DD236871A5 - Pflanzenschuetzende mittel - Google Patents

Pflanzenschuetzende mittel Download PDF

Info

Publication number: DD236871A5
Authority: DD; German Democratic Republic
Prior art keywords: alkyl; formula; alkoxy; substituted; ccl
Prior art date: 1984-09-11

Application number

DD85280484A

Other languages

German (de)

English (en)

Inventor

Guenther Heubach

Klaus Bauer

Hermann Bieringer

Original Assignee

Hoechst Ag,De

Priority date (The priority date 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 date listed.)

1984-09-11

Filing date

1985-09-10

Publication date

1986-06-25

1985-09-10 Application filed by Hoechst Ag,De filed Critical Hoechst Ag,De

1986-06-25 Publication of DD236871A5 publication Critical patent/DD236871A5/de

Links

239000011814 protection agent Substances 0.000 title abstract description 8
150000001875 compounds Chemical class 0.000 claims abstract description 59
-1 triazole compound Chemical class 0.000 claims abstract description 38
230000000694 effects Effects 0.000 claims abstract description 14
125000000217 alkyl group Chemical group 0.000 claims abstract description 11
125000003545 alkoxy group Chemical group 0.000 claims abstract description 10
229910052736 halogen Inorganic materials 0.000 claims abstract description 9
150000002367 halogens Chemical class 0.000 claims abstract description 9
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims abstract description 9
150000003839 salts Chemical class 0.000 claims abstract description 9
125000004414 alkyl thio group Chemical group 0.000 claims abstract description 8
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 8
244000038559 crop plants Species 0.000 claims abstract description 6
125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 6
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 6
231100000208 phytotoxic Toxicity 0.000 claims abstract description 6
230000000885 phytotoxic effect Effects 0.000 claims abstract description 6
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 5
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 3
125000003302 alkenyloxy group Chemical group 0.000 claims abstract 2
125000000000 cycloalkoxy group Chemical group 0.000 claims abstract 2
239000004009 herbicide Substances 0.000 claims description 34
230000002363 herbicidal effect Effects 0.000 claims description 26
239000000203 mixture Substances 0.000 claims description 22
239000000460 chlorine Substances 0.000 claims description 12
238000000034 method Methods 0.000 claims description 9
239000002253 acid Substances 0.000 claims description 8
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 6
150000002148 esters Chemical class 0.000 claims description 6
229910052801 chlorine Inorganic materials 0.000 claims description 4
229910052731 fluorine Inorganic materials 0.000 claims description 4
125000005843 halogen group Chemical group 0.000 claims description 4
229910052739 hydrogen Inorganic materials 0.000 claims description 4
239000001257 hydrogen Substances 0.000 claims description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 3
150000003558 thiocarbamic acid derivatives Chemical class 0.000 claims description 3
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 2
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 2
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 2
229910052794 bromium Inorganic materials 0.000 claims description 2
150000004657 carbamic acid derivatives Chemical class 0.000 claims description 2
239000011737 fluorine Substances 0.000 claims description 2
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims 1
KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims 1
GNVMUORYQLCPJZ-UHFFFAOYSA-M Thiocarbamate Chemical compound NC([S-])=O GNVMUORYQLCPJZ-UHFFFAOYSA-M 0.000 claims 1
125000004457 alkyl amino carbonyl group Chemical group 0.000 claims 1
125000001424 substituent group Chemical group 0.000 claims 1
239000004480 active ingredient Substances 0.000 abstract description 12
125000003342 alkenyl group Chemical group 0.000 abstract description 2
125000000753 cycloalkyl group Chemical group 0.000 abstract 2
125000000304 alkynyl group Chemical group 0.000 abstract 1
125000005133 alkynyloxy group Chemical group 0.000 abstract 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 50
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 45
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 39
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
241000196324 Embryophyta Species 0.000 description 15
