DE69413059T2 - Herbizide zusammensetzungen - Google Patents
Herbizide zusammensetzungenInfo
- Publication number
- DE69413059T2 DE69413059T2 DE69413059T DE69413059T DE69413059T2 DE 69413059 T2 DE69413059 T2 DE 69413059T2 DE 69413059 T DE69413059 T DE 69413059T DE 69413059 T DE69413059 T DE 69413059T DE 69413059 T2 DE69413059 T2 DE 69413059T2
- Authority
- DE
- Germany
- Prior art keywords
- herbicide
- formula
- triazine
- benzoylisoxazole
- weeds
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
Links
- 230000002363 herbicidal effect Effects 0.000 title claims abstract description 75
- 239000000203 mixture Substances 0.000 title claims abstract description 64
- 239000004009 herbicide Substances 0.000 claims abstract description 64
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 claims abstract description 33
- FGGUUGIYSOGQED-UHFFFAOYSA-N 1,2-oxazol-4-yl(phenyl)methanone Chemical class C=1C=CC=CC=1C(=O)C=1C=NOC=1 FGGUUGIYSOGQED-UHFFFAOYSA-N 0.000 claims abstract description 31
- MZZBPDKVEFVLFF-UHFFFAOYSA-N cyanazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)(C)C#N)=N1 MZZBPDKVEFVLFF-UHFFFAOYSA-N 0.000 claims abstract description 28
- MXWJVTOOROXGIU-UHFFFAOYSA-N atrazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)C)=N1 MXWJVTOOROXGIU-UHFFFAOYSA-N 0.000 claims abstract description 24
- FOXFZRUHNHCZPX-UHFFFAOYSA-N metribuzin Chemical compound CSC1=NN=C(C(C)(C)C)C(=O)N1N FOXFZRUHNHCZPX-UHFFFAOYSA-N 0.000 claims abstract description 19
- 239000005583 Metribuzin Substances 0.000 claims abstract description 16
- ODCWYMIRDDJXKW-UHFFFAOYSA-N simazine Chemical compound CCNC1=NC(Cl)=NC(NCC)=N1 ODCWYMIRDDJXKW-UHFFFAOYSA-N 0.000 claims abstract description 5
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims abstract description 3
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims abstract description 3
- 125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims abstract description 3
- 125000001188 haloalkyl group Chemical group 0.000 claims abstract description 3
- 229910052736 halogen Inorganic materials 0.000 claims abstract description 3
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 3
- 239000001257 hydrogen Substances 0.000 claims abstract description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 3
- 241000196324 Embryophyta Species 0.000 claims description 55
- 150000001875 compounds Chemical class 0.000 claims description 29
- 238000000034 method Methods 0.000 claims description 21
- -1 monoalkylamino Chemical group 0.000 claims description 13
- 230000012010 growth Effects 0.000 claims description 11
- 239000003085 diluting agent Substances 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 9
- 230000008569 process Effects 0.000 claims description 9
- 239000004094 surface-active agent Substances 0.000 claims description 8
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 7
- 241001148683 Zostera marina Species 0.000 claims description 6
- XBYZOHTXPQOOJM-UHFFFAOYSA-N 1,2-oxazol-3-yl(phenyl)methanone Chemical compound C=1C=CC=CC=1C(=O)C=1C=CON=1 XBYZOHTXPQOOJM-UHFFFAOYSA-N 0.000 claims description 5
- 239000000460 chlorine Substances 0.000 claims description 5
- 229910052801 chlorine Inorganic materials 0.000 claims description 5
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 4
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 4
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 4
- 240000008042 Zea mays Species 0.000 claims description 3
- 235000016383 Zea mays subsp huehuetenangensis Nutrition 0.000 claims description 3
- 235000002017 Zea mays subsp mays Nutrition 0.000 claims description 3
- 235000009973 maize Nutrition 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- 125000006310 cycloalkyl amino group Chemical group 0.000 claims description 2
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 238000002360 preparation method Methods 0.000 claims description 2
- 125000001424 substituent group Chemical group 0.000 claims description 2
- LMBFAGIMSUYTBN-MPZNNTNKSA-N teixobactin Chemical compound C([C@H](C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H](CCC(N)=O)C(=O)N[C@H]([C@@H](C)CC)C(=O)N[C@@H]([C@@H](C)CC)C(=O)N[C@@H](CO)C(=O)N[C@H]1C(N[C@@H](C)C(=O)N[C@@H](C[C@@H]2NC(=N)NC2)C(=O)N[C@H](C(=O)O[C@H]1C)[C@@H](C)CC)=O)NC)C1=CC=CC=C1 LMBFAGIMSUYTBN-MPZNNTNKSA-N 0.000 claims description 2
- 125000005843 halogen group Chemical group 0.000 claims 1
- RQVYBGPQFYCBGX-UHFFFAOYSA-N ametryn Chemical compound CCNC1=NC(NC(C)C)=NC(SC)=N1 RQVYBGPQFYCBGX-UHFFFAOYSA-N 0.000 abstract description 4
- 150000002367 halogens Chemical class 0.000 abstract description 2
- 238000001228 spectrum Methods 0.000 abstract description 2
- 150000003918 triazines Chemical class 0.000 abstract 1
