DE2210092A1 - Pesticides - Google Patents
PesticidesInfo
- Publication number
- DE2210092A1 DE2210092A1 DE19722210092 DE2210092A DE2210092A1 DE 2210092 A1 DE2210092 A1 DE 2210092A1 DE 19722210092 DE19722210092 DE 19722210092 DE 2210092 A DE2210092 A DE 2210092A DE 2210092 A1 DE2210092 A1 DE 2210092A1
- Authority
- DE
- Germany
- Prior art keywords
- formula
- species
- compounds
- alkyl
- methyl
- 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.)
- Pending
Links
- 239000000575 pesticide Substances 0.000 title claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 35
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- 229910052760 oxygen Inorganic materials 0.000 claims description 11
- 239000000969 carrier Substances 0.000 claims description 8
- 229910052717 sulfur Inorganic materials 0.000 claims description 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 7
- 239000000654 additive Substances 0.000 claims description 7
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 7
- 239000001301 oxygen Substances 0.000 claims description 7
- 239000011593 sulfur Substances 0.000 claims description 7
- 241000238631 Hexapoda Species 0.000 claims description 4
- 241001465754 Metazoa Species 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- SLFVYFOEHHLHDW-UHFFFAOYSA-N n-(trifluoromethyl)aniline Chemical compound FC(F)(F)NC1=CC=CC=C1 SLFVYFOEHHLHDW-UHFFFAOYSA-N 0.000 claims description 4
- 241000607479 Yersinia pestis Species 0.000 claims description 3
- 235000013311 vegetables Nutrition 0.000 claims description 3
- 238000002360 preparation method Methods 0.000 claims description 2
- 235000001674 Agaricus brunnescens Nutrition 0.000 claims 1
- 241000341511 Nematodes Species 0.000 claims 1
- 244000045947 parasite Species 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 description 42
- -1 ethyl propyl Chemical group 0.000 description 25
- 241000894007 species Species 0.000 description 20
- 239000000126 substance Substances 0.000 description 14
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 12
- 239000008187 granular material Substances 0.000 description 12
- 239000002253 acid Substances 0.000 description 11
- 238000012360 testing method Methods 0.000 description 11
- RYYWUUFWQRZTIU-UHFFFAOYSA-K thiophosphate Chemical compound [O-]P([O-])([O-])=S RYYWUUFWQRZTIU-UHFFFAOYSA-K 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 10
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
- 241000196324 Embryophyta Species 0.000 description 9
- 239000000203 mixture Substances 0.000 description 9
- 150000003839 salts Chemical class 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- 229910019142 PO4 Inorganic materials 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 8
- 239000000839 emulsion Substances 0.000 description 8
- 239000010452 phosphate Substances 0.000 description 8
- 241000233866 Fungi Species 0.000 description 7
- 239000013543 active substance Substances 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 7
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 7
- 239000000725 suspension Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- 239000005995 Aluminium silicate Substances 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- 235000012211 aluminium silicate Nutrition 0.000 description 6
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
- 239000012141 concentrate Substances 0.000 description 6
- 239000002270 dispersing agent Substances 0.000 description 6
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 6
- 229910052757 nitrogen Inorganic materials 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- 239000007921 spray Substances 0.000 description 6
- 239000004563 wettable powder Substances 0.000 description 6
- 241000238876 Acari Species 0.000 description 5
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 5
- 230000000895 acaricidal effect Effects 0.000 description 5
- 239000003513 alkali Substances 0.000 description 5
- 239000004495 emulsifiable concentrate Substances 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 5
- 230000000749 insecticidal effect Effects 0.000 description 5
- 239000003960 organic solvent Substances 0.000 description 5
- 239000006072 paste Substances 0.000 description 5
- 238000012545 processing Methods 0.000 description 5
- 239000002689 soil Substances 0.000 description 5
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 4
- 244000046052 Phaseolus vulgaris Species 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
- 239000000853 adhesive Substances 0.000 description 4
- 230000001070 adhesive effect Effects 0.000 description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 4
- 239000004202 carbamide Substances 0.000 description 4
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 239000003795 chemical substances by application Substances 0.000 description 4
- 239000007859 condensation product Substances 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- 235000013312 flour Nutrition 0.000 description 4
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
- 238000002156 mixing Methods 0.000 description 4
- 229920001223 polyethylene glycol Polymers 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 159000000000 sodium salts Chemical class 0.000 description 4
- 238000005507 spraying Methods 0.000 description 4
- 239000008096 xylene Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 3
- 241000221787 Erysiphe Species 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-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
- 241000258916 Leptinotarsa decemlineata Species 0.000 description 3
- 241001143352 Meloidogyne Species 0.000 description 3
- 241000244206 Nematoda Species 0.000 description 3
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
- 239000002202 Polyethylene glycol Substances 0.000 description 3
- 241001454293 Tetranychus urticae Species 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000011230 binding agent Substances 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 235000013339 cereals Nutrition 0.000 description 3
- 239000000460 chlorine Substances 0.000 description 3
- 229910052801 chlorine Inorganic materials 0.000 description 3
- 238000011161 development Methods 0.000 description 3
- 150000002148 esters Chemical class 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- CDBYLPFSWZWCQE-UHFFFAOYSA-L sodium carbonate Substances [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 3
- 230000009885 systemic effect Effects 0.000 description 3
- 239000000454 talc Substances 0.000 description 3
- 229910052623 talc Inorganic materials 0.000 description 3
- 241001124076 Aphididae Species 0.000 description 2
- 241001425390 Aphis fabae Species 0.000 description 2
- 241000283690 Bos taurus Species 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- STUSTWKEFDQFFZ-UHFFFAOYSA-N Chlordimeform Chemical compound CN(C)C=NC1=CC=C(Cl)C=C1C STUSTWKEFDQFFZ-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- SPJOZZSIXXJYBT-UHFFFAOYSA-N Fenson Chemical compound C1=CC(Cl)=CC=C1OS(=O)(=O)C1=CC=CC=C1 SPJOZZSIXXJYBT-UHFFFAOYSA-N 0.000 description 2
- 241000223221 Fusarium oxysporum Species 0.000 description 2
- 240000002024 Gossypium herbaceum Species 0.000 description 2
- 235000004341 Gossypium herbaceum Nutrition 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 239000005909 Kieselgur Substances 0.000 description 2
- 241000227653 Lycopersicon Species 0.000 description 2
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 2
- 241001518729 Monilinia Species 0.000 description 2
- 241001226034 Nectria <echinoderm> Species 0.000 description 2
- 241000190509 Ophiobolus Species 0.000 description 2
- 241000228143 Penicillium Species 0.000 description 2
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 2
- 241000222831 Phialophora <Chaetothyriales> Species 0.000 description 2
- RZKYEQDPDZUERB-UHFFFAOYSA-N Pindone Chemical compound C1=CC=C2C(=O)C(C(=O)C(C)(C)C)C(=O)C2=C1 RZKYEQDPDZUERB-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- 241001533598 Septoria Species 0.000 description 2
- 244000061456 Solanum tuberosum Species 0.000 description 2
- 241000228446 Taphrina Species 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- QUWSDLYBOVGOCW-UHFFFAOYSA-N Tetrasul Chemical compound C1=CC(Cl)=CC=C1SC1=CC(Cl)=C(Cl)C=C1Cl QUWSDLYBOVGOCW-UHFFFAOYSA-N 0.000 description 2
- 241000221561 Ustilaginales Species 0.000 description 2
- 240000006677 Vicia faba Species 0.000 description 2
- 235000010749 Vicia faba Nutrition 0.000 description 2
- 239000000642 acaricide Substances 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 2
- 239000002585 base Substances 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 235000019993 champagne Nutrition 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 239000013256 coordination polymer Substances 0.000 description 2
- 235000013601 eggs Nutrition 0.000 description 2
- FXBLJWDJXBQLEL-UHFFFAOYSA-N ethenyl dimethyl phosphate Chemical compound COP(=O)(OC)OC=C FXBLJWDJXBQLEL-UHFFFAOYSA-N 0.000 description 2
- 230000002349 favourable effect Effects 0.000 description 2
- 239000003337 fertilizer Substances 0.000 description 2
- 230000000855 fungicidal effect Effects 0.000 description 2
- JLYXXMFPNIAWKQ-UHFFFAOYSA-N gamma-hexachlorocyclohexane Natural products ClC1C(Cl)C(Cl)C(Cl)C(Cl)C1Cl JLYXXMFPNIAWKQ-UHFFFAOYSA-N 0.000 description 2
- JLYXXMFPNIAWKQ-GNIYUCBRSA-N gamma-hexachlorocyclohexane Chemical compound Cl[C@H]1[C@H](Cl)[C@@H](Cl)[C@@H](Cl)[C@H](Cl)[C@H]1Cl JLYXXMFPNIAWKQ-GNIYUCBRSA-N 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000000227 grinding Methods 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 208000015181 infectious disease Diseases 0.000 description 2
- 239000002917 insecticide Substances 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 2
- 239000002480 mineral oil Substances 0.000 description 2
- 230000001069 nematicidal effect Effects 0.000 description 2
- LQNUZADURLCDLV-UHFFFAOYSA-N nitrobenzene Chemical compound [O-][N+](=O)C1=CC=CC=C1 LQNUZADURLCDLV-UHFFFAOYSA-N 0.000 description 2
- FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
- 229920000151 polyglycol Polymers 0.000 description 2
- 239000010695 polyglycol Substances 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 229910000029 sodium carbonate Inorganic materials 0.000 description 2
- LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
- 230000000087 stabilizing effect Effects 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 235000015112 vegetable and seed oil Nutrition 0.000 description 2
- 239000008158 vegetable oil Substances 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- DNXHEGUUPJUMQT-UHFFFAOYSA-N (+)-estrone Natural products OC1=CC=C2C3CCC(C)(C(CC4)=O)C4C3CCC2=C1 DNXHEGUUPJUMQT-UHFFFAOYSA-N 0.000 description 1
- ZCVAOQKBXKSDMS-AQYZNVCMSA-N (+)-trans-allethrin Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)OC1C(C)=C(CC=C)C(=O)C1 ZCVAOQKBXKSDMS-AQYZNVCMSA-N 0.000 description 1
- QUZZCCGGEFBGTD-DUXPYHPUSA-N (2,3-dinitrophenyl) (e)-but-2-enoate Chemical compound C\C=C\C(=O)OC1=CC=CC([N+]([O-])=O)=C1[N+]([O-])=O QUZZCCGGEFBGTD-DUXPYHPUSA-N 0.000 description 1
- FHNKBSDJERHDHZ-UHFFFAOYSA-N (2,4-dimethylphenyl)methyl 2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate Chemical compound CC1(C)C(C=C(C)C)C1C(=O)OCC1=CC=C(C)C=C1C FHNKBSDJERHDHZ-UHFFFAOYSA-N 0.000 description 1
- OTKXWJHPGBRXCR-UHFFFAOYSA-N (2-chloro-4-nitrophenoxy)-dimethoxy-sulfanylidene-$l^{5}-phosphane Chemical compound COP(=S)(OC)OC1=CC=C([N+]([O-])=O)C=C1Cl OTKXWJHPGBRXCR-UHFFFAOYSA-N 0.000 description 1
- FSJYRLHKLVGCNH-UHFFFAOYSA-N (3-tert-butylphenyl) n-methylcarbamate Chemical compound CNC(=O)OC1=CC=CC(C(C)(C)C)=C1 FSJYRLHKLVGCNH-UHFFFAOYSA-N 0.000 description 1
- KPMWGGRSOPMANK-UHFFFAOYSA-N (6-chloro-1,3-benzodioxol-5-yl)methyl 2,2-dimethyl-3-(2-methylprop-1-enyl)cyclopropane-1-carboxylate Chemical compound CC1(C)C(C=C(C)C)C1C(=O)OCC(C(=C1)Cl)=CC2=C1OCO2 KPMWGGRSOPMANK-UHFFFAOYSA-N 0.000 description 1
- FZENGILVLUJGJX-NSCUHMNNSA-N (E)-acetaldehyde oxime Chemical compound C\C=N\O FZENGILVLUJGJX-NSCUHMNNSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- OCJBOOLMMGQPQU-UHFFFAOYSA-N 1,4-dichlorobenzene Chemical compound ClC1=CC=C(Cl)C=C1 OCJBOOLMMGQPQU-UHFFFAOYSA-N 0.000 description 1
- SVGYHIKXGFTUAG-UHFFFAOYSA-N 1-benzyl-2-(2-benzyl-4,4-dichlorocyclohexa-1,5-dien-1-yl)sulfanyl-5,5-dichlorocyclohexa-1,3-diene Chemical compound C=1C=CC=CC=1CC=1CC(Cl)(Cl)C=CC=1SC=1C=CC(Cl)(Cl)CC=1CC1=CC=CC=C1 SVGYHIKXGFTUAG-UHFFFAOYSA-N 0.000 description 1
- RMSGQZDGSZOJMU-UHFFFAOYSA-N 1-butyl-2-phenylbenzene Chemical group CCCCC1=CC=CC=C1C1=CC=CC=C1 RMSGQZDGSZOJMU-UHFFFAOYSA-N 0.000 description 1
- FMTFEIJHMMQUJI-NJAFHUGGSA-N 102130-98-3 Natural products CC=CCC1=C(C)[C@H](CC1=O)OC(=O)[C@@H]1[C@@H](C=C(C)C)C1(C)C FMTFEIJHMMQUJI-NJAFHUGGSA-N 0.000 description 1
- PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 description 1
- OWZPCEFYPSAJFR-UHFFFAOYSA-N 2-(butan-2-yl)-4,6-dinitrophenol Chemical compound CCC(C)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O OWZPCEFYPSAJFR-UHFFFAOYSA-N 0.000 description 1
- NTHGWXIWFHGPLK-UHFFFAOYSA-N 2-dimethoxyphosphinothioylsulfanyl-1-morpholin-4-ylethanone Chemical compound COP(=S)(OC)SCC(=O)N1CCOCC1 NTHGWXIWFHGPLK-UHFFFAOYSA-N 0.000 description 1
- BLTAWVIBZKXONU-UHFFFAOYSA-N 2-ethylsulfanylethoxy-dihydroxy-sulfanylidene-lambda5-phosphane Chemical compound CCSCCOP(O)(O)=S BLTAWVIBZKXONU-UHFFFAOYSA-N 0.000 description 1
- OIULAULHYHSZIN-UHFFFAOYSA-N 2-methoxy-4h-1,3,2$l^{5}-benzodioxaphosphinine 2-oxide Chemical compound C1=CC=C2OP(OC)(=O)OCC2=C1 OIULAULHYHSZIN-UHFFFAOYSA-N 0.000 description 1
- ZRDUSMYWDRPZRM-UHFFFAOYSA-N 2-sec-butyl-4,6-dinitrophenyl 3-methylbut-2-enoate Chemical compound CCC(C)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1OC(=O)C=C(C)C ZRDUSMYWDRPZRM-UHFFFAOYSA-N 0.000 description 1
- KNIUHBNRWZGIQQ-UHFFFAOYSA-N 7-diethoxyphosphinothioyloxy-4-methylchromen-2-one Chemical compound CC1=CC(=O)OC2=CC(OP(=S)(OCC)OCC)=CC=C21 KNIUHBNRWZGIQQ-UHFFFAOYSA-N 0.000 description 1
- 241000223600 Alternaria Species 0.000 description 1
- 241000213004 Alternaria solani Species 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 239000004254 Ammonium phosphate Substances 0.000 description 1
- 241000380490 Anguina Species 0.000 description 1
- 241001444083 Aphanomyces Species 0.000 description 1
- 241000294569 Aphelenchoides Species 0.000 description 1
- 241000239290 Araneae Species 0.000 description 1
- 241000238888 Argasidae Species 0.000 description 1
