DD260431A5 - Herbizide und pflanzenwuchsregulierende mittel - Google Patents

Herbizide und pflanzenwuchsregulierende mittel Download PDF

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Publication number: DD260431A5
Authority: DD; German Democratic Republic
Prior art keywords: hydrogen; phenyl; optionally; formula; methyl
Prior art date: 1986-02-04

Application number

DD87299667A

Other languages

German (de)

English (en)

Inventor

Reinhold Gehring

Otto Schallner

Joerg Stetter

Hans-Joachim Santel

Robert R Schmidt

Klaus Luerssen

Original Assignee

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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.)

1986-02-04

Filing date

1987-02-02

Publication date

1988-09-28

1987-02-02 Application filed by ��@��k�� filed Critical ��@��k��

1988-09-28 Publication of DD260431A5 publication Critical patent/DD260431A5/de

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239000003795 chemical substances by application Substances 0.000 title abstract description 16
239000004009 herbicide Substances 0.000 title abstract description 8
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 84
239000001257 hydrogen Substances 0.000 claims abstract description 84
125000000217 alkyl group Chemical group 0.000 claims abstract description 59
150000002431 hydrogen Chemical class 0.000 claims abstract description 53
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 50
ZVNYYNAAEVZNDW-UHFFFAOYSA-N 2-phenylpyrazol-3-amine Chemical class NC1=CC=NN1C1=CC=CC=C1 ZVNYYNAAEVZNDW-UHFFFAOYSA-N 0.000 claims abstract description 46
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 30
229910052736 halogen Inorganic materials 0.000 claims abstract description 28
150000002367 halogens Chemical class 0.000 claims abstract description 27
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 22
239000004480 active ingredient Substances 0.000 claims abstract description 12
125000000018 nitroso group Chemical group N(=O)* 0.000 claims abstract description 6
-1 phenoxy, phenylthio Chemical group 0.000 claims description 143
150000001875 compounds Chemical class 0.000 claims description 78
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 51
150000003254 radicals Chemical class 0.000 claims description 40
239000000460 chlorine Substances 0.000 claims description 31
239000000203 mixture Substances 0.000 claims description 31
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 29
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 29
125000001188 haloalkyl group Chemical group 0.000 claims description 28
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 24
229910052801 chlorine Inorganic materials 0.000 claims description 24
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 24
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 23
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 22
125000003545 alkoxy group Chemical group 0.000 claims description 22
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 22
229910052794 bromium Inorganic materials 0.000 claims description 22
UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims description 20
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 20
125000001424 substituent group Chemical group 0.000 claims description 18
125000005843 halogen group Chemical group 0.000 claims description 15
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 13
125000004663 dialkyl amino group Chemical group 0.000 claims description 13
125000004414 alkyl thio group Chemical group 0.000 claims description 12
150000003839 salts Chemical class 0.000 claims description 12
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 11
125000003282 alkyl amino group Chemical group 0.000 claims description 11
125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 11
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 11
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 11
229910052760 oxygen Inorganic materials 0.000 claims description 11
239000001301 oxygen Substances 0.000 claims description 11
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 11
125000003107 substituted aryl group Chemical group 0.000 claims description 11
229910052717 sulfur Chemical group 0.000 claims description 11
239000011593 sulfur Chemical group 0.000 claims description 11
125000003342 alkenyl group Chemical group 0.000 claims description 10
125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 10
