DE2157368A1 - Amidophenylguanidine, verfahren zu ihrer herstellung und ihre fungizide verwendung - Google Patents
Amidophenylguanidine, verfahren zu ihrer herstellung und ihre fungizide verwendungInfo
- Publication number
- DE2157368A1 DE2157368A1 DE2157368A DE2157368A DE2157368A1 DE 2157368 A1 DE2157368 A1 DE 2157368A1 DE 2157368 A DE2157368 A DE 2157368A DE 2157368 A DE2157368 A DE 2157368A DE 2157368 A1 DE2157368 A1 DE 2157368A1
- Authority
- DE
- Germany
- Prior art keywords
- carbon atoms
- alkyl
- alkoxy
- halogen
- active ingredient
- 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 12
- 230000000855 fungicidal effect Effects 0.000 title description 6
- 238000004519 manufacturing process Methods 0.000 title description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 42
- 125000000217 alkyl group Chemical group 0.000 claims description 20
- 125000003545 alkoxy group Chemical group 0.000 claims description 15
- 229910052736 halogen Inorganic materials 0.000 claims description 14
- 150000002367 halogens Chemical class 0.000 claims description 14
- 241000233866 Fungi Species 0.000 claims description 12
- 238000002360 preparation method Methods 0.000 claims description 9
- GEYOCULIXLDCMW-UHFFFAOYSA-N 1,2-phenylenediamine Chemical class NC1=CC=CC=C1N GEYOCULIXLDCMW-UHFFFAOYSA-N 0.000 claims description 6
- 235000001674 Agaricus brunnescens Nutrition 0.000 claims description 6
- 229910052739 hydrogen Inorganic materials 0.000 claims description 6
- 239000001257 hydrogen Substances 0.000 claims description 6
- 239000004606 Fillers/Extenders Substances 0.000 claims description 4
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 4
- 239000000417 fungicide Substances 0.000 claims description 4
- 150000002541 isothioureas Chemical class 0.000 claims description 4
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 4
- 239000003085 diluting agent Substances 0.000 claims description 3
- 150000007524 organic acids Chemical class 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000000304 alkynyl group Chemical group 0.000 claims description 2
- 150000007522 mineralic acids Chemical class 0.000 claims description 2
- 239000004094 surface-active agent Substances 0.000 claims description 2
- 150000002431 hydrogen Chemical class 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 description 60
- 241000196324 Embryophyta Species 0.000 description 27
- 206010061217 Infestation Diseases 0.000 description 27
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 21
- 239000007788 liquid Substances 0.000 description 18
- 239000002904 solvent Substances 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 16
- 230000009885 systemic effect Effects 0.000 description 15
- 239000000203 mixture Substances 0.000 description 12
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
- 239000002689 soil Substances 0.000 description 11
- -1 1 -Puryl Chemical group 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 9
- 239000002270 dispersing agent Substances 0.000 description 9
- 208000015181 infectious disease Diseases 0.000 description 8
- 125000002877 alkyl aryl group Chemical group 0.000 description 7
- 239000012141 concentrate Substances 0.000 description 7
- 241000220225 Malus Species 0.000 description 6
- 238000005266 casting Methods 0.000 description 6
- 238000011081 inoculation Methods 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- 229920000151 polyglycol Polymers 0.000 description 6
- 239000010695 polyglycol Substances 0.000 description 6
- 241000221785 Erysiphales Species 0.000 description 5
- 241000221787 Erysiphe Species 0.000 description 5
- 239000000654 additive Substances 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 239000003995 emulsifying agent Substances 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 239000011877 solvent mixture Substances 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- 241001465180 Botrytis Species 0.000 description 4
- 240000008067 Cucumis sativus Species 0.000 description 4
- 240000007594 Oryza sativa Species 0.000 description 4
