DE1955749A1 - Amidophenylguanidine,Verfahren zu ihrer Herstellung und ihre fungizide Verwendung - Google Patents
Amidophenylguanidine,Verfahren zu ihrer Herstellung und ihre fungizide VerwendungInfo
- Publication number
- DE1955749A1 DE1955749A1 DE19691955749 DE1955749A DE1955749A1 DE 1955749 A1 DE1955749 A1 DE 1955749A1 DE 19691955749 DE19691955749 DE 19691955749 DE 1955749 A DE1955749 A DE 1955749A DE 1955749 A1 DE1955749 A1 DE 1955749A1
- Authority
- DE
- Germany
- Prior art keywords
- carbon atoms
- active ingredient
- och
- alkyl
- plants
- 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
- 238000000034 method Methods 0.000 title claims description 9
- 238000002360 preparation method Methods 0.000 title claims description 8
- 230000000855 fungicidal effect Effects 0.000 title description 7
- 125000004432 carbon atom Chemical group C* 0.000 claims description 26
- 125000000217 alkyl group Chemical group 0.000 claims description 14
- -1 1 -Puryl Chemical group 0.000 claims description 13
- 241000233866 Fungi Species 0.000 claims description 12
- 125000003545 alkoxy group Chemical group 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical class NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 claims description 6
- 239000000417 fungicide Substances 0.000 claims description 5
- 239000004606 Fillers/Extenders Substances 0.000 claims description 3
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 3
- 239000003085 diluting agent Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 2
- 125000003118 aryl group Chemical group 0.000 claims description 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 2
- 239000004094 surface-active agent Substances 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims 4
- 239000004480 active ingredient Substances 0.000 description 74
- 241000196324 Embryophyta Species 0.000 description 39
- 206010061217 Infestation Diseases 0.000 description 29
- 238000012360 testing method Methods 0.000 description 27
- 239000002904 solvent Substances 0.000 description 20
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 17
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 17
- 239000007788 liquid Substances 0.000 description 16
- 150000001875 compounds Chemical class 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- 241000220225 Malus Species 0.000 description 13
- 239000002689 soil Substances 0.000 description 13
- 239000003795 chemical substances by application Substances 0.000 description 11
- 239000000203 mixture Substances 0.000 description 11
- 230000009885 systemic effect Effects 0.000 description 10
- 239000000654 additive Substances 0.000 description 8
- 238000011081 inoculation Methods 0.000 description 8
- 239000007921 spray Substances 0.000 description 8
- 235000001674 Agaricus brunnescens Nutrition 0.000 description 7
- 241000489964 Fusicladium Species 0.000 description 7
- 125000002877 alkyl aryl group Chemical group 0.000 description 7
- 239000012141 concentrate Substances 0.000 description 7
- 239000003995 emulsifying agent Substances 0.000 description 7
- 229920000151 polyglycol Polymers 0.000 description 7
- 239000010695 polyglycol Substances 0.000 description 7
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- 206010039509 Scab Diseases 0.000 description 6
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- 241000221785 Erysiphales Species 0.000 description 5
- 241000896242 Podosphaera Species 0.000 description 5
- 239000002270 dispersing agent Substances 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- 208000015181 infectious disease Diseases 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 230000001681 protective effect Effects 0.000 description 5
- 239000000758 substrate Substances 0.000 description 5