- 241000228212 Aspergillus Species 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 241000238660 Blattidae Species 0.000 description 1
- 241000123650 Botrytis cinerea Species 0.000 description 1
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- KVGLBTYUCJYMND-UHFFFAOYSA-N fonofos Chemical compound CCOP(=S)(CC)SC1=CC=CC=C1 KVGLBTYUCJYMND-UHFFFAOYSA-N 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- IVJISJACKSSFGE-UHFFFAOYSA-N formaldehyde;1,3,5-triazine-2,4,6-triamine Chemical compound O=C.NC1=NC(N)=NC(N)=N1 IVJISJACKSSFGE-UHFFFAOYSA-N 0.000 description 1
- 230000002464 fungitoxic effect Effects 0.000 description 1
- 238000005469 granulation Methods 0.000 description 1
- 230000003179 granulation Effects 0.000 description 1
- GOQYKNQRPGWPLP-UHFFFAOYSA-N heptadecan-1-ol Chemical class CCCCCCCCCCCCCCCCCO GOQYKNQRPGWPLP-UHFFFAOYSA-N 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical class CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 1
- GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
- 150000004679 hydroxides Chemical class 0.000 description 1
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 239000012442 inert solvent Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 150000007529 inorganic bases Chemical class 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- RNNBHZYEKNHLKT-UHFFFAOYSA-N isopropylmethylpyrazolyl dimethylcarbamate Chemical compound CC(C)N1N=C(C)C=C1OC(=O)N(C)C RNNBHZYEKNHLKT-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 239000004816 latex Substances 0.000 description 1
- 229920000126 latex Polymers 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 239000006028 limestone Substances 0.000 description 1
- 239000000395 magnesium oxide Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N magnesium oxide Inorganic materials [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- 235000012245 magnesium oxide Nutrition 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- AXZKOIWUVFPNLO-UHFFFAOYSA-N magnesium;oxygen(2-) Chemical compound [O-2].[Mg+2] AXZKOIWUVFPNLO-UHFFFAOYSA-N 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- GEPDYQSQVLXLEU-AATRIKPKSA-N methyl (e)-3-dimethoxyphosphoryloxybut-2-enoate Chemical compound COC(=O)\C=C(/C)OP(=O)(OC)OC GEPDYQSQVLXLEU-AATRIKPKSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- VCLYJTVFGQHHHD-UHFFFAOYSA-N methyl-(4-nitrophenoxy)-phenoxy-sulfanylidene-$l^{5}-phosphane Chemical compound C=1C=C([N+]([O-])=O)C=CC=1OP(=S)(C)OC1=CC=CC=C1 VCLYJTVFGQHHHD-UHFFFAOYSA-N 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 229960001952 metrifonate Drugs 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- KRTSDMXIXPKRQR-AATRIKPKSA-N monocrotophos Chemical compound CNC(=O)\C=C(/C)OP(=O)(OC)OC KRTSDMXIXPKRQR-AATRIKPKSA-N 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical class C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- GQPLMRYTRLFLPF-UHFFFAOYSA-N nitrous oxide Inorganic materials [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 description 1
- 231100001184 nonphytotoxic Toxicity 0.000 description 1
- 230000009965 odorless effect Effects 0.000 description 1
- 150000002903 organophosphorus compounds Chemical class 0.000 description 1
- 230000017448 oviposition Effects 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 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 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 230000003071 parasitic effect Effects 0.000 description 1
- LCCNCVORNKJIRZ-UHFFFAOYSA-N parathion Chemical compound CCOP(=S)(OCC)OC1=CC=C([N+]([O-])=O)C=C1 LCCNCVORNKJIRZ-UHFFFAOYSA-N 0.000 description 1
- RLBIQVVOMOPOHC-UHFFFAOYSA-N parathion-methyl Chemical compound COP(=S)(OC)OC1=CC=C([N+]([O-])=O)C=C1 RLBIQVVOMOPOHC-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000000546 pharmaceutical excipient Substances 0.000 description 1
- BULVZWIRKLYCBC-UHFFFAOYSA-N phorate Chemical compound CCOP(=S)(OCC)SCSCC BULVZWIRKLYCBC-UHFFFAOYSA-N 0.000 description 1
- LMNZTLDVJIUSHT-UHFFFAOYSA-N phosmet Chemical compound C1=CC=C2C(=O)N(CSP(=S)(OC)OC)C(=O)C2=C1 LMNZTLDVJIUSHT-UHFFFAOYSA-N 0.000 description 1
- UEZVMMHDMIWARA-UHFFFAOYSA-M phosphonate Chemical compound [O-]P(=O)=O UEZVMMHDMIWARA-UHFFFAOYSA-M 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- ATROHALUCMTWTB-OWBHPGMISA-N phoxim Chemical compound CCOP(=S)(OCC)O\N=C(\C#N)C1=CC=CC=C1 ATROHALUCMTWTB-OWBHPGMISA-N 0.000 description 1
- 229950001664 phoxim Drugs 0.000 description 1
- 230000003032 phytopathogenic effect Effects 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 229920002239 polyacrylonitrile Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- ODGAOXROABLFNM-UHFFFAOYSA-N polynoxylin Chemical compound O=C.NC(N)=O ODGAOXROABLFNM-UHFFFAOYSA-N 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 229920000036 polyvinylpyrrolidone Polymers 0.000 description 1
- 235000013855 polyvinylpyrrolidone Nutrition 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- TURAMGVWNUTQKH-UHFFFAOYSA-N propa-1,2-dien-1-one Chemical group C=C=C=O TURAMGVWNUTQKH-UHFFFAOYSA-N 0.000 description 1
- UMSVPCYSAUKCAZ-UHFFFAOYSA-N propane;hydrochloride Chemical compound Cl.CCC UMSVPCYSAUKCAZ-UHFFFAOYSA-N 0.000 description 1
- ZYHMJXZULPZUED-UHFFFAOYSA-N propargite Chemical compound C1=CC(C(C)(C)C)=CC=C1OC1C(OS(=O)OCC#C)CCCC1 ZYHMJXZULPZUED-UHFFFAOYSA-N 0.000 description 1
- 208000029561 pustule Diseases 0.000 description 1
- ROVGZAWFACYCSP-VUMXUWRFSA-N pyrethrin I Chemical compound CC1(C)[C@H](C=C(C)C)[C@H]1C(=O)O[C@@H]1C(C)=C(C\C=C/C=C)C(=O)C1 ROVGZAWFACYCSP-VUMXUWRFSA-N 0.000 description 1
- VJFUPGQZSXIULQ-XIGJTORUSA-N pyrethrin II Chemical compound CC1(C)[C@H](/C=C(\C)C(=O)OC)[C@H]1C(=O)O[C@@H]1C(C)=C(C\C=C/C=C)C(=O)C1 VJFUPGQZSXIULQ-XIGJTORUSA-N 0.000 description 1
- FBQQHUGEACOBDN-UHFFFAOYSA-N quinomethionate Chemical compound N1=C2SC(=O)SC2=NC2=CC(C)=CC=C21 FBQQHUGEACOBDN-UHFFFAOYSA-N 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 125000003548 sec-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 235000010288 sodium nitrite Nutrition 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
- 239000011877 solvent mixture Substances 0.000 description 1
- 238000002336 sorption--desorption measurement Methods 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000004659 sterilization and disinfection Methods 0.000 description 1
- XIUROWKZWPIAIB-UHFFFAOYSA-N sulfotep Chemical compound CCOP(=S)(OCC)OP(=S)(OCC)OCC XIUROWKZWPIAIB-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- MLGCXEBRWGEOQX-UHFFFAOYSA-N tetradifon Chemical compound C1=CC(Cl)=CC=C1S(=O)(=O)C1=CC(Cl)=C(Cl)C=C1Cl MLGCXEBRWGEOQX-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- RWRDLPDLKQPQOW-UHFFFAOYSA-N tetrahydropyrrole Substances C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 1
- RAOIDOHSFRTOEL-UHFFFAOYSA-N tetrahydrothiophene Chemical compound C1CCSC1 RAOIDOHSFRTOEL-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- ILERPRJWJPJZDN-UHFFFAOYSA-N thioquinox Chemical compound C1=CC=C2N=C(SC(=S)S3)C3=NC2=C1 ILERPRJWJPJZDN-UHFFFAOYSA-N 0.000 description 1
- 229960002447 thiram Drugs 0.000 description 1
- KUAZQDVKQLNFPE-UHFFFAOYSA-N thiram Chemical compound CN(C)C(=S)SSC(=S)N(C)C KUAZQDVKQLNFPE-UHFFFAOYSA-N 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- NFACJZMKEDPNKN-UHFFFAOYSA-N trichlorfon Chemical compound COP(=O)(OC)C(O)C(Cl)(Cl)Cl NFACJZMKEDPNKN-UHFFFAOYSA-N 0.000 description 1
- 239000002023 wood 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)
- General Health & Medical Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Dentistry (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Biochemistry (AREA)
- Molecular Biology (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
Description
SchädlingsbekämpfungsmittelPesticides
Die vorliegende Erfindung betrifft neue Trifluormethylphenylthlolphosphorsäureester, ihre Herstellung und Verwendung zur Schädlingsbekämpfung.The present invention relates to new trifluoromethylphenylthlolphosphoric acid esters, their manufacture and use for pest control.
Die Trif luormethylthjolphenylphosphor säure ester entsprechen, der Formel
XThe trifluoromethylthjolphenylphosphoric acid esters correspond to the formula
X
(D(D
worin R1 und R„ je Alkyl und X und Y je Sauerstoff oder Schwefel bedeuten.where R 1 and R "each signify alkyl and X and Y each signify oxygen or sulfur.
Die für R-, und Rp in Frage kommenden Alkylketten enthalten 1 bis K Kohlenstoffatome und können verzweigt oder geradkettig sein.The alkyl chains in question for R and Rp contain 1 to K carbon atoms and can be branched or straight-chain.
Beispiele solcher Alkylketten sind u.a. Methyl, Aethylj Propyl, Isopropyl, n-, i-, sek.- und tert. Butyl.Examples of such alkyl chains include methyl, ethyl propyl, isopropyl, n-, i-, sec- and tert. Butyl.
Von besonderer Bedeutung sind Verbindung derOf particular importance are the connections
Formel γ Formula γ
Ti Π ην Ti Π ην
/-s-Λ 9 / -s-Λ 9 (id(id
R/ R /
209840/1183209840/1183
worin R3 und R^ je C±-C Alkyl und X und Y je Sauerstoff oder Schwefel bedeuten.wherein R 3 and R ^ are each C ± -C alkyl and X and Y are each oxygen or sulfur.
Beispiele von Verbindungen der Formel (il) sind u.a.Examples of compounds of formula (II) are i.a.
CF3
R1 - s -<nT~^>
(in) CF 3
R 1 - s - <nT ~ ^> (in)
(V)(V)
worin R1, R", R111 jewherein R 1 , R ", R 111 each
OS0 OS 0
H H yH H y
(CH5O)2-P- ; (C2H5O)2-P- ; CnC3H7O)2-P- ;(CH 5 O) 2 -P-; (C 2 H 5 O) 2 -P-; CnC 3 H 7 O) 2 -P-;
? CH3Oj CH3Oj C2H5Oj (11C5H7O)2-P- ; P- ; P- oder P C2H5O (n)c H7O (1I)C3H7S ? CH 3 Oj CH 3 Oj C 2 H 5 Oj (11C 5 H 7 O) 2 -P- ; P-; P- or P C 2 H 5 O (n) c H 7 O (1I) C 3 H 7 S
Die Verbindungen der Formel I können nach an sich
bekannten Methoden hergestellt werden, in dem man z.B.:
a) ein Salz einer Verbindung der FormelThe compounds of the formula I can after per se
known methods can be produced in which, for example:
a) a salt of a compound of the formula
P-S-MP-S-M
r/r /
worin R ,R^,γ und Xdie für die Formel I angegebene Bedeutung
haben und M ein Metallatom, vorzugsweise ein Alkalimetallatom,
wie Natrium oder Kalium bedeutet, in einem Zweiphasensystem beiwherein R, R ^, γ and X have the meaning given for the formula I.
and M has a metal atom, preferably an alkali metal atom,
like sodium or potassium means, in a two-phase system
2098A0/11832098A0 / 1183
1O-1OO°C, vorzugsweise bei 20-700C, auf ein diazotiertes Trifluormethylanilin einwirken lässt. Diese Reaktion wird durch Kupfer katalysiert.10-1OO ° C, preferably at 20-70 0 C, can act on a diazotized trifluoromethylaniline. This reaction is catalyzed by copper.
Unter einem Zweiphasensystem wird dabei eine Lösung aus Wasser und einem mit Wasser nicht mischbaren organischen Lösungsmittel verstanden. Als derartige Lösungsmittel kommen z.B. Aether, Chloroform, Methylenchlorid, Aethylenchorid, Petroläther, Benzol, Toluol, Xylol, Chlorbenzol, Dichlorbenzol, Nitrobenzol in Frage. A two-phase system is understood to mean a solution of water and a water-immiscible organic solvent. Examples of such solvents are ether, chloroform, methylene chloride, ethylene chloride, petroleum ether, benzene, toluene, xylene, chlorobenzene, dichlorobenzene and nitrobenzene.
b) eine Verbindung der Formelb) a compound of the formula
P-H (VII)P-H (VII)
R2OR 2 O
mit der Verbindung der Formelwith the compound of the formula
Gl-S -^~s/ (VIII)Gl-S - ^ ~ s / (VIII)
in Gegenwart eines säurebindenden Mittels zur Reaktion bringt.reacts in the presence of an acid-binding agent.
In der Formel (VI) haben die Symbol R-,, Rp und X die für die Formel I angegebene Bedeutung.In the formula (VI), symbols R-, Rp and X have the meaning given for the formula I.
Als säurebindene Mittel kommen dabei beispielsweise folgende Basen in Betracht: tertiäre Amine, wie Triäthylamin, Dimethylanilin, Pyridin, Pyridinbasen; anorganische Basen, wie Hydroxide und Carbonate von Alkali- und Erdalkalimetallen, vorzugsweise Natrium- und Kaliumkarbonat. Diese Reaktion wird vorzugsweise in inerten Lösungsmitteln durchgeführt. Hierfür sind beispielsweise folgende geeignet: aromatische Kohlenwasserstoffe, The following bases, for example, can be used as acid-binding agents: tertiary amines, such as triethylamine, dimethylaniline, pyridine, pyridine bases; inorganic bases such as hydroxides and carbonates of alkali and alkaline earth metals, preferably sodium and potassium carbonate. This reaction is preferably carried out in inert solvents. For example, the following are suitable for this: aromatic hydrocarbons,
209840/1183209840/1183
wie Benzol, Toluol, Benzine, Chlorbenzol, Polychlorbenzole, Brombenzole; geeignete, chlorierte Alkane mit 1 bis 3 Kohlenstoffatome; Aether wie Dioxan; Tetrahydrofuran; Ester wie Essigsäureäthylester; Ketone, wie Methyläthylketon, Diäthylketon und Nitrile wie Acetonitril.such as benzene, toluene, benzines, chlorobenzene, polychlorobenzenes, bromobenzenes; suitable chlorinated alkanes having 1 to 3 carbon atoms; Ethers such as dioxane; Tetrahydrofuran; Esters such as ethyl acetate; Ketones such as methyl ethyl ketone, diethyl ketone and nitriles such as acetonitrile.
Dfe Ausgangsstoffe der Formeln (VI), (VII) und (VIII) sowie die Trifluormethylaniline sind bekannte Verbindungen, welche nach bekannten in der Literatur beschriebenen Verfahren hergestellt werden können. Die Diazotierung der Trifluormethylaniline wird nach an sich bekannten Methoden durchgeführt.Dfe starting materials of the formulas (VI), (VII) and (VIII) as well as the trifluoromethylanilines are known compounds which are obtained by known processes described in the literature can be produced. The diazotization of the trifluoromethylanilines is carried out according to methods known per se.
Die Wirkstoffe der Formel I eignen sich zur Bekämpfung der verschiedenartigsten tierischen und pflanzlichen Schädlinge. Sie können z.B. als Anthelminthika, Virizide, Fungistatika oder Bakteriostatika eingesetzt werden. Sie wirken aber vor allem gegen alle Entviicklungsstadien, wie Eier, Larven, Nymphen, Puppen und Adulte von Insekten und Vertretern der Ordnung Akarina, wie Milben und Zecken.The active ingredients of the formula I are suitable for combating a wide variety of animal and vegetable pests. They can be used, for example, as anthelmintics, viricides, fungistats or bacteriostats. they seem but above all against all stages of development, such as eggs, larvae, nymphs, pupae and adults of insects and representatives of the order Akarina, such as mites and ticks.
