DE2619304A1 - Neue schwefelhaltige formamidine, verwendung derselben und diese enthaltende land-, garten- und forstwirtschaftliche chemikalien - Google Patents
Neue schwefelhaltige formamidine, verwendung derselben und diese enthaltende land-, garten- und forstwirtschaftliche chemikalienInfo
- Publication number
- DE2619304A1 DE2619304A1 DE19762619304 DE2619304A DE2619304A1 DE 2619304 A1 DE2619304 A1 DE 2619304A1 DE 19762619304 DE19762619304 DE 19762619304 DE 2619304 A DE2619304 A DE 2619304A DE 2619304 A1 DE2619304 A1 DE 2619304A1
- Authority
- DE
- Germany
- Prior art keywords
- methyl
- carbon atoms
- formula
- alkyl radical
- thio
- 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.)
- Withdrawn
Links
- 239000000126 substance Substances 0.000 title claims description 3
- 150000001875 compounds Chemical class 0.000 claims description 85
- -1 alkyl radical Chemical class 0.000 claims description 69
- 125000000446 sulfanediyl group Chemical group *S* 0.000 claims description 37
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 34
- 125000004432 carbon atom Chemical group C* 0.000 claims description 32
- 241000607479 Yersinia pestis Species 0.000 claims description 21
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 claims description 18
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 12
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 12
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 claims description 12
- PNKUSGQVOMIXLU-UHFFFAOYSA-N Formamidine Chemical compound NC=N PNKUSGQVOMIXLU-UHFFFAOYSA-N 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- PVOAHINGSUIXLS-UHFFFAOYSA-N 1-Methylpiperazine Chemical compound CN1CCNCC1 PVOAHINGSUIXLS-UHFFFAOYSA-N 0.000 claims description 7
- 239000002253 acid Substances 0.000 claims description 7
- 125000005843 halogen group Chemical group 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- TXQKCKQJBGFUBF-UHFFFAOYSA-N 3,4,5-tribromo-1h-pyrazole Chemical compound BrC1=NNC(Br)=C1Br TXQKCKQJBGFUBF-UHFFFAOYSA-N 0.000 claims description 6
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 claims description 6
- 125000000217 alkyl group Chemical group 0.000 claims description 6
- 150000005840 aryl radicals Chemical class 0.000 claims description 6
- 238000002360 preparation method Methods 0.000 claims description 6
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical group O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims description 6
- FWMUJAIKEJWSSY-UHFFFAOYSA-N sulfur dichloride Chemical compound ClSCl FWMUJAIKEJWSSY-UHFFFAOYSA-N 0.000 claims description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 4
- DMBHHRLKUKUOEG-UHFFFAOYSA-N diphenylamine Chemical compound C=1C=CC=CC=1NC1=CC=CC=C1 DMBHHRLKUKUOEG-UHFFFAOYSA-N 0.000 claims description 4
- 150000001412 amines Chemical class 0.000 claims description 2
- 230000027455 binding Effects 0.000 claims description 2
- 238000009739 binding Methods 0.000 claims description 2
- BQJCRHHNABKAKU-KBQPJGBKSA-N morphine Chemical compound O([C@H]1[C@H](C=C[C@H]23)O)C4=C5[C@@]12CCN(C)[C@@H]3CC5=CC=C4O BQJCRHHNABKAKU-KBQPJGBKSA-N 0.000 claims 2
- 239000002516 radical scavenger Substances 0.000 claims 2
- HAYWNVRJEJDSGH-UHFFFAOYSA-N 4-chloro-2-methylbenzenecarboximidamide Chemical compound CC1=CC(Cl)=CC=C1C(N)=N HAYWNVRJEJDSGH-UHFFFAOYSA-N 0.000 claims 1
- 125000001309 chloro group Chemical group Cl* 0.000 claims 1
- 229960005181 morphine Drugs 0.000 claims 1