- 240000008067 Cucumis sativus Species 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 241000209140 Triticum Species 0.000 description 4
- 235000021307 Triticum Nutrition 0.000 description 4
- 238000005266 casting Methods 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 230000012010 growth Effects 0.000 description 4
- 150000002367 halogens Chemical group 0.000 description 4
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 229920001817 Agar Polymers 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 241000123650 Botrytis cinerea Species 0.000 description 3
- 241000221787 Erysiphe Species 0.000 description 3
- 208000031888 Mycoses Diseases 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 240000007594 Oryza sativa Species 0.000 description 3
- 241001337928 Podosphaera leucotricha Species 0.000 description 3
- 241001617088 Thanatephorus sasakii Species 0.000 description 3
- 241000228452 Venturia inaequalis Species 0.000 description 3
- 240000006677 Vicia faba Species 0.000 description 3
- 239000008272 agar Substances 0.000 description 3
- 201000010099 disease Diseases 0.000 description 3
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 3
- 235000021186 dishes Nutrition 0.000 description 3
- DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 3
- 230000002464 fungitoxic effect Effects 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 238000005507 spraying Methods 0.000 description 3
- 239000000454 talc Substances 0.000 description 3
- 229910052623 talc Inorganic materials 0.000 description 3
- HILAYQUKKYWPJW-UHFFFAOYSA-N 1-dodecylguanidine Chemical class CCCCCCCCCCCCN=C(N)N HILAYQUKKYWPJW-UHFFFAOYSA-N 0.000 description 2
- YIKWKLYQRFRGPM-UHFFFAOYSA-N 1-dodecylguanidine acetate Chemical compound CC(O)=O.CCCCCCCCCCCCN=C(N)N YIKWKLYQRFRGPM-UHFFFAOYSA-N 0.000 description 2
- SMNDYUVBFMFKNZ-UHFFFAOYSA-N 2-furoic acid Chemical compound OC(=O)C1=CC=CO1 SMNDYUVBFMFKNZ-UHFFFAOYSA-N 0.000 description 2
- 241001465180 Botrytis Species 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 241001480059 Erysiphaceae Species 0.000 description 2
- 241000896246 Golovinomyces cichoracearum Species 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 235000007164 Oryza sativa Nutrition 0.000 description 2
- 208000012868 Overgrowth Diseases 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 235000010749 Vicia faba Nutrition 0.000 description 2
- 230000000895 acaricidal effect Effects 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000003931 anilides Chemical class 0.000 description 2
- 235000013532 brandy Nutrition 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000004495 emulsifiable concentrate Substances 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 231100000162 fungitoxic Toxicity 0.000 description 2
- 230000035784 germination Effects 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 238000011534 incubation Methods 0.000 description 2
- 230000002401 inhibitory effect Effects 0.000 description 2
- 239000002054 inoculum Substances 0.000 description 2
- 231100000053 low toxicity Toxicity 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- RFDVMOUXHKTCDO-UHFFFAOYSA-N n-(2-aminophenyl)benzamide Chemical compound NC1=CC=CC=C1NC(=O)C1=CC=CC=C1 RFDVMOUXHKTCDO-UHFFFAOYSA-N 0.000 description 2
- 230000017074 necrotic cell death Effects 0.000 description 2
- 239000006072 paste Substances 0.000 description 2
- LCPDWSOZIOUXRV-UHFFFAOYSA-N phenoxyacetic acid Chemical compound OC(=O)COC1=CC=CC=C1 LCPDWSOZIOUXRV-UHFFFAOYSA-N 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 235000009566 rice Nutrition 0.000 description 2
- 239000011435 rock Substances 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 239000004575 stone Substances 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- GOJUJUVQIVIZAV-UHFFFAOYSA-N 2-amino-4,6-dichloropyrimidine-5-carbaldehyde Chemical group NC1=NC(Cl)=C(C=O)C(Cl)=N1 GOJUJUVQIVIZAV-UHFFFAOYSA-N 0.000 description 1