125000000304 alkynyl group Chemical group 0.000 claims description 10
125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 claims description 10
125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 claims description 10
229910052731 fluorine Inorganic materials 0.000 claims description 10
239000011737 fluorine Substances 0.000 claims description 10
UCFFGYASXIPWPD-UHFFFAOYSA-N methyl hypochlorite Chemical compound COCl UCFFGYASXIPWPD-UHFFFAOYSA-N 0.000 claims description 10
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 9
125000004184 methoxymethyl group Chemical group [H]C([H])([H])OC([H])([H])* 0.000 claims description 9
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 9
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 8
125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 8
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 8
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 claims description 8
125000004369 butenyl group Chemical group C(=CCC)* 0.000 claims description 8
125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 8
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 8
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 8
125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 8
125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims description 8
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 8
125000004092 methylthiomethyl group Chemical group [H]C([H])([H])SC([H])([H])* 0.000 claims description 8
125000001769 aryl amino group Chemical group 0.000 claims description 7
125000005110 aryl thio group Chemical group 0.000 claims description 7
125000004104 aryloxy group Chemical group 0.000 claims description 7
125000005997 bromomethyl group Chemical group 0.000 claims description 7
125000006341 heptafluoro n-propyl group Chemical group FC(F)(F)C(F)(F)C(F)(F)* 0.000 claims description 7
ZEIYBPGWHWECHV-UHFFFAOYSA-N nitrosyl fluoride Chemical compound FN=O ZEIYBPGWHWECHV-UHFFFAOYSA-N 0.000 claims description 7
UFUASNAHBMBJIX-UHFFFAOYSA-N propan-1-one Chemical compound CC[C]=O UFUASNAHBMBJIX-UHFFFAOYSA-N 0.000 claims description 7
229910052708 sodium Inorganic materials 0.000 claims description 7
125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 7
125000006000 trichloroethyl group Chemical group 0.000 claims description 7
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 7
229920002554 vinyl polymer Polymers 0.000 claims description 7
125000001478 1-chloroethyl group Chemical group [H]C([H])([H])C([H])(Cl)* 0.000 claims description 6
125000005999 2-bromoethyl group Chemical group 0.000 claims description 6
125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 claims description 6
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 6
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 6
229910052700 potassium Inorganic materials 0.000 claims description 6
239000011734 sodium Substances 0.000 claims description 6
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 5
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 5
125000001309 chloro group Chemical group Cl* 0.000 claims description 5
239000010941 cobalt Substances 0.000 claims description 5
229910052802 copper Inorganic materials 0.000 claims description 5
239000010949 copper Substances 0.000 claims description 5
125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
239000011630 iodine Substances 0.000 claims description 5
229910052740 iodine Inorganic materials 0.000 claims description 5
229910052742 iron Inorganic materials 0.000 claims description 5
WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 claims description 5
125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
239000011591 potassium Substances 0.000 claims description 5
125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 claims description 5
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 4
239000004606 Fillers/Extenders Substances 0.000 claims description 4
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 4
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 4
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 4
125000004687 alkyl sulfinyl alkyl group Chemical group 0.000 claims description 4
229910052788 barium Inorganic materials 0.000 claims description 4
DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 claims description 4
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 4
