DE2754287A1 - 1,3,5-triazapenta-1,4-diene, verfahren zu iher herstellung und ihre verwendung in der schaedlingsbekaempfung - Google Patents
1,3,5-triazapenta-1,4-diene, verfahren zu iher herstellung und ihre verwendung in der schaedlingsbekaempfungInfo
- Publication number
- DE2754287A1 DE2754287A1 DE19772754287 DE2754287A DE2754287A1 DE 2754287 A1 DE2754287 A1 DE 2754287A1 DE 19772754287 DE19772754287 DE 19772754287 DE 2754287 A DE2754287 A DE 2754287A DE 2754287 A1 DE2754287 A1 DE 2754287A1
- Authority
- DE
- Germany
- Prior art keywords
- triazapenta
- formula
- parts
- diene
- diene according
- 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- Withdrawn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
- 238000000034 method Methods 0.000 title claims description 7
- HLSFBFYQBSVXBS-UHFFFAOYSA-N n-(aminomethylidene)methanimidamide Chemical compound N=CNC=N HLSFBFYQBSVXBS-UHFFFAOYSA-N 0.000 title claims description 7
- 238000004519 manufacturing process Methods 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims description 21
- 239000000460 chlorine Substances 0.000 claims description 9
- 238000002360 preparation method Methods 0.000 claims description 6
- 241000238631 Hexapoda Species 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
- 241000607479 Yersinia pestis Species 0.000 claims description 4
- 239000000654 additive Substances 0.000 claims description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 239000000969 carrier Substances 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 229910052739 hydrogen Inorganic materials 0.000 claims description 4
- 239000001257 hydrogen Substances 0.000 claims description 4
- 150000002431 hydrogen Chemical class 0.000 claims description 4
- 241001465754 Metazoa Species 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 150000001993 dienes Chemical class 0.000 claims 1
- 125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims 1
- 239000000575 pesticide Substances 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 description 28
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
- 238000012360 testing method Methods 0.000 description 11
- 230000000694 effects Effects 0.000 description 10
- -1 methoxy, ethyl Chemical group 0.000 description 9
- 239000008187 granular material Substances 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000000839 emulsion Substances 0.000 description 6
- 230000000749 insecticidal effect Effects 0.000 description 6
- 239000005995 Aluminium silicate Substances 0.000 description 5
- 235000012211 aluminium silicate Nutrition 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 5
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 5
- 239000000203 mixture Substances 0.000 description 5
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- 230000000895 acaricidal effect Effects 0.000 description 4
- 239000004495 emulsifiable concentrate Substances 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 229920000151 polyglycol Polymers 0.000 description 4
- 239000010695 polyglycol Substances 0.000 description 4
- 239000002689 soil Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000007921 spray Substances 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- 239000008096 xylene Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 241000238876 Acari Species 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 241000426497 Chilo suppressalis Species 0.000 description 3
- 241000196324 Embryophyta Species 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 235000019993 champagne Nutrition 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 238000012545 processing Methods 0.000 description 3
- 239000000377 silicon dioxide Substances 0.000 description 3
- 230000009885 systemic effect Effects 0.000 description 3