- WZPUAGQZUJMMBW-UHFFFAOYSA-N 2-amino-4-chloro-N-phenyloctadecanamide Chemical compound NC(C(=O)NC1=CC=CC=C1)CC(CCCCCCCCCCCCCC)Cl WZPUAGQZUJMMBW-UHFFFAOYSA-N 0.000 description 1
- HFWAGNXIXZOFEB-UHFFFAOYSA-N 2-amino-N-phenyldodecanamide Chemical compound NC(C(=O)NC1=CC=CC=C1)CCCCCCCCCC HFWAGNXIXZOFEB-UHFFFAOYSA-N 0.000 description 1
- AVXFJSAZTALYFO-UHFFFAOYSA-N 2-amino-N-phenyloctadecanamide Chemical compound NC(C(=O)NC1=CC=CC=C1)CCCCCCCCCCCCCCCC AVXFJSAZTALYFO-UHFFFAOYSA-N 0.000 description 1
- CVDGZNXOEUTZSK-UHFFFAOYSA-N 2-amino-n-phenylbutanamide Chemical compound CCC(N)C(=O)NC1=CC=CC=C1 CVDGZNXOEUTZSK-UHFFFAOYSA-N 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- 125000000590 4-methylphenyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 241000223600 Alternaria Species 0.000 description 1
- 241000221198 Basidiomycota Species 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 229910014033 C-OH Inorganic materials 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 241000228437 Cochliobolus Species 0.000 description 1
- 229910014570 C—OH Inorganic materials 0.000 description 1
- 229910014569 C—OOH Inorganic materials 0.000 description 1
- 241000510928 Erysiphe necator Species 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 206010017533 Fungal infection Diseases 0.000 description 1
- 241000223218 Fusarium Species 0.000 description 1
- 241000223194 Fusarium culmorum Species 0.000 description 1
- 108010010803 Gelatin Proteins 0.000 description 1
- 241000896218 Golovinomyces orontii Species 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- GXCLVBGFBYZDAG-UHFFFAOYSA-N N-[2-(1H-indol-3-yl)ethyl]-N-methylprop-2-en-1-amine Chemical compound CN(CCC1=CNC2=C1C=CC=C2)CC=C GXCLVBGFBYZDAG-UHFFFAOYSA-N 0.000 description 1
- 241001329956 Nothopassalora personata Species 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 241000896238 Oidium Species 0.000 description 1
- 241000308483 Phialophora cinerescens Species 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 241000184297 Pseudocercospora musae Species 0.000 description 1
- 239000006004 Quartz sand Substances 0.000 description 1
- 240000004808 Saccharomyces cerevisiae Species 0.000 description 1
- BCKXLBQYZLBQEK-KVVVOXFISA-M Sodium oleate Chemical compound [Na+].CCCCCCCC\C=C/CCCCCCCC([O-])=O BCKXLBQYZLBQEK-KVVVOXFISA-M 0.000 description 1
- 241000579741 Sphaerotheca <fungi> Species 0.000 description 1
- 241000722093 Tilletia caries Species 0.000 description 1
- 241000510929 Uncinula Species 0.000 description 1
- 241001006642 Venturia pyrina Species 0.000 description 1
- 241001123669 Verticillium albo-atrum Species 0.000 description 1
- 235000002096 Vicia faba var. equina Nutrition 0.000 description 1
- 241000589652 Xanthomonas oryzae Species 0.000 description 1
- 239000000642 acaricide Substances 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 1
- 150000008052 alkyl sulfonates Chemical class 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 235000021016 apples Nutrition 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 239000008280 blood Substances 0.000 description 1
- 210000004369 blood Anatomy 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 150000008422 chlorobenzenes Chemical class 0.000 description 1
- 239000002361 compost Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 244000038559 crop plants Species 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- 231100000676 disease causative agent Toxicity 0.000 description 1
- 238000010410 dusting Methods 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 230000002538 fungal effect Effects 0.000 description 1
- 208000024386 fungal infectious disease Diseases 0.000 description 1
- 239000008273 gelatin Substances 0.000 description 1
