DD296819A5 - FUNGICIDAL AGENT WITH ADDITIONAL PLANT GROWTH-REGULATORY EFFECT (I) - Google Patents
FUNGICIDAL AGENT WITH ADDITIONAL PLANT GROWTH-REGULATORY EFFECT (I) Download PDFInfo
- Publication number
- DD296819A5 DD296819A5 DD31121287A DD31121287A DD296819A5 DD 296819 A5 DD296819 A5 DD 296819A5 DD 31121287 A DD31121287 A DD 31121287A DD 31121287 A DD31121287 A DD 31121287A DD 296819 A5 DD296819 A5 DD 296819A5
- Authority
- DD
- German Democratic Republic
- Prior art keywords
- atoms
- tridecyl
- iso
- alkyl
- chain
- Prior art date
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- 239000000417 fungicide Substances 0.000 title claims abstract description 15
- 230000000694 effects Effects 0.000 title claims abstract description 14
- 239000000203 mixture Substances 0.000 claims abstract description 16
- 230000002538 fungal effect Effects 0.000 claims abstract description 5
- -1 nitro, cyano, thiocyanato Chemical group 0.000 claims description 226
- 125000004432 carbon atom Chemical group C* 0.000 claims description 53
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 239000002904 solvent Substances 0.000 claims description 13
- 241000233866 Fungi Species 0.000 claims description 11
- 238000009472 formulation Methods 0.000 claims description 9
- 239000002253 acid Substances 0.000 claims description 8
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 8
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 125000003545 alkoxy group Chemical group 0.000 claims description 5
- 239000000969 carrier Substances 0.000 claims description 5
- 239000003795 chemical substances by application Substances 0.000 claims description 5
- 229910052757 nitrogen Inorganic materials 0.000 claims description 5
- 125000002252 acyl group Chemical group 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 125000001188 haloalkyl group Chemical group 0.000 claims description 4
- 150000001450 anions Chemical class 0.000 claims description 3
- 239000001257 hydrogen Substances 0.000 claims description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims description 3
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 3
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- 125000000623 heterocyclic group Chemical group 0.000 claims description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 2
- 231100001184 nonphytotoxic Toxicity 0.000 claims description 2
- 239000000546 pharmaceutical excipient Substances 0.000 claims description 2
- 125000004429 atom Chemical group 0.000 claims 1
- 230000000855 fungicidal effect Effects 0.000 abstract description 10
- 150000003839 salts Chemical class 0.000 abstract description 9
- 238000003898 horticulture Methods 0.000 abstract description 6
- 244000053095 fungal pathogen Species 0.000 abstract description 5
- 230000008635 plant growth Effects 0.000 abstract description 3
- 230000001105 regulatory effect Effects 0.000 abstract description 3
- 241000607479 Yersinia pestis Species 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 description 46
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 23
- 241000196324 Embryophyta Species 0.000 description 21
- 239000004480 active ingredient Substances 0.000 description 19
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 14
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 11
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 238000002360 preparation method Methods 0.000 description 7
- 239000000047 product Substances 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 6
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 6
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical class CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000008187 granular material Substances 0.000 description 6
- 238000002329 infrared spectrum Methods 0.000 description 6
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 6
- 229920000151 polyglycol Polymers 0.000 description 6
- 239000010695 polyglycol Substances 0.000 description 6
- FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 description 6
- 240000008067 Cucumis sativus Species 0.000 description 5
- 235000013339 cereals Nutrition 0.000 description 5
- 239000003814 drug Substances 0.000 description 5
- 229940079593 drug Drugs 0.000 description 5
- 208000015181 infectious disease Diseases 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
- TWFZGCMQGLPBSX-UHFFFAOYSA-N Carbendazim Natural products C1=CC=C2NC(NC(=O)OC)=NC2=C1 TWFZGCMQGLPBSX-UHFFFAOYSA-N 0.000 description 4
- 241000221785 Erysiphales Species 0.000 description 4
- 240000003768 Solanum lycopersicum Species 0.000 description 4
- 239000013543 active substance Substances 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 4
- 230000001276 controlling effect Effects 0.000 description 4
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
- 238000011161 development Methods 0.000 description 4
- 201000010099 disease Diseases 0.000 description 4
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 4
- 150000002170 ethers Chemical class 0.000 description 4
- 230000012010 growth Effects 0.000 description 4
- VLKZOEOYAKHREP-UHFFFAOYSA-N hexane Substances CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 4
- 230000003032 phytopathogenic effect Effects 0.000 description 4
- 238000005554 pickling Methods 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 239000000243 solution Substances 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- 241000123650 Botrytis cinerea Species 0.000 description 3
- 206010061217 Infestation Diseases 0.000 description 3
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 3
- 244000070406 Malus silvestris Species 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 3
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 3
- 244000046052 Phaseolus vulgaris Species 0.000 description 3
- 241000233622 Phytophthora infestans Species 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 125000002877 alkyl aryl group Chemical group 0.000 description 3
- 235000012211 aluminium silicate Nutrition 0.000 description 3
- 244000038559 crop plants Species 0.000 description 3
- 235000021186 dishes Nutrition 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- 238000002474 experimental method Methods 0.000 description 3
- 229910052500 inorganic mineral Inorganic materials 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 239000011707 mineral Substances 0.000 description 3
- 235000010755 mineral Nutrition 0.000 description 3
- 239000002689 soil Substances 0.000 description 3
- 238000005507 spraying Methods 0.000 description 3
- NHOWDZOIZKMVAI-UHFFFAOYSA-N (2-chlorophenyl)(4-chlorophenyl)pyrimidin-5-ylmethanol Chemical compound C=1N=CN=CC=1C(C=1C(=CC=CC=1)Cl)(O)C1=CC=C(Cl)C=C1 NHOWDZOIZKMVAI-UHFFFAOYSA-N 0.000 description 2
- WURBVZBTWMNKQT-UHFFFAOYSA-N 1-(4-chlorophenoxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)butan-2-one Chemical compound C1=NC=NN1C(C(=O)C(C)(C)C)OC1=CC=C(Cl)C=C1 WURBVZBTWMNKQT-UHFFFAOYSA-N 0.000 description 2
- ZBCYEVFVCCSZTN-UHFFFAOYSA-N 1-chloro-11-methyldodecane Chemical compound CC(C)CCCCCCCCCCCl ZBCYEVFVCCSZTN-UHFFFAOYSA-N 0.000 description 2
- ASZMYJSJEOGSBR-UHFFFAOYSA-N 1-chlorotridecane Chemical compound CCCCCCCCCCCCCCl ASZMYJSJEOGSBR-UHFFFAOYSA-N 0.000 description 2
- 125000004180 3-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(F)=C1[H] 0.000 description 2
- UHPMCKVQTMMPCG-UHFFFAOYSA-N 5,8-dihydroxy-2-methoxy-6-methyl-7-(2-oxopropyl)naphthalene-1,4-dione Chemical compound CC1=C(CC(C)=O)C(O)=C2C(=O)C(OC)=CC(=O)C2=C1O UHPMCKVQTMMPCG-UHFFFAOYSA-N 0.000 description 2
- 239000005995 Aluminium silicate Substances 0.000 description 2
- 235000007319 Avena orientalis Nutrition 0.000 description 2
- 244000075850 Avena orientalis Species 0.000 description 2
- 241001465180 Botrytis Species 0.000 description 2
- WCCXQZYSJWDCEB-UHFFFAOYSA-N CC(C)CCCCCCCCCCN1CCCC1 Chemical compound CC(C)CCCCCCCCCCN1CCCC1 WCCXQZYSJWDCEB-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- 240000007154 Coffea arabica Species 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 241000223218 Fusarium Species 0.000 description 2
- 244000043261 Hevea brasiliensis Species 0.000 description 2
- 240000005561 Musa balbisiana Species 0.000 description 2
- 208000031888 Mycoses Diseases 0.000 description 2
- 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 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 235000010627 Phaseolus vulgaris Nutrition 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- 244000061456 Solanum tuberosum Species 0.000 description 2