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 14
239000013256 coordination polymer Substances 0.000 description 14
239000013078 crystal Substances 0.000 description 13
238000002360 preparation method Methods 0.000 description 12
239000002904 solvent Substances 0.000 description 12
238000003756 stirring Methods 0.000 description 12
238000006243 chemical reaction Methods 0.000 description 10
239000000243 solution Substances 0.000 description 10
238000001816 cooling Methods 0.000 description 8
239000006188 syrup Substances 0.000 description 8
235000020357 syrup Nutrition 0.000 description 8
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 7
238000009472 formulation Methods 0.000 description 7
238000010992 reflux Methods 0.000 description 7
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 6
102100026197 C-type lectin domain family 2 member D Human genes 0.000 description 6
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
101000912615 Homo sapiens C-type lectin domain family 2 member D Proteins 0.000 description 6
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 6
239000004495 emulsifiable concentrate Substances 0.000 description 6
239000010437 gem Substances 0.000 description 6
239000000126 substance Substances 0.000 description 6
244000098338 Triticum aestivum Species 0.000 description 5
229960000583 acetic acid Drugs 0.000 description 5
239000013543 active substance Substances 0.000 description 5
239000002585 base Substances 0.000 description 5
238000009835 boiling Methods 0.000 description 5
150000001732 carboxylic acid derivatives Chemical class 0.000 description 5
235000013339 cereals Nutrition 0.000 description 5
239000012141 concentrate Substances 0.000 description 5
235000008504 concentrate Nutrition 0.000 description 5
239000008187 granular material Substances 0.000 description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
150000002905 orthoesters Chemical class 0.000 description 5
229920000151 polyglycol Polymers 0.000 description 5
239000010695 polyglycol Substances 0.000 description 5
239000000843 powder Substances 0.000 description 5
229910052708 sodium Inorganic materials 0.000 description 5
239000011734 sodium Substances 0.000 description 5
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 5
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
PQKBPHSEKWERTG-UHFFFAOYSA-N Fenoxaprop ethyl Chemical compound C1=CC(OC(C)C(=O)OCC)=CC=C1OC1=NC2=CC=C(Cl)C=C2O1 PQKBPHSEKWERTG-UHFFFAOYSA-N 0.000 description 4
241000209219 Hordeum Species 0.000 description 4
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
235000021307 Triticum Nutrition 0.000 description 4
239000012043 crude product Substances 0.000 description 4
239000003995 emulsifying agent Substances 0.000 description 4
239000000839 emulsion Substances 0.000 description 4
LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 4
PVFOMCVHYWHZJE-UHFFFAOYSA-N trichloroacetyl chloride Chemical compound ClC(=O)C(Cl)(Cl)Cl PVFOMCVHYWHZJE-UHFFFAOYSA-N 0.000 description 4
239000008096 xylene Substances 0.000 description 4
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 3
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
235000007340 Hordeum vulgare Nutrition 0.000 description 3
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
241001148683 Zostera marina Species 0.000 description 3
150000008065 acid anhydrides Chemical class 0.000 description 3
239000000729 antidote Substances 0.000 description 3
239000012954 diazonium Substances 0.000 description 3
150000001989 diazonium salts Chemical class 0.000 description 3
235000014113 dietary fatty acids Nutrition 0.000 description 3
239000006185 dispersion Substances 0.000 description 3
150000002170 ethers Chemical class 0.000 description 3
239000000194 fatty acid Substances 0.000 description 3
229930195729 fatty acid Natural products 0.000 description 3
238000000227 grinding Methods 0.000 description 3
239000000463 material Substances 0.000 description 3
238000002156 mixing Methods 0.000 description 3
SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical class CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 3
238000001953 recrystallisation Methods 0.000 description 3
239000000725 suspension Substances 0.000 description 3
BVKZMZBRCLNUBT-UHFFFAOYSA-N 1-(2,4-dichlorophenyl)-5-methyl-1,2,4-triazole-3-carboxylic acid Chemical compound CC1=NC(C(O)=O)=NN1C1=CC=C(Cl)C=C1Cl BVKZMZBRCLNUBT-UHFFFAOYSA-N 0.000 description 2
CMJUNAQINNWKAU-KTKRTIGZSA-N 2-[[(z)-2-oxononadec-10-enyl]amino]ethanesulfonic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)CNCCS(O)(=O)=O CMJUNAQINNWKAU-KTKRTIGZSA-N 0.000 description 2