- 235000013311 vegetables Nutrition 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- 241001124076 Aphididae Species 0.000 description 2
- 241001425390 Aphis fabae Species 0.000 description 2
- 241000283690 Bos taurus Species 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 241000272201 Columbiformes Species 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- 241000256113 Culicidae Species 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 241000256244 Heliothis virescens Species 0.000 description 2
- 241000243784 Meloidogyne arenaria Species 0.000 description 2
- 241000244206 Nematoda Species 0.000 description 2
- 244000046052 Phaseolus vulgaris Species 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 241001454294 Tetranychus Species 0.000 description 2
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 235000013601 eggs Nutrition 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 150000002191 fatty alcohols Chemical class 0.000 description 2
- 238000009472 formulation Methods 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 235000015112 vegetable and seed oil Nutrition 0.000 description 2
- 239000008158 vegetable oil Substances 0.000 description 2
- 239000004563 wettable powder Substances 0.000 description 2
- UXPPDBVMSPAPCL-UHFFFAOYSA-N 1-prop-1-ynoxyprop-1-yne Chemical compound CC#COC#CC UXPPDBVMSPAPCL-UHFFFAOYSA-N 0.000 description 1
- QQGRFMIMXPWKPM-UHFFFAOYSA-N 2,3,4-tributylphenol Chemical compound CCCCC1=CC=C(O)C(CCCC)=C1CCCC QQGRFMIMXPWKPM-UHFFFAOYSA-N 0.000 description 1
- 241000238660 Blattidae Species 0.000 description 1
- 241000907223 Bruchinae Species 0.000 description 1
- 241001260012 Bursa Species 0.000 description 1
- FIPWRIJSWJWJAI-UHFFFAOYSA-N Butyl carbitol 6-propylpiperonyl ether Chemical compound C1=C(CCC)C(COCCOCCOCCCC)=CC2=C1OCO2 FIPWRIJSWJWJAI-UHFFFAOYSA-N 0.000 description 1
- BNARGNJKJAZKNK-UHFFFAOYSA-N CC#COP(O)=O Chemical compound CC#COP(O)=O BNARGNJKJAZKNK-UHFFFAOYSA-N 0.000 description 1
- 241000257161 Calliphoridae Species 0.000 description 1
- 241001124134 Chrysomelidae Species 0.000 description 1
- 241001414835 Cimicidae Species 0.000 description 1
- 241000255749 Coccinellidae Species 0.000 description 1
- 241001466044 Delphacidae Species 0.000 description 1
- 241001481702 Dermanyssidae Species 0.000 description 1
- 241000131287 Dermestidae Species 0.000 description 1
- 241001414830 Diaspididae Species 0.000 description 1
- XTHFKEDIFFGKHM-UHFFFAOYSA-N Dimethoxyethane Chemical compound COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 1
- 241000255925 Diptera Species 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 235000009161 Espostoa lanata Nutrition 0.000 description 1
- 240000001624 Espostoa lanata Species 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N EtOH Substances CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- PNKUSGQVOMIXLU-UHFFFAOYSA-N Formamidine Chemical compound NC=N PNKUSGQVOMIXLU-UHFFFAOYSA-N 0.000 description 1
- 241000219146 Gossypium Species 0.000 description 1
- 240000002024 Gossypium herbaceum Species 0.000 description 1
- 235000004341 Gossypium herbaceum Nutrition 0.000 description 1
- 241000238816 Gryllidae Species 0.000 description 1
- 241001243087 Gryllotalpidae Species 0.000 description 1
- 241000256257 Heliothis Species 0.000 description 1
- 239000004354 Hydroxyethyl cellulose Substances 0.000 description 1
- 229920000663 Hydroxyethyl cellulose Polymers 0.000 description 1
- 206010061217 Infestation Diseases 0.000 description 1
- 241000238889 Ixodidae Species 0.000 description 1
- 241000258916 Leptinotarsa decemlineata Species 0.000 description 1
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 1
- 241001124557 Lymantriidae Species 0.000 description 1
- 241000257229 Musca <genus> Species 0.000 description 1
- 241000257226 Muscidae Species 0.000 description 1
- 241000721621 Myzus persicae Species 0.000 description 1