239000011777 magnesium Substances 0.000 claims description 4
229910052749 magnesium Inorganic materials 0.000 claims description 4
239000011135 tin Substances 0.000 claims description 4
229910052718 tin Inorganic materials 0.000 claims description 4
229910052725 zinc Inorganic materials 0.000 claims description 4
239000011701 zinc Substances 0.000 claims description 4
KKZUMAMOMRDVKA-UHFFFAOYSA-N 2-chloropropane Chemical group [CH2]C(C)Cl KKZUMAMOMRDVKA-UHFFFAOYSA-N 0.000 claims description 3
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical class [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 3
VEQPNABPJHWNSG-UHFFFAOYSA-N Nickel(2+) Chemical compound [Ni+2] VEQPNABPJHWNSG-UHFFFAOYSA-N 0.000 claims description 3
229910052784 alkaline earth metal Inorganic materials 0.000 claims description 3
150000001342 alkaline earth metals Chemical class 0.000 claims description 3
125000004688 alkyl sulfonyl alkyl group Chemical group 0.000 claims description 3
239000011575 calcium Substances 0.000 claims description 3
229910052791 calcium Inorganic materials 0.000 claims description 3
150000001767 cationic compounds Chemical class 0.000 claims description 3
229910001429 cobalt ion Inorganic materials 0.000 claims description 3
229910001453 nickel ion Inorganic materials 0.000 claims description 3
150000002892 organic cations Chemical class 0.000 claims description 3
229910052723 transition metal Inorganic materials 0.000 claims description 3
125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims description 3
229910052783 alkali metal Inorganic materials 0.000 claims description 2
150000001340 alkali metals Chemical class 0.000 claims description 2
239000004094 surface-active agent Substances 0.000 claims description 2
125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims 1
KURZCZMGELAPSV-UHFFFAOYSA-N [Br].[I] Chemical compound [Br].[I] KURZCZMGELAPSV-UHFFFAOYSA-N 0.000 claims 1
229920001577 copolymer Chemical class 0.000 claims 1
229940037201 oris Drugs 0.000 claims 1
125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 claims 1
230000002363 herbicidal effect Effects 0.000 abstract description 11
230000008635 plant growth Effects 0.000 abstract description 2
230000001105 regulatory effect Effects 0.000 abstract description 2
238000000034 method Methods 0.000 description 99
238000006243 chemical reaction Methods 0.000 description 52
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 45
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 43
241000196324 Embryophyta Species 0.000 description 39
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 36
239000003085 diluting agent Substances 0.000 description 35
238000002360 preparation method Methods 0.000 description 34
239000007858 starting material Substances 0.000 description 31
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 29
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 28
235000019441 ethanol Nutrition 0.000 description 22
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 21
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 21
239000003054 catalyst Substances 0.000 description 20
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 19
239000002253 acid Substances 0.000 description 19
239000002904 solvent Substances 0.000 description 18
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 16
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 16
239000000243 solution Substances 0.000 description 16
WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 15
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 14
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 14
239000000126 substance Substances 0.000 description 14
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
239000007795 chemical reaction product Substances 0.000 description 12
238000002955 isolation Methods 0.000 description 11
238000002844 melting Methods 0.000 description 11
230000008018 melting Effects 0.000 description 11
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 10
239000011230 binding agent Substances 0.000 description 10
150000002148 esters Chemical class 0.000 description 10
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 9
239000002585 base Substances 0.000 description 9
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
239000003960 organic solvent Substances 0.000 description 9
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 8