- 229920000159 gelatin Polymers 0.000 description 1
- 235000019322 gelatine Nutrition 0.000 description 1
- 235000011852 gelatine desserts Nutrition 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000002357 guanidines Chemical class 0.000 description 1
- 229940083094 guanine derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 125000002960 margaryl 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])C([H])([H])[H] 0.000 description 1
- HRDXJKGNWSUIBT-UHFFFAOYSA-N methoxybenzene Chemical group [CH2]OC1=CC=CC=C1 HRDXJKGNWSUIBT-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- JBJRVPVZADJOOX-UHFFFAOYSA-N n-(2-amino-4-methylphenyl)acetamide Chemical compound CC(=O)NC1=CC=C(C)C=C1N JBJRVPVZADJOOX-UHFFFAOYSA-N 0.000 description 1
- GIYCSTBRWXPCMX-UHFFFAOYSA-N n-(2-aminophenyl)-n-ethylacetamide Chemical compound CCN(C(C)=O)C1=CC=CC=C1N GIYCSTBRWXPCMX-UHFFFAOYSA-N 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 244000045947 parasite Species 0.000 description 1
- 230000003071 parasitic effect Effects 0.000 description 1
- 244000052769 pathogen Species 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229940096825 phenylmercury Drugs 0.000 description 1
- DCNLOVYDMCVNRZ-UHFFFAOYSA-N phenylmercury(.) Chemical compound [Hg]C1=CC=CC=C1 DCNLOVYDMCVNRZ-UHFFFAOYSA-N 0.000 description 1
- 230000003032 phytopathogenic effect Effects 0.000 description 1
- 238000005554 pickling Methods 0.000 description 1
- 230000008635 plant growth Effects 0.000 description 1
- 239000003495 polar organic solvent Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000001965 potato dextrose agar Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 230000000391 smoking effect Effects 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 230000004763 spore germination Effects 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 230000009897 systematic effect Effects 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 125000002948 undecyl 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])[H] 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
- C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members 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
- C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/40—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having a double or triple bond to nitrogen, e.g. cyanates, cyanamides
- A01N47/42—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having a double or triple bond to nitrogen, e.g. cyanates, cyanamides containing —N=CX2 groups, e.g. isothiourea
- A01N47/44—Guanidine; Derivatives thereof
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Furan Compounds (AREA)
Priority Applications (20)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE758607D BE758607A (fr) | 1969-11-06 | Nouvelles amidophenylguanidines, leur procede de preparation etleur application comme fongicides | |
| DE19691955749 DE1955749A1 (de) | 1969-11-06 | 1969-11-06 | Amidophenylguanidine,Verfahren zu ihrer Herstellung und ihre fungizide Verwendung |
| IL7035440A IL35440A (en) | 1969-11-06 | 1970-10-13 | Amidophenylguanidines, their production and use as fungicides |
| CH1549270A CH508603A (de) | 1969-11-06 | 1970-10-20 | Verfahren zur Herstellung von Amidophenylguanidinen und ihre fungizide Verwendung |
| ZA707167A ZA707167B (en) | 1969-11-06 | 1970-10-21 | Amidophenylguanidines and their use as fungicides |
| US083159A US3869503A (en) | 1969-11-06 | 1970-10-22 | Substituted amidophenylguanidines |
| RO64793A RO58034A (en, 2012) | 1969-11-06 | 1970-10-26 | |
| BG015931A BG17537A3 (bg) | 1969-11-06 | 1970-10-27 | Фунгицидно средство |
| GB52217/70A GB1282374A (en) | 1969-11-06 | 1970-11-03 | Amidophenylguanidines and their use as fungicides |
| HUBA2493A HU163069B (en, 2012) | 1969-11-06 | 1970-11-03 | |
| NL7016232A NL7016232A (en, 2012) | 1969-11-06 | 1970-11-05 | |