- JTMJJGAMTHKONV-UHFFFAOYSA-N n'-(2,4-dimethylphenyl)-n-(n-ethylanilino)sulfanyl-n-methylmethanimidamide Chemical compound C=1C=CC=CC=1N(CC)SN(C)C=NC1=CC=C(C)C=C1C JTMJJGAMTHKONV-UHFFFAOYSA-N 0.000 claims 1
- SMOYLFDBKHKTCC-UHFFFAOYSA-N n'-(2,4-dimethylphenyl)-n-methyl-n-piperidin-1-ylsulfanylmethanimidamide Chemical compound C=1C=C(C)C=C(C)C=1N=CN(C)SN1CCCCC1 SMOYLFDBKHKTCC-UHFFFAOYSA-N 0.000 claims 1
- JUOLCBXIGMKHJD-UHFFFAOYSA-N n'-(4-bromo-2-methylphenyl)-n-[di(propan-2-yl)amino]sulfanyl-n-methylmethanimidamide Chemical compound CC(C)N(C(C)C)SN(C)C=NC1=CC=C(Br)C=C1C JUOLCBXIGMKHJD-UHFFFAOYSA-N 0.000 claims 1
- HKQUNWBQYGBLMK-UHFFFAOYSA-N n'-(4-chloro-2-methylphenyl)-n-(n-ethylanilino)sulfanyl-n-methylmethanimidamide Chemical compound C=1C=CC=CC=1N(CC)SN(C)C=NC1=CC=C(Cl)C=C1C HKQUNWBQYGBLMK-UHFFFAOYSA-N 0.000 claims 1
- LFUCJUVICFPYOS-UHFFFAOYSA-N n'-(4-chloro-2-methylphenyl)-n-[di(propan-2-yl)amino]sulfanyl-n-methylmethanimidamide Chemical compound CC(C)N(C(C)C)SN(C)C=NC1=CC=C(Cl)C=C1C LFUCJUVICFPYOS-UHFFFAOYSA-N 0.000 claims 1
- KZEARZDBDZFLAH-UHFFFAOYSA-N n'-(4-chloro-2-methylphenyl)-n-methyl-n-morpholin-4-ylsulfanylmethanimidamide Chemical compound C=1C=C(Cl)C=C(C)C=1N=CN(C)SN1CCOCC1 KZEARZDBDZFLAH-UHFFFAOYSA-N 0.000 claims 1
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 56
- 239000000047 product Substances 0.000 description 49
- 239000002904 solvent Substances 0.000 description 32
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 24
- 239000000243 solution Substances 0.000 description 24
- 238000000921 elemental analysis Methods 0.000 description 20
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 18
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- 239000007787 solid Substances 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 15
- 239000011541 reaction mixture Substances 0.000 description 15
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 13
- 241000196324 Embryophyta Species 0.000 description 12
- 238000004458 analytical method Methods 0.000 description 11
- ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 10
- 230000000361 pesticidal effect Effects 0.000 description 10
- 238000001228 spectrum Methods 0.000 description 10
- 239000003795 chemical substances by application Substances 0.000 description 9
- 239000000203 mixture Substances 0.000 description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
- 241000238631 Hexapoda Species 0.000 description 7
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
- 239000012141 concentrate Substances 0.000 description 7
- 239000000575 pesticide Substances 0.000 description 7
- 239000007921 spray Substances 0.000 description 7
- 238000003756 stirring Methods 0.000 description 7
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 6
- 241000238876 Acari Species 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 5
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 239000006185 dispersion Substances 0.000 description 5
- 239000000839 emulsion Substances 0.000 description 5
- 238000002844 melting Methods 0.000 description 5
- 230000008018 melting Effects 0.000 description 5
- 239000008096 xylene Substances 0.000 description 5
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 4
- 238000005481 NMR spectroscopy Methods 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 4
- 239000013065 commercial product Substances 0.000 description 4
- 239000004495 emulsifiable concentrate Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- BWLUMTFWVZZZND-UHFFFAOYSA-N Dibenzylamine Chemical compound C=1C=CC=CC=1CNCC1=CC=CC=C1 BWLUMTFWVZZZND-UHFFFAOYSA-N 0.000 description 3