150000001298 alcohols Chemical class 0.000 description 8
150000001412 amines Chemical class 0.000 description 8
239000003995 emulsifying agent Substances 0.000 description 8
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 8
238000010626 work up procedure Methods 0.000 description 8
UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 7
TVSDZBUZBHRNBV-UHFFFAOYSA-N [2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl]hydrazine Chemical compound NNC1=C(F)C(F)=C(C(F)(F)F)C(F)=C1F TVSDZBUZBHRNBV-UHFFFAOYSA-N 0.000 description 7
229960000583 acetic acid Drugs 0.000 description 7
238000009472 formulation Methods 0.000 description 7
XZWCWXWGNGYETN-UHFFFAOYSA-N 2-[2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl]pyrazol-3-amine Chemical compound NC1=CC=NN1C1=C(F)C(F)=C(C(F)(F)F)C(F)=C1F XZWCWXWGNGYETN-UHFFFAOYSA-N 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
230000006378 damage Effects 0.000 description 6
JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 6
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 6
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 6
NFDXQGNDWIPXQL-UHFFFAOYSA-N 1-cyclooctyldiazocane Chemical compound C1CCCCCCC1N1NCCCCCC1 NFDXQGNDWIPXQL-UHFFFAOYSA-N 0.000 description 5
QDFXRVAOBHEBGJ-UHFFFAOYSA-N 3-(cyclononen-1-yl)-4,5,6,7,8,9-hexahydro-1h-diazonine Chemical compound C1CCCCCCC=C1C1=NNCCCCCC1 QDFXRVAOBHEBGJ-UHFFFAOYSA-N 0.000 description 5
BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical class OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 5
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 5
150000007513 acids Chemical class 0.000 description 5
239000012973 diazabicyclooctane Substances 0.000 description 5
230000000694 effects Effects 0.000 description 5
239000012362 glacial acetic acid Substances 0.000 description 5
239000008187 granular material Substances 0.000 description 5
150000007529 inorganic bases Chemical class 0.000 description 5
229910052500 inorganic mineral Inorganic materials 0.000 description 5
239000007788 liquid Substances 0.000 description 5
238000004519 manufacturing process Methods 0.000 description 5
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
150000007530 organic bases Chemical class 0.000 description 5
239000002244 precipitate Substances 0.000 description 5
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
229910000029 sodium carbonate Inorganic materials 0.000 description 5
239000002689 soil Substances 0.000 description 5
150000003512 tertiary amines Chemical class 0.000 description 5
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SUSRORUBZHMPCO-UHFFFAOYSA-N MC-4379 Chemical compound C1=C([N+]([O-])=O)C(C(=O)OC)=CC(OC=2C(=CC(Cl)=CC=2)Cl)=C1 SUSRORUBZHMPCO-UHFFFAOYSA-N 0.000 description 1
235000017945 Matricaria Nutrition 0.000 description 1
235000007232 Matricaria chamomilla Nutrition 0.000 description 1
239000012359 Methanesulfonyl chloride Substances 0.000 description 1
ZOKXTWBITQBERF-UHFFFAOYSA-N Molybdenum Chemical compound [Mo] ZOKXTWBITQBERF-UHFFFAOYSA-N 0.000 description 1
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239000003513 alkali Substances 0.000 description 1
229910000102 alkali metal hydride Inorganic materials 0.000 description 1
150000008046 alkali metal hydrides Chemical class 0.000 description 1
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150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
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PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
235000012211 aluminium silicate Nutrition 0.000 description 1
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239000008346 aqueous phase Substances 0.000 description 1
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239000012928 buffer substance Substances 0.000 description 1
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150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
150000001805 chlorine compounds Chemical class 0.000 description 1
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JXCGFZXSOMJFOA-UHFFFAOYSA-N chlorotoluron Chemical compound CN(C)C(=O)NC1=CC=C(C)C(Cl)=C1 JXCGFZXSOMJFOA-UHFFFAOYSA-N 0.000 description 1
VJYIFXVZLXQVHO-UHFFFAOYSA-N chlorsulfuron Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)Cl)=N1 VJYIFXVZLXQVHO-UHFFFAOYSA-N 0.000 description 1
235000020971 citrus fruits Nutrition 0.000 description 1
150000001868 cobalt Chemical class 0.000 description 1