- XLVAUNHFVBGFNI-UHFFFAOYSA-N N-(4-chloro-2-methylphenyl)-N-methylmethanimidamide Chemical compound N=CN(C)C1=CC=C(Cl)C=C1C XLVAUNHFVBGFNI-UHFFFAOYSA-N 0.000 description 1
- 241000256259 Noctuidae Species 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 241000488585 Panonychus Species 0.000 description 1
- 241001415279 Pseudococcidae Species 0.000 description 1
- 241000258921 Pulicidae Species 0.000 description 1
- 241000255893 Pyralidae Species 0.000 description 1
- 241001510071 Pyrrhocoridae Species 0.000 description 1
- 241001124072 Reduviidae Species 0.000 description 1
- 241001481703 Rhipicephalus <genus> Species 0.000 description 1
- 241000949016 Rhipicephalus bursa Species 0.000 description 1
- 241000238680 Rhipicephalus microplus Species 0.000 description 1
- 241000254062 Scarabaeidae Species 0.000 description 1
- 240000003768 Solanum lycopersicum Species 0.000 description 1
- 241000256248 Spodoptera Species 0.000 description 1
- 241000256250 Spodoptera littoralis Species 0.000 description 1
- 241000254107 Tenebrionidae Species 0.000 description 1
- 241000255588 Tephritidae Species 0.000 description 1
- 241001454293 Tetranychus urticae Species 0.000 description 1
- 241000896028 Tettigoniidae Species 0.000 description 1
- 241000130767 Tineidae Species 0.000 description 1
- 241000131339 Tipulidae Species 0.000 description 1
- 240000006677 Vicia faba Species 0.000 description 1
- 235000010749 Vicia faba Nutrition 0.000 description 1
- 239000000642 acaricide Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000000853 adhesive Substances 0.000 description 1
- 230000001070 adhesive effect Effects 0.000 description 1
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- DNEHKUCSURWDGO-UHFFFAOYSA-N aluminum sodium Chemical compound [Na].[Al] DNEHKUCSURWDGO-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000011230 binding agent Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 229920005551 calcium lignosulfonate Polymers 0.000 description 1
- RYAGRZNBULDMBW-UHFFFAOYSA-L calcium;3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfonatopropyl)phenoxy]propane-1-sulfonate Chemical compound [Ca+2].COC1=CC=CC(CC(CS([O-])(=O)=O)OC=2C(=CC(CCCS([O-])(=O)=O)=CC=2)OC)=C1O RYAGRZNBULDMBW-UHFFFAOYSA-L 0.000 description 1
- 150000004657 carbamic acid derivatives Chemical class 0.000 description 1
- 235000013877 carbamide Nutrition 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000003857 carboxamides Chemical class 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- FHIVAFMUCKRCQO-UHFFFAOYSA-N diazinon Chemical compound CCOP(=S)(OCC)OC1=CC(C)=NC(C(C)C)=N1 FHIVAFMUCKRCQO-UHFFFAOYSA-N 0.000 description 1
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 238000010410 dusting Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000003337 fertilizer Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 235000013305 food Nutrition 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 235000019447 hydroxyethyl cellulose Nutrition 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 230000001418 larval effect Effects 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- HNQIVZYLYMDVSB-UHFFFAOYSA-N methanesulfonimidic acid Chemical compound CS(N)(=O)=O HNQIVZYLYMDVSB-UHFFFAOYSA-N 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- RBXVOQPAMPBADW-UHFFFAOYSA-N nitrous acid;phenol Chemical class ON=O.OC1=CC=CC=C1 RBXVOQPAMPBADW-UHFFFAOYSA-N 0.000 description 1
- 150000002903 organophosphorus compounds Chemical class 0.000 description 1
- 239000006072 paste Substances 0.000 description 1
- 230000003032 phytopathogenic effect Effects 0.000 description 1
- 229960005235 piperonyl butoxide Drugs 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- FHQKDLNFTINTBW-UHFFFAOYSA-N prop-1-ynyl carbamate Chemical class CC#COC(N)=O FHQKDLNFTINTBW-UHFFFAOYSA-N 0.000 description 1
