DD258559A5 - Herbizide und pflanzenwuchsregulierende mittel - Google Patents

Herbizide und pflanzenwuchsregulierende mittel Download PDF

Info

Publication number: DD258559A5
Authority: DD; German Democratic Republic
Prior art keywords: case; carbon atoms; optionally; substituted; radical
Prior art date: 1985-10-31

Application number

DD86295696A

Other languages

German (de)

English (en)

Inventor

Reinhold Gehring

Otto Schallner

Joerg Stetter

Hans-Joachim Santel

Robert R Schmidt

Klaus Luerssen

Original Assignee

��@��k��

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.)

1985-10-31

Filing date

1986-10-29

Publication date

1988-07-27

1986-10-29 Application filed by ��@��k�� filed Critical ��@��k��

1988-07-27 Publication of DD258559A5 publication Critical patent/DD258559A5/de

Links

239000003795 chemical substances by application Substances 0.000 title claims abstract description 13
239000004009 herbicide Substances 0.000 title claims description 7
239000001257 hydrogen Substances 0.000 claims abstract description 38
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 38
239000000203 mixture Substances 0.000 claims abstract description 25
125000003342 alkenyl group Chemical group 0.000 claims abstract description 23
125000000304 alkynyl group Chemical group 0.000 claims abstract description 22
125000000547 substituted alkyl group Chemical group 0.000 claims abstract description 14
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 12
230000002363 herbicidal effect Effects 0.000 claims abstract description 10
125000000753 cycloalkyl group Chemical group 0.000 claims abstract description 7
125000004076 pyridyl group Chemical group 0.000 claims abstract description 4
-1 nitro, hydroxy Chemical group 0.000 claims description 114
239000000460 chlorine Substances 0.000 claims description 64
241000196324 Embryophyta Species 0.000 claims description 59
238000000034 method Methods 0.000 claims description 48
125000004432 carbon atom Chemical group C* 0.000 claims description 46
125000000217 alkyl group Chemical group 0.000 claims description 40
230000008569 process Effects 0.000 claims description 37
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 36
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 32
125000001424 substituent group Chemical group 0.000 claims description 26
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 25
229910052760 oxygen Inorganic materials 0.000 claims description 25
239000001301 oxygen Substances 0.000 claims description 25
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 24
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 24
229910052794 bromium Inorganic materials 0.000 claims description 24
229910052801 chlorine Inorganic materials 0.000 claims description 24
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 23
150000002431 hydrogen Chemical class 0.000 claims description 23
125000003545 alkoxy group Chemical group 0.000 claims description 21
125000001188 haloalkyl group Chemical group 0.000 claims description 21
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 21
238000002360 preparation method Methods 0.000 claims description 21
229910052736 halogen Inorganic materials 0.000 claims description 20
150000002367 halogens Chemical class 0.000 claims description 20
229910052757 nitrogen Inorganic materials 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 18
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 17
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 17
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 15
125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 15
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 14
239000011737 fluorine Substances 0.000 claims description 14
229910052731 fluorine Inorganic materials 0.000 claims description 14
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 14
125000004433 nitrogen atom Chemical group N* 0.000 claims description 14
125000004093 cyano group Chemical group *C#N 0.000 claims description 13
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 13
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 12
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 12
229910052717 sulfur Chemical group 0.000 claims description 12
239000011593 sulfur Chemical group 0.000 claims description 12
125000005843 halogen group Chemical group 0.000 claims description 11
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 10
125000003282 alkyl amino group Chemical group 0.000 claims description 9
125000004369 butenyl group Chemical group C(=CCC)* 0.000 claims description 9
125000004663 dialkyl amino group Chemical group 0.000 claims description 9
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 8
125000003178 carboxy group Chemical group [H]OC(*)=O 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
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 8