- 235000002595 Solanum tuberosum Nutrition 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
- 235000010749 Vicia faba Nutrition 0.000 description 2
- 235000002096 Vicia faba var. equina Nutrition 0.000 description 2
- 240000008042 Zea mays Species 0.000 description 2
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 2
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 229910052783 alkali metal Inorganic materials 0.000 description 2
- 150000001340 alkali metals Chemical class 0.000 description 2
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 2
- 150000003931 anilides Chemical class 0.000 description 2
- 235000021015 bananas Nutrition 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- VXIVSQZSERGHQP-UHFFFAOYSA-N chloroacetamide Chemical compound NC(=O)CCl VXIVSQZSERGHQP-UHFFFAOYSA-N 0.000 description 2
- PFIADAMVCJPXSF-UHFFFAOYSA-N chloroneb Chemical compound COC1=CC(Cl)=C(OC)C=C1Cl PFIADAMVCJPXSF-UHFFFAOYSA-N 0.000 description 2
- 229920003211 cis-1,4-polyisoprene Polymers 0.000 description 2
- 235000016213 coffee Nutrition 0.000 description 2
- 235000013353 coffee beverage Nutrition 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- 235000005822 corn Nutrition 0.000 description 2
- 230000001419 dependent effect Effects 0.000 description 2
- 230000008021 deposition Effects 0.000 description 2
- BIXZHMJUSMUDOQ-UHFFFAOYSA-N dichloran Chemical compound NC1=C(Cl)C=C([N+]([O-])=O)C=C1Cl BIXZHMJUSMUDOQ-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
- CJHXCRMKMMBYJQ-UHFFFAOYSA-N dimethirimol Chemical compound CCCCC1=C(C)NC(N(C)C)=NC1=O CJHXCRMKMMBYJQ-UHFFFAOYSA-N 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 235000005489 dwarf bean Nutrition 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 150000008282 halocarbons Chemical class 0.000 description 2
- 244000080020 horsebean Species 0.000 description 2
- 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 2
- 239000007788 liquid Substances 0.000 description 2
- 235000012054 meals Nutrition 0.000 description 2
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 2
- ZQEIXNIJLIKNTD-UHFFFAOYSA-N methyl N-(2,6-dimethylphenyl)-N-(methoxyacetyl)alaninate Chemical compound COCC(=O)N(C(C)C(=O)OC)C1=C(C)C=CC=C1C ZQEIXNIJLIKNTD-UHFFFAOYSA-N 0.000 description 2
- 150000002790 naphthalenes Chemical class 0.000 description 2
- 235000015097 nutrients Nutrition 0.000 description 2
- 239000002798 polar solvent Substances 0.000 description 2
- LCDCPQHFCOBUEF-UHFFFAOYSA-N pyrrolidine-1-carboxamide Chemical compound NC(=O)N1CCCC1 LCDCPQHFCOBUEF-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 235000009518 sodium iodide Nutrition 0.000 description 2
- 159000000000 sodium salts Chemical class 0.000 description 2
- 239000007787 solid Substances 0.000 description 2
- 238000003892 spreading Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- YFNCATAIYKQPOO-UHFFFAOYSA-N thiophanate Chemical compound CCOC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OCC YFNCATAIYKQPOO-UHFFFAOYSA-N 0.000 description 2
- 235000013311 vegetables Nutrition 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- GHYOCDFICYLMRF-UTIIJYGPSA-N (2S,3R)-N-[(2S)-3-(cyclopenten-1-yl)-1-[(2R)-2-methyloxiran-2-yl]-1-oxopropan-2-yl]-3-hydroxy-3-(4-methoxyphenyl)-2-[[(2S)-2-[(2-morpholin-4-ylacetyl)amino]propanoyl]amino]propanamide Chemical compound C1(=CCCC1)C[C@@H](C(=O)[C@@]1(OC1)C)NC([C@H]([C@@H](C1=CC=C(C=C1)OC)O)NC([C@H](C)NC(CN1CCOCC1)=O)=O)=O GHYOCDFICYLMRF-UTIIJYGPSA-N 0.000 description 1
- BQZRYUOIXPREMR-RLWSFTDUSA-N (4R,4aR,7aR,12bS)-9-methoxy-3-methyl-1,2,4,4a,5,6,7a,13-octahydro-4,12-methanobenzofuro[3,2-e]isoquinolin-7-one N,N-dimethyl-1-phenothiazin-10-ylpropan-2-amine N-(4-hydroxyphenyl)acetamide Chemical compound CC(=O)NC1=CC=C(O)C=C1.C1=CC=C2N(CC(C)N(C)C)C3=CC=CC=C3SC2=C1.C([C@H]1[C@H](N(CC[C@@]112)C)C3)CC(=O)[C@@H]1OC1=C2C3=CC=C1OC BQZRYUOIXPREMR-RLWSFTDUSA-N 0.000 description 1
- 125000003626 1,2,4-triazol-1-yl group Chemical group [*]N1N=C([H])N=C1[H] 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- PZBPKYOVPCNPJY-UHFFFAOYSA-N 1-[2-(allyloxy)-2-(2,4-dichlorophenyl)ethyl]imidazole Chemical compound ClC1=CC(Cl)=CC=C1C(OCC=C)CN1C=NC=C1 PZBPKYOVPCNPJY-UHFFFAOYSA-N 0.000 description 1
- JKOTZBXSNOGCIF-UHFFFAOYSA-N 1-bromopentadecane Chemical compound CCCCCCCCCCCCCCCBr JKOTZBXSNOGCIF-UHFFFAOYSA-N 0.000 description 1
- YAYNEUUHHLGGAH-UHFFFAOYSA-N 1-chlorododecane Chemical compound CCCCCCCCCCCCCl YAYNEUUHHLGGAH-UHFFFAOYSA-N 0.000 description 1
- CNDHHGUSRIZDSL-UHFFFAOYSA-N 1-chlorooctane Chemical compound CCCCCCCCCl CNDHHGUSRIZDSL-UHFFFAOYSA-N 0.000 description 1
- CMCBDXRRFKYBDG-UHFFFAOYSA-N 1-dodecoxydodecane Chemical compound CCCCCCCCCCCCOCCCCCCCCCCCC CMCBDXRRFKYBDG-UHFFFAOYSA-N 0.000 description 1
- 125000001637 1-naphthyl group Chemical group [H]C1=C([H])C([H])=C2C(*)=C([H])C([H])=C([H])C2=C1[H] 0.000 description 1
- 125000004214 1-pyrrolidinyl group Chemical group [H]C1([H])N(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 1
- 125000001462 1-pyrrolyl group Chemical group [*]N1C([H])=C([H])C([H])=C1[H] 0.000 description 1
- XUJLWPFSUCHPQL-UHFFFAOYSA-N 11-methyldodecan-1-ol Chemical compound CC(C)CCCCCCCCCCO XUJLWPFSUCHPQL-UHFFFAOYSA-N 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- KBLAMUYRMZPYLS-UHFFFAOYSA-N 2,3-bis(2-methylpropyl)naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(O)(=O)=O)=C(CC(C)C)C(CC(C)C)=CC2=C1 KBLAMUYRMZPYLS-UHFFFAOYSA-N 0.000 description 1
- 125000004201 2,4-dichlorophenyl group Chemical group [H]C1=C([H])C(*)=C(Cl)C([H])=C1Cl 0.000 description 1
- PYRKKGOKRMZEIT-UHFFFAOYSA-N 2-[6-(2-cyclopropylethoxy)-9-(2-hydroxy-2-methylpropyl)-1h-phenanthro[9,10-d]imidazol-2-yl]-5-fluorobenzene-1,3-dicarbonitrile Chemical compound C1=C2C3=CC(CC(C)(O)C)=CC=C3C=3NC(C=4C(=CC(F)=CC=4C#N)C#N)=NC=3C2=CC=C1OCCC1CC1 PYRKKGOKRMZEIT-UHFFFAOYSA-N 0.000 description 1
- RVGYVOMJXYSEEX-UHFFFAOYSA-N 2-bromo-n-(3,5-dichlorophenyl)propanamide Chemical compound CC(Br)C(=O)NC1=CC(Cl)=CC(Cl)=C1 RVGYVOMJXYSEEX-UHFFFAOYSA-N 0.000 description 1
- SRLNDHQCQMKRKL-UHFFFAOYSA-N 2-chloro-6,10-dimethylundecane Chemical compound CC(C)CCCC(C)CCCC(C)Cl SRLNDHQCQMKRKL-UHFFFAOYSA-N 0.000 description 1
- ZRTPLHDJASYNPE-UHFFFAOYSA-N 2-chloro-n-(3,5-dichlorophenyl)acetamide Chemical compound ClCC(=O)NC1=CC(Cl)=CC(Cl)=C1 ZRTPLHDJASYNPE-UHFFFAOYSA-N 0.000 description 1
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 1
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- LBTUTDYXOOUODJ-UHFFFAOYSA-N 2-pyrrolidin-1-ylacetamide Chemical compound NC(=O)CN1CCCC1 LBTUTDYXOOUODJ-UHFFFAOYSA-N 0.000 description 1
- 125000004362 3,4,5-trichlorophenyl group Chemical group [H]C1=C(Cl)C(Cl)=C(Cl)C([H])=C1* 0.000 description 1
- 125000006512 3,4-dichlorobenzyl group Chemical group [H]C1=C(Cl)C(Cl)=C([H])C(=C1[H])C([H])([H])* 0.000 description 1
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Abstract
Die Erfindung betrifft fungizide Mittel mit zusaetzlicher pflanzenwachstumsregulierender Wirkung, die N-Alkylpyrrolidinio-carbonsaeureamid-Salze der allgemeinen Formel I enthalten und zur Bekaempfung von pilzlichen Schaderregern in der Landwirtschaft und im Gartenbau verwendet werden koennen. Zusaetzlich besitzen die erfindungsgemaeszen Mittel pflanzenwachstumsregulierende Eigenschaften. Die Bedeutung von R1, R2, R3, R4 und X in der Formel (I) ist der Beschreibung zu entnehmen. Formel (I){fungizide Mittel; pflanzenwachstumsregulierende Wirkung; N-Alkylpyrrolidinio-carbonsaeureamid-Salze; pilzliche Schaderreger; Bekaempfung; Landwirtschaft; Gartenbau}The invention relates to fungicidal compositions having additional plant growth-regulating action, the N-alkylpyrrolidinio-carbonsaeureamid salts of the general formula I and can be used for the control of fungal pests in agriculture and horticulture. In addition, the compositions of the invention have plant growth regulating properties. The meaning of R1, R2, R3, R4 and X in the formula (I) can be taken from the description. Formula (I) {fungicidal agent; plant growth-regulating effect; N-Alkylpyrrolidinio-carboxylic acid amide salts; fungal pathogens; combating; Agriculture; Horticulture}
Description
Die Erfindung betrifft neue N-Alkylpyrrolidinio-carbonsäureamid-Salze und ihre Verwendung als fungizide Mittel in der Landwirtschaft und im Gartenbau mit zusätzlichen pflanzenwachstumsregulierenden Eigenschaften.The invention relates to novel N-alkylpyrrolidinio-carboxamide salts and their use as fungicidal agents in agriculture and horticulture with additional plant growth-regulating properties.