Die Verbindungen der Formel I können beispielsweise gegen folgende Insekten oder Vertretender Ordnung Akarina eingesetzt werden:The compounds of the formula I can, for example, be used against the following insects or of the order Acarina can be used:
Insekten der Familien: Teltigonidae, Gryllidae, Gryllotalpidae, Blattidae, Peduviidae, Phyrrohocoriae, Cimicidae, Delphacidae, Aphididae, Diaspididae, Pseudococcidae, Scarabaeidae, Dermestidae, Coccinellidae, Tenebrionidae, Chrysomelidae, Bruchidae, Tineidae, Noctindae, Lymatriidae, Pyralidae, GuIicidae, Tipulidae, Stomoxydae, Trypetidae, Muscidae, Calli-Insects of the families: Teltigonidae, Gryllidae, Gryllotalpidae, Blattidae, Peduviidae, Phyrrohocoriae, Cimicidae, Delphacidae, Aphididae, Diaspididae, Pseudococcidae, Scarabaeidae, Dermestidae, Coccinellidae, Tenebrionidae, Chrysomelidae, Bruchidae, Tineidae, Noctindae, Lymatriidae, Pyralidae, GuIicidae, Tipulidae, Stomoxydae, Trypetidae, Muscidae, Calli-
20984Q/ 1 18320984Q / 1 183
22 ι ΰ Ο 922 ι ΰ Ο 9
phoridae und Pulicidae sowie Akariden der Familien Ixodidae, Argasidae, Tetranyehidae und Dermanyssidae.phoridae and Pulicidae as well as acarids of the families Ixodidae, Argasidae, Tetranyehidae and Dermanyssidae.
Die insektizide und/oder akarizide Wirkung lässt sich durch Zusatz von andern Insektiziden und/oder Akariziden wesentlich verbreitern und an gegebene Umstände anpassen.The insecticidal and / or acaricidal effect can be substantially increased by adding other insecticides and / or acaricides broaden and adapt to given circumstances.
Als Zusätze eignen sich z.B. u.a. folgende Wirkstoffe:The following active ingredients, for example, are suitable as additives:
Bis-0,O-diäthylphosphorsäureanhydrid (TEPP) Dimethyl(2,2,2-trichlor-l-hydroxyäthy])phosphonat (TRICHLORFON) l,2-Dibrom-2,2-dichloräthy]diniethylphosphat (KALED) 2,2-Dichlorvinyidimethylphosphat (DICHLORPHOS) Z-Hethoxycarbamyl-l-nethylvinyldimethylphosphat (MEVINPHOS) Di«eihyl-l-inethyI-2-(raethylcarbamoyl)viny]pfiosphai_c_is_ (MONOCROTOPHOS) a-iDimethoxyphosphinyloxyJ-f^N-dimethyl-cis-crotonamid (DICROTOPHOS) 2-Chloro-2-di äihy1carbamoy1-1-meihy]vinyldi methyl phosphat (PHOSPHAHIDON) O,0-Diäthyl-O(oder S)-2-(äthylthio)-äthylthiophosphat (OEETON) S-Aethylthioäthyl-0,0-diiiiethyl-dithiophosphat (THIOnIETON) O.O-Diäthyl-S-äthylmercaptoirethyldithiophosphat (PHORATE) O1O-Dlithy1-5-2- gthylthio)äthyl dithiophosphat (DfSULFOTON) O,0-Dimethyl-S-2-(äthylsulfinyl)äthylthiophosphat (OXYDEMETONETHYL) 0,0-Dimethyl-S-(l,2-dicarbäthoxysthyI dithiophosphat (ItfALATHION) 6v0f0,0-Tetraäihyl-SfSl-aeihyIen-bfs- dithiophosphat (ETHION) O-Aethy1-S,S-d i propy1dithiophosphat OjO-Dimethyl-S-fN-methyl-N-formylcarbaiüoylinethyD-dithiophosphat (FORMOTHION) 0,0-Dimethyl-S-(N-methylcarbamoylmethyl)dithiophosphat (DIHETHOAT) 0,0-Dimethyl-O-p-nitrophenylthiophosphat (PARATHION-METHYL) 0,0-Diäthy1-0-p-nitropheny1thiophosphat (PARATHION) O-Aethy1-0-p-nitrophenylphenylthiophosphonat (EPN) 0,0-Dimethyl-0-(4-nitro-m-tolyl)thiophosphat (FENITROTHION) OjO-Dimethyl-O^^-S-trichlorphenylthiophosphat (RONNEL) 0~Aethyl-0,2,4,5-trichlorphenyläthylthiophosphonat (TRICHLORONAT) 0,O-Dimethyl-0-2,5-dichlor-4-broniphenylthiophosphat (BROMOPHOS) 0,0-Dinethyl-0-(2,5-dichlor-4-jodphenyl)-thiophosphat (JODOFENPHOS) 4-tert. Butyl^-chlorphenyl-N-tethyl-O-raethylanidophcsphat (CRUFOMAT) 0,0-DlmethyI-0-{3-methyl-4-methylmercaptopheny])thiophosphat (FENTHION) Isopropylamino-O-äthyl-O-^-methylmercapto-S-methylphenylJ-phosphat 0,0-Diäthyi-O-p- (nethylsulfinyl)phenyl -thiophosphat (FENSULFOTMON) 0-p-(Dimethylsulianido)phenyi 0,0-dimethylthiopnosphat (FAKPHUR) OjOjO'.O'-Tetra-ethyl-O.O'-thiodi-p-phenylenthiophosphat O-Aethy1-S-phenyl-äthyldithiophosphonat 0,0-Dimethyl-0-!i*nethylbenzyl-3-hydroxyf:r(?toriyl}p;iosphai 2-Chlor-l-(2,4-dichlorphenyl)vinyl-diäthylphosphat (CHLORFENVINPKOS) 2-Chlor-!-(2,A,5-trichlorphenyl)vinyl-dimeihyiphosphat 0-(2-Chlor-l-(2,5-dichlorphenyl)jvinyl-0,0-diäihyHhiophospiiai Phenylglyoxylonitriloxiin-O^-diäthylthJophosphat (PHOXIM)Bis-0, O-diethylphosphoric anhydride (TEPP) dimethyl (2,2,2-trichloro-1-hydroxyethy)) phosphonate (TRICHLORFON) 1,2-dibromo-2,2-dichloroethy] diniethyl phosphate (KALED) 2,2-dichlorovinyidimethylphosphate (DICHLORPHOS) Z-Hethoxycarbamyl-1-Nethylvinyldimethylphosphat (MEVINPHOS) Di «eihyl-1-inethyI-2- (methylcarbamoyl) viny] pfiosphai_c_is_ (MONOCROTOPHOS) a-iDimethoxyphosphICloxyJ-amid (DimethoxyphosphICloxyJ-f ^ N DimethoxyphosphICloxyJ-f ^ N-dimethoxyphosphICloxyJ-f ^ N Chloro-2-di-aihy1carbamoy1-1-meihy] vinyldimethyl phosphate (PHOSPHAHIDON) O, 0-diethyl-O (or S) -2- (ethylthio) ethylthiophosphate (OEETON) S-ethylthioethyl-0,0-diiiiethyl-dithiophosphate (THIOnIETON) OO-diethyl-S-ethyl mercaptoirethyldithiophosphate (PHORATE) O 1 O-Dlithy1-5-2- gthylthio) ethyl dithiophosphate (DfSULFOTON) O, 0-Dimethyl-S-2- (ethylsulfinyl) ethyl-ethylthiophosphate (.0.0-Ethylthiophosphate) -Dimethyl-S- (1,2-dicarbäthoxysthyI dithiophosphat (ItfALATHION) 6 v 0 f 0,0-Tetraäihyl-S f S l -aeihyIen-bfs- dithiophosphat (ETHION) O-Ethy1-S, Sd i propy1dithiophosphat OjO-Dimethyl -S-fN-methyl -N-formylcarbaiüoylinethyD-dithiophosphat (FORMOTHION) 0,0-Dimethyl-S- (N-methylcarbamoylmethyl) dithiophosphat (DIHETHOAT) 0,0-Dimethyl-Op-nitrophenylthiophosphat (PARATHION-METHYL) 0,0-Diethy1-0-p- nitropheny1thiophosphate (PARATHION) O-ethy1-0-p-nitrophenylphenylthiophosphonate (EPN) 0,0-dimethyl-0- (4-nitro-m-tolyl) thiophosphate (FENITROTHION) OjO-dimethyl-O ^^ - S-trichlorophenylthiophosphate (RONNEL ) 0 ~ ethyl-0,2,4,5-trichlorophenylethylthiophosphonate (TRICHLORONATE) 0, O-dimethyl-0-2,5-dichloro-4-broniphenylthiophosphate (BROMOPHOS) 0,0-dinethyl-0- (2,5- dichloro-4-iodophenyl) thiophosphate (IODOFENPHOS) 4-tert. Butyl-chlorophenyl-N-ethyl-O-raethylanidophosphate (CRUFOMAT) 0,0-DlmethyI-0- {3-methyl-4-methylmercaptopheny]) thiophosphate (FENTHION) isopropylamino-O-ethyl-O - ^ - methylmercapto-S -methylphenylJ-phosphate 0,0-diethyi-Op- (nethylsulfinyl) phenyl -thiophosphate (FENSULFOTMON) 0-p- (dimethylsulianido) phenyi 0,0-dimethylthiopnosphate (FAKPHUR) OjOjO'.O'-tetra-ethyl-O.O '-thiodi-p-phenylenethiophosphate O-ethyl-S-phenyl-ethyldithiophosphonate 0,0-dimethyl-0-! 4-dichlorophenyl) vinyl diethyl phosphate (CHLORFENVINPKOS) 2-chlorine -! - (2, A, 5-trichlorophenyl) vinyl dimethyl phosphate 0- (2-chloro-1- (2,5-dichlorophenyl) vinyl-0,0- diäihyHhiophospiiai Phenylglyoxylonitriloxiin-O ^ -diäthylthJophosphat (PHOXIM)
20984ύ/Τΐΰ320984ύ / Τΐΰ3
O.O-Diäthyl-O-O-chloM-inethyl-Z-oxo^-H-l-benzopyran-T-yl)-thiophosphat (COUMAPHOS) 2f3-p-0«oxandithiol-5,S-bis(0,0-diäthyldithiophosphat) (DIOXATHION) S-fie-Chior-Z-oxo-a-benzoxazolinyDmethyllOjO-diäthyldithiophosphat (PHOSALOH) 2-(0läthoxyphosphinylinino)-l,3-dithiolanOO-diethyl-OO-chloM-inethyl-Z-oxo ^ -Hl-benzopyran-T-yl) thiophosphate (COUMAPHOS) 2 f 3-p-0 «oxanedithiol-5, S-bis (0,0-diethyldithiophosphate) (DIOXATHION) S-fie-Chior-Z-oxo-a-benzoxazolinyDmethyllOjO-diethyldithiophosphate (PHOSALOH) 2- (0lethoxyphosphinylinino) -l, 3-dithiolane 0,0-Diuethyl-S-[2-ir,ethoxy-l,3,'i-thiadiazol-5-(*H)-onyl-(4)-iBethyl]dithiophosphat 0,0-Diaethyl-S^phthalimidonethyl-dithiophosphat (IMIDAN) 0,0-Diäihyl-0-(3,5,ß-trich)or-2-pyridyl)thiophosphat O,O-Diäthyl-O-2-pyraziny]thiophosphat (THIONAZIN) 0,0-Dläthyl-0-(2-isopropyM-methyl-6-pyriBidylJthiophosphat (DlAZINOH) O.O-Oiäthyl-O-te-chinoxalyOthiophosphat0,0-Diuethyl-S- [2-ir, ethoxy-1,3, 'i-thiadiazol-5 - (* H) -onyl- (4) -iBethyl] dithiophosphate 0,0-Diaethyl-S ^ phthalimidonethyl-dithiophosphat (IMIDAN) 0,0-diethyl-0- (3,5, β-trich) or-2-pyridyl) thiophosphate O, O-diethyl-O-2-pyraziny] thiophosphate (THIONAZINE) 0,0-Dläthyl-0- (2-isopropyM-methyl-6-pyriBidylJthiophosphat (DlAZINOH) O.O-diethyl-O-te-quinoxalyothiophosphate 0,0-D1aethy1-S-(4-oxo-l ,2,3-benzotriazin-3(4H)-y!inethyl )-dithiophosphat (AZINPHOSMETHYL) 0,0-Diäthyl-S-(4-oxo-l,2,3-benzotriazin-3(4H)-y1methyl)-dithiophosphat (AZINPHOSAETHYL) S-[(4,6-diaaiino-s-triazin-2-yl )methyl]-0,0-dimeihyldithiophosphat (BENAZON) O.O-Oiaethyl-O-ia-chloM-nitrophenyUthiophosphat (CHLORTHION) 0f0-DlBethy1-0(oder S)-2-(äthylthioä thyl Jthiophosphat (DEMETON-S-HETHYL)0,0-D1aethy1-S- (4-oxo-l, 2,3-benzotriazine-3 (4H) -y! Inethyl) -dithiophosphate (AZINPHOSMETHYL) 0,0-diethyl-S- (4-oxo-l, 2,3-Benzotriazine-3 (4H) -y1methyl) -dithiophosphate (AZINPHOSAETHYL) S - [(4,6-diaaiino-s-triazin-2-yl) methyl] -0,0-dimethyldithiophosphate (BENAZON) OO-Oiaethyl -O-ia-chloM-nitrophenyUthiophosphat (CHLORTHIONE) 0 f 0-DlBethy1-0 (or S) -2- (ethylthioethyl thiophosphate (DEMETON-S-HETHYL) 2-(0,0-Diiethyl-phosphoryl-thioirethyl)-5-iiethoxy-pyron-4-3f4-dichlorbenzyl-triphenylphosphon!iiichlorid 0,0-0iäthyl-S-(2,5-dichlorphenyHhioinethyl)dithiophosphat (PHENKAPTON) 0,0-D1äthyl-0-(*-methyl-cuinarinyl-7)-thiophosphat (POTASAN) 5-ABino-bis(dieethylap!ido)phosphinyl-3-phenyl-l,2fMriazol (TRIABIPHOS) ■ N-BethyT-5-(0,0-diBethylthiolphosphoryl)-3-thiavaleraraid (VAMIOOTHION) 0,0-Diäthyl-0-[2-dimethylamino-4-methylpyrtmidyl-(6)]-thiophosphat (DIOCTHYL) O.O-Dfiiethyl-S-fBethylcarbamoyliiiethyD-thiophosphat (OMETHOAT) O-Aethyl-O-iS-chinolinyD-phenylthiophosphonat (OXINOTHIOPHOS) O-Hethyl-S-Biethyl-anidothiophosphat (KONITOR) 0-Methyl-0-(2,5-dichlor-i-bro(iiphenyl)-benzothiophosphonat (PHOSVEL) 0,0,0,0-Tetrapropyldithiopyrophosphat2- (0,0-Diiethyl-phosphoryl-thioirethyl) -5-iiethoxy-pyrone-4-3 f 4-dichlorobenzyl-triphenylphosphonic chloride 0,0-0iethyl-S- (2,5-dichlorophenyHhioinethyl) dithiophosphate (PHENKAPTON) 0,0-D1ethyl-0 - (* - methyl-cuinarinyl-7) -thiophosphate (POTASAN) 5-ABino-bis (dieethylapido) phosphinyl-3-phenyl- 1,2 f mriazole (TRIABIPHOS) ■ N-BethyT -5- (0,0-diBethylthiolphosphoryl) -3-thiavaleraraid (VAMIOOTHION) 0,0-diethyl-0- [2-dimethylamino-4-methylpyrmidyl- (6)] thiophosphate (DIOCTHYL) OO-diethyl-S-f-methylcarbamoyliiiethyD thiophosphate (OMETHOAT) O-Aethyl-O-iS-quinolinyD-phenylthiophosphonate (OXINOTHIOPHOS) O-Hethyl-S-Biethyl-anidothiophosphate (KONITOR) 0-methyl-0- (2,5-dichloro-i-bro (iiphenyl) -benzothiophosphonate (PHOSVEL) 0,0,0,0-tetrapropyldithiopyrophosphate