125000000623 heterocyclic group Chemical group 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 7
125000005842 heteroatom Chemical group 0.000 claims description 7
125000005346 substituted cycloalkyl group Chemical group 0.000 claims description 7
125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims description 7
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical class [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 claims description 6
PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 claims description 6
125000000480 butynyl group Chemical group [*]C#CC([H])([H])C([H])([H])[H] 0.000 claims description 6
125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 claims description 6
125000002757 morpholinyl group Chemical group 0.000 claims description 6
125000003386 piperidinyl group Chemical group 0.000 claims description 6
125000000719 pyrrolidinyl group Chemical group 0.000 claims description 6
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 5
125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 5
125000002490 anilino group Chemical group [H]N(*)C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 claims description 5
125000004774 dichlorofluoromethyl group Chemical group FC(Cl)(Cl)* 0.000 claims description 5
125000004772 dichloromethyl group Chemical group [H]C(Cl)(Cl)* 0.000 claims description 5
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 5
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 claims description 4
RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 4
239000004606 Fillers/Extenders Substances 0.000 claims description 4
HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 claims description 4
125000004414 alkyl thio group Chemical group 0.000 claims description 4
239000010941 cobalt Substances 0.000 claims description 4
229910017052 cobalt Inorganic materials 0.000 claims description 4
GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 4
229910052802 copper Inorganic materials 0.000 claims description 4
239000010949 copper Substances 0.000 claims description 4
125000000582 cycloheptyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 4
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 4
239000011734 sodium Substances 0.000 claims description 4
125000003107 substituted aryl group Chemical group 0.000 claims description 4
125000006000 trichloroethyl group Chemical group 0.000 claims description 4
229910052725 zinc Inorganic materials 0.000 claims description 4
239000011701 zinc Substances 0.000 claims description 4
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 claims description 3
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 3
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 claims description 3
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 claims description 3
ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 claims description 3
239000013543 active substance Substances 0.000 claims description 3
125000005210 alkyl ammonium group Chemical group 0.000 claims description 3
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 3
125000001769 aryl amino group Chemical group 0.000 claims description 3
125000005110 aryl thio group Chemical group 0.000 claims description 3
125000004104 aryloxy group Chemical group 0.000 claims description 3
229910052788 barium Inorganic materials 0.000 claims description 3
DSAJWYNOEDNPEQ-UHFFFAOYSA-N barium atom Chemical compound [Ba] DSAJWYNOEDNPEQ-UHFFFAOYSA-N 0.000 claims description 3
125000005997 bromomethyl 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
125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 3
125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 3
125000005745 ethoxymethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])* 0.000 claims description 3
125000006125 ethylsulfonyl group Chemical group 0.000 claims description 3
239000011777 magnesium Substances 0.000 claims description 3
229910052749 magnesium Inorganic materials 0.000 claims description 3
125000004170 methylsulfonyl group Chemical group [H]C([H])([H])S(*)(=O)=O 0.000 claims description 3
229910052759 nickel Inorganic materials 0.000 claims description 3
JVJQPDTXIALXOG-UHFFFAOYSA-N nitryl fluoride Chemical compound [O-][N+](F)=O JVJQPDTXIALXOG-UHFFFAOYSA-N 0.000 claims description 3
125000004193 piperazinyl group Chemical group 0.000 claims description 3
239000005648 plant growth regulator Substances 0.000 claims description 3
239000011591 potassium Substances 0.000 claims description 3
229910052700 potassium Inorganic materials 0.000 claims description 3
229910052708 sodium Inorganic materials 0.000 claims description 3
125000006337 tetrafluoro ethyl group Chemical group 0.000 claims description 3
229910052718 tin Inorganic materials 0.000 claims description 3
239000011135 tin Substances 0.000 claims description 3