Es ist bekannt, N-Aralkylpyrrolidine und ihre Säureadditions-Salze als Fungizide zu verwenden (DE-PS 2727482, DE-PS 2830127, Angewandte Chemie 92 [1980], S. 17&-181).It is known to use N-aralkylpyrrolidines and their acid addition salts as fungicides (DE-PS 2727482, DE-PS 2830127, Angewandte Chemie 92 [1980], p. 17 & -181).
Bekannt ist ferner, daß quatemäre Ammoniumverbindungen von langkettigen N-Alkylpyrrolidinen mit niederen Alkyl-Substituenten fungizid wirksam sind (CS-PS 190691).It is also known that quaternary ammonium compounds of long-chain N-alkylpyrrolidines with lower alkyl substituents are fungicidally effective (CS-PS 190691).
Des weiteren ist bekannt, daß N-Alkyl-, N-Alkenyl- oder N-Alkinyl-substituierte N-Aralkylpyrrolidinium-Salze im Mittel zur Regulierung des Pflanzenwachstums beschrieben werden (DE-PS 2952382).Furthermore, it is known that N-alkyl, N-alkenyl or N-alkynyl-substituted N-Aralkylpyrrolidinium salts are described in the means for regulating plant growth (DE-PS 2952382).
Weiterhin sind quaternäre Salze von Pyrrolidino-alkancarbonsäure-aniliden mit niederen Alkyl-, Alkenyl-, Alkinyl- oderFurthermore, quaternary salts of pyrrolidino-alkanecarboxylic acid anilides with lower alkyl, alkenyl, alkynyl or
substituierten Alkylgruppen als Pflanzenwachstumsregulatoren bekannt (DE-PS 2657728, DE-PS 2915250, EP-PS 0014223, DD-PS 151036).Substituted alkyl groups known as plant growth regulators (DE-PS 2657728, DE-PS 2915250, EP-PS 0014223, DD-PS 151036).
Ferner ist bereits bekannt, N,N'-Bis-(1 -formamido^^-trichlorethyO-piperazin (Triforine) oder 2,6-Dichlor-4-nitranilin (Dicloran) als Wirkstoffe in fungiziden Mitteln zur Bekämpfung von pilzlichen Pflanzenkrankheiten zu verwenden (The Pesticide Manual, British Crop Protection Council; London, 1979).Furthermore, it is already known to use N, N'-bis (1-formamido) trichloroethylpiperazine (triforine) or 2,6-dichloro-4-nitraniline (diclorane) as active ingredients in fungicidal agents for combating fungal plant diseases (The Pesticide Manual, British Crop Protection Council, London, 1979).
Die Wirkung der genannten Verbindungen ist jedoch in bestimmten Indikationsbereichen, insbesondere bei niedrigen Aufwandmengen und -konzentrationen, nicht immer voll befriedigend. Außerdem zeigen sie eine recht hohe Selektivität gegenüber bestimmten Arten von pilzlichen Schaderregern, wodurch eine breite Anwendung dieser Mittel stark eingeschränkt wird. Nachteilig ist weiterhin, daß die Pflanzenverträglichkeit dieser Verbindungen in vielen Fällen nicht ausreichend ist.However, the action of the compounds mentioned is not always completely satisfactory in certain indication areas, in particular at low application rates and concentrations. In addition, they show a rather high selectivity against certain types of fungal pathogens, which greatly limits the broad use of these agents. A further disadvantage is that the plant compatibility of these compounds is not sufficient in many cases.
Ziel der ErfindungObject of the invention
Ziel der Erfindung ist die Entwicklung von neuen Verbindungen mit verbesserter fungizider Wirksamkeit und zusätzlichen wachstumsregulierenden Eigenschaften, ein Verfahren zu deren Herstellung sowie die Verwendung solcher fungiziden Mittel in der Landwirtschaft und im Gartenbau.The aim of the invention is the development of new compounds with improved fungicidal activity and additional growth-regulating properties, a process for their preparation and the use of such fungicides in agriculture and horticulture.
Darlegung des Wesens der ErfindungExplanation of the essence of the invention
Der Erfindung liegt die Aufgabe zugrunde, neue N-Alkylpyrrolidinio-carbonsäureamid-Salz enthaltende fungizide Mittel mit guter Wirksamkeit und breitem Wirkungsspektrum sowie einer möglichst hohen Pflanzenverträglichkeit und zusätzlichen pflanzenwachstumsregulierenden Eigenschaften bereitzustellen.The invention has for its object to provide novel N-alkylpyrrolidinio-carboxamide salt-containing fungicidal compositions with good efficacy and broad spectrum of activity and the highest possible plant tolerance and additional plant growth-regulating properties.
Erfindungsgemäß werden fungizide Mittel mit zusätzlicher pflanzenwachstumsregulierender Wirkung vorgeschlagen, die dadurch gekennzeichnet sind, daß sie mindestens ein N-Alkylpyrrolidinio-carbonsäureamid-Salz der allgemeinen Formel I,According to the invention fungicidal agents are proposed with additional plant growth-regulating effect, which are characterized in that they contain at least one N-alkylpyrrolidinio-carboxamide salt of the general formula I,
(D(D
in welcherin which
R1 geradkettiges oder verzweigtes Alkyl mit 6 bis 20 C-Atomen,R 1 straight-chain or branched alkyl having 6 to 20 C atoms,
R2 geradkettigesoderverzweigtesAlkylenmiti bis6C-Atomen,R 2 straight-chain or branched alkylene with up to 6 C atoms,
R3 und R4 unabhängig voneinander gleich oder verschieden Wasserstoff, geradkettiges oder verzweigtes Alkyl mit 1 bis 20 C-Atomen, ein durch Hydroxy, Alkoxy mit 1 bis 4 C-Atomen, Cyano oder Dialkylamino mit 2 bis 16 C-Atomen, substituiertes geradkettiges oder verzweigtes Alkyl mit 1 bis 6 C-Atomen, ein gegebenenfalls durch Halogen substituiertes Alkenyl mit 3 bis 6 C-Atomen, Cycloalkyl mit 3 bis 7 C-Atomen, Aryl, welches einfach oder mehrfach, gleich oder verschieden durch geradkettiges oder verzweigtes Alkyl mit 1 bis 6 C-Atomen, Alkoxy mit 1 bis 4 C-Atomen, Aryl-nieder-alkyl mit 7 bis 12 C-Atomen, Cycloalkyl mit 3 bis 7 C-Atomen, Acyl mit 1 bis 4 C-Atomen, Alkoxyalkyl mit 1 bis 8 C-Atomen, Aryl, Halogen, Halogenalkyl mit 1 bis4 C-Atomen, Halogenalkoxy mit 1 bis 4 C-Atomen, Alkylthio mit 1 bis 4 C-Atomen, Halogenalkylthio mit 1 bis4C-Atomen, Nitro, Cyano, Thiocyanate, NHCOR', NHCONR'R", COOR', CONR'R", SO2R'und/oder SO2NR1R", wobei R'und R" unabhängig voneinander für Wasserstoff, geradkettiges oder verzweigtes Alkyl mit 1 bis 6 C-Atomen, Cycloalkyl mit 3 bis 7 C-Atomen, Aryl oder Aryl-nieder-alkyl mit 7 bis 12 C-Atomen steht, substituiert sein kann, Aryl-nieder-alkyl mit 7 bis 12 C-Atomen, welches einfach oder mehrfach, gleich oder verschieden durch geradkettiges oder verzweigtes Alkyl mit 1 bis 6 C-Atomen, Alkoxy mit 1 bis 4 C-Atomen, Acyl mit 1 bis 4 C-Atomen, Halogen, Halogenalkyl mit 1 bis 4 C-Atomen, Nitro und/oder Cyano substituiert sein kann,R 3 and R 4 independently of one another are identical or different hydrogen, straight-chain or branched alkyl having 1 to 20 C atoms, a straight-chain radical substituted by hydroxyl, alkoxy having 1 to 4 C atoms, cyano or dialkylamino having 2 to 16 C atoms or branched alkyl having 1 to 6 carbon atoms, an optionally halogen-substituted alkenyl having 3 to 6 carbon atoms, cycloalkyl having 3 to 7 carbon atoms, aryl which is mono- or polysubstituted by identical or different straight-chain or branched alkyl 1 to 6 C atoms, alkoxy having 1 to 4 C atoms, aryl lower alkyl having 7 to 12 C atoms, cycloalkyl having 3 to 7 C atoms, acyl having 1 to 4 C atoms, alkoxyalkyl with 1 to 8 C atoms, aryl, halogen, halogenoalkyl having 1 to 4 C atoms, halogenoalkoxy having 1 to 4 C atoms, alkylthio having 1 to 4 C atoms, halogenoalkylthio having 1 to 4 C atoms, nitro, cyano, thiocyanates, NHCOR ', NHCONR'R ", COOR', CONR'R", SO 2 R 'and / or SO 2 NR 1 R ", where R' and R" independently represent water toff, straight-chain or branched alkyl having 1 to 6 C atoms, cycloalkyl having 3 to 7 C atoms, aryl or aryl-lower-alkyl having 7 to 12 C atoms, may be substituted aryl-lower-alkyl with 7 to 12 C atoms, which are monosubstituted or polysubstituted, identically or differently, by straight-chain or branched alkyl having 1 to 6 C atoms, alkoxy having 1 to 4 C atoms, acyl having 1 to 4 C atoms, halogen, haloalkyl having 1 up to 4 C atoms, nitro and / or cyano can be substituted,
R3 und R4 zusammen mit dem Stickstoffatom einen gegebenenfalls ein-oder zweifach durch Alkyl mit 1 bis 4 C-Atomen und/oder Halogen substituierten fünf-oder sechsgliedrigen heterocyclischen Ring darstellt, der gegebenenfalls noch ein oder zwei weitere Heteroatome enthält, undR 3 and R 4 together with the nitrogen atom represents a five- or six-membered heterocyclic ring which is optionally mono- or disubstituted by alkyl having 1 to 4 C atoms and / or halogen and optionally also contains one or two further heteroatoms, and
X" das Anion einer nicht phytotoxischen Säure bedeuten, neben den üblichen Lösungsmitteln, Trägerstoffen und/oder Formulierungshilfsstoffen enthalten.X "mean the anion of a non-phytotoxic acid, in addition to the usual solvents, carriers and / or formulation excipients included.