VIUDTWATMPPKEL-UHFFFAOYSA-N 3-(trifluoromethyl)aniline Chemical compound NC1=CC=CC(C(F)(F)F)=C1 VIUDTWATMPPKEL-UHFFFAOYSA-N 0.000 description 2
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
241000743985 Alopecurus Species 0.000 description 2
239000005995 Aluminium silicate Substances 0.000 description 2
235000007320 Avena fatua Nutrition 0.000 description 2
241000209764 Avena fatua Species 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
241000233866 Fungi Species 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 2
230000002378 acidificating effect Effects 0.000 description 2
229910052784 alkaline earth metal Inorganic materials 0.000 description 2
235000012211 aluminium silicate Nutrition 0.000 description 2
239000011230 binding agent Substances 0.000 description 2
SMLHHBQGIJMAIM-UHFFFAOYSA-N calcium;2-dodecylbenzenesulfonic acid Chemical compound [Ca].CCCCCCCCCCCCC1=CC=CC=C1S(O)(=O)=O SMLHHBQGIJMAIM-UHFFFAOYSA-N 0.000 description 2
239000004359 castor oil Substances 0.000 description 2
235000019438 castor oil Nutrition 0.000 description 2
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
238000001212 derivatisation Methods 0.000 description 2
239000002270 dispersing agent Substances 0.000 description 2
QUDVACRZWGPJNZ-UHFFFAOYSA-N ethyl 1-(2,4-dichlorophenyl)-5-methyl-1,2,4-triazole-3-carboxylate Chemical compound N1=C(C(=O)OCC)N=C(C)N1C1=CC=C(Cl)C=C1Cl QUDVACRZWGPJNZ-UHFFFAOYSA-N 0.000 description 2
150000002191 fatty alcohols Chemical class 0.000 description 2
239000003337 fertilizer Substances 0.000 description 2
ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 2
230000012010 growth Effects 0.000 description 2
239000004615 ingredient Substances 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
BACHBFVBHLGWSL-UHFFFAOYSA-N methyl 2-[4-(2,4-dichlorophenoxy)phenoxy]propanoate Chemical compound C1=CC(OC(C)C(=O)OC)=CC=C1OC1=CC=C(Cl)C=C1Cl BACHBFVBHLGWSL-UHFFFAOYSA-N 0.000 description 2
239000002480 mineral oil Substances 0.000 description 2
230000007935 neutral effect Effects 0.000 description 2
229920000847 nonoxynol Polymers 0.000 description 2
238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
239000003960 organic solvent Substances 0.000 description 2
239000000047 product Substances 0.000 description 2
BACHBFVBHLGWSL-JTQLQIEISA-N rac-diclofop methyl Natural products C1=CC(O[C@@H](C)C(=O)OC)=CC=C1OC1=CC=C(Cl)C=C1Cl BACHBFVBHLGWSL-JTQLQIEISA-N 0.000 description 2
150000003254 radicals Chemical class 0.000 description 2
239000011541 reaction mixture Substances 0.000 description 2
239000001632 sodium acetate Substances 0.000 description 2
235000017281 sodium acetate Nutrition 0.000 description 2
235000010288 sodium nitrite Nutrition 0.000 description 2
239000002689 soil Substances 0.000 description 2
239000007787 solid Substances 0.000 description 2
238000009331 sowing Methods 0.000 description 2
239000000454 talc Substances 0.000 description 2
229910052623 talc Inorganic materials 0.000 description 2
JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 2
231100000331 toxic Toxicity 0.000 description 2
230000002588 toxic effect Effects 0.000 description 2
PYOKUURKVVELLB-UHFFFAOYSA-N trimethyl orthoformate Chemical compound COC(OC)OC PYOKUURKVVELLB-UHFFFAOYSA-N 0.000 description 2
238000009736 wetting Methods 0.000 description 2
239000000080 wetting agent Substances 0.000 description 2
125000006526 (C1-C2) alkyl group Chemical group 0.000 description 1
125000006536 (C1-C2)alkoxy group Chemical group 0.000 description 1
125000006700 (C1-C6) alkylthio group Chemical group 0.000 description 1
125000006766 (C2-C6) alkynyloxy group Chemical group 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
XUJLWPFSUCHPQL-UHFFFAOYSA-N 11-methyldodecan-1-ol Chemical compound CC(C)CCCCCCCCCCO XUJLWPFSUCHPQL-UHFFFAOYSA-N 0.000 description 1
KQCMTOWTPBNWDB-UHFFFAOYSA-N 2,4-dichloroaniline Chemical compound NC1=CC=C(Cl)C=C1Cl KQCMTOWTPBNWDB-UHFFFAOYSA-N 0.000 description 1
DWDIDIITNMWCKN-UHFFFAOYSA-N 2-(N-ethoxy-C-propylcarbonimidoyl)-3-hydroxy-5-(2-phenylsulfanylpropyl)cyclohex-2-en-1-one Chemical compound C1C(=O)C(C(=NOCC)CCC)=C(O)CC1CC(C)SC1=CC=CC=C1 DWDIDIITNMWCKN-UHFFFAOYSA-N 0.000 description 1
OOLBCHYXZDXLDS-UHFFFAOYSA-N 2-[4-(2,4-dichlorophenoxy)phenoxy]propanoic acid Chemical compound C1=CC(OC(C)C(O)=O)=CC=C1OC1=CC=C(Cl)C=C1Cl OOLBCHYXZDXLDS-UHFFFAOYSA-N 0.000 description 1