S-iDiBethoxyphosphinyloxyJ-N-niethyl-N-nethoxy-cis-crotonanid 0,0-DiBethyl-S-(N-äthykarbaraoy]inethyl)dithiophosphat (ETHOAT-METHYL) 0,0-0iäthyl-S-(N-isopropylcarbamoy]ir,ethyl)-dithiophosphat (PROTHOAT) S-N-d-Cyano-l-methyläthyl )carbanoylmethyldiäthylthiolphosphat (CYANTHOAT) S-(2-AcetamidoäthyI )-G,0-diniethyldithiophosphat Hexaiethylphosphorsäuretriamid (HEMPA)S-iDiBethoxyphosphinyloxyJ-N-niethyl-N-nethoxy-cis-crotonanide 0,0-DiBethyl-S- (N-äthykarbaraoy] methyl) dithiophosphate (ETHOAT-METHYL) 0.0-0 diethyl-S- (N-isopropylcarbamoy] ir, ethyl) -dithiophosphate (PROTHOAT) S-N-d-Cyano-l-methylethyl) carbanoylmethyl diethylthiol phosphate (CYANTHOAT) S- (2-acetamidoethyl) -G, 0-diniethyldithiophosphate Hexaiethylphosphoric acid triamide (HEMPA) 0,0-DiBethyl-0-(2-chloM-nitrophenylJthiophosphat (DICAPTHON) O.O-Dinethyl-O-p-cyanophenyl thiophosphat (CYAfIOX) O-Aethyl-O-p-cyanophenylthiophosphonat 0,0-Diäthyl-0-2,A-dichlorphenylthiophosphat (DICHLORFENTHION) 0,2,4-Dichlorphenyl-ü-inethy 1 isopropylajnidothiophosphat 0,0-Dläthyl-0-2,5-dichlor-4-broinpheny]thiophosphat (BROMOPHOS-AETHYL) Diiiiethyl-p-(oethylthio)phenyl phosphat OjC-DUethyl-O-p-sulfamidophenyl thiophosphat Or{p-(p-Chlorphenyl>zopheny)]0,0-diiiiethylthiophosphat (AZOTHOAT) O-AethyI-S-4-chlorpheny1-äthy1d i thiophosphonat O-lsobutyl-Spjhlorphenyl-äthyldithiophosphonat 0,0-Dieethyl-S-p-chlorpheny1thiophosphat O.O-Diaethyl-S-ip-chlorphenylthiomethyD-dithiophosphat O.O-Diäthyl-p-chlorphenylinercaptoirethyl-dithiophosphat (CARBOPHENOTHION) 0,0-Diäthy1-S-p—chiorphenyIthiomethyl-thiophosphat O.O-DiBethyl-S-fcarbäthoxy-phenylinethylJdithiophosphat (PHENTHOAT) O1O-Di äthyl-S-(carbof1uoräthoxy-pheny1«ethyl)-d i thi ophosphat OfO-Diaethyl-S-(carboisopropoxy-pheny!niethyl )-dithiophosphat 0,0-Diäthyl-7-hydroxy-3,4-tetraseihyien-ccj(nariny1 -thiophosphat (COUBITHOAT)0,0-DiBethyl-0- (2-chloM-nitrophenyl thiophosphate (DICAPTHON) OO-Dinethyl-Op-cyanophenyl thiophosphate (CYAfIOX) O-ethyl-Op-cyanophenylthiophosphonate 0,0-diethyl-0-2, A-dichlorophenylthiophosphate (DICHLORO-THIophosphate ) 0,2,4-dichlorophenyl-u-inethy 1 isopropylaynidothiophosphate 0,0-dlethyl-0-2,5-dichloro-4-brominopheny] thiophosphate (BROMOPHOS-AETHYL) diiethyl-p- (ethylthio) phenyl phosphate OjC-DUethyl -Op-sulfamidophenyl thiophosphate Or {p- (p-chlorophenyl> zopheny)] 0,0-diiiiethylthiophosphate (AZOTHOAT) O-EthyI-S-4-chloropheny1-ethy1d i thiophosphonate O-lsobutyl-Spjhlorophenyl-ethyl-phosphonate-0,0 -Sp-chloropheny1thiophosphate OO-diaethyl-S-ip-chlorophenylthiomethyl-dithiophosphate OO-diethyl-p-chlorophenylinercaptoirethyl-dithiophosphate (CARBOPHENOTHION) 0,0 -diiethy1-Sp-chiorphenyIthiomethyl-thiophylbosphate-OO-D-PHiophosphine-S-phenylthiomethyl-thiophylbosphate-OO-Jd-PHO-phosphine-S-phenyIthiomethyl-thiophylbosphate-OO-ethoxy O 1 O-diethyl-S- (carbof1uoräthoxy-pheny1 «ethyl) -di thiophosphate O f O-Diaethyl-S- (carboisopropoxypheny! Niethyl) -dithiophos phat 0,0-diethyl-7-hydroxy-3,4-tetraseihyien-ccj (nariny1 -thiophosphate (COUBITHOAT)
0,0-0täthyl-0-(5-phenyl-3-isoQX3zoly]Jthiophosphat0,0-0-ethyl-0- (5-phenyl-3-isoQX3zoly] thiophosphate
209840/1209840/1
2-(Diäthoxyphosphinyl1iinoM-methyl-l,3-dithiolan2- (Diethoxyphosphinyl1iinoM-methyl-1,3-dithiolane
0,0-Dl«ethyI-0-(3,5,6-tnchlor-2-pyndyl)thiophosphat S- 2-(Aethylsulfony])äthyl dimethylthiolphosphat (DIOXYDEHETON-S-HETHYL) Oiäthyl-S- 2-(äthylsu1finyl)äthyl dithiophosphat (OXYDISULFOTON) Bis-OjO-diäthylthiophosphorsäureanhydrid (SULFOTEP) Di«ethyl-l,3-di(carbonethoxy)-]-propen-2-yl-phosphat 0,0-Dl «ethyl-0- (3,5,6-chloro-2-pyndyl) thiophosphate S- 2- (ethylsulfony]) ethyl dimethylthiolphosphate (DIOXYDEHETONE-S-HETHYL) diethyl-S- 2- (ethylsulfinyl ) ethyl dithiophosphate (OXYDISULFOTON) bis-OjO-diethylthiophosphoric anhydride (SULFOTEP) diethyl 1,3-di (carbonethoxy) -] - propen-2-yl phosphate
0,0-Di«ethyl-0-(2,2-dichlor-l-methoxy-vinyl)phosphat0,0-diethyl-0- (2,2-dichloro-1-methoxy-vinyl) phosphate
0,0-Diäthyl-0-(2,2-dichlor-l-chloräthoxyv1nyl)phosphat0,0-diethyl-0- (2,2-dichloro-1-chloroethoxyv1nyl) phosphate 0,0-DlBethyl-0-(2,2-dichlor-l-chloräthoxyviny1)phosphat0,0-DlBethyl-0- (2,2-dichloro-1-chloroethoxyviny1) phosphate 0-Aethyl-S,S-diphenyldithio]pljosphat0-ethyl-S, S-diphenyldithio] phosphate
0,0-Diäthyl-S-benzyMhiolphosphat0,0-diethyl-S-benzymhiolphosphate
0,0-Di«ethyl-S-(äthyIthioniethyl)dithiophosphat0,0-diethyl-S- (ethyithioniethyl) dithiophosphate
0,0-Oiiethyl-S-(norpholinylcarbainoyliethyl)dithiophosphat (MORPHOTHION)0,0-Oiiethyl-S- (norpholinylcarbainoyliethyl) dithiophosphate (MORPHOTHION)
0,0-Di«ethyl-S-(benzolsulfonyl)dithiophosphat0,0-diethyl-S- (benzenesulfonyl) dithiophosphate 0,0-Diiethy1-(S und O)-Ifhy1sulίiny1äthylthiophosphat0,0-Diiethy1- (S and O) -Ifhy1sulίiny1äthylthiophosphat
2-Methoxy-4H-1,3,2-benzodi oxaphosphorin-2-oxyd2-methoxy-4H-1,3,2-benzodioxaphosphorin-2-oxide
p/N'-tetraiethyldiaaidofluorphosphat (DIMEFOX)p / N'-tetraiethyldiaaidofluorophosphate (DIMEFOX)
0-IIethy1-0-(2-chlor-Mert. butyl-phenyl)-N-methylaaiidoth1ophosphat (HARLENE)0-IIethy1-0- (2-chloro-Mert. Butyl-phenyl) -N-methylaaiidoth1ophosphate (HARLENE) 0-Aethyl-0-(2,<-dichlorphenyl)-phenylthiophosphonat0-ethyl-0- (2, <- dichlorophenyl) -phenylthiophosphonate
0-lteihyl-0-(2-carbisopropoxyphenyl)-anidothiophosphatO-methyl-0- (2-carbisopropoxyphenyl) anidothiophosphate
0-Methyl-0-(2-i-propoxycarbonyl -1-aethylvinyI )äthylaniidothiophosphat0-methyl-0- (2-i-propoxycarbonyl -1-ethylvinyI) ethylaniidothiophosphate
^,B-Dinitro^-inethylphenol, Na-saiz [Oinitrocresol] Dinitrobutylphenol(2,2f,2" triäthanolaninsalz) 2 CyclohexyM^-Dinitrophenoi [Dinex] 2-(l-läethy]heptyl)-4,6 dinitrophenyl-crotonat [Oinocap] 2 sec.-butyl-AjG-dinitrophenyl-S-iiethyl-butenoat [Binapacryl] 2 sec.-butyMjß-dinitrophenyl-cyclopropionat 2 sec.-butyl-ijB-dinitrophenyl-isopropyl-carbonat [Dinobuton]^, B-Dinitro ^ -inethylphenol, Na-saiz [Oinitrocresol] Dinitrobutylphenol (2.2 f , 2 "triethanolanine salt) 2 CyclohexyM ^ -Dinitrophenoi [Dinex] 2- (1-l-ethy] heptyl) -4,6 dinitrophenyl-crotonate [Oinocap] 2 sec-butyl-AjG-dinitrophenyl-S-iiethyl-butenoate [Binapacryl] 2 sec-butyMjß-dinitrophenyl-cyclopropionate 2 sec-butyl-ijB-dinitrophenyl-isopropyl-carbonate [dinobutone]
209840/1183209840/1183
Verschiedene Pyrethrin I Pyrethrin Il 3-Allyl-2-methyl-A-oxo-Z-cyclopenten-l-yJ-chrysanthemumat (Allethrin) Various pyrethrin I pyrethrin II 3-allyl-2-methyl-A-oxo-Z-cyclopenten-l-yJ-chrysanthemumat (allethrin)
2,A-dimethy1benzyl-chrysanthemuraat (dimethrin)2, A-dimethylbenzyl-chrysanthemuraat (dimethrin) 2,3,4,5-tetrahydrophthal iraidotnethy]chrysanthemuraat2,3,4,5-tetrahydrophthal iraidotnethy] chrysanthemuraat 4-Chlorbenzyl-4-chlorphenylsulfid [Chlorbensid]4-chlorobenzyl-4-chlorophenyl sulfide [chlorine surfactant] 6-BethyI-2-oxo-l,3-dithiolo-[4,5-b]-chinoxalin [Quinomethionat]6-BethyI-2-oxo-1,3-dithiolo- [4,5-b] -quinoxaline [quinomethionate] (D-S-^-FurfuryO^-methyM-oxocyclopenW-enyldMcis + trans) chrysanthemum-monocarboxylat [Furethrin](D-S - ^ - FurfuryO ^ -methyM-oxocyclopenW-enyldMcis + trans) chrysanthemum monocarboxylate [furethrin] 2-Pivaloyl-indan-l,3-dion [Pindon]2-pivaloyl-indan-1,3-dione [pindon]
4-ChIorbenzyl-A-fluorphenyl-sulfid (Fluorbenside)4-chlorobenzyl-A-fluorophenyl sulfide (fluorosurfactants) 5,6-Dichlor-]-phenoxycarbanyl-2-trifluortnethyl-benzimidazol (Fenozaflor)5,6-dichloro -] - phenoxycarbanyl-2-trifluorotethylbenzimidazole (Fenozaflor) i-Chlorphenyl-p-chlorbenzolsulfonat (Ovex)i-chlorophenyl-p-chlorobenzenesulfonate (Ovex) p-Chlorphenyl-benzolsulfonat (Fenson)p-chlorophenyl benzenesulfonate (Fenson) p-Chlorpheny]-2,4,5-trich]orpheny]sulfon (Tetradifon)p-chlorpheny] -2,4,5-trich] orpheny] sulfon (Tetradifon) p-Chlorphenyl-2,4,5-trichlorphenylsulfid (Tetrasul)p-chlorophenyl-2,4,5-trichlorophenyl sulfide (Tetrasul) p-Chlorbenzyl-p-chlorphenyisulfid (Chlorbenside)p-chlorobenzyl-p-chlorophenyl sulfide (chlorine surfactants) 2-Thfo-l,3-dithiolo-(,5-6)chinoxal in (Thiochinox)2-Thfo-l, 3-dithiolo - (, 5-6) quinoxal in (Thioquinox)
l-0imethy1-2-(2'-(nethy)-A1-chlorphenyl)-formamidin (CHLORPHENAMIDIN) l-llethyl-2-(2t-methyl-41-chlorphenyl)-forinaniidin l-Methyl-2-(2t-methyl-4'-brompheny1)-formamidinl-0imethy1-2- (2 '- (nethy) -A 1 -chlorophenyl) -formamidine (chlorphenamidine) l-llethyl-2- (2-methyl-4 t 1 -chlorophenyl) -forinaniidin l-methyl-2- ( 2 t -methyl-4'-bromopheny1) -formamidine l-«!ethyl-2-(2',V-dir;ethylphenyl)-foriramidin 1-n-Butyl-l-methyl-2-(2l-methyl-V-chlorphenyl )-f ormamidin I-Hethy 1 -1 -{2' -me thy 1 -4' -c h 1 oran i 1 i η o-!re thy i en) 2-(2''-methyl-41'-chlorphenyl)-forraamidin l-n-Butyl-2-(2'-methyl-4'-chlorphenyl-iinino)-pyrrol idinl - «! ethyl-2- (2 ', V-dir; ethylphenyl) -foriramidine 1-n-butyl-l-methyl-2- (2 l -methyl-V-chlorophenyl) -formamidine I-Hethy 1 - 1 - {2 '-me thy 1 -4' -ch 1 oran i 1 i η o-! Re thy i en) 2- (2 "- methyl-4 1 '-chlorphenyl) -forraamidine in-butyl-2 - (2'-methyl-4'-chlorophenyl-iinino) -pyrrolidine
Harnstoffurea
l-Naphthyl-N-methylcarbamat (CARBARYL)l-naphthyl-N-methylcarbamate (CARBARYL) 2-Butinyl-A-chlorphenylcarbamat2-butynyl-A-chlorophenyl carbamate 4-Di«iethylamino-3,5-xy Iy 1-N-methy lcarbamat4-Di «ethylamino-3,5-xy Iy 1-N-methyl carbamate
4-«ethyHhio-3,5-xylyl-N-nethylcarbaaat (METHlOCARB)4- «ethyHhio-3,5-xylyl-N-nethylcarbaaat (METHlOCARB) 3,A,5-TrimethyIpheny1-N-methyIcarbaraat3, A, 5-trimethylphenyl-N-methylcarbarate 2-Chlorphenyl-N-methy)carbamat (CFMC)2-chlorophenyl-N-methy) carbamate (CFMC) 5-Chloro-6-oxo-2-norborran-carbonitril-0-(n:ethylcarbai>ioyl)-oxiai5-chloro-6-oxo-2-norborran-carbonitrile-0- (n: ethylcarbai> ioyl) -oxiai l-(Dimethylcarbamoyl)-5-3iethyl-3-pyra2olyl-N,N-diinethylc3rbaii)at (DIMETILAN)1- (Dimethylcarbamoyl) -5-3iethyl-3-pyra2olyl-N, N-diinethylc3rbaii) at (DIMETILAN) 2,3-0ihydro-2,2-dimethyl-7-benzofuranyl-N-niethylcarbamat (CARBOFURAN)2,3-0ihydro-2,2-dimethyl-7-benzofuranyl-N-diethylcarbamate (CARBOFURAN)
8-Chinaldy1-N-nethylcarbamat und seine Salze8-Quinaldy1-N-methylcarbamate and its salts
■-{l-AethylpropyUphenyl-N-methylcarbaiiiat■ - {1-AethylpropyUphenyl-N-methylcarbaiiat 3,5-Di-tert.butyl-N-methylcarbamat3,5-di-tert-butyl-N-methylcarbamate ■-(l-Methylbutyl)phenyl-N-methylcarbainat■ - (1-methylbutyl) phenyl-N-methylcarbainate 2-Isopropy 1 phenyl -fi-methy 1 carbanat2-isopropy 1 phenyl-fi-methyl 1 carbanate 2-sec.Butyl phenyl-N-methy Icarbaraat2-sec.Butyl phenyl-N-methy Icarbaraat ■-Toiyl-N-nethylcarbamat■ -Toiyl-N-methyl carbamate
2,3-Xy1y1-N-methy1carbamat2,3-Xy1y1-N-methylcarbamate