125000004784 trichloromethoxy group Chemical group ClC(O*)(Cl)Cl 0.000 claims description 3
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 claims description 3
125000001478 1-chloroethyl group Chemical group [H]C([H])([H])C([H])(Cl)* 0.000 claims description 2
125000005999 2-bromoethyl group Chemical group 0.000 claims description 2
125000001340 2-chloroethyl group Chemical group [H]C([H])(Cl)C([H])([H])* 0.000 claims description 2
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 claims description 2
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
125000003754 ethoxycarbonyl group Chemical group C(=O)(OCC)* 0.000 claims description 2
125000001153 fluoro group Chemical group F* 0.000 claims description 2
125000004438 haloalkoxy group Chemical group 0.000 claims description 2
125000006341 heptafluoro n-propyl group Chemical group FC(F)(F)C(F)(F)C(F)(F)* 0.000 claims description 2
229910052740 iodine Inorganic materials 0.000 claims description 2
UCFFGYASXIPWPD-UHFFFAOYSA-N methyl hypochlorite Chemical group COCl UCFFGYASXIPWPD-UHFFFAOYSA-N 0.000 claims description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
239000004094 surface-active agent Substances 0.000 claims description 2
229910052723 transition metal Inorganic materials 0.000 claims description 2
150000003624 transition metals Chemical class 0.000 claims description 2
125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 2
YPFNIPKMNMDDDB-UHFFFAOYSA-K 2-[2-[bis(carboxylatomethyl)amino]ethyl-(2-hydroxyethyl)amino]acetate;iron(3+) Chemical compound [Fe+3].OCCN(CC([O-])=O)CCN(CC([O-])=O)CC([O-])=O YPFNIPKMNMDDDB-UHFFFAOYSA-K 0.000 claims 1
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 claims 1
239000003513 alkali Substances 0.000 claims 1
125000006193 alkinyl group Chemical group 0.000 claims 1
WGQKYBSKWIADBV-UHFFFAOYSA-O benzylaminium Chemical compound [NH3+]CC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-O 0.000 claims 1
239000004480 active ingredient Substances 0.000 abstract description 15
230000008635 plant growth Effects 0.000 abstract description 3
230000001105 regulatory effect Effects 0.000 abstract description 3
125000004435 hydrogen atom Chemical class [H]* 0.000 abstract 1
150000001875 compounds Chemical class 0.000 description 47
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 32
150000003254 radicals Chemical class 0.000 description 30
238000006243 chemical reaction Methods 0.000 description 23
239000003630 growth substance Substances 0.000 description 23
239000002253 acid Substances 0.000 description 19
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 18
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 18
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 18
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 18
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 17
239000003085 diluting agent Substances 0.000 description 17
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 15
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 15
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
235000019441 ethanol Nutrition 0.000 description 13
239000000126 substance Substances 0.000 description 13
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
239000007858 starting material Substances 0.000 description 12
239000011230 binding agent Substances 0.000 description 11
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 10
238000003306 harvesting Methods 0.000 description 10
239000002904 solvent Substances 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
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 9
235000013399 edible fruits Nutrition 0.000 description 9
238000009472 formulation Methods 0.000 description 9
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 8
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
150000001412 amines Chemical class 0.000 description 8
239000002585 base Substances 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
230000006378 damage Effects 0.000 description 7
239000003960 organic solvent Substances 0.000 description 7
239000002689 soil Substances 0.000 description 7
NFDXQGNDWIPXQL-UHFFFAOYSA-N 1-cyclooctyldiazocane Chemical compound C1CCCCCCC1N1NCCCCCC1 NFDXQGNDWIPXQL-UHFFFAOYSA-N 0.000 description 6
238000005160 1H NMR spectroscopy Methods 0.000 description 6
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 6
WADSJYLPJPTMLN-UHFFFAOYSA-N 3-(cycloundecen-1-yl)-1,2-diazacycloundec-2-ene Chemical compound C1CCCCCCCCC=C1C1=NNCCCCCCCC1 WADSJYLPJPTMLN-UHFFFAOYSA-N 0.000 description 6
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 6
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
150000001298 alcohols Chemical class 0.000 description 6
239000002168 alkylating agent Substances 0.000 description 6
229940100198 alkylating agent Drugs 0.000 description 6
