1707672A CH578304A5 (en) | 1972-11-23 | 1972-11-23 | S-(1-benzotriazolyl) dithiophosphates - with insecticidal, acaricidal, fungicidal and nematocidal activity |
Publications (1)
Publication Number | Publication Date |
---|---|
CH578304A5 true CH578304A5 (en) | 1976-08-13 |
Family
ID=4422570
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CH1707672A CH578304A5 (en) | 1972-11-23 | 1972-11-23 | S-(1-benzotriazolyl) dithiophosphates - with insecticidal, acaricidal, fungicidal and nematocidal activity |
Country Status (2)
Country | Link |
---|---|
BE (1) | BE807636A (en) |
CH (1) | CH578304A5 (en) |
-
1972
- 1972-11-23 CH CH1707672A patent/CH578304A5/en not_active IP Right Cessation
-
1973
- 1973-11-22 BE BE138016A patent/BE807636A/en unknown
Also Published As
Publication number | Publication date |
---|---|
BE807636A (en) | 1974-05-22 |
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