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3-lsopropy 1 pheny 1-N-methylcarbaniat 3-tert.Butylphenyl-N-methylcarbamat 3-sec.-Buty Ipheny1-N-nethy1carbamat 3-lsopropy1-5-methy1pheny1-N-methylcarbamat (PROMECARB) 3,5-Diisopropyipheny1-N-methylcarbamat 2-Chlor-5-isopropy]phenyl-N-methylcarbamat 2-Chlor-4,5-dimethy1phenyl-N-methylcarbamat'3-Isopropy 1 pheny 1-N-methylcarbaniate 3-tert-Butylphenyl-N-methylcarbamate 3-sec -Buty Ipheny1-N-methy1carbamate 3-Isopropy1 -5-methy1pheny1-N-methylcarbamate (PROMECARB) 3,5-Diisopropyipheny1- N-methylcarbamate 2-chloro-5-isopropy] phenyl-N-methylcarbamate 2-chloro-4,5-dimethylphenyl-N-methylcarbamate '
2-(l,3-Dioxolan-2-yl)phenyf-M-methylcarbamat (DIOXACARB) 2-(4,5-0i!T.ethyl-!,3-dHXoTan-2-yl)ph3nvl-fl-5iethylcarban!at 2-(1,3-Di oxo 1an-2-y1)phenyi-N,N-d i methy1carbamat 2-(1,3-Di thiolar-2-y i _n,N-ciimethy"IcarDamat 2-(l,3-Dithiolar-2-yOpfe."yi-N,S-d?n;etiiy!carbanat 2-Uopropoxyphenyl-N-n:ethy]cartanat (ARPROCARB) 2-(2-Propinyloxy)phenyl-N-ir,ethylcarban-at 3-CZ-Propinyloxy)pheny1-N-nethylcarbamat 2-Dimethyl3rnnophenyl-N-ir.ethylcarbaniat 2-DIaT lylaminophepyl-N-^ethylcarbairat 4-Diallylaisino-3,5-xy1y]-f.'-[re%karbaniat (ALLYXiCARB) 4-Benzothienyi-N-methy 1carbamat 2,3-Dihydro-2-methy]-7-benzofuranyl-N-:nethyl carbamat 3-Methyl-l-phenylpyrazol-5-yl-N,N-dimethylcarbamat l-lsopropyl-3-methyIpyrazo1-5-y1-N,N-d!methy 1carbamat (ISOLAN) 2-Dimethy!a,T,ino-5,6-dimeihylpyrimidin-4-yl-N,N-dimethyl-carbamat S-HethyM-dinethylaminornethyleniminophenyl-N-methylcarbamat 3,^-Dimethylphenyl-N-methylcarbamat 2-Cyclopentyl-N-methylcarbamat 3-Diniethylamino-nethyleniniinophenyl-N-methylcarbainat (FORMETANATE) und seine Salze l-Methylthio-äthylimino-N-methylcarbamat (ETHOMYL) 2-Meihy I carbanioy i ox i ra ino-1,3-d i thiolan S-Methyl-Z-methylcarbaraoyloxiraino-ljS-oxythiolan 2-(l -Methoxy-2-propoxy Jpheny1-N-methyl carbamat 2-(l-Butin-3-yl-oxy)phenyl-N-methy]carbamat l-UJmethylcarbamyl-l-methylthio-O-rsethylcarbamyl-formoxim l-(2l-Cyanoäthylthio)-0-methylcarbamyl-acetaldoxim 1-Methy lthio-O-carbasiyl -acetal dox im 0-(3-sec.-Butyl phenyl)-N-pheny1th i o-N-methy1carbamat 2,5-DiraethyI-l,3-dithioland-2-(0-methylcarbamyl)-aldoxim) O-2-Diphenyl-N-methylcarbamat2- (1,3-Dioxolan-2-yl) phenyf-M-methylcarbamate (DIOXACARB) 2- (4,5-0i! T.ethyl - !, 3-dHXoTan-2-yl) ph3nvl- f l-5iethylcarban ! at 2- (1,3-Di oxo-1an-2-y1) phenyi-N, Nd i methy1carbamat 2- (1,3-Di thiolar-2-yin, N-ciimethy "IcarDamat 2- (1,3 -Dithiolar-2-yOpfe. "Yi-N, Sd ? N; etiiy! Carbanate 2-uropropoxyphenyl-Nn: ethy] cartanate (ARPROCARB) 2- (2-propinyloxy) phenyl-N-ir, ethylcarbanate 3-CZ Propynyl oxy) pheny1-N-methylcarbamate 2-dimethyl3rnnophenyl-N-ir.ethylcarbaniate 2-DIaT lylaminophepyl-N- ^ ethylcarbairate 4-diallylaisino-3,5-xy1y] -f .'- [re% carbanate (ALLYXiCARB) 4 -Benzothienyi-N-methy 1-carbamate 2,3-dihydro-2-methy] -7-benzofuranyl-N-: methyl carbamate 3-methyl-l-phenylpyrazol-5-yl-N, N-dimethylcarbamate l-isopropyl-3- methyIpyrazo1-5-y1-N, Nd! methy 1carbamat (ISOLAN) 2-Dimethy! a, T, ino-5,6-dimethylpyrimidin-4-yl-N, N-dimethyl-carbamate S-HethyM-dinethylaminornethyleniminophenyl-N- methylcarbamate 3, ^ - dimethylphenyl-N-methylcarbamate 2-cyclopentyl-N-methylcarbamate 3-diniethylamino-ethyleninophenyl-N-methylcarbainate (FO RMETANATE) and its salts l-methylthio-ethylimino-N-methylcarbamate (ETHOMYL) 2-Meihy I carbanioy i ox i ra ino-1,3-di thiolane S-methyl-Z-methylcarbaraoyloxiraino-ljS-oxythiolane 2- (l - Methoxy-2-propoxy Jpheny1-N-methyl carbamate 2- (l-butyn-3-yl-oxy) phenyl-N-methy] carbamate l-methylcarbamyl-l-methylthio-O-rsethylcarbamyl-formoxime l- (2 l - Cyanoethylthio) -0-methylcarbamyl-acetaldoxime 1-methylthio-O-carbasiyl-acetal dox in 0- (3-sec-butylphenyl) -N-phenylthio-N-methylcarbamate 2,5-diraethyI-1,3-dithioland -2- (0-methylcarbamyl) aldoxime) O-2-diphenyl-N-methylcarbamate
2-(N-Hethylcarbaniy!-oximino)-3-chlor-bicyclo[2.2.l]heptan 2-(N-Methylcarbaüiyl-oximino)-bicyclo[2.2.l]heptan 3-lxopropyl pheny l-N-Trethyl-N-chloracetyl -carbamat 3-lsopropylpheny1-N-methy1-N-methylihi oraethy1-carbamat O-iZjZ-Dimethyl-i-chlor^^-dihydro-T-benzofuranyD-N-nethyl carbamat 0-(2,2,4-Triisethyl 2,3-dihydro-7-benzofuranyi)-N-niethyl carbamat O-Naphthyl-Fi-Eethyl-iJ-acetyl-carbanat 0-5,6,7,8-Tetrahydroraphthyl-N-nethyl-carbamat 3-lsopropy 1 —4-riethy i thi o-phenyl-N-methy I carbamat 3,5-D i nethy1-4-me thoxy-pheny i-N-methy1carbamat 3~Methoxymethoxy-phenyl-H-tneihylcarbamax 3—Al 1 y 1 oxy pheny 1 -N-iiethy ] carbania t 2-Propargyioxyir.ethoxy-preny]-fi-methyl-carb2!üai 2—Αϊ lyloxypHeny I—'»-"letnyl—carbamf.i 4-Methoxycartc:])'l an ino-5-isopropyl pheny i«-fi"r:ji"hyl-f;arfeT'">2- (N-Methylcarbaniy! -Oximino) -3-chlorobicyclo [2.2.1] heptane 2- (N-Methylcarbaniyl-oximino) -bicyclo [2.2.1] heptane 3-lxopropyl pheny lN-Trethyl-N-chloroacetyl carbamate 3-isopropylpheny1-N-methy1-N-methylihi oraethy1-carbamate O-iZjZ-Dimethyl-i-chloro ^^ - dihydro-T-benzofuranyD-N-methyl carbamate 0- (2,2,4-triisethyl 2, 3-dihydro-7-benzofuranyi) -N-niethyl carbamate O-naphthyl-Fi-ethyl-iJ-acetyl-carbanate 0-5,6,7,8 -tetrahydroraphthyl-N-ethyl-carbamate 3-isopropy 1-4- riethy i thi o-phenyl-N-methy I carbamat 3,5-D i nethy1-4-methoxy-pheny iN-methy1carbamat 3 ~ Methoxymethoxy-phenyl-H-tneihylcarbamax 3-Al 1 y 1 oxy pheny 1 -N- iiethy] carbania t 2-propargyioxyir.ethoxy-preny] -fi-methyl-carb2! üai 2-Αϊ lyloxypheny I - '»-" letnyl-carbamf.i 4-methoxycartc:])' l an ino-5-isopropyl pheny i «-fi" r: ji "hyl-f; arfeT '">
3,5-DlnethyI-4-Bethoxycarbony]an i no-phenyI-N-methy1-carbaeat3,5-methylene I-4-bethoxycarbony] an i no-phenyI-N-methy1-carbaeate 2-Y-Methylthiopropylt*enyl-(i-aethyl-carbaB3t2-Y-methylthiopropylt * enyl- (i-ethyl-carbaB3t
2-Chlor-5-tert-buty1-pheny1-N-eethy]-carbamat2-chloro-5-tert-buty1-pheny1-N-ethyl] carbamate 4-(Methyl-propargylaiino)-3,5-xylyl-N-raethyl-carbamat4- (methyl-propargylaiino) -3,5-xylyl-N -raethyl-carbamate
4-{Methyl-ß-chloranylamino)-3,5-xylyl-N-methyl-carbaBat4- (methyl-β-chloranylamino) -3,5-xylyl-N-methyl-carbate l-(ß-Aethoxycarbonyläthyl )-3-raethyl-5-pyr3zolyl-N,N-diBethyl-carbaitat1- (β-ethoxycarbonylethyl) -3-raethyl-5-pyr3zolyl-N, N-di-methylcarbaitate
1,3-Bls(carbaBoyHhio)-2-(N,N-diinethylaBino)-propanhydrochlorid1,3-Bls (carbaBoyHhio) -2- (N, N-diinethylaBino) propane hydrochloride
2-^ethyl-propargylaainoj-phenyl-N-iiethylcarbainat2- ^ ethyl-propargylaainoj-phenyl-N-iiethylcarbainat 2-[Methyl-propargyla»ino]-pheny1-N-methy1carbama t2- [methyl-propargyla »ino] -pheny1-N-methy1carbama t 2-[Dipropargylaiino]-phenyl-N-Eethylcarbanat2- [Dipropargylaiino] phenyl-N-ethylcarbanate 4-[D1propargylaeino]-3-toly 1-fi-roethylcarbaraat4- [D1propargylaeino] -3-toly 1-fi-roethylcarbaraat 4-[DipropargylaBino]3,5-xylyl-N-ir.ethylcarbainat4- [DipropargylaBino] 3,5-xylyl-N-ir.ethylcarbainate 2-[AHy l-lsopropylaBinoJ-phenyl-N-me thy lcarbamat2- [AHy l-IsopropylaBinoJ-phenyl-N-methy lcarbamate 3-[A1 lyl-Jsopropylaaino]-phenyl-M-raethylcarba,T5at3- [A1 lyl-Isopropylaaino] -phenyl-M-raethylcarba, T5at
Chlorierte Kohlenwasserstoffe γ-Hexachlorcyclohexan [GAMmEXAHE; LINDAN; γ HCH] Chlorinated hydrocarbons γ-hexachlorocyclohexane [GAMmEXAHE; LINDAN; γ HCH] !^^^^^,B.e-Octachlor-^a^.T^a'tetrahydro^^-Bethylenindan [CHLORDAN] 1,4,5,6,7,8,8-Heptachloro, 3α, V7,7tt-tetrahydro-4,7-«ethylenindan [HEPTACHLOR] !^,S^.IO.in-hexachlor-l.^ia.S.S.ea-hexahydro-endo^.i-exo-S.e-diBiethanonaphthalin [AlDRIl] l.Z^^.IO.lO-hexachlor-e^-epoxy-l^^a.S^^.S^a-oxtahydro-exo-l.^-endo-S.B-diBethanonaphthann [DIELDRIN] 1,2,3,4,10,10-hexachlor-6,7-epoxy-l,4,4i,5l6,7,8,8a-octahydro-endo-endo-5,B-diMthanonaphthaHn [ENDRIN]! ^^^^^, Be-Octachlor- ^ a ^ .T ^ a'tetrahydro ^^ - Bethyleneindane [CHLORDAN] 1,4,5,6,7,8,8-Heptachloro, 3α, V7,7tt-tetrahydro -4,7- «ethylenindan [HEPTACHLOR]! ^, S ^ .IO.in-hexachlor-l. ^ Ia.SSea-hexahydro-endo ^ .i-exo-Se-diBiethanonaphthalin [AlDRIl] lZ ^^. IO. lO-hexachlor-e ^ -epoxy-l ^^ aS ^^. S ^ a-oxtahydro-exo-l. ^ - endo-SB-diBethanonaphthann [DIELDRIN] 1,2,3,4,10,10-hexachlor- 6,7-epoxy-l, 4,4i, 5 l 6,7,8,8a-octahydro-endo-endo-5, B-diMthanonaphthaHn [ENDRIN]
Ausserdem besitzen die neuen Verbindungen der Formel I nematozide Eigenschaften und können beispielsweise zur Bekämpfung folgender pflanzenparasitä'rer Nematoden eingesetzt v/erden: Meloidogyne Arten, Heterodera Arten, Ditylenchus Arten, Pratylenchus Arten, Paratylenchus Arten, Anguina Arten, Helicotylenchus Arten, Tylenchorhynchus Arten, Radopholus Arten, Belonolaismus Arten, Trichodorus Arten, Longidorus Arten, Aphelenchoides Arten, Xiphinema Arten.In addition, the new compounds of the formula I have nematocidal properties and can be used, for example, to combat The following plant parasitic nematodes are used: Meloidogyne species, Heterodera species, Ditylenchus species, Pratylenchus Species, Paratylenchus species, Anguina species, Helicotylenchus species, Tylenchorhynchus species, Radopholus species, Belonolaismus species, Trichodorus species, Longidorus species, Aphelenchoides species, Xiphinema species.
Die Verbindungen der Formel I weisen neben den oben erwähnten Eigenschaften in sehr geringen Aufwandmengen auch eine günstige Wirksamkeit gegen Vertreter der Abteilung Thallophyta auf. So zeigen einige dieser Verbindungen bakterizide Wirkung. Sie sind aber vor allem gegen Fungi, insbesondere gegen die folgenden Klassen, Ordnungen bzv/. Arten angehörenden phytopathogenen Pilze wirksam:In addition to the properties mentioned above, the compounds of the formula I also have a favorable activity against representatives of the Thallophyta department when applied in very small amounts. Some of these compounds show bactericidal activity. But you are above all against fungi, especially against the following classes, orders or /. Species belonging to phytopathogenic fungi effective:
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Oomycetes. wie Plasmodiophora-Arten, Aphanomyces-Arten, Oomycetes. such as Plasmodiophora species, Aphanomyces species,
Pythium-Arten, Phytopthora-Arten (Phytophthora tnfestans, Phytophthora cactorum), Plasmopara-Arten (Plasmopara viticola), 3remia-Arten (Brernia lactucae), Peronospor-a-Arten (Peronospora tabacina), Pseudoperonospora-Arten (Pseudoperonospora humuli).Pythium species, Phytopthora species (Phytophthora tnfestans, Phytophthora cactorum), Plasmopara species (Plasmopara viticola), 3remia species (Brernia lactucae), Downy mildew a species (Peronospora tabacina), Pseudoperonospora species (Pseudoperonospora humuli).
Zyfro^iycetes, v/ie Rhizopus-Arten. Zyfro ^ iycetes, v / ie Rhizopus species.