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
239000012973 diazabicyclooctane Substances 0.000 description 6
230000000694 effects Effects 0.000 description 6
150000002148 esters Chemical class 0.000 description 6
XTHFKEDIFFGKHM-UHFFFAOYSA-N ethylene glycol dimethyl ether Natural products COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 6
239000008187 granular material Substances 0.000 description 6
239000000843 powder Substances 0.000 description 6
230000009105 vegetative growth Effects 0.000 description 6
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 5
KOPFEFZSAMLEHK-UHFFFAOYSA-N 1h-pyrazole-5-carboxylic acid Chemical class OC(=O)C=1C=CNN=1 KOPFEFZSAMLEHK-UHFFFAOYSA-N 0.000 description 5
241000219146 Gossypium Species 0.000 description 5
230000012010 growth Effects 0.000 description 5
238000002955 isolation Methods 0.000 description 5
239000003208 petroleum Substances 0.000 description 5
230000000704 physical effect Effects 0.000 description 5
229920000742 Cotton Polymers 0.000 description 4
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 4
241000208125 Nicotiana Species 0.000 description 4
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 4
241000209140 Triticum Species 0.000 description 4
235000021307 Triticum Nutrition 0.000 description 4
150000001408 amides Chemical class 0.000 description 4
230000008901 benefit Effects 0.000 description 4
DIKBFYAXUHHXCS-UHFFFAOYSA-N bromoform Chemical compound BrC(Br)Br DIKBFYAXUHHXCS-UHFFFAOYSA-N 0.000 description 4
235000013339 cereals Nutrition 0.000 description 4
239000007795 chemical reaction product Substances 0.000 description 4
125000001309 chloro group Chemical group Cl* 0.000 description 4
230000018109 developmental process Effects 0.000 description 4
239000000839 emulsion Substances 0.000 description 4
150000002170 ethers Chemical class 0.000 description 4
229910052500 inorganic mineral Inorganic materials 0.000 description 4
150000002576 ketones Chemical class 0.000 description 4
235000010755 mineral Nutrition 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
150000003839 salts Chemical class 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
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VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
UIIMBOGNXHQVGW-DEQYMQKBSA-M Sodium bicarbonate-14C Chemical compound [Na+].O[14C]([O-])=O UIIMBOGNXHQVGW-DEQYMQKBSA-M 0.000 description 1
241000488874 Sonchus Species 0.000 description 1
235000017967 Sphenoclea zeylanica Nutrition 0.000 description 1
244000273618 Sphenoclea zeylanica Species 0.000 description 1
240000006694 Stellaria media Species 0.000 description 1
244000269722 Thea sinensis Species 0.000 description 1
244000299461 Theobroma cacao Species 0.000 description 1
235000009470 Theobroma cacao Nutrition 0.000 description 1
GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
WHKUVVPPKQRRBV-UHFFFAOYSA-N Trasan Chemical compound CC1=CC(Cl)=CC=C1OCC(O)=O WHKUVVPPKQRRBV-UHFFFAOYSA-N 0.000 description 1
241000219422 Urtica Species 0.000 description 1
240000005592 Veronica officinalis Species 0.000 description 1
241000219873 Vicia Species 0.000 description 1
BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical class ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
241000405217 Viola <butterfly> Species 0.000 description 1
241001506766 Xanthium Species 0.000 description 1
241000607479 Yersinia pestis Species 0.000 description 1
241000209149 Zea 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
239000000205 acacia gum Substances 0.000 description 1
235000010489 acacia gum Nutrition 0.000 description 1
150000008065 acid anhydrides Chemical class 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
230000009471 action Effects 0.000 description 1
230000010933 acylation Effects 0.000 description 1
238000005917 acylation reaction Methods 0.000 description 1
230000006978 adaptation Effects 0.000 description 1
239000000654 additive Substances 0.000 description 1
239000000853 adhesive Substances 0.000 description 1
230000001070 adhesive effect Effects 0.000 description 1
244000193174 agave Species 0.000 description 1
230000001476 alcoholic effect Effects 0.000 description 1
HFVAFDPGUJEFBQ-UHFFFAOYSA-M alizarin red S Chemical compound [Na+].O=C1C2=CC=CC=C2C(=O)C2=C1C=C(S([O-])(=O)=O)C(O)=C2O HFVAFDPGUJEFBQ-UHFFFAOYSA-M 0.000 description 1
229910000102 alkali metal hydride Inorganic materials 0.000 description 1
150000008046 alkali metal hydrides Chemical class 0.000 description 1
150000001340 alkali metals Chemical class 0.000 description 1
229910052784 alkaline earth metal Inorganic materials 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
150000008051 alkyl sulfates Chemical class 0.000 description 1
125000005278 alkyl sulfonyloxy group Chemical group 0.000 description 1
125000004419 alkynylene group Chemical group 0.000 description 1
PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
235000012211 aluminium silicate Nutrition 0.000 description 1
125000003277 amino group Chemical group 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
150000008064 anhydrides Chemical class 0.000 description 1
125000000129 anionic group Chemical group 0.000 description 1
239000007864 aqueous solution Substances 0.000 description 1
125000005279 aryl sulfonyloxy group Chemical group 0.000 description 1
229960000892 attapulgite Drugs 0.000 description 1
230000003416 augmentation Effects 0.000 description 1
ZOMSMJKLGFBRBS-UHFFFAOYSA-N bentazone Chemical compound C1=CC=C2NS(=O)(=O)N(C(C)C)C(=O)C2=C1 ZOMSMJKLGFBRBS-UHFFFAOYSA-N 0.000 description 1
HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 1
KXHPPCXNWTUNSB-UHFFFAOYSA-M benzyl(trimethyl)azanium;chloride Chemical compound [Cl-].C[N+](C)(C)CC1=CC=CC=C1 KXHPPCXNWTUNSB-UHFFFAOYSA-M 0.000 description 1
235000021028 berry Nutrition 0.000 description 1
229910052796 boron Inorganic materials 0.000 description 1
238000009395 breeding Methods 0.000 description 1
230000001488 breeding effect Effects 0.000 description 1
230000001680 brushing effect Effects 0.000 description 1
125000005569 butenylene group Chemical group 0.000 description 1
125000005622 butynylene group Chemical group 0.000 description 1
150000004649 carbonic acid derivatives Chemical class 0.000 description 1
239000001768 carboxy methyl cellulose Substances 0.000 description 1
235000010948 carboxy methyl cellulose Nutrition 0.000 description 1
239000008112 carboxymethyl-cellulose Substances 0.000 description 1
230000015556 catabolic process Effects 0.000 description 1
230000008859 change Effects 0.000 description 1
FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical compound OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
229940106681 chloroacetic acid Drugs 0.000 description 1
150000008422 chlorobenzenes Chemical class 0.000 description 1
238000012505 colouration Methods 0.000 description 1
235000005822 corn Nutrition 0.000 description 1
244000038559 crop plants Species 0.000 description 1
239000002837 defoliant Substances 0.000 description 1
238000006731 degradation reaction Methods 0.000 description 1
239000002274 desiccant Substances 0.000 description 1
GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
MGXPSYQWCVTGNH-UHFFFAOYSA-N dibenzylazanium;methyl sulfate Chemical compound COS([O-])(=O)=O.C=1C=CC=CC=1C[NH2+]CC1=CC=CC=C1 MGXPSYQWCVTGNH-UHFFFAOYSA-N 0.000 description 1
235000014113 dietary fatty acids Nutrition 0.000 description 1
238000010790 dilution Methods 0.000 description 1
239000012895 dilution Substances 0.000 description 1
231100000676 disease causative agent Toxicity 0.000 description 1
239000010459 dolomite Substances 0.000 description 1
229910000514 dolomite Inorganic materials 0.000 description 1
238000010410 dusting Methods 0.000 description 1
239000004495 emulsifiable concentrate Substances 0.000 description 1
230000001804 emulsifying effect Effects 0.000 description 1
238000005538 encapsulation Methods 0.000 description 1
238000005516 engineering process Methods 0.000 description 1
ARFLASKVLJTEJD-UHFFFAOYSA-N ethyl 2-bromopropanoate Chemical compound CCOC(=O)C(C)Br ARFLASKVLJTEJD-UHFFFAOYSA-N 0.000 description 1
QDSCNNCJPLTQLA-UHFFFAOYSA-N ethyl 2-ethoxy-3,4-dihydro-2h-quinoline-1-carboxylate Chemical compound C1=CC=C2N(C(=O)OCC)C(OCC)CCC2=C1 QDSCNNCJPLTQLA-UHFFFAOYSA-N 0.000 description 1
FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 1
239000000194 fatty acid Substances 0.000 description 1
229930195729 fatty acid Natural products 0.000 description 1
235000013312 flour Nutrition 0.000 description 1
RZILCCPWPBTYDO-UHFFFAOYSA-N fluometuron Chemical compound CN(C)C(=O)NC1=CC=CC(C(F)(F)F)=C1 RZILCCPWPBTYDO-UHFFFAOYSA-N 0.000 description 1
238000005187 foaming Methods 0.000 description 1
230000000855 fungicidal effect Effects 0.000 description 1
229960002449 glycine Drugs 0.000 description 1
DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
IKDUDTNKRLTJSI-UHFFFAOYSA-N hydrazine monohydrate Substances O.NN IKDUDTNKRLTJSI-UHFFFAOYSA-N 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
230000006872 improvement Effects 0.000 description 1
230000036512 infertility Effects 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
229910001411 inorganic cation Inorganic materials 0.000 description 1
239000001023 inorganic pigment Substances 0.000 description 1
229910001867 inorganic solvent Inorganic materials 0.000 description 1
239000003049 inorganic solvent Substances 0.000 description 1
230000000749 insecticidal effect Effects 0.000 description 1
230000002452 interceptive effect Effects 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
239000011630 iodine Substances 0.000 description 1
239000012948 isocyanate Substances 0.000 description 1