Überraschenderweise wurde gefunden, daß die erfindungsgemäßen N-Alkylpyrrolidinio-carbonsäureamid-Salze der allgemeinen Formel I eine starke fungizide Wirksamkeit und ein breites Wirkungsspektrum besitzen und sich insbesondere zur Bekämpfung von phytopathogenen Pilzen an Kulturpflanzen und pflanzlichen Vorratsgütern eignen.Surprisingly, it has been found that the N-alkylpyrrolidinio-carboxamide salts of the general formula I according to the invention have a strong fungicidal activity and a broad activity spectrum and are particularly suitable for controlling phytopathogenic fungi on crop plants and vegetable stocks.
Die Wirkstoffe zeigen eine gute Pflanzenverträglichkeit bei den zur Bekämpfung von Pflanzenkrankheiten erforderlichen Aufwandmengen. Zusätzlich können die erfindungsgemäßen Verbindungen mit ihren wachstumsregulierenden Eigenschaften Kulturpflanzen in gewünschter Weise positiv beeinflussen.The active compounds show good plant compatibility in the amounts required for controlling plant diseases. In addition, the compounds according to the invention, with their growth-regulating properties, can positively influence crop plants in the desired manner.
N-Alkyl-cycloammonio-carbonsäureamid-Salze anderer Ringgröße, deren Ringe auch substituiert sein können, besitzen ähnliche fungizide und wachstumsregulierende Eigenschaften wie die erfindungsgemäßen Wirkstoffe.N-alkyl-cycloammonio-carboxamide salts of other ring size, whose rings may also be substituted, have similar fungicidal and growth-regulating properties as the active compounds according to the invention.
Weiterhin wurde gefunden, daß die N-Alkylpyrrolidinio-carbonsäureamid-Salze der allgemeinen Formel I erhalten werden, indem man ein N-Alkylpyrrolidin der Formel IlFurthermore, it has been found that the N-alkylpyrrolidinio-carboxamide salts of the general formula I are obtained by reacting an N-alkylpyrrolidine of the formula II
о-о-
(II)(II)
worin R1 die in der allgemeinen Formel I angegebene Bedeutung besitzt, mit einer Verbindung der Formel III,wherein R 1 has the meaning given in the general formula I, with a compound of formula III,
R3 R 3
X - R2 - CO - N^ (|||) X - R 2 - CO - N ^ (|||)
R4 R 4
worin R2, R3, R* die in der allgemeinen Formel I angegebene Bedeutung besitzen und X für Halogen steht, umsetztwherein R 2 , R 3 , R * have the meaning given in the general formula I and X is halogen reacted
oder alternativ ein Pyrrolidino-carbonsäureamid der Formel IV,or alternatively a pyrrolidino-carboxamide of the formula IV,
N-R-CO-NN-R-CO-N
(IV)(IV)
worin R2, R3 und R4 die in der allgemeinen Formel I angegebene Bedeutung besitzen, mit einer Verbindung der Formel V,in which R 2 , R 3 and R 4 have the meaning given in the general formula I, with a compound of the formula V,
R'-X (V)R'-X (V)
worin R1 die in der allgemeinen Formel I angegebene Bedeutung besitzt und X für Halogen steht, umsetzt.wherein R 1 has the meaning given in the general formula I and X is halogen reacted.
N-Alkylpyrrolidine der Formel Il sind z.B. n-Octyl-, n-Dodecyl-, n-Tridecyl-, iso-Tridecyl-, Pentadecyl- oder n-Didecylpyrrolidin. Halogencarbonsäureamide der Formel III sind beispielsweise Chloracetamid, Chloressigsäure-N-Ci-CM-alkylamid, -N-2-cyanoethylamid, -Ν,Ν-diethylamid, -N,N-Bis-(2-cyanoethyl)-amid, -N-cyclohexylamid, -anilid, -4-chloranilid, -3,5-dichloranilid, 3,5-dichlor-4-methoxy-anilid 1 H-1,2,4-triazol-1-y|-amid, 2-Brompropionsäure-3,5-dichlor-anilid, -2,6-dibrom-4-nitranilid, -N-methyl-2,6-dichlor-4-cyano-anilid oder ^,e-dibrom-^nitroanilid, -N-methyl^.fJ-dichloM-cyanoanilid oder -2,6-dibrom-4-thiocyanato-anilid.N-alkylpyrrolidines of the formula II are e.g. n-octyl, n-dodecyl, n-tridecyl, iso-tridecyl, pentadecyl or n-didecylpyrrolidine. Halogenocarboxamides of the formula III are, for example, chloroacetamide, chloroacetic acid-N-C 1 -C 4 -alkylamide, -N-2-cyanoethylamide, -Ν, Ν-diethylamide, -N, N-bis (2-cyanoethyl) -amide, -N- cyclohexylamide, anilide, 4-chloroanilide, 3,5-dichloroanilide, 3,5-dichloro-4-methoxy-anilide 1 H-1,2,4-triazol-1-yl-amide, 2-bromopropionic acid 3,5-dichloroanilide, -2,6-dibromo-4-nitranilide, -N-methyl-2,6-dichloro-4-cyanoanilide or ^, e-dibromo-nitroanilide, -N-methyl ^ .fJ-dichloM-cyanoanilide or -2,6-dibromo-4-thiocyanato-anilide.
Pyrrolidino-carbonsäureamide der Formel IV sind z. B. Pyrrolidino-essigsäureamid, -essigsäure-N-C^Cao-alkylamid, -essigsäure-bis-(2-cyanoethyl)-amid, -essigsäure-N-cyclohexylamid, -essigsäure-anilid, -essigsäure-4-chloranilid, -essigsäure-S^-dichloranilid^essigsäure-S.S-dichloM-methoxyanilid.^-propionsäure-S^-dichloranilid,-г-ргоріопваиге-г.б-аіЬгот-А-nitroanilid, ^-propionsäure^e-dibrom^-thiocyanatooder^-propionsäure-N-methyl^.e-dichloM-cyanoanilid. Alkylhalogenide der Formel V sind beispielsweise n-Octylchlorid, n-Dodecylchlorid, n-Tridecylchlorid, iso-Tridecylchlorid, 1,5,9-Trimethyldecylchlorid, Pentadecyl brom id oder Didecylbromid.Pyrrolidino-carboxamides of the formula IV are z. B. Pyrrolidinoacetic acid amide, acetic acid NC ^ Caoalkylamide, acetic acid bis (2-cyanoethyl) amide, acetic acid N-cyclohexylamide, acetic acid anilide, acetic acid 4-chloroanilide, acetic acid S ^ -dichloroanilide-acetic acid-SS-dichloro-methoxyanilide. ^ -Propionic acid-S, -dichloroanilide, -g-ргоріопваиге-г.б-агЬто-А-nitroanilide,--propionic acid,--dibromo-thiocyanato or--propionic acid -N-methyl ^ .e dichloM-cyanoanilid. Alkyl halides of the formula V are, for example, n-octyl chloride, n-dodecyl chloride, n-tridecyl chloride, isotridecyl chloride, 1,5,9-trimethyldecyl chloride, pentadecyl bromide or didecyl bromide.