UFMZWBIQTDUYBN-UHFFFAOYSA-N cobalt dinitrate Chemical compound [Co+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O UFMZWBIQTDUYBN-UHFFFAOYSA-N 0.000 description 1
229910001981 cobalt nitrate Inorganic materials 0.000 description 1
235000016213 coffee Nutrition 0.000 description 1
235000013353 coffee beverage Nutrition 0.000 description 1
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FBCCMZVIWNDFMO-UHFFFAOYSA-N dichloroacetyl chloride Chemical compound ClC(Cl)C(Cl)=O FBCCMZVIWNDFMO-UHFFFAOYSA-N 0.000 description 1
235000014113 dietary fatty acids Nutrition 0.000 description 1
125000001664 diethylamino group Chemical group [H]C([H])([H])C([H])([H])N(*)C([H])([H])C([H])([H])[H] 0.000 description 1
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238000005538 encapsulation Methods 0.000 description 1
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XCLXGCQTGNGHJQ-UHFFFAOYSA-N ethyl 2-[4-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]oxyphenoxy]propanoate Chemical compound C1=CC(OC(C)C(=O)OCC)=CC=C1OC1=NC=C(C(F)(F)F)C=C1Cl XCLXGCQTGNGHJQ-UHFFFAOYSA-N 0.000 description 1
KTMGNAIGXYODKQ-UHFFFAOYSA-N ethyl 2-cyano-3-ethoxyprop-2-enoate Chemical compound CCOC=C(C#N)C(=O)OCC KTMGNAIGXYODKQ-UHFFFAOYSA-N 0.000 description 1
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238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
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230000002140 halogenating effect Effects 0.000 description 1
238000003306 harvesting Methods 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
150000004679 hydroxides Chemical class 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
239000005457 ice water Substances 0.000 description 1
239000001023 inorganic pigment Substances 0.000 description 1
239000003049 inorganic solvent Substances 0.000 description 1
230000000749 insecticidal effect Effects 0.000 description 1
239000002917 insecticide Substances 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
NRXQIUSYPAHGNM-UHFFFAOYSA-N ioxynil Chemical compound OC1=C(I)C=C(C#N)C=C1I NRXQIUSYPAHGNM-UHFFFAOYSA-N 0.000 description 1
RBTARNINKXHZNM-UHFFFAOYSA-K iron trichloride Chemical compound Cl[Fe](Cl)Cl RBTARNINKXHZNM-UHFFFAOYSA-K 0.000 description 1
PUIYMUZLKQOUOZ-UHFFFAOYSA-N isoproturon Chemical compound CC(C)C1=CC=C(NC(=O)N(C)C)C=C1 PUIYMUZLKQOUOZ-UHFFFAOYSA-N 0.000 description 1
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239000004579 marble Substances 0.000 description 1
230000004060 metabolic process Effects 0.000 description 1
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239000002184 metal Substances 0.000 description 1
VHCNQEUWZYOAEV-UHFFFAOYSA-N metamitron Chemical compound O=C1N(N)C(C)=NN=C1C1=CC=CC=C1 VHCNQEUWZYOAEV-UHFFFAOYSA-N 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
HAMGRBXTJNITHG-UHFFFAOYSA-N methyl isocyanate Chemical compound CN=C=O HAMGRBXTJNITHG-UHFFFAOYSA-N 0.000 description 1
239000001923 methylcellulose Substances 0.000 description 1
235000010981 methylcellulose Nutrition 0.000 description 1
FOXFZRUHNHCZPX-UHFFFAOYSA-N metribuzin Chemical compound CSC1=NN=C(C(C)(C)C)C(=O)N1N FOXFZRUHNHCZPX-UHFFFAOYSA-N 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
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239000011733 molybdenum Substances 0.000 description 1
229910052901 montmorillonite Inorganic materials 0.000 description 1
PSHKMPUSSFXUIA-UHFFFAOYSA-N n,n-dimethylpyridin-2-amine Chemical compound CN(C)C1=CC=CC=N1 PSHKMPUSSFXUIA-UHFFFAOYSA-N 0.000 description 1
JIKUXBYRTXDNIY-UHFFFAOYSA-N n-methyl-n-phenylformamide Chemical compound O=CN(C)C1=CC=CC=C1 JIKUXBYRTXDNIY-UHFFFAOYSA-N 0.000 description 1
229940042880 natural phospholipid Drugs 0.000 description 1
239000005645 nematicide Substances 0.000 description 1
229910052759 nickel Inorganic materials 0.000 description 1
SNICXCGAKADSCV-UHFFFAOYSA-N nicotine Chemical compound CN1CCCC1C1=CC=CN=C1 SNICXCGAKADSCV-UHFFFAOYSA-N 0.000 description 1
150000002823 nitrates Chemical class 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
GQPLMRYTRLFLPF-UHFFFAOYSA-N nitrous oxide Inorganic materials [O-][N+]#N GQPLMRYTRLFLPF-UHFFFAOYSA-N 0.000 description 1
235000014571 nuts Nutrition 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
239000011368 organic material Substances 0.000 description 1
229910052625 palygorskite Inorganic materials 0.000 description 1