- XBPCUCUWBYBCDP-UHFFFAOYSA-N Dicyclohexylamine Chemical compound C1CCCCC1NC1CCCCC1 XBPCUCUWBYBCDP-UHFFFAOYSA-N 0.000 description 3
- 241001465754 Metazoa Species 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 235000013601 eggs Nutrition 0.000 description 3
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 3
- 238000010183 spectrum analysis Methods 0.000 description 3
- 238000004809 thin layer chromatography Methods 0.000 description 3
- GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 3
- SHCFCJUJGBRSPO-UHFFFAOYSA-N 1-cyclohexylcyclohexan-1-amine Chemical compound C1CCCCC1C1(N)CCCCC1 SHCFCJUJGBRSPO-UHFFFAOYSA-N 0.000 description 2
- 241000254173 Coleoptera Species 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- 241000255777 Lepidoptera Species 0.000 description 2
- OJGMBLNIHDZDGS-UHFFFAOYSA-N N-Ethylaniline Chemical compound CCNC1=CC=CC=C1 OJGMBLNIHDZDGS-UHFFFAOYSA-N 0.000 description 2
- AFBPFSWMIHJQDM-UHFFFAOYSA-N N-methylaniline Chemical compound CNC1=CC=CC=C1 AFBPFSWMIHJQDM-UHFFFAOYSA-N 0.000 description 2
- WCUXLLCKKVVCTQ-UHFFFAOYSA-M Potassium chloride Chemical compound [Cl-].[K+] WCUXLLCKKVVCTQ-UHFFFAOYSA-M 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- 241001521235 Spodoptera eridania Species 0.000 description 2
- 241001454293 Tetranychus urticae Species 0.000 description 2
- 239000000443 aerosol Substances 0.000 description 2
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 2
- NEHMKBQYUWJMIP-UHFFFAOYSA-N chloromethane Chemical compound ClC NEHMKBQYUWJMIP-UHFFFAOYSA-N 0.000 description 2
- 239000006071 cream Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- 235000013399 edible fruits Nutrition 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- 239000003906 humectant Substances 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 201000002266 mite infestation Diseases 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- XNLICIUVMPYHGG-UHFFFAOYSA-N pentan-2-one Chemical compound CCCC(C)=O XNLICIUVMPYHGG-UHFFFAOYSA-N 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000000725 suspension Substances 0.000 description 2
- GSDYHLKAHLTKKL-UHFFFAOYSA-N (n-cyclohexylanilino) thiohypochlorite Chemical compound C=1C=CC=CC=1N(SCl)C1CCCCC1 GSDYHLKAHLTKKL-UHFFFAOYSA-N 0.000 description 1
- QXKPABNWQSEPEM-UHFFFAOYSA-N 2,3-dimethylbenzenecarboximidamide Chemical compound CC1=CC=CC(C(N)=N)=C1C QXKPABNWQSEPEM-UHFFFAOYSA-N 0.000 description 1
- XHRCFGDFESIFRG-UHFFFAOYSA-N 2-chloro-n-ethyl-n-[(2-methylphenyl)methyl]ethanamine Chemical compound ClCCN(CC)CC1=CC=CC=C1C XHRCFGDFESIFRG-UHFFFAOYSA-N 0.000 description 1
- 241000254175 Anthonomus grandis Species 0.000 description 1
- 241001124076 Aphididae Species 0.000 description 1
- 241000239223 Arachnida Species 0.000 description 1
- 241000239290 Araneae Species 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- 239000004338 Dichlorodifluoromethane Substances 0.000 description 1
- 102100022404 E3 ubiquitin-protein ligase Midline-1 Human genes 0.000 description 1
- 101710102210 E3 ubiquitin-protein ligase Midline-1 Proteins 0.000 description 1
- 206010061217 Infestation Diseases 0.000 description 1
- 239000005949 Malathion Substances 0.000 description 1
- 244000141359 Malus pumila Species 0.000 description 1
- 241000124008 Mammalia Species 0.000 description 1
- JIIOLEGNERQDIP-UHFFFAOYSA-N N'-(2,4-dimethylphenyl)-N-methylformamidine Chemical compound CN=CNC1=CC=C(C)C=C1C JIIOLEGNERQDIP-UHFFFAOYSA-N 0.000 description 1