Die Umsetzung zu den erfindungsgemäßen Verbindungen der Formel I werden gegebenenfalls in Gegenwart eines Lösungsoder Verdünnungsmittels bei einer Temperatur im Bereich zwischen 10 und 1800C, vorzugsweise zwischen 30 und 15O0C, durchgeführt. Die Ausgangsstoffe der Formel Il bzw. der Formel IV werden in stöchiometrischen Mengen mit einer Verbindung der Formel III bzw. der Formel V oder bevorzugt mit einem Überschuß von 10 bis 100% an einer Verbindung der Formel III bzw. der Formel V über die stöchiometrische Menge hinaus, bezogen auf die Ausgangsstoffe der Formel Il bzw. der Formel IV, umgesetzt.The conversion to the novel compounds of formula I are optionally carried out in the presence of a solvent or diluent at a temperature in the range between 10 and 180 0 C, preferably between 30 and 15O 0 C. The starting materials of the formula II or of the formula IV are used in stoichiometric amounts with a compound of the formula III or of the formula V or preferably with an excess of 10 to 100% of a compound of the formula III or of the formula V over the stoichiometric amount also, based on the starting materials of the formula II or the formula IV, implemented.
Als bevorzugte Lösungs- oder Verdünnungsmittel können beispielsweise aliphatische oder aromatische, gegebenenfalls halogenierte Kohlenwasserstoffe, wie n-Pentan, Cyclohexan, Benzen, Toluen, Chlorbenzen, Chloroform oder Methylenchlorid; aliphatische Ketone, wie Aceton, Methylethylketon oder Cyclohexanon; Ether, wie Diethylether, Tetrahydrofuran oder Dioxan; Alkohole, wie Methanol, Ethanol, Propanole, Butanole oder Hexanole; Nitrile, wie Acetonitril; Ester, wie Essigsäuremethylester; Amide, wie Dimethylformamid, Dimethylacetamid oder N-Methyl-pyrrolidon; Dimethylsulfoxid oder Wasser oder Gemische dieser Lösungsmittel verwendet werden.As preferred solvents or diluents, for example, aliphatic or aromatic, optionally halogenated hydrocarbons, such as n-pentane, cyclohexane, benzene, toluene, chlorobenzene, chloroform or methylene chloride; aliphatic ketones, such as acetone, methyl ethyl ketone or cyclohexanone; Ethers, such as diethyl ether, tetrahydrofuran or dioxane; Alcohols, such as methanol, ethanol, propanols, butanols or hexanols; Nitriles, such as acetonitrile; Esters, such as methyl acetate; Amides, such as dimethylformamide, dimethylacetamide or N-methyl-pyrrolidone; Dimethyl sulfoxide or water or mixtures of these solvents can be used.
Die Isolierung der erfindungsgemäßen Verbindungen der allgemeinen Formel I aus den Reaktionsgemischen ist nicht unbedingt erforderlich, da sie auch ohne weitere Reinigungsoperation zur Herstellung fungizider Zubereitungen einsetzbar sind. Die Ausgangsverbindungen zur Herstellung der erfindungsgemäßen Verbindungen sind an sich bekannt oder können nach bekannten Verfahren hergestellt werden.The isolation of the compounds of the general formula I according to the invention from the reaction mixtures is not absolutely necessary since they can also be used without further purification to prepare fungicidal preparations. The starting compounds for the preparation of the compounds according to the invention are known per se or can be prepared by known processes.
Die erfindungsgemäßen Wirkstoffe der allgemeinen Formel I besitzen eine starke Wirksamkeit gegen Mikroorganismen und können dementsprechend zur Bekämpfung von pilzlichen Schaderregern in der Landwirtschaft und im Gartenbau Verwendung finden. Mit den Wirkstoffen können an Pflanzen oder Pflanzenteilen auftretende unerwünschte Pilze bekämpft werden. Die Wirkstoffe der allgemeinen Forme) I eignen sich ferner als Beizmittel гиг Behandlung von Saatgut und PflanzensteckHngen zum Schutz vor Pilzinfektionen und können gegen im Erdboden auftretende phytopathogene Pilze eingesetzt werden. Zusätzlich beeinflussen die Wirkstoffe bei ihrer Anwendung die Wachstumsprozesse von Kulturpflanzen in positiver Weise.The active compounds of the general formula I according to the invention have a strong activity against microorganisms and can accordingly be used for combating fungal pathogens in agriculture and horticulture. With the active substances occurring on plants or parts of plants undesirable fungi can be combated. The active compounds of the general formula (I) are also suitable as mordants for treating seed and plant patches for protection against fungal infections and can be used against phytopathogenic fungi occurring in the soil. In addition, the active ingredients in their application influence the growth processes of crops in a positive way.
Die erfindungsgemäßen Wirkstoffe eignen sich besonders zur Verhütung und Heilung von Pflanzenkrankheiten, die durch Pilze verursacht werden, wiez. B. Erysiphe graminis (Getreidemehltau), Erysiphe cichoracearum (Gurkenmehltau), Erysiphe polygoni (Bohnenmehltau), Podosphaera leucotricha (Apfelmehltau), Sphaerotheca pannosa (Rosenmehltau), Uncinula necator (Rebenmehltau); Rostkrankheiten, wie solche der Gattungen Puccinia,Uromyces oder Hemileia, insbesondere Puccinia graminis (Getreideschwarzrost), Puccinia coronata (Haferkronenrost), Puccinia sorghi (Maisrost), Puccinia recondita (Getreidebraunrost), Uromyces fabae (Buschbohnenrost), Hemileia vastatrix (Kaffeerost); Botrytis cinerea an Reben und Erdbeeren; Monilia fructigena an Äpfeln; Plasmopara viticola an Reben; Mycosphaerella musicola an Bananen; Corticum salmonicolor an Hevea; Ganoderma pseudoferreum an Hevea; Exobasidium vexans an Tee; Phytophthora infestans an Kartoffeln und Tomaten; Alternaria solani an Tomaten. Ferner sind verschiedene dieser Wirkstoffe auch unterschiedlich wirksam gegen phytopathogen Pilze, wie z. B. Ustilago avenae (Flugbrand), Ophiobolus graminis (Getreidefußkrankheiten), Septoria nodorum (Getreideblatt- und Spelzenbräune), Venturia inaequalis (Apfelschorf) sowie weitere pilzliche Krankheitserreger, wie Rhizoctonia, Tilletia, Helminthosporium, Peronospora, Pythium, Alternaria, Mucor, Sclerotinia, Fusarium, Pseudocercosporella und Cladosporium. Besonders interessant sind die erfindungsgemäßen Wirkstoffe für die Bekämpfung einer Vielzahl von Pilzkrankheiten an verschiedenen Kulturpflanzen oder ihren Samen, insbesondere Weizen, Roggen, Gerste, Hafer, Reis, Mais, Baumwolle, Soja, Kaffee, Bananen, Zuckerrohr, Obst, Zierpflanzen im Gartenbau, Gemüse, wie Gurken, Bohnen oder Kürbisgewächse. Zusätzlich können die erfindungsgemäßen Wirkstoffe mit ihren pflanzenwachstumsregulierenden Eigenschaften die Entwicklung von Kulturpflanzen in gewünschter Weise positiv beeinflussen. Die Wirkungen der Verbindungen sind im wesentlichen von dem Zeitpunkt der Anwendung, bezogen auf das Entwicklungsstadium des Samens oder der Pflanzen, von cion auf die Pflanzen oder ihre Umgebung ausgebrachten Wirkstoffmengen und von der Art der Applikation abhängig. Weiterhin erbringen die Wirkstoffe auch eine gute Wirksamkeit gegen holzverfärbende und holzzerstörende Pilze, wie z. B. Pullaria pullulans, Aspergillus niger, Polystictus versicolor oder Chaetomium globosum.The active compounds according to the invention are particularly suitable for the prevention and cure of plant diseases caused by fungi, such as. B. Erysiphe graminis (powdery mildew), Erysiphe cichoracearum (cucumber powdery mildew), Erysiphe polygoni (bean powdery mildew), Podosphaera leucotricha (apple powdery mildew), Sphaerotheca pannosa (rose mildew), Uncinula necator (vineyard mildew); Rust diseases, such as those of the genera Puccinia, Uromyces or Hemileia, in particular Puccinia graminis (cereal rust rust), Puccinia coronata (oat crown rust), Puccinia sorghi (corn rust), Puccinia recondita (cereal rust), Uromyces fabae (bush bean rust), Hemileia vastatrix (coffee rust); Botrytis cinerea on vines and strawberries; Monilia fructigena on apples; Plasmopara viticola on vines; Mycosphaerella musicola on bananas; Corticum salmonicolor on Hevea; Ganoderma pseudoferreum on Hevea; Exobasidium vexans to tea; Phytophthora infestans on potatoes and tomatoes; Alternaria solani on tomatoes. Furthermore, various of these agents are also different effective against phytopathogenic fungi, such. B. Ustilago avenae (flare), Ophiobolus graminis (cereal foot diseases), Septoria nodorum (cereal and fennel tan), Venturia inaequalis (apple scab) and other fungal pathogens, such as Rhizoctonia, Tilletia, Helminthosporium, Peronospora, Pythium, Alternaria, Mucor, Sclerotinia, Fusarium, Pseudocercosporella and Cladosporium. Particularly interesting are the active compounds according to the invention for combating a variety of fungal diseases on various crops or their seeds, especially wheat, rye, barley, oats, rice, corn, cotton, soybeans, coffee, bananas, sugarcane, fruit, ornamentals in horticulture, vegetables like cucumbers, beans or cucurbits. In addition, the active compounds according to the invention, with their plant growth-regulating properties, can positively influence the development of crop plants in the desired manner. The effects of the compounds are essentially dependent on the time of application, based on the stage of development of the seed or plants, of cion applied to the plants or their environment, and the mode of administration. Furthermore, the active ingredients also provide good activity against wood-discoloring and wood-destroying fungi, such. Pullaria pullulans, Aspergillus niger, Polystictus versicolor or Chaetomium globosum.