- 125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000001172 regenerating effect Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- KZOJQMWTKJDSQJ-UHFFFAOYSA-M sodium;2,3-dibutylnaphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S([O-])(=O)=O)=C(CCCC)C(CCCC)=CC2=C1 KZOJQMWTKJDSQJ-UHFFFAOYSA-M 0.000 description 1
- SRAWNDFHGTVUNZ-UHFFFAOYSA-M sodium;3,6-dibutylnaphthalene-1-sulfonate Chemical compound [Na+].[O-]S(=O)(=O)C1=CC(CCCC)=CC2=CC(CCCC)=CC=C21 SRAWNDFHGTVUNZ-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- ZOKXUAHZSKEQSS-UHFFFAOYSA-N tribufos Chemical compound CCCCSP(=O)(SCCCC)SCCCC ZOKXUAHZSKEQSS-UHFFFAOYSA-N 0.000 description 1
- 150000003672 ureas Chemical class 0.000 description 1
- 244000045561 useful plants Species 0.000 description 1
- 239000000080 wetting agent Substances 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
- A01N41/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom
- A01N41/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a sulfur atom bound to a hetero atom containing a sulfur-to-oxygen double bond
- A01N41/04—Sulfonic acids; Derivatives thereof
- A01N41/06—Sulfonic acid amides
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH1549776A CH621235A5 (en) | 1976-12-09 | 1976-12-09 | A pesticide. |
| CH124477 | 1977-02-02 | ||
| CH1358677 | 1977-11-08 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2754287A1 true DE2754287A1 (de) | 1978-06-15 |
Family
ID=27172819
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19772754287 Withdrawn DE2754287A1 (de) | 1976-12-09 | 1977-12-06 | 1,3,5-triazapenta-1,4-diene, verfahren zu iher herstellung und ihre verwendung in der schaedlingsbekaempfung |
Country Status (12)
| Country | Link |
|---|---|
| US (1) | US4140795A (enExample) |
| JP (1) | JPS5373527A (enExample) |
| AU (1) | AU3137277A (enExample) |
| CA (1) | CA1082734A (enExample) |
| DE (1) | DE2754287A1 (enExample) |
| EG (1) | EG13127A (enExample) |
| ES (1) | ES464847A1 (enExample) |
| FR (1) | FR2373523A1 (enExample) |
| GB (1) | GB1586246A (enExample) |
| IL (1) | IL53558A (enExample) |
| NL (1) | NL7713440A (enExample) |
| TR (1) | TR19805A (enExample) |
Families Citing this family (4)
| 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 |
| US4356191A (en) * | 1981-06-03 | 1982-10-26 | The Upjohn Company | Animal feed and process |
| US5304573A (en) * | 1990-11-17 | 1994-04-19 | Nihon Nohyaku Co., Ltd. | Hydrazone derivatives, processes for production thereof, and uses thereof |
| JP4532339B2 (ja) * | 2005-05-18 | 2010-08-25 | アグロカネショウ株式会社 | 有害生物の防除に有効なトリフルオロメチルスルホニルアミジン誘導体 |
Family Cites Families (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE949285C (de) * | 1953-05-07 | 1956-09-20 | Bayer Ag | Verfahren zur Herstellung von N-Sulfonylformamidinen |
| DE2029298C3 (de) * | 1970-06-13 | 1980-04-17 | Bayer Ag, 5090 Leverkusen | Aminophenylamidine, Verfahren zu ihrer Herstellung und diese enthaltende Arzneimittel |
| DE2306918A1 (de) * | 1973-02-13 | 1974-08-15 | Bayer Ag | Benzaldehyd-sulfonylhydrazone, verfahren zu ihrer herstellung und ihre verwendung zur bekaempfung von hasenartigen und nagetieren |
| DE2405546A1 (de) * | 1974-02-06 | 1975-08-21 | Bayer Ag | Verfahren zur herstellung von neuen 1-aryl-4-amino-1,3-diaza-butadienen oeoiie ihre verwendung als acaricide und insekticide |
| GB1448165A (en) * | 1974-08-23 | 1976-09-02 | Pfizer Ltd | 1-substituted-5-substituted phenyl-3-methyl-1,3,5-triazapenta- 1,4-dienes and acaricidal and insecticidal compositions containing them |
| IL49140A (en) * | 1975-03-05 | 1979-10-31 | Ciba Geigy Ag | N-(3,5-bis-trifluoromethylphenyl)-n'-sulfonyl-iso(thio)ureas,their production and insecticidal compositions containing them |
| US4056570A (en) * | 1975-05-07 | 1977-11-01 | Stauffer Chemical Company | Acylformanidine insecticidal and miticidal compounds |
-
1977