- XTUVJUMINZSXGF-UHFFFAOYSA-N N-methylcyclohexylamine Chemical compound CNC1CCCCC1 XTUVJUMINZSXGF-UHFFFAOYSA-N 0.000 description 1
- PAMIQIKDUOTOBW-UHFFFAOYSA-N N-methylcyclohexylamine Natural products CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 description 1
- 231100000674 Phytotoxicity Toxicity 0.000 description 1
- 108010021119 Trichosanthin Proteins 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 235000021016 apples Nutrition 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- CJJOSEISRRTUQB-UHFFFAOYSA-N azinphos-methyl Chemical group C1=CC=C2C(=O)N(CSP(=S)(OC)OC)N=NC2=C1 CJJOSEISRRTUQB-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 229960005286 carbaryl Drugs 0.000 description 1
- CVXBEEMKQHEXEN-UHFFFAOYSA-N carbaryl Chemical compound C1=CC=C2C(OC(=O)NC)=CC=CC2=C1 CVXBEEMKQHEXEN-UHFFFAOYSA-N 0.000 description 1
- 239000000969 carrier Substances 0.000 description 1
- 241001233037 catfish Species 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 230000001684 chronic effect Effects 0.000 description 1
- 235000020971 citrus fruits Nutrition 0.000 description 1
- ONCCWDRMOZMNSM-FBCQKBJTSA-N compound Z Chemical compound N1=C2C(=O)NC(N)=NC2=NC=C1C(=O)[C@H]1OP(O)(=O)OC[C@H]1O ONCCWDRMOZMNSM-FBCQKBJTSA-N 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 239000000356 contaminant Substances 0.000 description 1
- 230000003111 delayed effect Effects 0.000 description 1
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 1
- 235000019404 dichlorodifluoromethane Nutrition 0.000 description 1
- 239000002283 diesel fuel Substances 0.000 description 1
- JXSJBGJIGXNWCI-UHFFFAOYSA-N diethyl 2-[(dimethoxyphosphorothioyl)thio]succinate Chemical compound CCOC(=O)CC(SP(=S)(OC)OC)C(=O)OCC JXSJBGJIGXNWCI-UHFFFAOYSA-N 0.000 description 1
- 125000002147 dimethylamino group Chemical group [H]C([H])([H])N(*)C([H])([H])[H] 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 235000018927 edible plant Nutrition 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 230000009969 flowable effect Effects 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 239000012535 impurity Substances 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 239000013067 intermediate product Substances 0.000 description 1
- 231100000566 intoxication Toxicity 0.000 description 1
- 230000035987 intoxication Effects 0.000 description 1
- 235000021581 juice product Nutrition 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 230000001665 lethal effect Effects 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- 229960000453 malathion Drugs 0.000 description 1
- 239000002609 medium Substances 0.000 description 1
- 229940050176 methyl chloride Drugs 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 235000010755 mineral Nutrition 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- 239000007764 o/w emulsion Substances 0.000 description 1
- 229920002113 octoxynol Polymers 0.000 description 1
- 239000002674 ointment Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 239000003209 petroleum derivative Substances 0.000 description 1
- 239000001103 potassium chloride Substances 0.000 description 1
- 235000011164 potassium chloride Nutrition 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- CYJUHOMVLKQQMZ-UHFFFAOYSA-N pyrrol-1-yl thiohypochlorite Chemical compound ClSN1C=CC=C1 CYJUHOMVLKQQMZ-UHFFFAOYSA-N 0.000 description 1