JJKWHOSQTYYFAE-UHFFFAOYSA-N 2-methoxyacetyl chloride Chemical compound COCC(Cl)=O JJKWHOSQTYYFAE-UHFFFAOYSA-N 0.000 description 1
FOGYNLXERPKEGN-UHFFFAOYSA-N 3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfopropyl)phenoxy]propane-1-sulfonic acid Chemical compound COC1=CC=CC(CC(CS(O)(=O)=O)OC=2C(=CC(CCCS(O)(=O)=O)=CC=2)OC)=C1O FOGYNLXERPKEGN-UHFFFAOYSA-N 0.000 description 1
125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 1
QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 1
241000209761 Avena Species 0.000 description 1
235000007319 Avena orientalis Nutrition 0.000 description 1
241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 1
241001465180 Botrytis Species 0.000 description 1
BMTAFVWTTFSTOG-UHFFFAOYSA-N Butylate Chemical compound CCSC(=O)N(CC(C)C)CC(C)C BMTAFVWTTFSTOG-UHFFFAOYSA-N 0.000 description 1
125000004399 C1-C4 alkenyl group Chemical group 0.000 description 1
125000000882 C2-C6 alkenyl group Chemical group 0.000 description 1
229920000742 Cotton Polymers 0.000 description 1
241000221785 Erysiphales Species 0.000 description 1
244000068988 Glycine max Species 0.000 description 1
235000010469 Glycine max Nutrition 0.000 description 1
241000219146 Gossypium Species 0.000 description 1
239000005909 Kieselgur Substances 0.000 description 1
RJUFJBKOKNCXHH-UHFFFAOYSA-N Methyl propionate Chemical compound CCC(=O)OC RJUFJBKOKNCXHH-UHFFFAOYSA-N 0.000 description 1
101100420779 Mus musculus Scimp gene Proteins 0.000 description 1
241001291960 Myroides Species 0.000 description 1
240000007594 Oryza sativa Species 0.000 description 1
235000007164 Oryza sativa Nutrition 0.000 description 1
YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
RVGRUAULSDPKGF-UHFFFAOYSA-N Poloxamer Chemical compound C1CO1.CC1CO1 RVGRUAULSDPKGF-UHFFFAOYSA-N 0.000 description 1
229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
229920001214 Polysorbate 60 Polymers 0.000 description 1
239000004372 Polyvinyl alcohol Substances 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
241000221535 Pucciniales Species 0.000 description 1
240000000111 Saccharum officinarum Species 0.000 description 1
235000007201 Saccharum officinarum Nutrition 0.000 description 1
241000209056 Secale Species 0.000 description 1
235000007238 Secale cereale Nutrition 0.000 description 1
229920002125 Sokalan® Polymers 0.000 description 1
240000006394 Sorghum bicolor Species 0.000 description 1
235000011684 Sorghum saccharatum Nutrition 0.000 description 1
235000021536 Sugar beet Nutrition 0.000 description 1
241000317942 Venturia <ichneumonid wasp> Species 0.000 description 1
240000008042 Zea mays Species 0.000 description 1
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 1
235000002017 Zea mays subsp mays Nutrition 0.000 description 1
YQSGAPRTTCXZBP-UHFFFAOYSA-N [2-(1,3-benzothiazol-2-yloxy)phenyl] hydrogen carbonate Chemical compound OC(=O)OC1=CC=CC=C1OC1=NC2=CC=CC=C2S1 YQSGAPRTTCXZBP-UHFFFAOYSA-N 0.000 description 1
BKAOCUJXRWCECQ-UHFFFAOYSA-N [4-(trifluoromethyl)phenyl] 2-phenoxypent-2-eneperoxoate Chemical compound O(C1=CC=CC=C1)C(C(=O)OOC1=CC=C(C=C1)C(F)(F)F)=CCC BKAOCUJXRWCECQ-UHFFFAOYSA-N 0.000 description 1
238000005903 acid hydrolysis reaction Methods 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
230000000274 adsorptive effect Effects 0.000 description 1
239000003513 alkali Substances 0.000 description 1
238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
125000006193 alkinyl group Chemical group 0.000 description 1
125000002877 alkyl aryl group Chemical group 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
229910021529 ammonia Inorganic materials 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
229940075522 antidotes Drugs 0.000 description 1
239000000010 aprotic solvent Substances 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
239000003849 aromatic solvent Substances 0.000 description 1
239000000440 bentonite Substances 0.000 description 1
229910000278 bentonite Inorganic materials 0.000 description 1
SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
CIZVQWNPBGYCGK-UHFFFAOYSA-N benzenediazonium Chemical class N#[N+]C1=CC=CC=C1 CIZVQWNPBGYCGK-UHFFFAOYSA-N 0.000 description 1
VAIZTNZGPYBOGF-UHFFFAOYSA-N butyl 2-(4-{[5-(trifluoromethyl)pyridin-2-yl]oxy}phenoxy)propanoate Chemical compound C1=CC(OC(C)C(=O)OCCCC)=CC=C1OC1=CC=C(C(F)(F)F)C=N1 VAIZTNZGPYBOGF-UHFFFAOYSA-N 0.000 description 1
239000011575 calcium Substances 0.000 description 1
159000000007 calcium salts Chemical class 0.000 description 1
239000000969 carrier Substances 0.000 description 1
239000003054 catalyst Substances 0.000 description 1