Ferner zeigen die erfindungsgemäßen Wirkstoffe der allgemeinen Formel I eine gute Aktivität gegen Schimmelpilze, wie z. B. Penicillium-, Fusarium- oder Aspergillus-Arten, die einen Verderb von hochfeuchtigkeitshaltigen landwirtschaftlichen Produkten oder Verarbeitungsprodukten landwirtschaftlicher Erzeugnisse während der Lagerung oder Zwischenlagerung verursachen. Derartig zu behandelnde Produkte umfassen z.B. Äpfel, Apfelsinen, Mandarinen, Zitronen, Pampelmusen, Erdnüsse, Getreide und Getreideprodukte oder Hülsenfrüchte und -schrot.Furthermore, the active compounds of the general formula I according to the invention show a good activity against molds, such. Penicillium, Fusarium or Aspergillus species causing spoilage of high moisture agricultural products or processed agricultural products during storage or intermediate storage. Such products to be treated include e.g. Apples, oranges, mandarins, lemons, grapefruits, peanuts, cereals and cereal products or pulses and meal.
Die erfindungsgemäßen Wirkstoffe sind neben ihrem breiten fungiziden Wirkungsspektrum auch unterschiedlich gegen phytopathogene Bakterien, wie beispielsweise Xanthomonas- oder Erwinia-Arten, wirksam.The active compounds according to the invention, in addition to their broad spectrum of fungicidal activity, are also effective against phytopathogenic bacteria, such as, for example, Xanthomonas or Erwinia species.
Einige der Wirkstoffe zeigen auch eine Wirkung gegen humanpathogene Pilze, wie z. B. Trichophyten- und Candida-Arten. Ein Teil der Wirkstoffe der allgemeinen Formel I zeichnet sich neben der protektiven Wirkung durch eine systematische Wirkungsentfaltung aus. So werden sie sowohl über die Wurzel als auch über die Blätter aufgenommen und im Pflanzengewebe transportiert oder über das Saatgut den oberirdischen Teilen der Pflanze zugeführt.Some of the active ingredients also show an action against human pathogenic fungi, such. B. Trichophyten and Candida species. A part of the active compounds of the general formula I is distinguished not only by the protective action but also by a systematic development of activity. Thus, they are absorbed both via the root and the leaves and transported in the plant tissue or fed via the seed to the aerial parts of the plant.
Die erfindungsgemäßen Wirkstoffe sind ferner geeignet zur Bekämpfung resistenter Stämme pilzlicher Schaderreger, die gegen bekannte fungizide Wirkstoffe, wie z. B. Wirkstoffe aus der Gruppe der Dicarboximid-Fungizide, wie beispielsweise 5-Methyl-5-vinyl-S-O^-dichlorphenyD^^-dioxo-i^-oxazolidinlVinclozolinJoderS-Methyl-S-methoxymethyl-S-O^-dichlorphenyD-I.S-oxazolidin-2,4-dion (Myclozolin); Wirkstoffe aus der Gruppe der Benzimidazol- oder Thiophanat-Fungizide, wie beispielsweise i-in-ButylcarbamoyD-benzimidazol^-yl-carbaminsäuremethylesterfBenomyl), Benzimidazol-2-yl-carbaminsäuremethylester (Carbendazim) oder 1,2-Bis-(3-ethoxycarbonyl-2-thioureido)-benzen (Thiophanat); Wirkstoffe aus der Gruppe der Azol-Fungizide, wie beispielsweise 1-(4-Chlorphenoxy-3,3-dimethyl-1-(1 H-1,2,4-triazol-1-yl)-butan-2-on (Triadimefon) oder 1-/2'-(2",4"-Dichlorphenyl)-2'-(propenyloxy)-ethyl/-1,3-imidazol (Imazalil); Wirkstoffe aus der Gruppe der aromatischen Kohlenwasserstoffe enthaltenden Fungizide, wie beispielsweise 2,5-Dichlor-1,4-dimethoxy-benzen (Chloroneb) oder 2,6-Dichlor-4-nitro-anilin (Dichloran); Wirkstoffe aus der Gruppe der Acylalanin-Fungizide, wie beispielsweise DL-N-(2,6-dimethylphenyl)-N-(2'-methoxyacetyl)-alanin-methylester(Metalaxyl)oderDL-N-(2,6-dimethylphenyl)-N-(2-furoyl)-alaninmethylester(Furalaxyl) oder Wirkstoffe aus der Gruppe der Pyrimidin-Fungizide, wie beispielsweise 5-Butyl-2-dimethylamino-4-hydroxy-6-methyl-pyrimidin (Dimethirimol) oder 2-Chlorphenyl-4-chlorphenyl-pyrimidin-5-yl-methanol (Fenarimol), Resistenzerscheinungen zeigen.The active compounds according to the invention are also suitable for controlling resistant strains of fungal pathogens which are resistant to known fungicidal active compounds, such as. B. Active ingredients from the group of dicarboximide fungicides, such as 5-methyl-5-vinyl-SO ^ -DichlorphenyD ^^ - dioxo-i ^ -oxazolidinlVinclozolinJoderS-methyl-S-methoxymethyl-SO ^ -DichlorphenyD-IS-oxazolidin- 2,4-dione (myclozoline); Active substances from the group of the benzimidazole or thiophanate fungicides, such as, for example, i-in-butylcarbamoy-D-benzimidazole-1-methylcarboxylate fbenomyl), benzimidazol-2-yl-carbamic acid methyl ester (carbendazim) or 1,2-bis (3-ethoxycarbonyl) 2-thioureido) -benzene (thiophanate); Agents from the group of azole fungicides, such as 1- (4-chlorophenoxy-3,3-dimethyl-1- (1 H-1,2,4-triazol-1-yl) -butan-2-one (Triadimefon ) or 1/2 '- (2 ", 4" -dichlorophenyl) -2' - (propenyloxy) ethyl / -1,3-imidazole (imazalil); active compounds from the group of aromatic hydrocarbons containing fungicides, such as 2 , 5-dichloro-1,4-dimethoxybenzene (chloroneb) or 2,6-dichloro-4-nitroaniline (dichloran); acylalanine fungicide group active ingredients such as DL-N- (2,6 -dimethylphenyl) -N- (2'-methoxyacetyl) -alanine methyl ester (metalaxyl) or DL-N- (2,6-dimethylphenyl) -N- (2-furoyl) alanine methyl ester (Furalaxyl) or agents from the group of pyrimidine Fungicides, such as 5-butyl-2-dimethylamino-4-hydroxy-6-methyl-pyrimidine (dimethirimol) or 2-chlorophenyl-4-chlorophenyl-pyrimidin-5-yl-methanol (fenarimol) show resistance phenomena.
Die in der allgemeinen Formel I der erfindungsgemäßen Wirkstoffe aufgeführten Anionen X- sind für die fungizide Wirkung nicht ausschlaggebend.The anions X listed in the general formula I the novel active ingredients - are not decisive for the fungicidal action.
Die erfindungsgemäßen Wirkstoffe können in die üblichen Formulierungen überführt werden, wie Lösungen, Emulsionen, Spritzpulver, Suspensionen, Pulver, Stäubemittel, Schäume, Pasten, lösliche Pulver, Granulate, mit Wirkstoff imprägnierte Natur- und synthetische Stoffe, Feinstverkapselungen in polymeren Stoffen und in Hüllmassen für Saatgut sowie ULV-KaIt- und Warmnebel-Formulierungen.The active compounds according to the invention can be converted into the customary formulations, such as solutions, emulsions, wettable powders, suspensions, powders, dusts, foams, pastes, soluble powders, granules, natural and synthetic substances impregnated with active substance, very fine encapsulations in polymeric substances and in encapsulants Seeds and ULV KaIt and warm mist formulations.
Die Herstellung dieser Formulierungen kann in bekannter Weise erfolgen, z. B. durch Vermischen oder Vermählender erfindungsgemäßen Wirkstoffe der allgemeinen Formel I mit Lösungsmitteln und/oder Trägerstoffen, gegebenenfalls unter Verwendung von oberflächenaktiven Mitteln, wie Emulgiermitteln und/oder Dispergiermitteln.The preparation of these formulations can be carried out in a known manner, for. B. by mixing or Vermählender the active compounds of general formula I according to the invention with solvents and / or carriers, optionally with the use of surfactants, such as emulsifiers and / or dispersants.