- KWVAMPIMKWMCGP-UHFFFAOYSA-N pyrrolidin-1-yl thiohypochlorite Chemical compound ClSN1CCCC1 KWVAMPIMKWMCGP-UHFFFAOYSA-N 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000012265 solid product Substances 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
- WCLDITPGPXSPGV-UHFFFAOYSA-N tricamba Chemical compound COC1=C(Cl)C=C(Cl)C(Cl)=C1C(O)=O WCLDITPGPXSPGV-UHFFFAOYSA-N 0.000 description 1
- ILWRPSCZWQJDMK-UHFFFAOYSA-N triethylazanium;chloride Chemical compound Cl.CCN(CC)CC ILWRPSCZWQJDMK-UHFFFAOYSA-N 0.000 description 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 description 1
- 238000009827 uniform distribution Methods 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/18—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member
- C07D207/22—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having one double bond between ring members or between a ring member and a non-ring member with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D207/24—Oxygen or sulfur atoms
- C07D207/26—2-Pyrrolidones
- C07D207/273—2-Pyrrolidones with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to other ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D207/00—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom
- C07D207/02—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D207/30—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members
- C07D207/32—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
- C07D207/325—Heterocyclic compounds containing five-membered rings not condensed with other rings, with one nitrogen atom as the only ring hetero atom with only hydrogen or carbon atoms directly attached to the ring nitrogen atom having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms with substituted hydrocarbon radicals directly attached to the ring nitrogen atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/12—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/56—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D295/00—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms
- C07D295/22—Heterocyclic compounds containing polymethylene-imine rings with at least five ring members, 3-azabicyclo [3.2.2] nonane, piperazine, morpholine or thiomorpholine rings, having only hydrogen atoms directly attached to the ring carbon atoms with hetero atoms directly attached to ring nitrogen atoms
- C07D295/26—Sulfur atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyrrole Compounds (AREA)
- Hydrogenated Pyridines (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/575,247 US3998969A (en) | 1975-05-07 | 1975-05-07 | Formamidine insecticides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2619304A1 true DE2619304A1 (de) | 1976-11-18 |
Family
ID=24299514
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19762619304 Withdrawn DE2619304A1 (de) | 1975-05-07 | 1976-04-30 | Neue schwefelhaltige formamidine, verwendung derselben und diese enthaltende land-, garten- und forstwirtschaftliche chemikalien |
Country Status (19)
| Country | Link |
|---|---|
| US (2) | US3998969A (enExample) |
| JP (1) | JPS51138625A (enExample) |
| AR (1) | AR220666A1 (enExample) |
| AU (1) | AU1273976A (enExample) |
| BE (1) | BE841578A (enExample) |
| BR (1) | BR7602704A (enExample) |
| CA (1) | CA1074796A (enExample) |
| DE (1) | DE2619304A1 (enExample) |
| DK (1) | DK202576A (enExample) |
| ES (1) | ES447319A1 (enExample) |
| FR (1) | FR2310345A1 (enExample) |
| GB (1) | GB1479874A (enExample) |
| IT (1) | IT1059446B (enExample) |
| MX (1) | MX3513E (enExample) |
| NL (1) | NL7604719A (enExample) |
| NZ (1) | NZ180538A (enExample) |