150000002513 isocyanates Chemical class 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
239000000787 lecithin Substances 0.000 description 1
235000010445 lecithin Nutrition 0.000 description 1
239000004579 marble Substances 0.000 description 1
XIGAUIHYSDTJHW-UHFFFAOYSA-N mefenacet Chemical compound N=1C2=CC=CC=C2SC=1OCC(=O)N(C)C1=CC=CC=C1 XIGAUIHYSDTJHW-UHFFFAOYSA-N 0.000 description 1
125000005948 methanesulfonyloxy group Chemical group 0.000 description 1
229920000609 methyl cellulose Polymers 0.000 description 1
239000001923 methylcellulose Substances 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
238000002156 mixing Methods 0.000 description 1
229910052750 molybdenum Inorganic materials 0.000 description 1
239000011733 molybdenum Substances 0.000 description 1
229910052901 montmorillonite Inorganic materials 0.000 description 1
SWWDQDFDZLKDIK-UHFFFAOYSA-N n-[2-[2,6-dichloro-4-(trifluoromethyl)phenyl]-4-nitropyrazol-3-yl]propanamide Chemical compound CCC(=O)NC1=C([N+]([O-])=O)C=NN1C1=C(Cl)C=C(C(F)(F)F)C=C1Cl SWWDQDFDZLKDIK-UHFFFAOYSA-N 0.000 description 1
ABTVFZFMTSAHPI-UHFFFAOYSA-N n-amino-n-(methylamino)ethanamine Chemical class CCN(N)NC ABTVFZFMTSAHPI-UHFFFAOYSA-N 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
229940042880 natural phospholipid Drugs 0.000 description 1
239000005645 nematicide Substances 0.000 description 1
230000000802 nitrating effect Effects 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
235000014571 nuts Nutrition 0.000 description 1
238000005580 one pot reaction Methods 0.000 description 1
239000002420 orchard Substances 0.000 description 1
150000002892 organic cations Chemical class 0.000 description 1
239000011368 organic material Substances 0.000 description 1
239000012074 organic phase 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
125000006340 pentafluoro ethyl group Chemical group FC(F)(F)C(F)(F)* 0.000 description 1
239000012071 phase Substances 0.000 description 1
150000003904 phospholipids Chemical class 0.000 description 1
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
239000002798 polar solvent Substances 0.000 description 1
229920000642 polymer Polymers 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
230000002028 premature Effects 0.000 description 1
230000001737 promoting effect Effects 0.000 description 1
TVDSBUOJIPERQY-UHFFFAOYSA-N prop-2-yn-1-ol Chemical compound OCC#C TVDSBUOJIPERQY-UHFFFAOYSA-N 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
239000003531 protein hydrolysate Substances 0.000 description 1
239000008262 pumice Substances 0.000 description 1
125000003226 pyrazolyl group Chemical group 0.000 description 1
239000010453 quartz Substances 0.000 description 1
239000013558 reference substance Substances 0.000 description 1
230000002787 reinforcement Effects 0.000 description 1
239000005871 repellent Substances 0.000 description 1
230000002940 repellent Effects 0.000 description 1
239000011435 rock Substances 0.000 description 1
238000007127 saponification reaction Methods 0.000 description 1
230000007226 seed germination Effects 0.000 description 1
229910052624 sepiolite Inorganic materials 0.000 description 1
235000019355 sepiolite Nutrition 0.000 description 1
238000004904 shortening Methods 0.000 description 1
150000004760 silicates Chemical class 0.000 description 1
239000000377 silicon dioxide Substances 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
229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
235000017557 sodium bicarbonate Nutrition 0.000 description 1
239000012312 sodium hydride Substances 0.000 description 1
229910000104 sodium hydride Inorganic materials 0.000 description 1
235000010288 sodium nitrite Nutrition 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
229940035044 sorbitan monolaurate Drugs 0.000 description 1
238000009331 sowing Methods 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
239000007921 spray Substances 0.000 description 1
230000000638 stimulation Effects 0.000 description 1
238000003756 stirring Methods 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
230000002123 temporal effect Effects 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
IOGXOCVLYRDXLW-UHFFFAOYSA-N tert-butyl nitrite Chemical compound CC(C)(C)ON=O IOGXOCVLYRDXLW-UHFFFAOYSA-N 0.000 description 1
JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 description 1
DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 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
OGIDPMRJRNCKJF-UHFFFAOYSA-N titanium oxide Inorganic materials [Ti]=O OGIDPMRJRNCKJF-UHFFFAOYSA-N 0.000 description 1
230000005068 transpiration Effects 0.000 description 1
XKFPGUWSSPXXMF-UHFFFAOYSA-N tributyl(methyl)phosphanium Chemical compound CCCC[P+](C)(CCCC)CCCC XKFPGUWSSPXXMF-UHFFFAOYSA-N 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
239000002023 wood Substances 0.000 description 1