238000012512 characterization method Methods 0.000 description 1
CSPPKDPQLUUTND-UHFFFAOYSA-N chembl3186232 Chemical compound CCON=C(CCC)C1=C(O)CC(CC(C)SCC)CC1=O CSPPKDPQLUUTND-UHFFFAOYSA-N 0.000 description 1
239000007795 chemical reaction product Substances 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
239000007859 condensation product Substances 0.000 description 1
230000001276 controlling effect Effects 0.000 description 1
235000005822 corn Nutrition 0.000 description 1
FBCCMZVIWNDFMO-UHFFFAOYSA-N dichloroacetyl chloride Chemical compound ClC(Cl)C(Cl)=O FBCCMZVIWNDFMO-UHFFFAOYSA-N 0.000 description 1
ISOLMABRZPQKOV-UHFFFAOYSA-N diethyl 2-acetamidopropanedioate Chemical compound CCOC(=O)C(NC(C)=O)C(=O)OCC ISOLMABRZPQKOV-UHFFFAOYSA-N 0.000 description 1
239000003085 diluting agent Substances 0.000 description 1
BADXJIPKFRBFOT-UHFFFAOYSA-N dimedone Chemical class CC1(C)CC(=O)CC(=O)C1 BADXJIPKFRBFOT-UHFFFAOYSA-N 0.000 description 1
239000000428 dust Substances 0.000 description 1
238000000921 elemental analysis Methods 0.000 description 1
230000001804 emulsifying effect Effects 0.000 description 1
HVCNNTAUBZIYCG-UHFFFAOYSA-N ethyl 2-[4-[(6-chloro-1,3-benzothiazol-2-yl)oxy]phenoxy]propanoate Chemical compound C1=CC(OC(C)C(=O)OCC)=CC=C1OC1=NC2=CC=C(Cl)C=C2S1 HVCNNTAUBZIYCG-UHFFFAOYSA-N 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
150000004665 fatty acids Chemical class 0.000 description 1
239000000945 filler Substances 0.000 description 1
238000011049 filling Methods 0.000 description 1
239000000706 filtrate Substances 0.000 description 1
230000000855 fungicidal effect Effects 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
208000037824 growth disorder Diseases 0.000 description 1
230000009036 growth inhibition Effects 0.000 description 1
238000003306 harvesting Methods 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
239000005457 ice water Substances 0.000 description 1
239000012442 inert solvent Substances 0.000 description 1
238000002347 injection Methods 0.000 description 1
239000007924 injection Substances 0.000 description 1
150000007529 inorganic bases Chemical class 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
239000000155 melt Substances 0.000 description 1
230000004060 metabolic process Effects 0.000 description 1
229910052751 metal Inorganic materials 0.000 description 1
239000002184 metal Substances 0.000 description 1
MFSWTRQUCLNFOM-UHFFFAOYSA-N methyl 2-(4-{[3-chloro-5-(trifluoromethyl)pyridin-2-yl]oxy}phenoxy)propanoate Chemical compound C1=CC(OC(C)C(=O)OC)=CC=C1OC1=NC=C(C(F)(F)F)C=C1Cl MFSWTRQUCLNFOM-UHFFFAOYSA-N 0.000 description 1
SWFHBCLLOXLJSC-UHFFFAOYSA-N methyl 5-(2-methylprop-1-enyl)-1-[3-(trifluoromethyl)phenyl]-1,2,4-triazole-3-carboxylate Chemical compound N1=C(C(=O)OC)N=C(C=C(C)C)N1C1=CC=CC(C(F)(F)F)=C1 SWFHBCLLOXLJSC-UHFFFAOYSA-N 0.000 description 1
229940017219 methyl propionate Drugs 0.000 description 1
235000010446 mineral oil Nutrition 0.000 description 1
229920002113 octoxynol Polymers 0.000 description 1
238000005580 one pot reaction Methods 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
239000008188 pellet Substances 0.000 description 1
230000000149 penetrating effect Effects 0.000 description 1
230000003032 phytopathogenic effect Effects 0.000 description 1
239000004584 polyacrylic acid Substances 0.000 description 1
229920001522 polyglycol ester Polymers 0.000 description 1
229920002451 polyvinyl alcohol Polymers 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
159000000001 potassium salts Chemical class 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
239000002243 precursor Substances 0.000 description 1
125000005554 pyridyloxy group Chemical group 0.000 description 1
239000010453 quartz Substances 0.000 description 1
230000001105 regulatory effect Effects 0.000 description 1
239000012262 resinous product Substances 0.000 description 1
235000009566 rice Nutrition 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
239000004576 sand Substances 0.000 description 1
229920005552 sodium lignosulfonate Polymers 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
238000005507 spraying Methods 0.000 description 1
239000012258 stirred mixture Substances 0.000 description 1
230000036435 stunted growth Effects 0.000 description 1
230000002459 sustained effect Effects 0.000 description 1
208000024891 symptom Diseases 0.000 description 1
LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 description 1
239000004563 wettable powder Substances 0.000 description 1