| PL (1) | PL102995B1 (enExample) |
| YU (3) | YU115676A (enExample) |
| ZA (1) | ZA762108B (enExample) |
Families Citing this family (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2724764A1 (de) * | 1976-06-04 | 1977-12-15 | Ciba Geigy Ag | N-sulfonyl-diaminosulfide, verfahren zur deren herstellung und diese enthaltende mittel |
| NL7712749A (nl) * | 1976-11-30 | 1978-06-01 | Ciba Geigy | Werkwijze voor het bereiden van nieuwe amidinen en de toepassing van deze verbindingen bij de bestrijding van schadelijke organismen. |
| US4413013A (en) * | 1979-06-22 | 1983-11-01 | The Upjohn Company | Sulfonamide compounds, compositions and methods for combatting insects |
| US4356194A (en) * | 1981-06-03 | 1982-10-26 | The Upjohn Company | Animal feed and process |
| US5200427A (en) * | 1984-07-27 | 1993-04-06 | The Board Of Trustees Of The Univ. Of Illinois | Porphyric insecticides |
| KR100920771B1 (ko) | 2007-09-04 | 2009-10-08 | 한국화학연구원 | 새로운 불소함유 페닐포름아미딘 유도체 및 살충제로서 이의 용도 |
Family Cites Families (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3803134A (en) * | 1962-03-08 | 1974-04-09 | Ciba Geigy Ag | N-heterocyclic derivatives of phenyl-formamidines and -acetamidines |
| DE1598133B2 (de) * | 1966-09-01 | 1974-05-22 | Boehringer Mannheim Gmbh, 6800 Mannheim | Verfahren und diagnostisches Mittel zur Bestimmung von Hydroperoxiden bzw. peroxidatisch wirksamen Substanzen |
| BE792338A (fr) * | 1971-12-07 | 1973-06-06 | Ciba Geigy | Phenyl-formamidines et produits pesticides qui en contiennent |
| NL7600124A (nl) * | 1975-01-16 | 1976-07-20 | Ciba Geigy | Werkwijze voor het bereiden van preparaten voor het bestrijden van schadelijke organismen. |
-
1975
- 1975-05-07 US US05/575,247 patent/US3998969A/en not_active Expired - Lifetime
-
1976
- 1976-03-24 CA CA248,685A patent/CA1074796A/en not_active Expired
- 1976-03-29 AR AR262698A patent/AR220666A1/es active
- 1976-04-07 AU AU12739/76A patent/AU1273976A/en not_active Expired
- 1976-04-07 NZ NZ180538A patent/NZ180538A/xx unknown
- 1976-04-08 ZA ZA762108A patent/ZA762108B/xx unknown
- 1976-04-09 MX MX76162U patent/MX3513E/es unknown
- 1976-04-12 GB GB14776/76A patent/GB1479874A/en not_active Expired
- 1976-04-24 ES ES447319A patent/ES447319A1/es not_active Expired
- 1976-04-30 BR BR2704/76A patent/BR7602704A/pt unknown
- 1976-04-30 IT IT49279/76A patent/IT1059446B/it active
- 1976-04-30 DE DE19762619304 patent/DE2619304A1/de not_active Withdrawn
- 1976-05-04 PL PL1976189289A patent/PL102995B1/pl unknown
- 1976-05-04 NL NL7604719A patent/NL7604719A/xx not_active Application Discontinuation
- 1976-05-06 DK DK202576A patent/DK202576A/da not_active Application Discontinuation
- 1976-05-06 FR FR7613642A patent/FR2310345A1/fr active Granted
- 1976-05-07 BE BE166834A patent/BE841578A/xx not_active IP Right Cessation
- 1976-05-07 YU YU01156/76A patent/YU115676A/xx unknown
- 1976-05-07 JP JP51051996A patent/JPS51138625A/ja active Pending
- 1976-09-14 US US05/723,076 patent/US4066765A/en not_active Expired - Lifetime
-
1981
- 1981-04-07 YU YU00776/81A patent/YU77681A/xx unknown
-
1982
- 1982-04-07 YU YU00777/82A patent/YU77782A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| AR220666A1 (es) | 1980-11-28 |
| ZA762108B (en) | 1977-04-27 |
| GB1479874A (en) | 1977-07-13 |
| YU115676A (en) | 1982-10-31 |
| ES447319A1 (es) | 1977-07-01 |
| BR7602704A (pt) | 1976-11-16 |
| YU77681A (en) | 1982-10-31 |
| FR2310345B1 (enExample) | 1979-09-28 |
| MX3513E (es) | 1981-01-14 |
| CA1074796A (en) | 1980-04-01 |