| ES385211A ES385211A1 (es) | 1969-11-06 | 1970-11-05 | Procedimiento para la obtencion de amidofenilguanidinas. |
| DK563870AA DK126499B (da) | 1969-11-06 | 1970-11-05 | Fungicidt aktive amidophenylguanidiner. |
| AT999970A AT303751B (de) | 1969-11-06 | 1970-11-06 | Verfahren zur Herstellung von neuen Amidophenylguanidinen |
| PL1970144296A PL69661B1 (en, 2012) | 1969-11-06 | 1970-11-06 | |
| JP45097535A JPS4936705B1 (en, 2012) | 1969-11-06 | 1970-11-06 | |
| FR7039983A FR2069114A5 (en, 2012) | 1969-11-06 | 1970-11-06 | |
| JP45097536A JPS4811015B1 (en, 2012) | 1969-11-06 | 1970-11-06 | |
| US337183A US3881018A (en) | 1969-11-06 | 1973-03-01 | Substituted amidophenylguanidine fungicides |
| MY1973142A MY7300142A (en) | 1969-11-06 | 1973-12-31 | Aminophenylguanidines and their use as fungicides |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19691955749 DE1955749A1 (de) | 1969-11-06 | 1969-11-06 | Amidophenylguanidine,Verfahren zu ihrer Herstellung und ihre fungizide Verwendung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1955749A1 true DE1955749A1 (de) | 1971-05-13 |
Family
ID=5750236
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19691955749 Pending DE1955749A1 (de) | 1969-11-06 | 1969-11-06 | Amidophenylguanidine,Verfahren zu ihrer Herstellung und ihre fungizide Verwendung |
Country Status (18)
| Country | Link |
|---|---|
| US (1) | US3869503A (en, 2012) |
| JP (2) | JPS4811015B1 (en, 2012) |
| AT (1) | AT303751B (en, 2012) |
| BE (1) | BE758607A (en, 2012) |
| BG (1) | BG17537A3 (en, 2012) |
| CH (1) | CH508603A (en, 2012) |
| DE (1) | DE1955749A1 (en, 2012) |
| DK (1) | DK126499B (en, 2012) |
| ES (1) | ES385211A1 (en, 2012) |
| FR (1) | FR2069114A5 (en, 2012) |
| GB (1) | GB1282374A (en, 2012) |
| HU (1) | HU163069B (en, 2012) |
| IL (1) | IL35440A (en, 2012) |
| MY (1) | MY7300142A (en, 2012) |
| NL (1) | NL7016232A (en, 2012) |
| PL (1) | PL69661B1 (en, 2012) |
| RO (1) | RO58034A (en, 2012) |
| ZA (1) | ZA707167B (en, 2012) |
Families Citing this family (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS50141412U (en, 2012) * | 1974-05-08 | 1975-11-21 | ||
| US4088780A (en) * | 1974-05-15 | 1978-05-09 | Bayer Aktiengesellschaft | Substituted phenylguanidines and processes for their preparation and use |
| USRE29508E (en) * | 1974-06-13 | 1978-01-03 | Eli Lilly And Company | Ring-substituted N-(2,2-difluoroalkanoyl)-o-phenylenediamine compounds |
| DE2609994A1 (de) * | 1976-03-10 | 1977-09-15 | Bayer Ag | 2-formylamino-phenylguanidine, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
| JPS52160210U (en, 2012) * | 1976-05-29 | 1977-12-05 | ||
| DE2651467A1 (de) * | 1976-11-11 | 1978-05-18 | Bayer Ag | Substituierte o-phenylendiaminderivate, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
| CH645359A5 (de) * | 1978-11-20 | 1984-09-28 | Ciba Geigy Ag | Lagerstabile, konzentrierte waessrige loesung von benzimidazolium-aufhellern. |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3564041A (en) * | 1967-04-26 | 1971-02-16 | Upjohn Co | 1,2,3-trihydrocarbylguanidine-1-carboxylates |
-
0
- BE BE758607D patent/BE758607A/xx unknown
-
1969
- 1969-11-06 DE DE19691955749 patent/DE1955749A1/de active Pending
-
1970
- 1970-10-13 IL IL7035440A patent/IL35440A/en unknown
- 1970-10-20 CH CH1549270A patent/CH508603A/de not_active IP Right Cessation
- 1970-10-21 ZA ZA707167A patent/ZA707167B/xx unknown
- 1970-10-22 US US083159A patent/US3869503A/en not_active Expired - Lifetime
- 1970-10-26 RO RO64793A patent/RO58034A/ro unknown
- 1970-10-27 BG BG015931A patent/BG17537A3/xx unknown
- 1970-11-03 HU HUBA2493A patent/HU163069B/hu unknown
- 1970-11-03 GB GB52217/70A patent/GB1282374A/en not_active Expired
- 1970-11-05 DK DK563870AA patent/DK126499B/da unknown
- 1970-11-05 ES ES385211A patent/ES385211A1/es not_active Expired