CHIFOSRWCNZCFN-UHFFFAOYSA-N pendimethalin Chemical compound CCC(CC)NC1=C([N+]([O-])=O)C=C(C)C(C)=C1[N+]([O-])=O CHIFOSRWCNZCFN-UHFFFAOYSA-N 0.000 description 1
GSEOSWAMPBKOLE-UHFFFAOYSA-N phenyl n-[2-[2,3,5,6-tetrafluoro-4-(trifluoromethyl)phenyl]pyrazol-3-yl]carbamate Chemical compound FC1=C(F)C(C(F)(F)F)=C(F)C(F)=C1N1C(NC(=O)OC=2C=CC=CC=2)=CC=N1 GSEOSWAMPBKOLE-UHFFFAOYSA-N 0.000 description 1
150000004031 phenylhydrazines Chemical class 0.000 description 1
235000021317 phosphate Nutrition 0.000 description 1
150000003904 phospholipids Chemical class 0.000 description 1
150000003013 phosphoric acid derivatives Chemical class 0.000 description 1
UXCDUFKZSUBXGM-UHFFFAOYSA-N phosphoric tribromide Chemical compound BrP(Br)(Br)=O UXCDUFKZSUBXGM-UHFFFAOYSA-N 0.000 description 1
229920000642 polymer Polymers 0.000 description 1
239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
239000011118 polyvinyl acetate Substances 0.000 description 1
229920002689 polyvinyl acetate Polymers 0.000 description 1
229920002451 polyvinyl alcohol Polymers 0.000 description 1
239000011736 potassium bicarbonate Substances 0.000 description 1
229910000028 potassium bicarbonate Inorganic materials 0.000 description 1
235000015497 potassium bicarbonate Nutrition 0.000 description 1
TYJJADVDDVDEDZ-UHFFFAOYSA-M potassium hydrogencarbonate Chemical compound [K+].OC([O-])=O TYJJADVDDVDEDZ-UHFFFAOYSA-M 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
239000002243 precursor Substances 0.000 description 1
238000002953 preparative HPLC Methods 0.000 description 1
RZWZRACFZGVKFM-UHFFFAOYSA-N propanoyl chloride Chemical compound CCC(Cl)=O RZWZRACFZGVKFM-UHFFFAOYSA-N 0.000 description 1
239000003531 protein hydrolysate Substances 0.000 description 1
239000008262 pumice Substances 0.000 description 1
150000003217 pyrazoles Chemical class 0.000 description 1
239000010453 quartz Substances 0.000 description 1
238000001953 recrystallisation Methods 0.000 description 1
238000007363 ring formation reaction Methods 0.000 description 1
239000011435 rock Substances 0.000 description 1
229910052624 sepiolite Inorganic materials 0.000 description 1
235000019355 sepiolite Nutrition 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
235000015424 sodium Nutrition 0.000 description 1
239000001632 sodium acetate Substances 0.000 description 1
235000017281 sodium acetate Nutrition 0.000 description 1
ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
239000011780 sodium chloride Substances 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical class O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 1
238000009331 sowing Methods 0.000 description 1
238000003892 spreading Methods 0.000 description 1
238000003756 stirring Methods 0.000 description 1
150000003462 sulfoxides Chemical class 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
230000002195 synergetic effect Effects 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
235000013616 tea Nutrition 0.000 description 1
IROINLKCQGIITA-UHFFFAOYSA-N terbutryn Chemical compound CCNC1=NC(NC(C)(C)C)=NC(SC)=N1 IROINLKCQGIITA-UHFFFAOYSA-N 0.000 description 1
ZFXYFBGIUFBOJW-UHFFFAOYSA-N theophylline Chemical compound O=C1N(C)C(=O)N(C)C2=C1NC=N2 ZFXYFBGIUFBOJW-UHFFFAOYSA-N 0.000 description 1
229960000278 theophylline Drugs 0.000 description 1
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 1
OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
150000003624 transition metals Chemical class 0.000 description 1
230000005068 transpiration Effects 0.000 description 1
ZSDSQXJSNMTJDA-UHFFFAOYSA-N trifluralin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O ZSDSQXJSNMTJDA-UHFFFAOYSA-N 0.000 description 1
238000009369 viticulture Methods 0.000 description 1
235000014101 wine Nutrition 0.000 description 1
239000002023 wood Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/88—Nitrogen atoms, e.g. allantoin
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/38—Nitrogen atoms
- 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
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/18—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, directly attached to a heterocyclic or cycloaliphatic ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
- C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
- C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D231/38—Nitrogen atoms
- C07D231/40—Acylated on said nitrogen atom