Classifications

- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/32—Ingredients for reducing the noxious effect of the active substances to organisms other than pests, e.g. toxicity reducing compositions, self-destructing compositions
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D249/00—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms
- C07D249/02—Heterocyclic compounds containing five-membered rings having three nitrogen atoms as the only ring hetero atoms not condensed with other rings
- C07D249/08—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles
- C07D249/10—1,2,4-Triazoles; Hydrogenated 1,2,4-triazoles 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/06—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing only aliphatic carbon atoms

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
General Health & Medical Sciences (AREA)
Health & Medical Sciences (AREA)
Pest Control & Pesticides (AREA)
Agronomy & Crop Science (AREA)
Plant Pathology (AREA)
Toxicology (AREA)
Engineering & Computer Science (AREA)
Dentistry (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Environmental Sciences (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)

DD85280484A 1984-09-11 1985-09-10 Pflanzenschuetzende mittel DD236871A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE3433249		1984-09-11

Publications (1)

Publication Number	Publication Date
DD236871A5 true DD236871A5 (de)	1986-06-25

Family

ID=6245074

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD85280484A DD236871A5 (de)	1984-09-11	1985-09-10	Pflanzenschuetzende mittel

Country Status (4)

Country	Link
DD (1)	DD236871A5 (fr)
LT (1)	LT3371B (fr)
MA (1)	MA20520A1 (fr)
ZA (1)	ZA856909B (fr)

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE1123321B (de)	1957-11-29	1962-02-08	Upjohn Company Eine Ges Nach D	Verfahren zur Herstellung von therapeutisch wirksamen Steroidverbindungen

1985
- 1985-09-09 MA MA20746A patent/MA20520A1/fr unknown
- 1985-09-10 DD DD85280484A patent/DD236871A5/de not_active IP Right Cessation
- 1985-09-10 ZA ZA856909A patent/ZA856909B/xx unknown
1993
- 1993-06-25 LT LTIP710A patent/LT3371B/lt not_active IP Right Cessation