Classifications

- 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
- 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
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond

Landscapes

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

DD86295696A 1985-10-31 1986-10-29 Herbizide und pflanzenwuchsregulierende mittel DD258559A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19853538731 DE3538731A1 (de)	1985-10-31	1985-10-31	1-aryl-4-nitro-pyrazole

Publications (1)

Publication Number	Publication Date
DD258559A5 true DD258559A5 (de)	1988-07-27

Family

ID=6284912

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD86295696A DD258559A5 (de)	1985-10-31	1986-10-29	Herbizide und pflanzenwuchsregulierende mittel

Country Status (12)

Country	Link
US (1)	US4810283A (fr)
EP (1)	EP0224019A3 (fr)
JP (1)	JPS62108865A (fr)
KR (1)	KR870003993A (fr)
AU (1)	AU6417086A (fr)
BR (1)	BR8605333A (fr)
DD (1)	DD258559A5 (fr)
DE (1)	DE3538731A1 (fr)
DK (1)	DK519586A (fr)
HU (1)	HUT42685A (fr)
IL (1)	IL80440A0 (fr)
ZA (1)	ZA868265B (fr)

Families Citing this family (14)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE3402308A1 (de) *	1984-01-24	1985-08-01	Bayer Ag, 5090 Leverkusen	Herbizide mittel auf basis von pyrazolderivaten
DE3600950A1 (de) *	1986-01-15	1987-07-16	Bayer Ag	5-acylamido-1-aryl-pyrazole
US5258511A (en) *	1989-03-11	1993-11-02	Bayer Aktiengesellschaft	Pyrazoloazepinones and methods of using such pyrazoloazepinones to dye synthetic fibers and to pigment pastes, paints, printing inks, colored paper and colored macromolecular substances
JP2624899B2 (ja) *	1991-02-20	1997-06-25	オークラ輸送機株式会社	センサ取付部材
HRP970348A2 (en) *	1996-07-17	1998-04-30	Bayer Ag	New nitropyrazole esters, process for their preparation and their use for the preparation of nytropyrazolamides
US6541273B1 (en)	1999-11-12	2003-04-01	Aventis Cropscience, S.A.	Multiple sorbent cartridges for solid phase extraction
DE602004022985D1 (de) *	2003-12-24	2009-10-15	Bayer Cropscience Ag	Regulation des pflanzenwachstums
PE20141468A1 (es)	2010-12-21	2014-11-05	Bayer Cropscience Lp	Mutantes tipo papel de lija de bacillus y metodos de uso de los mismo para mejorar el crecimiento vegetal, promover la salud de plantas y controlar enfermedades y plagas
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.
CA2894399A1 (fr)	2012-12-06	2014-06-12	Quanticel Pharmaceuticals, Inc.	Inhibiteurs de l'histone demethylase
AR097245A1 (es) *	2013-08-09	2016-03-02	Kyoyu Agri Co Ltd	Derivado de pirazolilpirazol sustituido y su empleo como herbicida
JP6128556B2 (ja) *	2013-08-13	2017-05-17	協友アグリ株式会社	置換ピラゾリルピラゾール誘導体とその除草剤としての使用
JP6128555B2 (ja) *	2013-08-13	2017-05-17	協友アグリ株式会社	置換ピラゾリルピラゾール誘導体とその除草剤としての使用
JP6097655B2 (ja) *	2013-08-13	2017-03-15	協友アグリ株式会社	置換ピラゾリルピラゾール誘導体とその除草剤としての使用