- 1977-12-01 US US05/856,369 patent/US4140795A/en not_active Expired - Lifetime
- 1977-12-05 NL NL7713440A patent/NL7713440A/xx not_active Application Discontinuation
- 1977-12-06 EG EG673/77A patent/EG13127A/xx active
- 1977-12-06 TR TR19805A patent/TR19805A/xx unknown
- 1977-12-06 DE DE19772754287 patent/DE2754287A1/de not_active Withdrawn
- 1977-12-07 FR FR7736831A patent/FR2373523A1/fr active Granted
- 1977-12-07 ES ES464847A patent/ES464847A1/es not_active Expired
- 1977-12-07 CA CA292,550A patent/CA1082734A/en not_active Expired
- 1977-12-07 IL IL53558A patent/IL53558A/xx unknown
- 1977-12-08 GB GB51166/77A patent/GB1586246A/en not_active Expired
- 1977-12-08 JP JP14771277A patent/JPS5373527A/ja active Pending
- 1977-12-08 AU AU31372/77A patent/AU3137277A/en active Pending
Also Published As
| Publication number | Publication date |
|---|---|
| AU3137277A (en) | 1979-06-14 |
| GB1586246A (en) | 1981-03-18 |
| US4140795A (en) | 1979-02-20 |
| FR2373523B1 (enExample) | 1980-06-13 |
| ES464847A1 (es) | 1979-01-01 |
| TR19805A (tr) | 1979-12-28 |
| FR2373523A1 (fr) | 1978-07-07 |
| IL53558A0 (en) | 1978-03-10 |
| NL7713440A (nl) | 1978-06-13 |
| EG13127A (en) | 1981-03-31 |
| IL53558A (en) | 1981-06-29 |
| JPS5373527A (en) | 1978-06-30 |
| CA1082734A (en) | 1980-07-29 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE2303185C2 (de) | Thiophosphorsäurephenylester, Verfahren zu ihrer Herstellung sowie diese enthaltende Schädlingsbekämpfungsmittel | |
| DE2447095A1 (de) | Harnstoffphosphonate, verfahren zu ihrer herstellung und ihre verwendung | |
| DE2754287A1 (de) | 1,3,5-triazapenta-1,4-diene, verfahren zu iher herstellung und ihre verwendung in der schaedlingsbekaempfung | |
| DE2451588A1 (de) | Derivate des 1,2,4-oxadiazols, verfahren zu ihrer herstellung und ihre verwendung | |
| DE2647368A1 (de) | Alpha-(1-pyrrolyl)-carbonsaeure-3- phenoxy-benzylester, verfahren zu ihrer herstellung und ihre verwendung | |
| DE2139046C3 (de) | Formamidine und ihre Salze, Herstellung derselben und diese enthaltende Mittel zur Bekämpfung von Insekten und Vertretern der Ordnung Akarina | |
| DE2422324C2 (de) | Diphenyläther-phosphorverbindungen, Verfahren zu ihrer Herstellung und diese enthaltende Schädlingsbekämpfungsmittel | |
| DE2350696A1 (de) | Neue ester | |
| CH580910A5 (enExample) | ||
| AT328795B (de) | Schadlingsbekampfungsmittel | |
| DE2754310A1 (de) | 1,3,5-triazapenta-1,4-diene, verfahren zu ihrer herstellung und ihre verwendung in der schaedlingsbekaempfung | |
| DE2354586A1 (de) | Neue ester | |
| CH621235A5 (en) | A pesticide. | |
| DE2755481A1 (de) | Phenyl-diformamidine und ihre salze mit anorganischen und organischen saeuren, verfahren zu ihrer herstellung und ihre verwendung in der schaedlingsbekaempfung | |
| CH608692A5 (en) | Pesticide comprising an N,N'-dicarbamic acid sulphide derivative as active ingredient | |
| DE2356453A1 (de) | Alkylendithiophosphorsaeureester, verfahren zu ihrer herstellung und ihre verwendung | |
| DE2800086A1 (de) | 1,3,5-triazapenta-1,4-diene, verfahren zu ihrer herstellung und ihre verwendung in der schaedlingsbekaempfung | |
| DE2801072A1 (de) | Carbamidosulfonylphenyl-formamidine, verfahren zu ihrer herstellung und ihre verwendung in der schaedlingsbekaempfung | |
| CH623992A5 (en) | A pesticide | |
| DE2430758A1 (de) | Oxadiazolylverbindungen, verfahren zu ihrer herstellung und ihre verwendung zur schaedlingsbekaempfung | |
| CH622409A5 (en) | A pesticide | |
| CH631867A5 (en) | A pesticide | |
| CH626875A5 (en) | A pesticide which contains, as active ingredient, a carbonylaminocarbonylphenylformamidine | |
| CH620341A5 (en) | Pesticides | |
| CH600760A5 (en) | Antiparasitic isobutyronitrile-phenyl-formamidine sulphides |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| OI | Miscellaneous see part 1 | ||
| 8139 | Disposal/non-payment of the annual fee |