Ascon;ycetes, vile Eurotiales, z.B. Aspergillus'-Arten, Penicillium-Arten (Penicillium digitatum, Penicillium italicutn), Taphrinales, z.B. Taphrina-Arten (Taphrina deformane), Erysiphales, z.B. Erysiphe-Arten (Erysiphe cichcrace- Ascon; ycetes, vile Eurotiales, e.g. Aspergillus' species, Penicillium species (Penicillium digitatum, Penicillium italicutn), Taphrinales, e.g. Taphrina species (Taphrina deformane), Erysiphales, e.g. Erysiphe species (Erysiphe cichcrace-
arusn, Erysiphe grarainis, Podosphaera leucotricha), Sphaerothcca-Artcn (Sphacrotheca pannosa), Uncinula-arusn, Erysiphe grarainis, Podosphaera leucotricha), Sphaerothcca species (Sphacrotheca pannosa), Uncinula
Arten (Uncinula necator),Species (Uncinula necator),
Helotiales, vie Monilinia-Arten (Monilinia [Sclerotiniaj fructicola, Monilinia laxa), Dlplocarpon-Artcn (Diplocarpon rosae), Pseudopeziza-Arten,Helotiales, vie Monilinia species (Monilinia [Sclerotiniaj fructicola, Monilinia laxa), Dlplocarpon species (Diplocarpon rosae), Pseudopeziza species,
Sphaeriales, wie Nectria-Arten (Nectria gallißena), Ceratocystis-Arten,Sphaeriales, such as Nectria species (Nectria gallißena), Ceratocystis species,
Pseudosphaeriales, wie Venturia-Arten (Venturia inaequalis), Mycosphaerella-Arten, Ophiobolus-Arten (Ophiobolus graminus), Cochliobolus-Arten [Helminthosporium] miyabeanus), Cercospora-Arten (Cercospora beticola, Cercospora musae).Pseudosphaeriales, such as Venturia species (Venturia inaequalis), Mycosphaerella species, Ophiobolus species (Ophiobolus graminus), Cochliobolus species [Helminthosporium] miyabeanus), Cercospora species (Cercospora beticola, Cercospora musae).
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Basldiomycetes, wie Aphyllophorales, z.B. Pellicularia-Arten (Pellicularia filamentora = [Rhizoctonia sonlani]), Uredinales, z.B. Puccinia-Arten (Puccinia triticina), Uromyces-Arten (Uromyces phaseoli), Hemileia-Arten (Hemlleia vastatrix), Cronartium-Artcn (Cronartium ribicola), Phraernidium-Artcn (Phraßmidium cubcorticiurn}, Gymnosporangium-Arten. Basldiomycetes, such as Aphyllophorales, e.g. Pellicularia species (Pellicularia filamentora = [Rhizoctonia sonlani]), Uredinales, e.g. Puccinia species (Puccinia triticina), Uromyces species (Uromyces phaseoli), Hemileia species (Hemlleia vastatrix), Cronartium species Cronartium ribicola), Phraernidium species (Phraßmidium cubcorticiurn}, Gymnosporangium species.
Pcnteromycotos = (Fungi imperfecti) Pcnteromycotos = (Fungi imperfecti)
z.B. Piricularia-Arten (Piricularia oryzac),Cbri!iespora-Arten. Thielaviopsis-Arten, Clasterosporium-Arten, Bctry tis-Arten (Botrytis cinerea), CladoGporiutn-ArUcn, Alternaria-Arten (Alternaria solani), Verticilliuni-Arten (Vcrbiclllium albo-atrum), Phialophora-Arten,e.g. Piricularia species (Piricularia oryzac), Cbri! iespora species. Thielaviopsis species, Clasterosporium species, Bctry tis species (Botrytis cinerea), CladoGporiutn-ArUcn, Alternaria species (Alternaria solani), Verticilliuni species (Vcrbiclllium albo-atrum), Phialophora species,
Melanconiales, z.B. Collctotrichusn-Arten, Fusarium-Arten (Fusarium oxysporum, Fusarium nivale)^ Glocosporium-Arten (Cloeocporium fructieenum),Melanconiales, e.g. Collctotrichusn species, Fusarium species (Fusarium oxysporum, Fusarium nivale) ^ Glocosporium species (Cloeocporium fructieenum),
Sphacropsidales, z.B. Septoria-Arten (Septoria apicola).Sphacropsidales, e.g. Septoria species (Septoria apicola).
Diplodia-Arten (Diplodia natalensis), Mycelia sterilia, z.B. Sclerotium-Arten (Sclcrotium.Diplodia species (Diplodia natalensis), Mycelia sterilia, e.g. Sclerotium species (Sclcrotium.
rolfsii).rolfsii).
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Die Verbindungen der Formel I zeigen ebenfalls eine fungitoxische Wirkung bei Pilzen, die die Pflanzen vom Boden her angreifen und teilweise Tracheomycose verursachen, wie z.B. Fusarium cubense, Fusarium dianthi, Verticillium alboatrum und Phialophora einereceus.The compounds of formula I also show a fungitoxic effect on fungi that the plants from Attack the soil and sometimes cause tracheomycosis, such as Fusarium cubense, Fusarium dianthi, Verticillium alboatrum and Phialophora einereceus.
Ferner können die neuen Wirkstoffe zur Behandlung von Saatgut, Früchten, Knollen etc. zum Schutz vor Pilzinfektionen beispielsweise durch Brandpilze aller Art, wieThe new active ingredients can also be used to treat seeds, fruits, tubers, etc. to protect against fungal infections for example through all kinds of smut fungi, such as
Ustilaginales, z.B. Ustilago-Arten'(Ustilage avenae),
Tilletia-Arten (Tilletia tritici), Urocystis- und .Tuburcinia-Arten
Phoma-Arten (Phoma betae)Ustilaginales, for example Ustilago species (Ustilage avenae), Tilletia species (Tilletia tritici), Urocystis and .Tuburcinia species
Phoma species (Phoma betae)
eingesetzt werden.can be used.
Dank ihrer bioziden Eigenschaften eignen sich dieThanks to their biocidal properties, the
Verbindungen der Formel I zur Desinfektion und zum Schützen verschiedenartiger Materialien vor' dem Befall durch Bakterien und Pilze. Hierbei erweist es sich als besonders vorteilhaft, dass die Verbindungen der Formel I gegenüber Warmblütern bei den Konzentrationen, wie sie für die Desinfektion und den Materialschutz erforderlich sind, keine giftigen Nebenerscheinungen aufweisen.Compounds of the formula I for disinfecting and protecting various materials from infestation Bacteria and fungi. It proves to be particularly advantageous that the compounds of the formula I over Warm-blooded animals at the concentrations required for disinfection and material protection, none have toxic side effects.
Die Verbindungen der Formel I können neben den erwähnten Insektiziden und Akariziden auch mit andern Fungizidenj Fungistatika oder Bakteriostatika in verschiedenen Mischungsverhältnissen formuliert werden, wobei Verbindungsgemische mit Vorteilen gegenüber den Einzelkomponenten entstehen. Zur Formulierung mit den Wirkstoffen der Formel I eignen sich z.B.: 209840/1183 In addition to the insecticides and acaricides mentioned, the compounds of the formula I can also be used with others Fungizidenj Fungistatika or bacteriostatika in different Mixing ratios are formulated, with compound mixtures having advantages over the individual components develop. For formulation with the active ingredients of the formula I are, for example: 209840/1183
Dodecylgu3nidiRace<ai (CCCINi) Pentschlornitrobenicl iGülSTOZESE) Penlachlcrphenol (fCP)Dodecylgu3nidiRace <ai (CCCINi) Pentschlornitrobenicl iGülSTOZESE) Penlachlic phenol (fCP)
2-(l-Mhyl-n-propyl)4,5-diniirc?hen)M-2-re!hyl6rotoP3t (BtKAPACRYL) 2- (l-Mhyl-n-propyl) 4,5-diniirc? Hen) M-2-re! Hyl6rotoP3t (BtKAPACRYL)
2-(l-i'eU.yl-n-hcpiyl)-i,6-dinilrcrher.yicrolcnat (OIKCCA?) . ·2- (l-i'eU.yl-n-hcpiyl) -i, 6-dinilhrcrher.yicrolcnat (OIKCCA?). ·
?,6-Dichlor-i-nitrc3-ilin (CICHLCS:1;) i^^.C-Tstrachlor-Lenzochinon (1,0 (CKLCRAKIL) ?, 6-dichloro-i-nitrc3-iline (CICHLCS: 1 ;) i ^^. C-Tstrachloro-lenzoquinone (1.0 (CKLCRAKIL)
li-t'elhylsulfonal-fi-trichlorrcihylthio-chJcra.niiinli-t'elhylsulfonal-fi-trichlororcihylthio-chJcra.niiin
0,0-DiäthyI-S-benzyl-thiolptiosphat0,0-diethyI-S-benzyl-thiolptiosphate
l-0xy-3-acetyl-6-cethyl-cyclohexen-(5)dion-(2,O (OEHYDROACETIC ACID)l-oxy-3-acetyl-6-ethyl-cyclohexen- (5) dione- (2, O (OEHYDROACETIC ACID) 8~Hydroxych'.nol in (8-CjJ.'.OLITiOL)8 ~ Hydroxych'.nol in (8-CjJ. '. OLITiOL) i-DjF.ci'iylaaino-S-^cthyl-S-n-butyl-i-hydroxy-pyrinidini-DjF.ci'iylaaino-S- ^ cthyl-S-n-butyl-i-hydroxy-pyrinidine
2-Acthylasir.o-ß-!;ethyl-5n-buiyl-^-hydroxypyrinfdin2-Acthylasir.o-ß- !; ethyl-5n-buiyl- ^ - hydroxypyrinfdin i.a-Dlcyano-l^-dHhia-anthrachinon (DITHI^.O.'J)i.a-Dlcyano-l ^ -dHhia-anthraquinone (DITHI ^ .O.'J) 2-«-Th5azolyi)-bcn2ii.Jc!azol2 - «- Th5azolyi) -bcn2ii.Jc! Azole
3,5-Dir.etSyHelrah/oro-),3,5-thiadiazin-2-ihion (DAZOXlT)3,5-Dir.etSyHelrah / oro -), 3,5-thiadiazin-2-ihione (DAZOXlT) 2t 3-D i hydro-5-carbo/an i1i do-c-ce thy I-1,4-oxa thin2 t 3-D i hydro-5-carbo / an i1i do-c-ce thy I-1,4-oxa thin
Die Verbindungen der Formel I können für sich allein oder zusammen mit geeigneten Trägern und/oder Zuschlagstoffen eingesetzt werden· Geeignete Träger und 2uscniagStoffe können fest oder flüssig sein und entsprechen den in der Formulierungstechnik üblichen Stoffen wie z.B. natürlichen oder regenerierten Stoffen, Lösungs-, Disper- gier-, Netz-, Haft-, Verdickungs-, Binde- und/oder Düngemitteln. The compounds of formula I can be used alone or together with suitable carriers and / or additives · Suitable carriers and 2 USCN i a g SUBSTANCES can be solid or liquid and correspond to the substances common in formulation practice, such as natural or regenerated substances , Solvents, dispersants, wetting agents, adhesives, thickeners, binders and / or fertilizers.
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 gehört, verarbeitet werden. Ferner sind "cattle dips", d.h. Viehbäder, und "spray" For application, the compounds of formula (I) to dusts, emulsion concentrates, granulates, dispersions, sprays may be solutions or slurries on in a conventional formulation, are processed belongs in the application technology for general knowledge. There are also "cattle dips", ie cattle baths, and "spray"
2098AO/11832098AO / 1183
races", d.h. Sprühgänge, in denen wässerige Zubereitungen verwendet werden, zu erwähnen.races ", i.e. spray courses in which aqueous preparations are used be to mention.
Die Herstellung erfindungsgemässer Mittel erfolgt in an sich bekannter Weise durch inniges Vermischen und/oder Vermählen 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:The agents according to the invention are produced in in a manner known per se by intimate mixing and / or grinding of active ingredients of the formula I with the suitable carriers, optionally with the addition of the active ingredients inert dispersants or solvents. The active ingredients can be used in the following processing forms are available and used:
feste Aufarbeitungsformen: Stäubemittel, Streumittel,solid processing forms: dusts, grit,
Granulate, Umhüllungsgranulate, Imprägnierungsgranulate und HomogengranulateGranules, coated granules, impregnation granules and homogeneous granules
flüssige Aufarbeitungsformen:liquid processing forms:
a) in Wasser dispergierbarea) dispersible in water
Wirkstoffkonzenträte: Spritzpulver (wettable powder),Active ingredient concentrates: wettable powder,
Pasten, Emulsionen;Pastes, emulsions;
b) Lösungenb) Solutions
Zur Herstellung fester Aufarbeitungsformen (Stäubemittel, Streumittel) werden die Wirkstoffe mit festen Trägerstoffen vermischt. Als Trägerstoffe kommen zum Beispiel Kaolin, Talkum, Bolus, Löss, Kreide, Kalkstein, Kalkgries, Ataclay, Dolomit, Diatomeenerde, gefällte Kieselsäure, Erdalkalisilikate, Natrium- und Kaliumaluminiumsilikate (Feldspate und Glimmer), Calcium- und Magnesiumsulfate, Magnesiumoxid, gemahlene Kunststoffe, Düngemittel, wie Ammoniumsulfat, Ammoniumphosphat, Ammoniumnitrat, Harnstoff, gemahlene pflanzliche Produkte, wie Getreidemehl, Baumrindenmehl, Holzmehl, Nussschalenmehl, Cellulosepulver, Rückstände von Pflanzenextraktionen, Aktivkohle etc., je für sich oder als Mischungen untereinander in Frage. . . .A *The active ingredients are mixed with solid carriers for the production of solid processing forms (dusts, grit). Carriers include kaolin, talc, bolus, loess, chalk, limestone, lime grit, ataclay, dolomite, diatomaceous earth, precipitated silica, alkaline earth silicates, sodium and potassium aluminum silicates (feldspar and mica), calcium and magnesium sulfates, magnesium oxide, ground plastics, Fertilizers such as ammonium sulfate, ammonium phosphate, ammonium nitrate, urea, ground vegetable products such as grain flour, tree bark flour, wood flour, nutshell flour, cellulose powder, residues from plant extractions, activated charcoal, etc., each individually or as mixtures with one another. . . . A *
209840/1183209840/1183
Granulate lassen sich sehr einfach herstellen, indem man einen Wirkstoff der Formel I in einem organischen Lösungsmittel löst und die so erhaltene Lösung auf ein granuliertes Mineral, z.B. Attapulgit, SiO?, Granicalcium, Bentonit usw. aufbringt und dann das organische Lösungsmittel wieder verdampft.Granules can be produced very easily by dissolving an active ingredient of the formula I in an organic solvent and applying the solution obtained in this way to a granulated mineral, for example attapulgite, SiO ? , Granicalcium, bentonite etc. and then the organic solvent evaporates again.
Es können auch Polymerengranulate dadurch hergestellt werden, dass die Wirkstoffe der Formel I mit polymerisierbaren Verbindungen vermischt werden (Harnstoff/Formaldehyd; Dicyandiamid/ Formaldehyd; Melamin/Pormaldehyd oder andere), worauf eine schonende Polymerisation durchgeführt wird, von der die Aktivsubstanzen unberührt bleiben, und wobei noch während, der Gelbildung die Granulierung vorgenommen wird. Günstiger ist es, fertige, poröse Pölymerengranulate (Harnstoff/Formaldehyd, Polyacrylnitril, Polyester und andere) mit bestimmter Oberfläche und günstigem voraus bestimmbaren Adsorptions/Desorptionsverhältnis mit den Wirkstoffen z.B. in Form ihrer Lösungen (in einem niedrig siedenden Lösungsmittel) zu imprägnieren und das Lösungsmittel zu entfernen. Derartige Polymerengranulate können in Form von Mikrogranulaten mit Schüttgewicht von vorzugsweise 3OO g/Liter bis 600 -g/Liter auch mit Hilfe von Zerstäubern ausgebracht werden. Das Zerstäuben kann über ausgedehnte Flächen von Nutzpflanzenkulturen mit Hilfe von Flugzeugen durchgeführt werden.Polymer granules can also be produced by mixing the active ingredients of the formula I with polymerizable Compounds are mixed (urea / formaldehyde; dicyandiamide / Formaldehyde; Melamine / formaldehyde or others), after which a gentle polymerization is carried out, from which the active substances Remaining untouched, and with the granulation still occurring during the gel formation is made. It is cheaper to use finished, porous polymer granules (Urea / formaldehyde, polyacrylonitrile, polyester and others) with a specific surface and favorable predictability Adsorption / desorption ratio with the active ingredients, e.g. in the form of their solutions (in a low-boiling solvent) to impregnate and remove the solvent. Such polymer granules can be used in the form of micro-granules Bulky weight of preferably 300 g / liter to 600 g / liter as well be applied with the help of atomizers. The atomization can be done over large areas of crops with the help of Aircraft are carried.