- 201000010099 disease Diseases 0.000 description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000007921 spray Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 241000489964 Fusicladium Species 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 241000896242 Podosphaera Species 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 241000589652 Xanthomonas oryzae Species 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- 239000000969 carrier Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 3
- 239000002609 medium Substances 0.000 description 3
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 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
- 229920001817 Agar Polymers 0.000 description 2
- 241000894006 Bacteria Species 0.000 description 2
- 241000123650 Botrytis cinerea 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
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
- 241001465754 Metazoa Species 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
- 241001337928 Podosphaera leucotricha Species 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- 206010039509 Scab Diseases 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 2
- 240000006677 Vicia faba Species 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 235000010419 agar Nutrition 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 150000008051 alkyl sulfates Chemical class 0.000 description 2
- 229940045714 alkyl sulfonate alkylating agent Drugs 0.000 description 2
- 150000008052 alkyl sulfonates Chemical class 0.000 description 2
- FPIPGXGPPPQFEQ-OVSJKPMPSA-N all-trans-retinol Chemical compound OC\C=C(/C)\C=C\C=C(/C)\C=C\C1=C(C)CCCC1(C)C FPIPGXGPPPQFEQ-OVSJKPMPSA-N 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 235000021186 dishes Nutrition 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 230000002538 fungal effect Effects 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 239000001963 growth medium Substances 0.000 description 2
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 150000002576 ketones Chemical class 0.000 description 2
- 231100000053 low toxicity Toxicity 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 230000017066 negative regulation of growth Effects 0.000 description 2
- 235000015097 nutrients Nutrition 0.000 description 2
- 239000006072 paste Substances 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 230000001681 protective effect Effects 0.000 description 2
- 235000009566 rice Nutrition 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
- 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 2
- LDVVMCZRFWMZSG-OLQVQODUSA-N (3ar,7as)-2-(trichloromethylsulfanyl)-3a,4,7,7a-tetrahydroisoindole-1,3-dione Chemical compound C1C=CC[C@H]2C(=O)N(SC(Cl)(Cl)Cl)C(=O)[C@H]21 LDVVMCZRFWMZSG-OLQVQODUSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-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
- QRKJNCRCYBKANP-UHFFFAOYSA-N 2-amino-n-phenylacetamide Chemical compound NCC(=O)NC1=CC=CC=C1 QRKJNCRCYBKANP-UHFFFAOYSA-N 0.000 description 1
- RUBYQYMLYZMHQR-UHFFFAOYSA-N 2-amino-n-phenylpropanamide Chemical compound CC(N)C(=O)NC1=CC=CC=C1 RUBYQYMLYZMHQR-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-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
- 241000235349 Ascomycota 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
- 239000005745 Captan Substances 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 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
- 235000009849 Cucumis sativus Nutrition 0.000 description 1
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 241000510928 Erysiphe necator Species 0.000 description 1
- 241000345386 Fabia Species 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- 241000223218 Fusarium Species 0.000 description 1
- 241000206672 Gelidium Species 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- 241000896246 Golovinomyces cichoracearum Species 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- 208000031888 Mycoses Diseases 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
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 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
- 208000030852 Parasitic disease Diseases 0.000 description 1
- 239000001888 Peptone Substances 0.000 description 1
- 108010080698 Peptones Proteins 0.000 description 1
- 241000308483 Phialophora cinerescens Species 0.000 description 1
- 241000184297 Pseudocercospora musae Species 0.000 description 1