Landscapes

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

DD87299667A 1986-02-04 1987-02-02 Herbizide und pflanzenwuchsregulierende mittel DD260431A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19863603291 DE3603291A1 (de)	1986-02-04	1986-02-04	5-amino-1-phenyl-pyrazole

Publications (1)

Publication Number	Publication Date
DD260431A5 true DD260431A5 (de)	1988-09-28

Family

ID=6293287

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD87299667A DD260431A5 (de)	1986-02-04	1987-02-02	Herbizide und pflanzenwuchsregulierende mittel

Country Status (16)

Country	Link
US (1)	US4787930A (tr)
EP (1)	EP0235558A3 (tr)
JP (1)	JPS62190168A (tr)
KR (1)	KR870007897A (tr)
CN (1)	CN87100874A (tr)
AU (1)	AU6829587A (tr)
BR (1)	BR8700478A (tr)
DD (1)	DD260431A5 (tr)
DE (1)	DE3603291A1 (tr)
DK (1)	DK55887A (tr)
HU (1)	HUT45694A (tr)
IE (1)	IE870284L (tr)
IL (1)	IL81446A0 (tr)
NZ (1)	NZ219135A (tr)
TR (1)	TR23238A (tr)
ZA (1)	ZA87760B (tr)

Families Citing this family (17)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3420985A1 (de) *	1983-10-15	1985-04-25	Bayer Ag, 5090 Leverkusen	Substituierte 5-acylamino-1-phenylpyrazole
US5256634A (en) *	1984-01-24	1993-10-26	Bayer Aktiengesellschaft	Herbicidal agents based on pyrazole derivatives
DE3402308A1 (de) *	1984-01-24	1985-08-01	Bayer Ag, 5090 Leverkusen	Herbizide mittel auf basis von pyrazolderivaten
DE3706993A1 (de) *	1987-03-05	1988-09-15	Bayer Ag	5-amino-3-halogenalkyl-1-aryl-pyrazole
DE3725661A1 (de) *	1987-08-03	1989-02-23	Bayer Ag	1-arylpyrazole
DE3808896A1 (de) *	1988-03-17	1989-09-28	Hoechst Ag	Pflanzenschuetzende mittel auf basis von pyrazolcarbonsaeurederivaten
US5167691A (en) *	1991-10-03	1992-12-01	Fmc Corporation	Herbicidal 5-amino-1-phenyl pyrazole compounds
US5198014A (en) *	1991-11-20	1993-03-30	Fmc Corporation	Herbicidal beta-pyrazolylacrylic acid compound
US5556873A (en) *	1993-02-24	1996-09-17	Rhone-Poulenc Inc.	Pesticidal 1-aryl-5-(substituted alkyl (thio) amido)pyrazoles
US5585329A (en) *	1995-04-28	1996-12-17	Rhone-Poulenc Inc.	Plant growth promotion using 3-cyano-1-phenylpyrazoles such as fipronil
US5707934A (en) *	1995-04-28	1998-01-13	Rhone-Poulenc Inc.	Plant growth regulation using 3-cyano-1-phenylpyrazoles such as fipronil
GB0016787D0 (en)	2000-07-07	2000-08-30	Pfizer Ltd	Compounds useful in therapy
WO2005030128A2 (en) *	2003-09-23	2005-04-07	Merck & Co., Inc.	Pyrazole modulators of metabotropic glutamate receptors
EP1550370A1 (en) *	2003-12-24	2005-07-06	Bayer CropScience GmbH	Plant growth regulation
KR20060115904A (ko) *	2003-12-24	2006-11-10	바이엘 크롭사이언스 게엠베하	식물 성장 조절
EP2654433B1 (en)	2010-12-21	2017-08-30	Bayer Cropscience LP	Sandpaper mutants of bacillus and methods of their use to enhance plant growth, promote plant health and control diseases and pests
MX2014002890A (es)	2011-09-12	2015-01-19	Bayer Cropscience Lp	Metodo para mejorar la salud y/o promover el crecimiento de una planta y/o mejorar la maduracion de frutos.

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3420985A1 (de) *	1983-10-15	1985-04-25	Bayer Ag, 5090 Leverkusen	Substituierte 5-acylamino-1-phenylpyrazole
DE3402308A1 (de) *	1984-01-24	1985-08-01	Bayer Ag, 5090 Leverkusen	Herbizide mittel auf basis von pyrazolderivaten
DE3423582A1 (de) *	1984-06-27	1986-01-09	Bayer Ag, 5090 Leverkusen	Substituierte 5-acylamino-1-phenylpyrazole