Granulate sind auch durch Kompaktieren des Trägermaterials mit den Wirk- und Zusatzstoffen und anschliessendem Zerkleinern erhältlich.Granules are also made by compacting the carrier material with the active ingredients and additives and then comminuting available.
Diesen Gemischen können ferner den Wirkstoff stabilisierende Zusätze und/oder nichtionische, anionaktive und kationaktive Stoffe zugegeben werden, die beispielsweise die HaftfestigkeitThese mixtures can also contain additives stabilizing the active ingredient and / or nonionic, anionic and cationic active substances Substances are added, for example the adhesive strength
209840/1183209840/1183
der Wirkstoffe auf Pflanzen -und Pflanzenteilen verbessern (Haft- und Klebemittel) und/oder eine bessere Benetzbarkeit (Netzmittel) sowie Dispergierbarkeit (Dispergatoren) gewährleisten.improve the active ingredients on plants and plant parts (adhesive and adhesives) and / or ensure better wettability (wetting agents) and dispersibility (dispersants).
Beispielsweise kommen folgende Stoffe in Frage: Olein-Kalk-Mi schling, Cellulosederivate (Methylcellulose, Carboxymethylcellulose), Hydroxyäthylenglykoläther von Mono- und Dialkylphenolen mit 5-15 Aethylenoxidresteii pro Molekül und 8-9 Kohlenstoffatomen im Alkylrest, Ligninsulfonsäure, deren Alkali- und Erdalkalisalze, Polyäthylenglykoläther (Carbowachs), Pettalkoholpolyglykoläther mit 5-20 Aethylenoxidresten pro Molekül und 8-18 Kohlenstoffatomen im Fettalkoholteil, Kondensationsprodukte von Aethylenoxid, Propylenoxid, Polyvinylpyrrolidone, Polyvinylalkohole, Kondensationsprodukte von Harnstoff-Formaldehyd sowie Latex-Produkte.For example, the following substances are possible: olein-lime-Mi loop, cellulose derivatives (methyl cellulose, carboxymethyl cellulose), Hydroxyethylene glycol ethers of mono- and dialkylphenols with 5-15 Aethylenoxidresteii per molecule and 8-9 carbon atoms in the alkyl radical, ligninsulphonic acid, its alkali and alkaline earth salts, polyethylene glycol ether (Carbowax), Pettalkoholpolyglykoläther with 5-20 ethylene oxide residues per molecule and 8-18 carbon atoms in the fatty alcohol part, condensation products of ethylene oxide, propylene oxide, Polyvinylpyrrolidones, polyvinyl alcohols, condensation products of urea-formaldehyde and latex products.
In Wasser dispergierbare Wirkstoffkonzentrate, d.h. Spritzpulver (wettable powder), Pasten und Emulsionskonzentrate stellen . Mittel dar, die mit Wasser auf jede gewünschte Konzentration verdünnt Werden können. Sie bestehen aus Wirkstoff, Trägerstoff, gegebenenfalls den Wirkstoff stabilisierenden Zusätzen, oberflächenaktiven Substanzen und Antischaummitteln und gegebenenfalls Lösungsmi tteln.Active ingredient concentrates dispersible in water, i.e. wettable powders, pastes and emulsion concentrates place . Represent means that can be diluted with water to any desired concentration. They consist of an active ingredient, a carrier, optionally additives stabilizing the active substance, surface-active substances and antifoams, and optionally Solvents.
Die Spritzpulver (wettable powder) und Pasten werden erhalten, indem man die Wirkstoffe mit Dispergiermitteln und pulverförmigen Trägerstoffen in geeigneten Vorrichtungen bis zur Homogenität vermischt und vermahlt. Als Trägerstoffe kommen beispielsweise die vorstehend für die festen Aufarbeitungsformen erwähnten in Frage, In machen Fällen ist es vorteilhaft $ Mischungen verschiedener Trägerstoffe zu verwenden» Als Dispergatoren können beispielsweise verwendet werden: Kondensationsprodukte von sulfoniertemThe wettable powders and pastes are obtained by mixing and grinding the active ingredients with dispersants and pulverulent carriers in suitable devices until homogeneous. Suitable excipients are, for example, those mentioned above for the solid processing forms in question, in some cases, it is advantageous $ mixtures of different carriers to use "The dispersants can be used, for example: condensation products of sulfonated
209840/1183209840/1183
Naphthalin und sulfonierten Naphthalinderivaten mit Formaldehyd, Kondenstionsprodukte des Naphthalins bzw. der Naphthalinsulfonsäuren mit Phenol und Formaldehyd sowie Alkali-, Ammonium- und Erdalkalisalze von Ligninsulfonsäure, weiter Alkylarylsulfonate, Alkali- und Erdalkalimetallsalze der Dibutylnaphthalinsulfonsaure, Fettalkoholsulfate, wie Salze sulfatierter Hexadecanole, Heptadecanole, Octadecanole und Salze von sulfatiertem Fettalkoholglykoläther, das Natriumsalz von QLe ylmethyltaurid, ditertiäre Aethylenglykole, Dialkyldilaurylarnmoniumchlorid^und fettsaure Alkali- und Erdalkalisalze. Naphthalene and sulfonated naphthalene derivatives with formaldehyde, condensation products of naphthalene or naphthalene sulfonic acids with phenol and formaldehyde as well as alkali, ammonium and alkaline earth salts of lignosulphonic acid, further alkylarylsulphonates, alkali and alkaline earth metal salts of dibutylnaphthalenesulfonic acid, fatty alcohol sulfates, such as salts of sulfated hexadecanols, heptadecanols, octadecanols and salts of sulfated fatty alcohol glycol ethers, the sodium salt of QLe ylmethyltauride, ditertiary ethylene glycols, Dialkyldilaurylammonium chloride and fatty acid alkali and alkaline earth salts.
Als Antischaummittel kommen zum Beispiel Silicone in Frage.Silicones, for example, can be used as antifoam agents.
Die Wirkstoffe werden mit den oben aufgeführten Zusätzen so vermischt, vermählen, gesiebt und passiert, dass bei den Spritzpulvern der festen Anteil eine Korngrösse von 0,02 bis 0,04 und bei den Pasten von 0,03 mm nicht überschreitet. Zur Herstellung von Emulsionskonzentraten und Pasten werden Dispergiermittel, wie sie in den vorangehenden Abschnitten aufgeführt wurden, organische Lösungsmittel und Wasser verwendet. Als Lösungsmittel kommen beispielsweise Alkohole, Benzol, Xylole, Toluol, Dimethylsulf oxid und im Bereich von 120 bis 350 C siedende Mineralölfraktionen in Frage. Die Lösungsmittel müssen praktisch geruchlos, nicht phytotoxisch und den Wirkstoffen gegenüber inert sein.The active ingredients are mixed, ground, sieved and passed with the additives listed above in the same way as with the wettable powders the solid part has a grain size of 0.02 to 0.04 and at the pastes does not exceed 0.03 mm. For production of Emulsion concentrates and pastes are dispersants as listed in the previous sections, organic Solvent and water used. As solvents, for example, alcohols, benzene, xylenes, toluene, dimethyl sulfoxide and come Mineral oil fractions boiling in the range from 120 to 350 C are suitable. The solvents must be practically odorless, non-phytotoxic and inert to the active ingredients.
Ferner können die erfindungsgemässen Mittel in Form von Lösungen angewendet werden. Hierzu wird der Wirkstoff bzw. werden mehrere V/irkstoffe der allgemeinen Formel I in geeigneten organischen: Lösungsmitteln, Lösungsmittelgemischen oder V/asser gelöst,The agents according to the invention can also be used in the form of Solutions are applied. For this purpose, the active ingredient or several active ingredients of the general formula I are used in suitable organic: Solvents, solvent mixtures or dissolved in water,
209840/1183209840/1183
Als organische Lösungsmittel können aliphatische und aromatische Kohlenwasserstoffe, deren chlorierte Derivate, AlkyInaphthaline, Mineralöle allein oder als Mischung untereinander verwendet werden.As organic solvents, aliphatic and aromatic hydrocarbons, their chlorinated derivatives, alkyinaphthalenes, Mineral oils can be used alone or as a mixture with one another.
Der Gehalt an Wirkstoff in den oben beschriebenen Mitteln liegt zwischen 0,1 bis 95$, dabei ist zu erwähnen, dass bei der Applikation aus dem Flugzeug oder mittels anderer geeigneter Applikationsgeräte Konzentrationen bis zu 99,5$ oder sogar reiner Wirkstoff eingesetzt werden können.The content of active ingredient in the agents described above is between $ 0.1 and $ 95, it should be mentioned that the Application from the aircraft or by means of other suitable application devices, concentrations of up to $ 99.5 or even more pure Active ingredient can be used.
Die Wirkstoffe der Formel I können beispielsweise wie folgt formuliert werden:The active ingredients of the formula I can, for example, be formulated as follows:
Stäubemittel: Zur Herstellung eines a) 5$igen und b) 2$igen Stäubemittels werden die folgenden Stoffe verwendet:Dust: For the production of a) 5 and b) 2 dusts the following substances are used:
a) 5 Teile Wirkstoff·
95 Teile Talkum;a) 5 parts of active ingredient
95 parts of talc;
b) 2 Teile Wirkstoffb) 2 parts of active ingredient
1 Teil hochdisperse Kieselsäure, 97 Teile Talkum1 part of highly disperse silica, 97 parts of talc
Die Wirkstoffe werden mit den Trägerstoffen vermischt und vermählen.The active ingredients are mixed and ground with the carrier substances.
Granulat: Zur Herstellung eines 5$igen Granulates werden die folgenden Stoffe verwendet:Granulate: To produce a 5 $ granulate, the following Substances used:
— 5 Teile Wirkstoff- 5 parts of active ingredient
0,25 Teile Epichlorhydrin,
•Q>?3 Teile Cetylpolyglykoläther,
3,50 Teile Polyäthylenglykol
91 Teile Kaolin (Korngrösse 0,3 - 0,8 mm).0.25 part of epichlorohydrin,
• Q> 3 parts cetyl polyglycol ether, 3.50 parts polyethylene glycol
91 parts of kaolin (grain size 0.3-0.8 mm).
D.vv Aktivcubstanr. wird mit Epichlorhydrin vermischt und mit 6 Teilen Aceton gelöst, hierauf wird Polyäthylenglykol undD.vv Aktivcubstanr. is mixed with epichlorohydrin and dissolved with 6 parts of acetone, then polyethylene glycol and
2 0 9 8 U ü / 1 1 P 32 0 9 8 U ü / 1 1 P 3
Ce ty I])C lyglykc-j ;'tlK.r : ny ..· Kaolin aufgesprüht, und anr. Spritzpulver: Zur Herste:^Ce ty I]) C lyglykc-j; 'tlK.r: ny .. · Kaolin sprayed on, and anr. Wettable powder: For the manufacture: ^
d) IO %\ cen Spritzpulversd) IO % \ cen spray powder
40 5 140 5 1
54 2554 25
-Te-Natriumsalz,
.: nsulf onsäure-Natriumsalz,-Te sodium salt,
.: nsulfonic acid sodium salt,
' :;o erhaltene Lösung wird auf ■ ■:■'.-:;·..■ I das Aceton im Vakuum verdampft. , — ,·.) 4Obigen, b) und c) 25^i gen ; - ' ende Bestandteile verwendet:':; O obtained solution is adjusted to ■ ■: ■' evaporated .- :; · .. ■ I, the acetone in vacuo. , -, ·.) 4Obigen, b) and c) 25 ^ i gen; - 'End components used:
Teile Wirkst oft TeileParts Do often make parts
Te j 3 Dibuty jin'ij)!:' ];: Teile Jo eecDsäure; Te.i]c- WirkstoffTe j 3 Dibuty jin'ij) !: '];: Parts of Jo eecDäure; Te.i] c active ingredient
4,5 Teile Ca] ei um-Li cn: ru^ulf onat, 1,9 Toi De Champagne-Kr·"·: de/Hydroxyäthylcellulose-4.5 parts Ca] ei um-Li cn: ru ^ ulfonat, 1.9 Toi De Champagne-Kr · "·: de / Hydroxyethylcellulose-
Gemi scli (l:l ), Gemi scli (l: l) ,
3,5 Teile Natrium-dibutyl-naphthalinsulfonat, 19,5 Teile Kieselsäure, 19,5 Teile Champagne-Kreide, 28,1 Teile Kaolin; 25 Teile Wirkstoff 2,5 Teile Isooctylphenoxy-polyoxyäthylen-äthanol, 1,7 Teile Champagne-Kreide/Hydroxyäthylcellulose-3.5 parts of sodium dibutyl naphthalene sulfonate, 19.5 parts silica, 19.5 parts Champagne chalk, 28.1 parts of kaolin; 25 parts of active ingredient 2.5 parts of isooctylphenoxy-polyoxyethylene-ethanol, 1.7 parts champagne chalk / hydroxyethyl cellulose
Gemi sch (l: 1),Mixed (l: 1),
8,3 Teile Natriumaluminiumsilikat, 16,5 T-. ilc Kieselgur, 46 Teile Kaolin; 10 TeiIe Wirkstoff 3 Teile Gemisch der Natriumsalze von gesättigten8.3 parts sodium aluminum silicate, 16.5 T-. ilc diatomaceous earth, 46 parts of kaolin; 10 parts active ingredient 3 parts mixture of the sodium salts of saturated
Fe 11a1koho1su1fa ten, 5 Teile IJa phtha 1 insul fön säure -Formaldehyd -Kondensat,Fe 11a1koho1su1fa ten, 5 parts IJa phtha 1 insul fön acid formaldehyde condensate,
8282
Teile Kaolin.Share kaolin.
20Θ8Α0/ 118320Θ8Α0 / 1183
BAD ORIGINALBATH ORIGINAL
Die V/irkstoffe werden in geeigneten Mischern mib den Zuschlagstoffen innig vermischt und auf entsprechenden Mühlen und Walzen vermählen. Man erhält Spritzpulver, die sich mit Wasser zuThe active ingredients are mixed in suitable mixers Aggregates are intimately mixed and ground on appropriate mills and rollers. You get wettable powder, which can be mixed with water
Suspensionen jeder gewünschten Konzentration verdünnen lassen. Emulgierbare Konzentrate: Zur Herstellung eines a) lO^igen und b) 25/^igen emulgierbaren Konzentrates werden folgende Stoffe verwendet:Allow suspensions to be diluted to any desired concentration. Emulsifiable concentrates: For the production of a) lO ^ igen and b) 25 / ^ igen emulsifiable concentrates are the following substances used:
a) IO Teile Wirkstoffa) IO parts active ingredient
3.4 Teile epoxydiertes Pflanzenöl,3.4 parts epoxidized vegetable oil,
13*4 Teile eines Kurnbinationsemulgators, bestehend aus Pettalküho !.polyglykolether und Alkylarylsulfonat-Calcium-Salz, 13 * 4 parts of a combination emulsifier, consisting of Pettalküho! .Polyglycol ether and alkylarylsulfonate calcium salt,
40 Teile Dimethylformamid, 4-3,2 Teile Xylol;40 parts dimethylformamide, 4-3.2 parts xylene;
b) 25 Teile Wirkstoffb) 25 parts of active ingredient
2.5 Teile epoxydiertes Pflanzenöl,2.5 parts epoxidized vegetable oil,
10 Teile eines Alkylarylsulfonat-Fettalkoholpoly-10 parts of an alkylarylsulfonate fatty alcohol poly
glykoläther-Gernisches,
5 Teile Dimethylformamid, 57,5 Teile Xylol.glycol ether-Gernisches,
5 parts of dimethylformamide, 57.5 parts of xylene.
Aus diesen Konzentraten können durch Verdünnen mit Wasser Emulsionen jeder gewünschten Konzentration hergestellt werden.