- 244000061456 Solanum tuberosum Species 0.000 description 1
- 235000002595 Solanum tuberosum Nutrition 0.000 description 1
- 241000579741 Sphaerotheca <fungi> Species 0.000 description 1
- 244000269722 Thea sinensis Species 0.000 description 1
- 241000510929 Uncinula Species 0.000 description 1
- 241000228452 Venturia inaequalis Species 0.000 description 1
- 241001006642 Venturia pyrina Species 0.000 description 1
- 241000219873 Vicia Species 0.000 description 1
- 235000010749 Vicia faba Nutrition 0.000 description 1
- 235000002096 Vicia faba var. equina Nutrition 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical class ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- 230000000895 acaricidal effect Effects 0.000 description 1
- 239000000642 acaricide Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000008272 agar Substances 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 229940100198 alkylating agent Drugs 0.000 description 1
- 239000002168 alkylating agent Substances 0.000 description 1
- 239000011717 all-trans-retinol Substances 0.000 description 1
- 235000019169 all-trans-retinol Nutrition 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
- 125000004429 atom Chemical group 0.000 description 1
- 229960000892 attapulgite Drugs 0.000 description 1
- 230000001580 bacterial effect Effects 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 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
- 244000309464 bull Species 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 229940117949 captan Drugs 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 150000008422 chlorobenzenes Chemical class 0.000 description 1
- 244000038559 crop plants Species 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 239000008121 dextrose Substances 0.000 description 1
- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
- ZFTFAPZRGNKQPU-UHFFFAOYSA-N dicarbonic acid Chemical compound OC(=O)OC(O)=O ZFTFAPZRGNKQPU-UHFFFAOYSA-N 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- FFYPMLJYZAEMQB-UHFFFAOYSA-N diethyl pyrocarbonate Chemical compound CCOC(=O)OC(=O)OCC FFYPMLJYZAEMQB-UHFFFAOYSA-N 0.000 description 1
- 238000010410 dusting Methods 0.000 description 1
- 235000013399 edible fruits Nutrition 0.000 description 1
- 239000004495 emulsifiable concentrate Substances 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- DQYBDCGIPTYXML-UHFFFAOYSA-N ethoxyethane;hydrate Chemical compound O.CCOCC DQYBDCGIPTYXML-UHFFFAOYSA-N 0.000 description 1
- 125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 description 1
- VZUNIZBFOIERAB-UHFFFAOYSA-N ethyl n-[methylsulfanyl-(propanoylamino)methylidene]carbamate Chemical compound CCOC(=O)NC(SC)=NC(=O)CC VZUNIZBFOIERAB-UHFFFAOYSA-N 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 244000053095 fungal pathogen Species 0.000 description 1
- 230000001408 fungistatic effect Effects 0.000 description 1
- 230000002464 fungitoxic effect Effects 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 230000009036 growth inhibition Effects 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
- 150000008282 halocarbons Chemical class 0.000 description 1
- LFXAECSQJSRSTP-UHFFFAOYSA-N hydron;methyl carbamimidothioate;iodide Chemical compound I.CSC(N)=N LFXAECSQJSRSTP-UHFFFAOYSA-N 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 238000011534 incubation Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 230000000749 insecticidal effect Effects 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 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
- ICGKKNKTOSEAHZ-UHFFFAOYSA-N methyl N-propanoylcarbamimidothioate hydroiodide Chemical compound I.C(CC)(=O)NC(SC)=N ICGKKNKTOSEAHZ-UHFFFAOYSA-N 0.000 description 1
- 229920000609 methyl cellulose Polymers 0.000 description 1
- OAQFTVPOKDOFLY-UHFFFAOYSA-N methyl n-[(cyclohexanecarbonylamino)-methylsulfanylmethylidene]carbamate Chemical compound COC(=O)NC(SC)=NC(=O)C1CCCCC1 OAQFTVPOKDOFLY-UHFFFAOYSA-N 0.000 description 1
- XQLWPOXMLSCQLM-UHFFFAOYSA-N methyl n-[methylsulfanyl-(propanoylamino)methylidene]carbamate Chemical compound CCC(=O)N=C(SC)NC(=O)OC XQLWPOXMLSCQLM-UHFFFAOYSA-N 0.000 description 1
- 239000001923 methylcellulose Substances 0.000 description 1
- 235000010981 methylcellulose Nutrition 0.000 description 1