| PL102995B1 (pl) | 1979-05-31 |
| US3998969A (en) | 1976-12-21 |
| NL7604719A (nl) | 1976-11-09 |
| IT1059446B (it) | 1982-05-31 |
| JPS51138625A (en) | 1976-11-30 |
| BE841578A (fr) | 1976-11-08 |
| US4066765A (en) | 1978-01-03 |
| DK202576A (da) | 1976-11-08 |
| FR2310345A1 (fr) | 1976-12-03 |
| AU1273976A (en) | 1977-10-13 |
| NZ180538A (en) | 1978-07-28 |
| YU77782A (en) | 1982-10-31 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE69028461T2 (de) | Triazin-derivate und unkrautvertilgungsmittel daraus | |
| DE2216838C2 (de) | Ketoximcarbamate, Verfahren zu ihrer Herstellung und ihre Verwendung | |
| DE1299294B (de) | Carbamoyloxime und Verfahren zu ihrer Herstellung | |
| DE2541116C2 (de) | 1-(Substituierte-benzoyl)-3-(substituierte-pyrazinyl)-harnstoffe, Verfahren zu ihrer Herstellung und sie enthaltendes insektizides Mittel | |
| DE2509416C2 (de) | Dinitrobenzotrifluoride, Verfahren zu deren Herstellung und diese enthaltende pestizide Zusammensetzungen | |
| DE2654314A1 (de) | Asymmetrische bis-carbamoylsulfidverbindungen und verfahren zu ihrer herstellung | |
| DE2619303A1 (de) | Neue schwefelhaltige bisformamidine, verfahren zu ihrer herstellung und verwendung derselben sowie diese enthaltende land-, garten- und forstwirtschaftliche chemikalien | |
| DE2619304A1 (de) | Neue schwefelhaltige formamidine, verwendung derselben und diese enthaltende land-, garten- und forstwirtschaftliche chemikalien | |
| DD149890A5 (de) | Schimmelbekaempfungsmittel und-verfahren | |
| DE2530287A1 (de) | Insekticide | |
| DD233293A5 (de) | Mittel zur verzoegerung der wirkung herbizider praeparate | |
| DE2123277A1 (de) | Insektizide Mittel | |
| DE2813281C2 (de) | N-substituierte Bis-Carbamoyloximinodisulfidverbindungen, Verfahren zu ihrer Herstellung und diese Verbindungen enthaltende Pestizide | |
| DE2920182A1 (de) | Salze von thiazolyliden-oxo-propionitrilen, insektizide mittel enthaltend diese salze sowie verfahren zu ihrer herstellung | |
| DE2222464A1 (de) | Carbamoyloximderivat,dessen Herstellung und dessen Verwendung als Pesticid | |
| DE2436957A1 (de) | Carbaminsaeure-derivate | |
| DE2524578A1 (de) | Barbitursaeurederivate, verfahren zu ihrer herstellung und ihre verwendung als herbizide | |
| DE1567142A1 (de) | Pestizide Mittel | |
| EP0023976B1 (de) | N-Aryl-N'-acryloyl-ureide, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Mikrobizide | |
| EP0007066B1 (de) | 4-Alkyl- und 4-Allyl-merkapto-, sulfinyl- und sulfonyl-methyl-2-amino-6-N,N'-dimethylcarbamoyloxy-pyrimidine, Verfahren zu ihrer Herstellung, Mittel welche diese Pyrimidine enthalten und deren Verwendung zur Bekämpfung von Insekten | |
| DE2823355A1 (de) | Sulfonamide, verwendung derselben bei der bekaempfung von zu den gliederfuessern gehoerigen schaedlingen und diese enthaltende pestizide mittel | |
| DE2628574A1 (de) | Neue pestizide verbindungen und verfahren zu ihrer herstellung | |
| DE2655212A1 (de) | Aminothiocarbamate, verfahren zu ihrer herstellung und diese enthaltende pestizide | |
| DE2341810A1 (de) | Substituierte oxazolidine | |
| DE2548898A1 (de) | Benzothiazolderivate, verfahren zu ihrer herstellung und ihre verwendung als herbizide |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8126 | Change of the secondary classification |
Ipc: A01N 41/12 |
|
| 8128 | New person/name/address of the agent |
Representative=s name: HENKEL, G., DR.PHIL. FEILER, L., DR.RER.NAT. HAENZ |
|
| 8110 | Request for examination paragraph 44 | ||
| 8139 | Disposal/non-payment of the annual fee |