Sprühmittel: Zur Herstellung eines 5 ^igen Sprüh- .. , .
mittels werden die folgenden Bestandte_ie verwendet:
5 Teile Wirkstoff,
1 Teil Epichlorhydrin,
94 Teile Benzin (Siedegronzen 16O -0 Emulsions of any desired concentration can be prepared from these concentrates by diluting them with water. Spray: For the production of a 5 ^ igen spray ..,. by means of the following ingredients are used: 5 parts active ingredient,
1 part epichlorohydrin,
94 parts of gasoline (Boiling Gronzen 16O - 0
\ 's\ 's
32,2 g 3-AmLnobenzotrifluorid werden in 200 ml Wasser mit 60 ml Konz. Salzsäure in das Chlorhydrat überführt und auf übliehe Weise mit 14 g Hatriumnitrit in 60 ml Wasser diazotiert.32.2 g of 3-amlnobenzotrifluoride are converted into the chlorohydrate in 200 ml of water with 60 ml of conc. Hydrochloric acid and diazotized in the usual way with 14 g of sodium nitrite in 60 ml of water.
Anschliessend wird während einer Stunde bei 0-2 C Stick stoff durch die Lösung geleitet, um eventuell vorhandene nitrose Gase zu entfernen.Then stick material is passed through the solution for one hour at 0-2 C in order to remove any nitrous gases that may be present.
Dann wird nacheinander 50 ml Chlorbenz-· L, eine Lösung von 44,8 g Kai Inrrisa Lz der DLäthyld i thiophosphoric' ire, 10,6 g Natriumcarbonat in 100 ml Wasser und zuletzt 0,2 Teile Ki:pforpulv^r zugesetzt, fiese Miochung wird während 2 Stunden auf C or.·/arm ι,.Then successively 50 ml of chlorobenzene, a solution of 44.8 g of Kai Inrrisa Lz der DLäthyld i thiophosphoric 'ire, 10.6 g of sodium carbonate in 100 ml of water and finally 0.2 part of Ki: pforpulv ^ r added, nasty Miochung is set to C or. · / Arm ι ,. for 2 hours.
Nach der in an sich bekannter Weise eifDlgence:: Aufarbeitung erhält man den Wirkstoff der FormeLAfter working up in a manner known per se, the active ingredient of the form L is obtained
CFCF
1,5261.526
Auf analoge Weise werden auch die folgenden Verbindungen hergestellt:The following compounds manufactured:
CF_CF_
' — οι? '- οι?
° 1, 538 ° 1, 538
H 0 / ! H 0 /!
CP.CP.
((1Oc3H7C)2-P-S-^V((1Oc 3 H 7 C) 2 -PS- ^ V
1,5141.514
CF.CF.
(Do3H7O(Thu 3 H 7 O
S 73 P. 73
(CH(CH
S CP3S CP 3
lt521lt521
rOrO
1,5421,542
■ o■ o
1,5331.533
,0, 0
1,5111.511
\H\H
,0, 0
1,5271.527
0 9 8 4 0/11830 9 8 4 0/1183
insektizide Frassf'ift-V.Mrku.nn;insecticidal Frassf'ift-V.Mrku.nn;
Baumwollpflanzen und Kartoffelstauden wurden mit einer 0,05/5-ißen wässrigen Wirkstoffemulsion (erhalten aus einem 10/o-igen emulgierbaren Konzentrat) besprüht.Cotton plants and potato plants were treated with a 0.05 / 5% aqueous active substance emulsion (obtained from a 10 / o-strength emulsifiable concentrate) sprayed.
Nach dem Antrocknen des Belages wurden die Baumwollpflanzen mit Dlsdercus fasciatus Nymphen und die Kartoffelstauden mit Kartoffelkäfer-Larven (Leptinotarsa decemlineata) besetzt. Der Versuch wurde bei 240C und 60# relativer Luftfeuchtigkeit durchgeführt.After the covering had dried on, the cotton plants were populated with Dlsdercus fasciatus nymphs and the potato plants with Colorado beetle larvae (Leptinotarsa decemlineata). The experiment was carried out at 24 ° C. and 60 ° relative humidity.
Die Verbindungen gemäss Beispiel 1 zeigten im obigen Test eine gute insektizide Frassgift-Wirkung gegen Disdercus fasciatus und Leptinotarsa decemlineata.The compounds according to Example 1 showed in the above Test a good insecticidal food poison effect against Disdercus fasciatus and Leptinotarsa decemlineata.
Zur Feststellung der systemischen Wirkung werden bewurzelte Bohnenpflanzen (Vicia fabae) in eine O,Ol#ige wässrige Wirkstofflösung (erhalten aus einem lO^igen emulgierbaren Konzentrat) eingestellt. Nach 2h Stunden wurden auf die oberirdischen Pflanzenteile Blattläuse (Aphis fabae) gesetzt. Durch eine spezielle Einrichtung waren die Tiere vor der Kontakt- und Gaswirkung geschützt. Der Versuch wurde bei 24° und 70% relativer Luftfeuchtigkeit durchgeführt.To determine the systemic effect, rooted bean plants (Vicia fabae) are placed in an O, O, aqueous active ingredient solution (obtained from a 10 ^ emulsifiable concentrate). After 2 hours, aphids (Aphis fabae) were placed on the above-ground parts of the plant. The animals were protected from contact and gas effects by a special device. The experiment was carried out at 24 ° and 70% relative humidity.
209840/1183209840/1183
Im obigen Test zeigten die Verbindunge gemäss Beispiel 1 eine gute systemisch-insektizide Wirkung gegen Aphis fabae.In the above test, the compounds according to Example 1 showed a good systemic insecticidal action against Aphis fabae.
Beispiel '■%
Akarizide Wirkung Example '■%
Acaricidal effect
a) Wirkung: auf Mühen (Tetranychus urticae) a) Effect: on effort (Tet r anychus urticae)
Zur Prüfung der akariziden Wirkung wurden Bohnenblätter., die durch Adulte, Ruhestadien und Eier der roten Spinnmilbe (Tetranychus urticae) befallen sind, mit einer O,O5/2-igen wässrigen Emulsion der zu prüfenden Substanz (hergestellt aus einem 25/c-igen emulgierbaren Konzentrat) behandelt. Nach 6 Tagen wurde der Versuch ausgewertet. Als Versuchstiere dienten gegen Phosphorsäureester resistente Stämme der roten Spinnmilbe.Bean leaves were used to test the acaricidal effect., infested by adults, dormant stages and eggs of the red spider mite (Tetranychus urticae), with an O, O5 / 2-igen aqueous emulsion of the substance to be tested (made from a 25 / c-strength emulsifiable concentrate). The experiment was evaluated after 6 days. Strains of the red strains resistant to phosphoric acid esters were used as test animals Spider mite.
b) Wirkung auf Zecken (Boophilus microplus) und deren Entv/icklungsstadien b) Effect on ticks ( Boophilus microplus) and their stages of development
Für den folgenden Versuch wurden je 10 adulte, legereife Zecken J5 Minuten lang in wässrige Wirkstoffernulsionen (Konzentrationen lOO, 200, 400 und 800 ppm) getaucht.For the following experiment, 10 adults each were ready to lay Ticks in aqueous drug emulsions for 5 minutes (Concentrations 100, 200, 400 and 800 ppm) immersed.
Dann wurden die Zecken bei 270C und 80^ relativer Luftfeuchtigkeit gehalten. Am 5·* 10· und I5. Tag wurde die Eiablage bestimmt.Then the ticks were kept at 27 0 C and 80 ^ relative humidity. On 5 * 10 and 15. On the day of the egg laying was determined.
Die nach den oben angegebenen Tests a) und b) geprüften Verbindungen cc:näGs Beispiel 1 zeigten gute Wirkung sogen Tetranychus urticae und Ütraphilus microplus.The compounds cc: NaGs Example 1 tested according to the tests a) and b) given above showed a good effect so-called Tetranychus urticae and Ütraphilus microplus.
209840/1183209840/1183
' Beispiel 5'Example 5
a) Wirkung gegen Botirytis cinerea auf Vicia faba a) Action against Botirytis cinerea on Vicia faba
In Petrischalen, die mit befeuchtetem Filterpapier ausgelegt worden sind, wurden je drei voll entwickelte, gleichgrosse Blätter von Vicia faba gelegt, die mit einer aus der als 10%-iges Spritzpulver formulierten Wirksubstanz hei'gestcllten Brühe (0,05% Aktivsubstanz-Gehalt) mit einem Sprühapparat tropfnass besprüht wurden. Als die Blätter wieder trocken waren, wurden sie mit einer frisch bereiteten, standardisierten Sporensuspension des Pilzes (Konzentration: 1001OOO Sporen/ml) infiziert und 48 Stunden in einer feuchten Atmosphäre bei 20 C gehalten. Nach dieser Zeit wiesen sie schwarze, zunächst punktförmige Flecken auf, die sich rasch ausbreiteten. Anzahl und Grosse der Infektionsstellen dienten als Bewerti.ngsnassstab für die Wirksamkeit der Prüfsubstanz.Three fully developed leaves of the same size from Vicia faba were placed in Petri dishes, which had been lined with moistened filter paper. were sprayed dripping wet with a sprayer. When the leaves were dry again, they were prepared fresh with a standardized spore suspension of the fungus (concentration: 100 1 OOO spores / ml) infected and maintained for 48 hours in a humid atmosphere at 20 C. After this time, they showed black, initially point-like spots that spread rapidly. The number and size of the infection sites served as an assessment wet rod for the effectiveness of the test substance.
b) Wirkung gegen Erysiphs cichoracearun auf Cucuils sntivus b) Action against Erysiphs cichoracearun on Cucuils sntivus
Junge Cucumis sativus-Pflanzen wurden nah dem Besprühen mit einer 0,05%-igen Suspension des als Spritzpulver formulierten Wirkstoffes und nach dem Antrocknen des Spritzbclages mit einer Sporensuspension des Pilzes besprüht. Nach 8 Ta^ η im Gewächshaus bei ca. 23°C wurde der Befallsgrad (Anteil er vom Hycelbelag überzogenen Blattoberfläche) auf den infi:. arten, behandelten BIaLLern, im Vergleich zu unbchanuelten, infizierLcn Kontrollen ermittelt.Young Cucumis sativus plants were sprayed close to the spraying with a 0.05% suspension of the active ingredient formulated as a wettable powder and, after the spray coating had dried on, sprayed with a spore suspension of the fungus. After 8 Ta ^ η in a greenhouse at about 23 ° C, the degree of infection (percentage of he Hycelbelag coated sheet surface) on the infi :. species, treated balls compared to non-channeled, infected controls.
2098A0/11832098A0 / 1183
c) Wirkung gegen Uroniyces appendix ulate s auf Phaseolus yulgaris_ c) Action against Uroniyces appendix ulate s on Phaseolus yulgaris_
Phaseolus vulgaris-Pflanzen im Zv/eiblatt stadium wurden mit einer Suspension der als Spritzpulver formulierten Substanz bis zur Tropfnässe" besprüht (Konzentration: 0,05% Aktivsubstanz). Nach dera Antrocknen des Spritzbelages wurden die Pflanzen mit einer frischen Sporensuspension des Bohnenrostes infiziert und anschliessend für einen Tag in einer feuchten Kammer und 12 Tage im Gewächshaus bei 2O-22°C gehalten.Phaseolus vulgaris plants in the Zv / egg-leaf stage were sprayed with a suspension of the substance formulated as a wettable powder to runoff point (concentration: 0.05% active substance). After the spray coating had dried on, the plants were infected with a fresh spore suspension of the bean grate and then kept in a humid chamber for one day and in a greenhouse at 20-22 ° C. for 12 days.
Anzahl und Grosse der Rostpusteln dienten als Bewertungsmassstab für die Wirksamkeit der Prüfsubstanzen.The number and size of the rust pustules were used as a benchmark for the effectiveness of the test substances.
d) Wirkung gegen Phytophthora infestans auf Solanum Lycopersicumd) Action against Phytophthora infestans on Solanum Lycope rsicum
S. Lycopexsicuni-Pflanzen der gleichen Sorte und im gleichen Entwicklungsstadium wurden mit einer Brühe von 0,05% Aktivsubstanz behandelt (hergestellt aus der zu einem Spritzpulver aufgearbeiteten Wirksubstanz}. Nach dem Antrocknen des Spritzbelages wurden die Pflanzen mit einer Zoosporen-Suspension von Ph. infestans tropfnass besprüht. Sie blieben dann für 6 Tage im Gewächshaus bei 18-2O°C und hoher Luftfeuchtigkeit (95-100%) und ze5.gten nach dieser Zeit typische Blattflecken. Aufgrund ihrer Anzahl und Grosse erfolgte die Beurteilung der geprüften Substanz.S. Lycopexsicuni plants of the same cultivar and in the same Stage of development were with a broth of 0.05% active ingredient treated (made from the active substance processed into a wettable powder). After the spray coating has dried on the plants were sprayed dripping wet with a zoospore suspension of Ph. infestans. They then stayed for 6 days in a greenhouse at 18-2O ° C and high humidity (95-100%) and showed typical leaf spots after this time. Because of The number and size of the tested substance were assessed.
Die Verbindungen geinäss Beispiel 1 zeigen in den obigen Tests a) bis d) fungizide Wirkung.The compounds according to Example 1 show in the above Tests a) to d) fungicidal effect.
209840/1183209840/1183
Zur Prüfung der Wirkung gegen Bodennematoden wurden die Wirkstoffe in der jeweils angegebenen Konzentration in durch Wurzelzellen-Nematoden (Meloidogyne Avenaria) infizierte Erde gegeben und innig vermischt. In die so vorbereitete Erde wurden in einer Versuchsreihe unmittelbar danach Tomatensetzlinge gepflanzt und in einer zweiten Versuchsreihe nach 8 Tagen V/artezeit Tomaten eingesät.To test the action against soil nematodes, the active ingredients were in the given concentration in Root cell nematodes (Meloidogyne Avenaria) infected soil given and intimately mixed. Immediately afterwards tomato seedlings were placed in the soil prepared in this way in a test series planted and in a second series of experiments sown tomatoes after 8 days before the season.
Zur Beurteilung der nematoziden Wirkung wurden 28 Tage nach dem Pflanzen bzw. nach der Saat die an den Wurzeln vorhandenen Gallen ausgezählt.The nematocidal effect was assessed for 28 days after planting or after sowing, the galls present on the roots are counted.
In diesem Test zeigten die Wirkstoffe gemäss Beispiel 1 eine gute Wirkung gegen Meloidogyne Avenaria.In this test, the active ingredients according to Example 1 showed a good effect against Meloidogyne Avenaria.
209840/ 1183209840/1183
Claims (1)
/
E2TPSM
/
E 2 T
12. Verwendung von Verbindungen der FormelR, and R ^ each denote alkyl and X and Y each denote oxygen or sulfur, and contain suitable carriers and / or other additives.
12. Use of compounds of the formula
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CH433971 | 1971-03-24 | ||
CH149772 | 1972-02-01 |
Publications (1)
Publication Number | Publication Date |
---|---|
DE2210092A1 true DE2210092A1 (en) | 1972-09-28 |
Family
ID=25687829
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
DE19722210092 Pending DE2210092A1 (en) | 1971-03-24 | 1972-03-02 | Pesticides |
Country Status (4)
Country | Link |
---|---|
DE (1) | DE2210092A1 (en) |
FR (1) | FR2130597A1 (en) |
IT (1) | IT953548B (en) |
NL (1) | NL7203906A (en) |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE3201227A1 (en) * | 1982-01-16 | 1983-07-28 | Basf Ag, 6700 Ludwigshafen | 2-TRIFLUORMETHYLPHENYL- (DI) -THIOPHOSPHORIC ACID ESTER, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE FOR CONTROLLING Pests |
-
1972
- 1972-03-02 DE DE19722210092 patent/DE2210092A1/en active Pending
- 1972-03-22 IT IT2226172A patent/IT953548B/en active
- 1972-03-23 NL NL7203906A patent/NL7203906A/xx unknown
- 1972-03-23 FR FR7210190A patent/FR2130597A1/en active Granted
Also Published As
Publication number | Publication date |
---|---|
FR2130597B1 (en) | 1974-09-13 |
NL7203906A (en) | 1972-09-26 |
IT953548B (en) | 1973-08-10 |
FR2130597A1 (en) | 1972-11-03 |
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