- 244000005700 microbiome Species 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 229910052901 montmorillonite Inorganic materials 0.000 description 1
- IWAXFIOOFMLCCI-UHFFFAOYSA-N n-(2-aminophenyl)-2-phenoxyacetamide Chemical compound NC1=CC=CC=C1NC(=O)COC1=CC=CC=C1 IWAXFIOOFMLCCI-UHFFFAOYSA-N 0.000 description 1
- PRZZSWCUIWZUHO-UHFFFAOYSA-N n-(2-aminophenyl)-4-chlorobenzamide Chemical compound NC1=CC=CC=C1NC(=O)C1=CC=C(Cl)C=C1 PRZZSWCUIWZUHO-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
- RFDVMOUXHKTCDO-UHFFFAOYSA-N n-(2-aminophenyl)benzamide Chemical compound NC1=CC=CC=C1NC(=O)C1=CC=CC=C1 RFDVMOUXHKTCDO-UHFFFAOYSA-N 0.000 description 1
- VVWCJSVUWOIXAD-UHFFFAOYSA-N n-carbamothioylpropanamide Chemical compound CCC(=O)NC(N)=S VVWCJSVUWOIXAD-UHFFFAOYSA-N 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000002828 nitro derivatives Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- TWNQGVIAIRXVLR-UHFFFAOYSA-N oxo(oxoalumanyloxy)alumane Chemical compound O=[Al]O[Al]=O TWNQGVIAIRXVLR-UHFFFAOYSA-N 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 230000003071 parasitic effect Effects 0.000 description 1
- 244000052769 pathogen Species 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- 235000019319 peptone Nutrition 0.000 description 1
- 239000000575 pesticide Substances 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 229940096825 phenylmercury Drugs 0.000 description 1
- DCNLOVYDMCVNRZ-UHFFFAOYSA-N phenylmercury(.) Chemical class [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
- 239000003495 polar organic solvent Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 239000002244 precipitate Substances 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 125000004368 propenyl group Chemical group C(=CC)* 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002568 propynyl group Chemical group [*]C#CC([H])([H])[H] 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 239000011435 rock Substances 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
- 150000004760 silicates Chemical class 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 230000000391 smoking effect Effects 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical compound [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 239000013589 supplement Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Furan Compounds (AREA)
Priority Applications (10)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| BE791553D BE791553A (fr) | 1971-11-19 | Nouvelles amidophenylguanidines, leur procede de preparation etleur application comme fongicides | |
| DE2157368A DE2157368A1 (de) | 1971-11-19 | 1971-11-19 | Amidophenylguanidine, verfahren zu ihrer herstellung und ihre fungizide verwendung |
| US00303301A US3835164A (en) | 1971-11-19 | 1972-11-02 | N-alkoxycarbonyl-n{40 -acyl-n{41 12-acylamidophenyl-guanidines |
| NL7215528A NL7215528A (OSRAM) | 1971-11-19 | 1972-11-16 | |
| IL40859A IL40859A0 (en) | 1971-11-19 | 1972-11-16 | Amidophenylguanidines,process for their preparation and their fungicidal use |
| ZA728165A ZA728165B (en) | 1971-11-19 | 1972-11-17 | Amidophenylguanidines process for their preparation and their fungicidal use |
| FR7241029A FR2161715A5 (OSRAM) | 1971-11-19 | 1972-11-17 | |
| JP47114856A JPS4861632A (OSRAM) | 1971-11-19 | 1972-11-17 | |
| BR8086/72A BR7208086D0 (pt) | 1971-11-19 | 1972-11-17 | Processo para a obtencao de amido fenil guanidina e composicao fungicida a base das mesmas |
| JP47114855A JPS4861437A (OSRAM) | 1971-11-19 | 1972-11-17 |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2157368A DE2157368A1 (de) | 1971-11-19 | 1971-11-19 | Amidophenylguanidine, verfahren zu ihrer herstellung und ihre fungizide verwendung |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE2157368A1 true DE2157368A1 (de) | 1973-05-24 |
Family
ID=5825516
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2157368A Pending DE2157368A1 (de) | 1971-11-19 | 1971-11-19 | Amidophenylguanidine, verfahren zu ihrer herstellung und ihre fungizide verwendung |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US3835164A (OSRAM) |
| JP (2) | JPS4861437A (OSRAM) |
| BE (1) | BE791553A (OSRAM) |
| BR (1) | BR7208086D0 (OSRAM) |
| DE (1) | DE2157368A1 (OSRAM) |
| FR (1) | FR2161715A5 (OSRAM) |
| IL (1) | IL40859A0 (OSRAM) |