- 1970-11-05 NL NL7016232A patent/NL7016232A/xx unknown
- 1970-11-06 FR FR7039983A patent/FR2069114A5/fr not_active Expired
- 1970-11-06 JP JP45097536A patent/JPS4811015B1/ja active Pending
- 1970-11-06 AT AT999970A patent/AT303751B/de not_active IP Right Cessation
- 1970-11-06 PL PL1970144296A patent/PL69661B1/pl unknown
- 1970-11-06 JP JP45097535A patent/JPS4936705B1/ja active Pending
-
1973
- 1973-12-31 MY MY1973142A patent/MY7300142A/xx unknown
Also Published As
| Publication number | Publication date |
|---|---|
| DK126499B (da) | 1973-07-23 |
| GB1282374A (en) | 1972-07-19 |
| HU163069B (en, 2012) | 1973-06-28 |
| IL35440A (en) | 1973-11-28 |
| US3869503A (en) | 1975-03-04 |
| JPS4936705B1 (en, 2012) | 1974-10-02 |
| BG17537A3 (bg) | 1973-11-10 |
| MY7300142A (en) | 1973-12-31 |
| ES385211A1 (es) | 1973-04-01 |
| IL35440A0 (en) | 1970-12-24 |
| ZA707167B (en) | 1971-07-28 |
| FR2069114A5 (en, 2012) | 1971-09-03 |
| CH508603A (de) | 1971-06-15 |
| JPS4811015B1 (en, 2012) | 1973-04-10 |
| NL7016232A (en, 2012) | 1971-05-10 |
| AT303751B (de) | 1972-12-11 |
| PL69661B1 (en, 2012) | 1973-08-31 |
| BE758607A (fr) | 1971-05-06 |
| RO58034A (en, 2012) | 1975-06-15 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0001414B1 (de) | Diastereomere Formen A von Triazolyl-O,N-acetalen und ihre Verwendung als Fungizide | |
| CH625793A5 (en, 2012) | ||
| EP0137868A1 (de) | 1-Substituierte Imidazol-5-carbonsäurederivate, ihre Herstellung sowie ihre Verwendung als Biozide | |
| DE1955750A1 (de) | Ureidophenylguanidine,Verfahren zu ihrer Herstellung und ihre fungizide Verwendung | |
| DE2325156A1 (de) | Fungizide und mikrobizide mittel | |
| EP0225886B1 (de) | Neue pyridaziniumverbindungen, verfahren zu deren herstellung und diese enthaltende fungizide und algizide mittel | |
| DE2600799A1 (de) | Acylierte triazolyl-0,n-acetale, verfahren zu ihrer herstellung und ihre verwendung als fungizide | |
| DE2547954C2 (en, 2012) | ||
| DE2140863A1 (de) | Aminobenzimidazolcarbonsaeure-derivate, verfahren zu ihrer herstellung und ihre systemisch-fungizide und bakterizide verwendung | |
| CH618974A5 (en, 2012) | ||
| DE2136923A1 (de) | Substituierte benzthiazole, verfahren zu ihrer herstellung und ihre verwendung als fungizide und bakterizide | |
| DE2431073A1 (de) | Fungizides mittel | |
| DE1955749A1 (de) | Amidophenylguanidine,Verfahren zu ihrer Herstellung und ihre fungizide Verwendung | |
| DE1960029A1 (de) | Ureidophenylthioharnstoffe,Verfahren zu ihrer Herstellung und ihre fungizide Verwendung | |
| DE3218176A1 (de) | Jodpropargylammoniumsalze, verfahren zu ihrer herstellung und ihre verwendung als schaedlingsbekaempfungsmittel | |
| DE1209798B (de) | Insektizid, akarizid und fungizid wirksame Mittel | |
| DE3145846A1 (de) | Cycloalkyl-((alpha)-triazolyl-ss-hydroxy)-ketone, verfahren zu ihrer herstellung sowie ihre verwendung als fungizide und pflanzenwachstumsregulatoren | |
| DE2334352B2 (de) | Im Heterocyclus halogenierte 1-(1,2,4-Triazol-l yl)-l-phenoxy-33dimethyl-butan-2-on- Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Fungizide | |
| EP0002679A1 (de) | 1-Halogen-1-propin-3-ole, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Fungizide | |
| DE2128700C2 (de) | Fungitoxische Mittel | |
| DE2025412A1 (de) | Amidophenylisothiohamstoffe, Verfahren zu ihrer Herstellung und ihre fungizide Verwendung | |
| DE2025413A1 (de) | Ureidophenylisothioharnstoffe, Verfahren zu ihrer Herstellung und ihre fungizide Verwendung | |
| DE1960027A1 (de) | Amidophenylthioharnstoffe,Verfahren zu ihrer Herstellung und ihre fungizide Verwendung | |
| DE2604761A1 (de) | Acylierte imidazolyl-o,n-acetale, verfahren zu ihrer herstellung und ihre verwendung als fungizide | |
| DE1936130A1 (de) | Benzimidazol-Derivate,Verfahren zu ihrer Herstellung und ihre fungizide Verwendung |