Also Published As

Publication number	Publication date
LT3371B (en)	1995-08-25
ZA856909B (en)	1986-04-30
LTIP710A (en)	1995-01-31
MA20520A1 (fr)	1986-04-01

Legal Events

Date	Code	Title	Description
1997-05-22	ENJ	Ceased due to non-payment of renewal fee

Publication	Publication Date	Title
EP0174562B1 (fr)	1991-01-09	Agents pour la protection de plantes basés sur des dérivés de 1,2,4- briazole ainsi que dérivés 1,2,4-triazole
EP0269806B1 (fr)	1991-02-27	Dérivés d'acide phénylpyrazolcarbonique, leur préparation et leur utilisation comme agents régulateurs de croissance des plantes et antidote
DE3817192A1 (de)	1989-11-30	1,2,4-triazolderivate enthaltende pflanzenschuetzende mittel sowie neue derivate des 1,2,4-triazols
US4671818A (en)	1987-06-09	Compositions containing heterocyclic compounds and their use as herbicides
DE1695786A1 (de)	1971-04-29	Biocide Mittel
EP0030676A1 (fr)	1981-06-24	Dérivés d'acide phénoxybenzoique, procédé pour leur préparation et leur utilisation comme herbicides et comme agents de régulation de la croissance des plantes
EP0561845B1 (fr)	1995-03-08	4-oxo-4h-benzopyrannes pyrido-anneles, leur procede de fabrication et leur utilisation comme antidotes
EP0368212B1 (fr)	1995-09-20	Agents herbicides, contenant des dérivés des acides 2-(4-hétéroaryloxy)- ou 2-(4-aryloxy)-phénoxy-acétiques ou -propioniques et/ou des dérivés de la cyclohexénone comme matières actives et des dérivés du naphtalène comme antidotes
EP0310555B1 (fr)	1993-02-10	Dérivés de l'acide 1,5-diphényl-1,2,4-triazole-3 carboxylique pour la protection de plantes cultivées contre l'action phytotoxique d'herbicides
EP0014900B1 (fr)	1982-06-02	Esters carbonylalkyliques d'acides phénoxycarboxyliques, procédé pour leur préparation et leur utilisation comme herbicides ainsi comme défoliants et desséchants
EP0224823A2 (fr)	1987-06-10	Dérivés de la quinoléine et leur utilité pour contrôler la croissance non voulue des plantes
EP0379003B1 (fr)	1995-01-25	Dérivés de l'acide thiophène-2-carboxylique, procédé pour leur préparation et leur utilisation pour la lutte contre la croissance indésirable des plantes
EP0409118B1 (fr)	1994-10-12	Pyrazolines et leur application antidotique
EP0135838A2 (fr)	1985-04-03	3-Phényl-4-méthoxy carbonylepyrazoles, leur procédé de préparation et leur utilisation dans la lutte contre la croissance de plantes indésirables
EP0151744B1 (fr)	1989-04-26	1-Acylimidazolinones, procédé de leur préparation et leur application dans l'agriculture
EP0170906B1 (fr)	1990-03-07	Agents protecteurs des plantes basés sur les oxime-esters
DE3818848A1 (de)	1989-12-07	Pyridazinonderivate, verfahren zu ihrer herstellung, sie enthaltende mittel und ihre verwendung im pflanzenschutz
EP0254222B1 (fr)	1992-08-26	Composés quinoléinoxy, leur procédé de synthèse et leur utilisation comme antidotes
EP0170905B1 (fr)	1988-04-27	Esters d'acides alpha-acyloximino-alcanephosphoniques (et phosphiniques), leur préparation et leur utilisation dans la protection des plantes
EP0189800A2 (fr)	1986-08-06	Composés contenant des groupes thiocyanatomethylthio
EP0142757A2 (fr)	1985-05-29	Dérivés phénoxyalcanoyles, procédé de préparation et utilisation comme agent de protection des plantes
EP0153583A1 (fr)	1985-09-04	Isoindoles, procédés pour leur préparation et leur application en agriculture
EP0144749A2 (fr)	1985-06-19	Imidazolinones-2-aryl substitués, procédé de leur préparation et leur application dans la protection des plantes
DE2732924A1 (de)	1979-02-08	Herbizide mittel
LT3371B (en)	1995-08-25	Method of cultured plants protection from phytotoxic herbicide effect