| NL (1) | NL7215528A (OSRAM) |
| ZA (1) | ZA728165B (OSRAM) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5089333A (OSRAM) * | 1973-12-13 | 1975-07-17 | ||
| DE2609994A1 (de) * | 1976-03-10 | 1977-09-15 | Bayer Ag | 2-formylamino-phenylguanidine, verfahren zu ihrer herstellung sowie ihre verwendung als arzneimittel |
-
0
- BE BE791553D patent/BE791553A/xx unknown
-
1971
- 1971-11-19 DE DE2157368A patent/DE2157368A1/de active Pending
-
1972
- 1972-11-02 US US00303301A patent/US3835164A/en not_active Expired - Lifetime
- 1972-11-16 IL IL40859A patent/IL40859A0/xx unknown
- 1972-11-16 NL NL7215528A patent/NL7215528A/xx unknown
- 1972-11-17 ZA ZA728165A patent/ZA728165B/xx unknown
- 1972-11-17 JP JP47114855A patent/JPS4861437A/ja active Pending
- 1972-11-17 JP JP47114856A patent/JPS4861632A/ja active Pending
- 1972-11-17 FR FR7241029A patent/FR2161715A5/fr not_active Expired
- 1972-11-17 BR BR8086/72A patent/BR7208086D0/pt unknown
Also Published As
| Publication number | Publication date |
|---|---|
| BR7208086D0 (pt) | 1973-09-18 |
| ZA728165B (en) | 1973-07-25 |
| IL40859A0 (en) | 1973-01-30 |
| JPS4861437A (OSRAM) | 1973-08-28 |
| FR2161715A5 (OSRAM) | 1973-07-06 |
| NL7215528A (OSRAM) | 1973-05-22 |
| BE791553A (fr) | 1973-05-17 |
| JPS4861632A (OSRAM) | 1973-08-29 |
| US3835164A (en) | 1974-09-10 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP0025949A1 (de) | Acylierte Triazolyl-gamma-fluorpinakolyl-Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Fungizide | |
| DE1955750A1 (de) | Ureidophenylguanidine,Verfahren zu ihrer Herstellung und ihre fungizide Verwendung | |
| DE2335020C3 (de) | 1-(1,2,4-Triazol-1-yl)-2-phenoxy-4,4-dimethyl-pentan-3-on-Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Fungizide | |
| DE2600799A1 (de) | Acylierte triazolyl-0,n-acetale, verfahren zu ihrer herstellung und ihre verwendung als fungizide | |
| DE2547954C2 (OSRAM) | ||
| DE2206010A1 (de) | 1-aminosulfonyl-2-amino-benzimidazole, verfahren zu ihrer herstellung und ihre fungizide verwendung | |
| DE2140863A1 (de) | Aminobenzimidazolcarbonsaeure-derivate, verfahren zu ihrer herstellung und ihre systemisch-fungizide und bakterizide verwendung | |
| DE2431073A1 (de) | Fungizides mittel | |
| DE2714290A1 (de) | Fungizide mittel | |
| DE2136923A1 (de) | Substituierte benzthiazole, verfahren zu ihrer herstellung und ihre verwendung als fungizide und bakterizide | |
| DE2243626A1 (de) | N-sulfenylierte carbamidoxime, verfahren zu ihrer herstellung und ihre fungizide und bakterizide verwendung | |
| DE2334352C3 (de) | Im Heterocyclus halogenierte 1-(1,2,4-Triazol-1-yl)-1-phenoxy-3,3-dimethyl-butan-2-on- Derivate, Verfahren zu ihrer Herstellung und ihre Verwendung als Fungizide | |
| DE2253324A1 (de) | 1-alkoxycarbonyl-2- eckige klammer auf bis-(alkoxycarbonyl)-amino eckige klammer zu -benzimidazole, verfahren zu ihrer herstellung, sowie ihre verwendung als fungizide | |
| DE2624529A1 (de) | Aminomethylazol-derivate, verfahren zu ihrer herstellung sowie ihre verwendung als fungizide und zur regulierung des pflanzenwachstums | |
| EP0142653A1 (de) | 1-Azolyl-substituierte Oximether | |
| DE3145846A1 (de) | Cycloalkyl-((alpha)-triazolyl-ss-hydroxy)-ketone, verfahren zu ihrer herstellung sowie ihre verwendung als fungizide und pflanzenwachstumsregulatoren | |
| DE1955749A1 (de) | Amidophenylguanidine,Verfahren zu ihrer Herstellung und ihre fungizide Verwendung | |
| DE2632603A1 (de) | Halogenierte 1-triazolyl-butan-derivate, verfahren zu ihrer herstellung und ihre verwendung als fungizide | |
| DE2157368A1 (de) | Amidophenylguanidine, verfahren zu ihrer herstellung und ihre fungizide verwendung | |
| DE2604761A1 (de) | Acylierte imidazolyl-o,n-acetale, verfahren zu ihrer herstellung und ihre verwendung als fungizide | |
| EP0154273B1 (de) | Fungizide Mittel | |
| DE2025412A1 (de) | Amidophenylisothiohamstoffe, Verfahren zu ihrer Herstellung und ihre fungizide Verwendung | |
| DE2740848A1 (de) | Substituierte n-phenyl-bernsteinsaeureimide, verfahren zu ihrer herstellung sowie ihre verwendung als fungizide | |
| DE3049439A1 (de) | N-sulfenylierte biurete, verfahren zu ihrer herstellung und ihre verwendung als fungizide | |
| DE1960027A1 (de) | Amidophenylthioharnstoffe,Verfahren zu ihrer Herstellung und ihre fungizide Verwendung |