Als flüssige Lösungsmittel können Aromaten, wie Toluen, Xylen oder Alkylnaphthalene; chlorierte Aromaten oder chlorierte aliphatische Kohlenwasserstoffe, wie Chlorbenzene, Chlorethylene oder Methylenchlorid; aliphatische Kohlenwasserstoffe, wie Cyclohexan oder Paraffine, z. B. Erdölfraktionen; Alkohole, wie Butanole oder Glykole sowie deren Ester und Ether; Ketone, wie Aceton, Methylethylketon, Methylisobutylketon oder Cyclohexanon; stark polare Lösungsmittel, wie Wasser, Dimethylformamid oder Dimethylsulfoxid verwendet werden. Ebenso können verflüssigte Lösungsmittel, die unter Normalbedingungen gasförmig sind, wie z. B. Aerosol-Treibgase, wie Halogenkohlenwasserstoffe, Propan, Butan, Stickstoff und Kohlendioxid, eingesetzt werden.As liquid solvents, aromatics such as toluene, xylene or alkylnaphthalenes; chlorinated aromatics or chlorinated aliphatic hydrocarbons, such as chlorobenzene, chloroethylene or methylene chloride; aliphatic hydrocarbons such as cyclohexane or paraffins, e.g. B. petroleum fractions; Alcohols, such as butanols or glycols, and their esters and ethers; Ketones, such as acetone, methyl ethyl ketone, methyl isobutyl ketone or cyclohexanone; strong polar solvents such as water, dimethylformamide or dimethyl sulfoxide can be used. Likewise, liquefied solvents which are gaseous under normal conditions, such as. As aerosol propellants, such as halogenated hydrocarbons, propane, butane, nitrogen and carbon dioxide, are used.
Als feste Trägerstoffe kommen z.B. natürliche Gesteinsmehle, wie Kaoline, Tonerden, Talkum, Kreide, Quarz, Montmorillonit oder Diatomeenerde und synthetische Gesteinsmehle, wie hochdisperse Kieselsäure, Aluminiumoxid und Silikate, in Frage. Als feste Trägerstoffe für Granulate können z. B. gebrochene und fraktionierte natürliche Gesteinsmehle, wie Calcit, Marmor, Bims, Dolomit sowie synthetische Granulate aus anorganischen oder organischen Mehlen, sowie Granulate aus organischen Materialien, wie Sägemehl, Cellulosepulver, Baumrinden- und Nußschalenmehl, verwendet werden.As solid carriers are e.g. ground natural minerals, such as kaolins, clays, talc, chalk, quartz, montmorillonite or diatomaceous earth, and ground synthetic minerals, such as finely divided silica, alumina and silicates. As solid carriers for granules z. B. crushed and fractionated natural minerals, such as calcite, marble, pumice, dolomite and synthetic granules of inorganic or organic meals, and granules of organic materials, such as sawdust, cellulose powder, tree bark and Nussschalenmehl be used.
sulfatierter Hexadecanole, Heptadecanole oder Octadecanole, Salze von sulfatierten Fettalkoholglykolethern,sulfated hexadecanols, heptadecanols or octadecanols, salts of sulfated fatty alcohol glycol ethers,
wie Gummiarabicum, Polyvinylalkohol und Polyvinylacetat, verwendet werden.such as gum arabic, polyvinyl alcohol and polyvinyl acetate.
erfindungsgemäßen Wirkstoffen der allgemeinen Formel I auf Pilze oder die vor Pilzbefall zu schützenden Gegenstände inwirksamer Menge einwirken läßt.active compounds of the general formula I according to the invention act on fungi or the objects to be protected against fungal attack in an effective amount.
werden.become.
3kg Wirkstoff pro Hektar.3kg of active ingredient per hectare.
vorzugsweise 0,01 bis 10 g, benötigt.preferably 0.01 to 10 g, needed.
landwirtschaftlicher Erzeugnisse betragen die benötigten Wirkstoffmengen 0,01 bis 100g je Kilogramm Behandlungsgut,vorzugsweise 0,1 bis 50g.agricultural products amount to the required amounts of active ingredient 0.01 to 100 g per kilogram of material to be treated, preferably 0.1 to 50g.
am Wirkungsort erforderlich.required at the place of action.
erfindungsgemäßen Verbindungen der allgemeinen Formel I belegen.prove compounds of general formula I according to the invention.
25,4g N-iso-Tridecyl-pyrrolidin und 9,4g Chloracetamid werden unter Zugabe einer katalytischer! Menge Natriumjodid in 100ml25.4 g of N-isotridecylpyrrolidine and 9.4 g of chloroacetamide are added with the addition of a catalytic! Amount of sodium iodide in 100ml
in wenig Aceton gelöst und mit η-Hexan bis zur vollständigen Abscheidung versetzt. Nach Einengen im Vakuum erhält man 28geines gelbbraunen Harzes (Verbindung Nr.7).dissolved in a little acetone and mixed with η-hexane until complete deposition. After concentration in vacuo to give 28geines yellow-brown resin (compound no.7).
25,4g N-iso-Tridecyl-pyrrolidin und 24g Chloressigsäure-3,5-dichloranilid werden in 100ml n-Butanol unter Zugabe einerkatalytischer) Menge Natriumjodid 24 Stunden zum Rückfluß erwärmt. Man kühlt ab und destilliert das Lösungsmittel im25.4 g of N-isotridecylpyrrolidine and 24 g of chloroacetic acid 3,5-dichloroanilide are refluxed in 100 ml of n-butanol with the addition of a catalytic amount of sodium iodide for 24 hours. It is cooled and the solvent is distilled in
versetzt. Die ölige Phase wird abgetrennt und im Vakuum von Lösungsmittelresten befreit. Man erhält 41 g eines gelbbraunenadded. The oily phase is separated and freed from solvent residues in vacuo. This gives 41 g of a tan
24g Pyrrolidino-essigsäure-4-chloranilid und 22g iso-Tridecyl-chlorid (Gemisch verschiedener C^-C^-Alkylchloride, das 60 bis70% n-Tridecylchlorid enthält) in 100ml n-Butanol werden 24 Stunden zum Rückfluß erhitzt. Nach dem Abkühlen wird das24 g of pyrrolidinoacetic acid 4-chloroanilide and 22 g of isotridecyl chloride (mixture of various C 1 -C 4 -alkyl chlorides containing 60 to 70% of n-tridecyl chloride) in 100 ml of n-butanol are heated to reflux for 24 hours. After cooling, the
η-Hexan versetzt. Die ölige Phase wird abgetrennt und im Vakuum von Lösungsmittelresten befreit. Man erhält 48g eineshellbraunen Harzes (Verbindung Nr.55).η-hexane added. The oily phase is separated and freed from solvent residues in vacuo. This gives 48 g of a light brown resin (compound no.55).
sich bekannten Verfahren hergestellt werden.known methods are produced.
IT— GO-NIT-GO-N
R4 R 4
Cl Cl Cl Cl Cl Cl Cl Cl Cl Cl Cl Cl Cl Cl Cl Cl Cl Br Br Br Br Br Cl Br Cl Cl Cl Cl Br ClCl Cl Cl Cl Cl Cl Cl Cl Cl Cl Cl Br Br Br Br Br Cl Br Cl Cl Cl Cl Br Cl
Cl ClCl Cl
Nr. R1 R2 R3 R4 XNo. R 1 R 2 R 3 R 4 X
7 3300,2 960,2930,2870,1700,15647 3300.2 960, 2930, 2870, 1700, 1564
12 3 350,3 200,2 960,2 930,2 850,1 670,1 560,1 470,1 38012 3 350.3 200.2 960.2 930.2 850.1 670.1 560.1 470.1 380
44 3 380,2 960,2 930,2 870,1 700,1 610,1 560,1 505,1 450,1 320,1 26044 3 380.2 960.2 930.2 870.1 700.1 610.1 560.1 505.1 450.1 320.1 260
55 3 370,2 955,2 930,2 870,1 700,1 615,1 560,1 500,1 465,1 310,1 255,1 100,83555 3 370.2 955.2 930.2 870.1 700.1 615.1 560.1 500.1 465.1 310.1 255.1 100.835
79 3 380,2 965,2 925,2 880,1 705,1 600,1 565,145079 3 380.2 965.2 925.2 880.1 705.1 600.1 565.1450
104 3 380,2 965,2 935,2 880,1 700,1 540,1 460,1 380104 3 380.2 965.2 935.2 880.1 700.1 540.1 460.1 380
Die erfindungsgemäßen Verbindungen der allgemeinen Formel I können beispielsweise in Form folgender Zubereitungen zur Anwendung kommen:The compounds of the general formula I according to the invention can be used, for example, in the form of the following preparations:
I. BeispielI. Example
Lösungskonzentrate: Man vermischt 80 Gewichtsteile der Verbindung 12 mit 20 Gewichtsteilen N-Methyl-2-pyrrolidon. Es wird eine Lösung erhalten, die zur Anwendung in Form kleinster Tropfen geeignet ist.Solution concentrates: 80 parts by weight of compound 12 are mixed with 20 parts by weight of N-methyl-2-pyrrolidone. A solution is obtained which is suitable for use in the form of very small drops.