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
MA19540A1 (fr) *	1981-07-17	1983-04-01	May & Baker Ltd	Derives du n-phenylpyrazole
DE3402308A1 (de) *	1984-01-24	1985-08-01	Bayer Ag, 5090 Leverkusen	Herbizide mittel auf basis von pyrazolderivaten

1985
- 1985-10-31 DE DE19853538731 patent/DE3538731A1/de not_active Withdrawn
1986
- 1986-10-16 AU AU64170/86A patent/AU6417086A/en not_active Abandoned
- 1986-10-20 EP EP86114490A patent/EP0224019A3/fr not_active Withdrawn
- 1986-10-24 JP JP61252103A patent/JPS62108865A/ja active Pending
- 1986-10-28 IL IL80440A patent/IL80440A0/xx unknown
- 1986-10-29 DD DD86295696A patent/DD258559A5/de not_active IP Right Cessation
- 1986-10-30 DK DK519586A patent/DK519586A/da not_active Application Discontinuation
- 1986-10-30 KR KR860009123A patent/KR870003993A/ko not_active Withdrawn
- 1986-10-30 HU HU864563A patent/HUT42685A/hu unknown
- 1986-10-30 BR BR8605333A patent/BR8605333A/pt unknown
- 1986-10-30 US US06/925,639 patent/US4810283A/en not_active Expired - Fee Related
- 1986-10-30 ZA ZA868265A patent/ZA868265B/xx unknown

Also Published As

Publication number	Publication date
EP0224019A3 (fr)	1987-10-14
DK519586A (da)	1987-05-01
US4810283A (en)	1989-03-07
DE3538731A1 (de)	1987-05-07
BR8605333A (pt)	1987-08-04
IL80440A0 (en)	1987-01-30
DK519586D0 (da)	1986-10-30
HUT42685A (en)	1987-08-28
KR870003993A (ko)	1987-05-06
ZA868265B (en)	1987-07-29
EP0224019A2 (fr)	1987-06-03
AU6417086A (en)	1987-05-07
JPS62108865A (ja)	1987-05-20

Legal Events

Date	Code	Title	Description
1995-08-31	ENJ	Ceased due to non-payment of renewal fee

Publication	Publication Date	Title
DE3618717A1 (de)	1987-12-10	5- acylamino-pyrazol-derivate
DD253172A5 (de)	1988-01-13	Herbizide mittel
EP0205024A2 (fr)	1986-12-17	Amino-5-hétérocyclyl-4-pyridyl-1-pyrazole
EP0167028B1 (fr)	1988-03-09	Amino-5-hétérocyclique-4-phényl-1-pyrazoles
DE3603291A1 (de)	1987-08-06	5-amino-1-phenyl-pyrazole
DD258559A5 (de)	1988-07-27	Herbizide und pflanzenwuchsregulierende mittel
DD228157A5 (de)	1985-10-09	Herbizide mittel
DE3609542A1 (de)	1987-10-01	5-acylamino-pyrazol-derivate
EP0205022B1 (fr)	1990-01-10	Aryl-1-alkoximinoalkylamino-5-pyrazoles
US4685957A (en)	1987-08-11	1-aryl-5-iminoaminopyrazoles, compositions containing them, and herbicidal method of using them
DE3543034A1 (de)	1987-06-11	5-perfluoracylamino-4-nitro-1-aryl-pyrazol-salze
DE3707551A1 (de)	1988-09-22	Substituierte 1-arylpyrazole
DE3543035A1 (de)	1987-06-11	5-fluoracylamino-4-nitro-1-aryl-pyrazole
DD238909A5 (de)	1986-09-10	Herbizide mittel
EP0222253B1 (fr)	1989-04-05	5-Amino-1-aryl-pyrazoles substitués
DE3637710A1 (de)	1988-05-11	5-acylamino-pyrazol-derivate
DE3545347A1 (de)	1987-07-02	1-aryl-pyrazole
DD258558A5 (de)	1988-07-27	1-aryl-5-hydrazino-pyrazole
DE3707686A1 (de)	1988-09-22	4-cyano-1-aryl-pyrazole
EP0205023A2 (fr)	1986-12-17	Aryl-1-hétérocyclyl-4-pyrazoles
EP0297427A2 (fr)	1989-01-04	Aryl-1-pyrazoles
DD248271A5 (de)	1987-08-05	Herbizide mittel