1986
- 1986-02-04 DE DE19863603291 patent/DE3603291A1/de not_active Withdrawn
1987
- 1987-01-16 US US07/004,353 patent/US4787930A/en not_active Expired - Fee Related
- 1987-01-26 EP EP87101037A patent/EP0235558A3/de not_active Withdrawn
- 1987-02-02 NZ NZ219135A patent/NZ219135A/xx unknown
- 1987-02-02 DD DD87299667A patent/DD260431A5/de not_active IP Right Cessation
- 1987-02-02 TR TR79/87A patent/TR23238A/tr unknown
- 1987-02-02 IL IL81446A patent/IL81446A0/xx unknown
- 1987-02-03 HU HU87366A patent/HUT45694A/hu unknown
- 1987-02-03 ZA ZA87760A patent/ZA87760B/xx unknown
- 1987-02-03 DK DK055887A patent/DK55887A/da not_active Application Discontinuation
- 1987-02-03 BR BR8700478A patent/BR8700478A/pt unknown
- 1987-02-03 IE IE870284A patent/IE870284L/xx unknown
- 1987-02-04 AU AU68295/87A patent/AU6829587A/en not_active Abandoned
- 1987-02-04 KR KR870000875A patent/KR870007897A/ko not_active Withdrawn
- 1987-02-04 JP JP62022617A patent/JPS62190168A/ja active Pending
- 1987-02-04 CN CN198787100874A patent/CN87100874A/zh active Pending

Also Published As

Publication number	Publication date
US4787930A (en)	1988-11-29
CN87100874A (zh)	1987-08-19
HUT45694A (en)	1988-08-29
IE870284L (en)	1987-08-04
DE3603291A1 (de)	1987-08-06
NZ219135A (en)	1989-11-28
IL81446A0 (en)	1987-09-16
KR870007897A (ko)	1987-09-22
AU6829587A (en)	1987-08-06
DK55887D0 (da)	1987-02-03
JPS62190168A (ja)	1987-08-20
DK55887A (da)	1987-08-05
ZA87760B (en)	1987-09-30
TR23238A (tr)	1989-07-21
BR8700478A (pt)	1987-12-08
EP0235558A2 (de)	1987-09-09
EP0235558A3 (de)	1987-10-21

Legal Events

Date	Code	Title	Description
1995-04-27	PJ	Ceased due to non-payment of renewal fee (addendum to changes before extension act)

Publication	Publication Date	Title
EP0154115B1 (de)	1988-10-26	Herbizide Mittel auf Basis von Pyrazolderivaten
EP0205024A2 (de)	1986-12-17	5-Amino-4-heterocyclyl-1-pyridyl-pyrazole
EP0248315A2 (de)	1987-12-09	5-Acylamino-pyrazol-Derivate
DD253172A5 (de)	1988-01-13	Herbizide mittel
EP0207285A1 (de)	1987-01-07	5-Amino-1-pyridyl-pyrazole
DE3728278A1 (de)	1988-06-23	Herbizide und fungizide mittel auf basis von substituierten pyrazolin-5-on derivaten
EP0335156A1 (de)	1989-10-04	5-Amino-1-phenylpyrazole
EP0138149B1 (de)	1989-01-18	Substituierte 5-Acylamino-1-phenylpyrazole
EP0235558A2 (de)	1987-09-09	5-Amino-1-phenyl-pyrazole
EP0302328A2 (de)	1989-02-08	l-Arylpyrazole
DD258559A5 (de)	1988-07-27	Herbizide und pflanzenwuchsregulierende mittel
EP0303153A2 (de)	1989-02-15	1-Arylpyrazole
EP0242573A1 (de)	1987-10-28	5-Acylamino-pyrazol-Derivate
DD247371A5 (de)	1987-07-08	Herbizide mittel
EP0281883A1 (de)	1988-09-14	Substituierte 1-Arylpyrazole
DD242165A5 (de)	1987-01-21	Herbizide mittel
DD238909A5 (de)	1986-09-10	Herbizide mittel
EP0204242A2 (de)	1986-12-10	1-Aryl-4-cyano-5-halogenpyrazole
EP0222253B1 (de)	1989-04-05	Substituierte 5-Amino-1-aryl-pyrazole
EP0171544A1 (de)	1986-02-19	Substituierte 5-Acylamino-1-phenylpyrazole
EP0269839A1 (de)	1988-06-08	5-Acylamino-pyrazol-Derivate
DD256640A5 (de)	1988-05-18	Herbizide und pflanzenwuchsregulierende mittel
DD258558A5 (de)	1988-07-27	1-aryl-5-hydrazino-pyrazole
EP0173323A1 (de)	1986-03-05	Amidinoazole
DE3707686A1 (de)	1988-09-22	4-cyano-1-aryl-pyrazole