II. BeispielII. Example
Emulgierbare Konzentrate: 25 Gewichtsteile der Verbindung 55 werden mit 2,5 Gewichtsteilen epoxydierten Pflanzenöles, 10 Gewichtsteilen eines Alkylarylsulfonat/Fettalkoholpolyglykolether-Gemisches, 5 Gewichtsteilen Dimethylformamid und 57,5 Gewichtsteilen Xylen vermischt. Aus diesem Konzentrat können durch Verdünnen mit Wasser Emulsionen jeder gewünschten Konzentration hergestellt werden.Emulsifiable concentrates: 25 parts by weight of compound 55 are mixed with 2.5 parts by weight of epoxidized vegetable oil, 10 parts by weight of an alkylarylsulfonate / fatty alcohol polyglycol ether mixture, 5 parts by weight of dimethylformamide and 57.5 parts by weight of xylene. From this concentrate emulsions of any desired concentration can be prepared by dilution with water.
III. BeispielIII. example
Spritzpuler: 40 Gewichtsteile der Verbindung 79 werden mit 5 Gewichtsteilen des Natrium-Salzes einer Ligninsulfonsäure aus einer Sulfitablauge, 1 Gewichtsteil Natrium-Salz der Di-iso-butylnaphthalen-sulfonsäure und 54 Gewichtsteilen Kieselsäuregel gut vermischt und in einer entsprechenden Mühle vermählen. Man erhält ein Spritzpulver, das mit Wasser zu Suspensionen jeder gewünschten Konzentration verdünnt werden kann.Spritzpuler: 40 parts by weight of compound 79 are mixed well with 5 parts by weight of the sodium salt of a lignosulfonic acid from a sulfite liquor, 1 part by weight of sodium salt of di-iso-butylnaphthalen-sulfonic acid and 54 parts by weight of silica gel and ground in an appropriate mill. A spray powder is obtained which can be diluted with water to give suspensions of any desired concentration.
IV. BeispielIV. Example
Stäubemittel: 5 Gewichtsteile der Verbindung 79 werden mit 95 Gewichtsteilen feinteiligen Kaolins innig vermischt und vermählen. Die Stäubemittel können in dieser Form zur Anwendung verstäubt werden.Dusts: 5 parts by weight of compound 79 are intimately mixed and ground with 95 parts by weight of finely divided kaolin. The dusts can be dusted in this form for use.
V.BeispielV.Beispiel
Granulate: 5 Gewichtsteile der Verbindung 44 werden mit 0,25 Gewichtsteilen Epichlorhydrin vermischt und mit 6 Gewichtsteilen Aceton gelöst. Danach werden 3,5 Gewichtsteile Polyethylenglykol und 0,25 Gewichtsteile Cetylpolyglykolether zugesetzt. Die so erhaltene Lösung wird auf Kaolin aufgesprüht. Anschließend wird das Aceton in Vakuum verdampft. Es wird ein Mikrogranulat erhalten, das in dieser Form zur Anwendung kommen kann.Granules: 5 parts by weight of compound 44 are mixed with 0.25 part by weight of epichlorohydrin and dissolved with 6 parts by weight of acetone. Thereafter, 3.5 parts by weight of polyethylene glycol and 0.25 parts by weight of cetyl polyglycol ether are added. The resulting solution is sprayed on kaolin. Subsequently, the acetone is evaporated in vacuo. It is obtained a micro-granules that can be used in this form.
Die nachfolgenden Beispiele sollen die Erfindung weiter erläutern, ohne sie jedoch einzuschränken, und die biologische Wirkung der Verbindungen der allgemeinen Formel I belegen:The following examples are intended to further illustrate the invention without, however, restricting it, and to demonstrate the biological activity of the compounds of general formula I:
Botrytis-Test (Botrytis cinerea/Ackerbohne [Vicia faba]-Blattfieder)Botrytis test (Botrytis cinerea / field bean [Vicia faba] leaffed)
Abgeschnittene Blattfeder von in Topfen angezogenen Ackerbohnenpflanzen (Vicia faba) der Sorte „Fribo" im Vierblattstadium werden kurzzeitig in Wirkstoffzubereitungen getaucht, die aus 1 Gewichtsteil Wirkstoff, 100 Gewichtsteilen Aceton und 0,25 Gewichtsteilen Alkylarylpolyglykolether hergestellt und mit Wasser auf die gewünschte Wirkstoff konzentration verdünnt werden. Nach Antrocknen des Spritzbelages werden die Blätter mit einer Konidiensuspension von Botrytis cinerea inokuliert, die durch Abschwemmen von 12 bis 16 Tage alten Pilzkulturen auf Malzagar-Nährmedium (2% Malz) gewonnen wird. Die Ackerbohne-Blattfieder werden in einer Inkubationskabine in Schalen bei einer Temperatur von 22°C und 90 bis 100% relativer Luftfeuchtigkeit gehalten.Cropped leaf spring of potted bean plants (Vicia faba) of the variety "Fribo" in the four-leaf stage are briefly dipped in active ingredient preparations, which are prepared from 1 part by weight of active ingredient, 100 parts by weight of acetone and 0.25 parts by weight of alkylaryl polyglycol ether and diluted with water to the desired active ingredient concentration After the spray coating has dried on, the leaves are inoculated with a conidia suspension of Botrytis cinerea, which is obtained by washing 12 to 16-day-old fungal cultures on malt agar nutritive medium (2% malt) in an incubation cabin in dishes Temperature of 22 ° C and maintained at 90 to 100% relative humidity.
Nach 2 Tagen wird der Botrytis-Befall der Ackerbohne-Blattfieder bestimmt. Die angegangenen Infektionen wurden ausgezählt und mit einem Faktor für die Infektionsstärke (Boniturskala von 1 = kein Befall, bis 5 = sehr starker Befall) multipliziert. Der daraus resultierende Wert wurde in % Infektionsangang angegeben und daraus in Relation zur unbehandelten Kontrolle der Wirkungsgrad berechnet.After 2 days, the Botrytis infestation of field bean leaflet is determined. The infections were counted and multiplied by a factor for the strength of infection (rating scale from 1 = no infestation, to 5 = very severe infestation). The resulting value was given in% Infektionsangang and calculated in relation to the untreated control of the efficiency.
Die Ergebnisse der Versuche zeigten, daß beispielsweise die Verbindungen Nr.44,55 und 104 bei Anwendung in einer Wirkstoff konzentration von 500 mg χ Γ1 eine bessere Wirkung (Wirkungsgrad von 90 bis 100%) als der bekannte Wirkstoff Dicloran (2,6-Dichlor-4-nitranilin) (Wirkungsgrad 65%) erreichen.The results of the experiments showed that, for example, the compounds Nos. 44.55 and 104 when used in an active compound concentration of 500 mg χ Γ 1 a better effect (efficiency of 90 to 100%) than the known active ingredient diclorane (2,6- Dichloro-4-nitraniline) (efficiency 65%) reach.
ausgelegten Blattscheiben gegossen werden. Nach 2 Stunden wird die überstehende Flüssigkeit abgegossen. Die Schalenwerden bei 15 bis 200C unter Belichtung aufbewahrt. Nach 3 bis 4 Tagen erfolgt die Auswertung durch Ermittlung des Anteilsnekrotischer Blattfläche je Blattscheibe. Aus der Testung einer Konzentrationsreihe wird die Infektionshemmung bestimmt.designed leaf discs are poured. After 2 hours, the supernatant liquid is poured off. The dishes are stored at 15 to 20 ° C under exposure. After 3 to 4 days, the evaluation is carried out by determining the proportion of necrotic leaf area per leaf disc. From the testing of a concentration series, the infection inhibition is determined.
5mg x Γ1 eine 90- bis 100%ige Wirkung erreichten.5mg x Γ 1 achieved a 90 to 100% effect.
werden mit Wirkstoffzubereitungen besprüht, die aus 1 Gewichtsteil Wirkstoff, 100 Gewichtsteilen Aceton und0,25 Gewichtsteilen Alkylarylpolyglykolether hergestellt und mit Wasser auf die gewünschte Wirkstoffkonzentration verdünntwerden.are sprayed with drug formulations prepared from 1 part by weight of active ingredient, 100 parts by weight of acetone and 0.25 parts by weight of alkylaryl polyglycol ether and diluted with water to the desired drug concentration.
unbehandelten Kontrollpflanzen Längenmessungen vorgenommen.untreated control plants length measurements made.
1 250mg χ Γ1 das Längenwachstum von Gurkenpflanzen um 5% hemmten.1 250mg χ Γ 1 inhibited the growth of cucumber plants by 5%.
Claims (3)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DD31121287A DD296819A5 (en) | 1987-12-24 | 1987-12-24 | FUNGICIDAL AGENT WITH ADDITIONAL PLANT GROWTH-REGULATORY EFFECT (I) |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DD31121287A DD296819A5 (en) | 1987-12-24 | 1987-12-24 | FUNGICIDAL AGENT WITH ADDITIONAL PLANT GROWTH-REGULATORY EFFECT (I) |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DD296819A5 true DD296819A5 (en) | 1991-12-19 |
Family
ID=5595695
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DD31121287A DD296819A5 (en) | 1987-12-24 | 1987-12-24 | FUNGICIDAL AGENT WITH ADDITIONAL PLANT GROWTH-REGULATORY EFFECT (I) |
Country Status (1)
| Country | Link |
|---|---|
| DD (1) | DD296819A5 (en) |
-
1987
- 1987-12-24 DD DD31121287A patent/DD296819A5/en unknown
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