- 229940126062 Compound A Drugs 0.000 description 19
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 description 19
- 238000002474 experimental method Methods 0.000 description 15
- 239000000654 additive Substances 0.000 description 11
- 239000002689 soil Substances 0.000 description 10
- 230000000996 additive effect Effects 0.000 description 9
- 241000207890 Ipomoea purpurea Species 0.000 description 8
- 230000002195 synergetic effect Effects 0.000 description 8
- 244000088461 Panicum crus-galli Species 0.000 description 7
- 235000011999 Panicum crusgalli Nutrition 0.000 description 7
- 230000004071 biological effect Effects 0.000 description 7
- 239000000243 solution Substances 0.000 description 7
- 244000237956 Amaranthus retroflexus Species 0.000 description 6
- 235000013479 Amaranthus retroflexus Nutrition 0.000 description 6
- 239000007787 solid Substances 0.000 description 6
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 6
- 230000000694 effects Effects 0.000 description 5
- 239000000463 material Substances 0.000 description 5
- 239000007921 spray Substances 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- 240000006995 Abutilon theophrasti Species 0.000 description 4
- 244000152970 Digitaria sanguinalis Species 0.000 description 4
- 235000010823 Digitaria sanguinalis Nutrition 0.000 description 4
- 240000003461 Setaria viridis Species 0.000 description 4
- 235000002248 Setaria viridis Nutrition 0.000 description 4
- 240000006410 Sida spinosa Species 0.000 description 4
- 244000067505 Xanthium strumarium Species 0.000 description 4
- 239000004480 active ingredient Substances 0.000 description 4
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 4
- 239000000969 carrier Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000004033 plastic Substances 0.000 description 4
- 229920003023 plastic Polymers 0.000 description 4
- 244000104272 Bidens pilosa Species 0.000 description 3
- 235000010662 Bidens pilosa Nutrition 0.000 description 3
- 244000062995 Cassia occidentalis Species 0.000 description 3
- 235000001948 Cassia occidentalis Nutrition 0.000 description 3
- 244000048459 Euphorbia cyathophora Species 0.000 description 3
- 241000207783 Ipomoea Species 0.000 description 3
- 235000021506 Ipomoea Nutrition 0.000 description 3
- 231100000674 Phytotoxicity Toxicity 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 230000009036 growth inhibition Effects 0.000 description 3
- 125000002816 methylsulfanyl group Chemical group [H]C([H])([H])S[*] 0.000 description 3
- 230000008635 plant growth Effects 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 238000011160 research Methods 0.000 description 3
- 241000894007 species Species 0.000 description 3
- 239000003381 stabilizer Substances 0.000 description 3
- 239000004563 wettable powder Substances 0.000 description 3
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 description 2
- HFBHPHBIBAUDNE-UHFFFAOYSA-N 2h-1,2,4-triazin-3-one Chemical compound O=C1N=CC=NN1 HFBHPHBIBAUDNE-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- 239000005995 Aluminium silicate Substances 0.000 description 2
- AFIIBUOYKYSPKB-UHFFFAOYSA-N Aziprotryne Chemical compound CSC1=NC(NC(C)C)=NC(N=[N+]=[N-])=N1 AFIIBUOYKYSPKB-UHFFFAOYSA-N 0.000 description 2
- 239000001692 EU approved anti-caking agent Substances 0.000 description 2
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 2
- DDUIUBPJPOKOMV-UHFFFAOYSA-N Methoprotryne Chemical compound COCCCNC1=NC(NC(C)C)=NC(SC)=N1 DDUIUBPJPOKOMV-UHFFFAOYSA-N 0.000 description 2
- 240000000111 Saccharum officinarum Species 0.000 description 2
- 235000007201 Saccharum officinarum Nutrition 0.000 description 2
- 241000232088 Setaria <nematode> Species 0.000 description 2
- 239000005621 Terbuthylazine Substances 0.000 description 2
- 230000009471 action Effects 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 239000002671 adjuvant Substances 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 235000012211 aluminium silicate Nutrition 0.000 description 2
- 239000003086 colorant Substances 0.000 description 2
- 230000007797 corrosion Effects 0.000 description 2
- 238000005260 corrosion Methods 0.000 description 2
- 239000007822 coupling agent Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 239000003112 inhibitor Substances 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 239000000575 pesticide Substances 0.000 description 2
- ISEUFVQQFVOBCY-UHFFFAOYSA-N prometon Chemical compound COC1=NC(NC(C)C)=NC(NC(C)C)=N1 ISEUFVQQFVOBCY-UHFFFAOYSA-N 0.000 description 2
- AAEVYOVXGOFMJO-UHFFFAOYSA-N prometryn Chemical compound CSC1=NC(NC(C)C)=NC(NC(C)C)=N1 AAEVYOVXGOFMJO-UHFFFAOYSA-N 0.000 description 2
- WJNRPILHGGKWCK-UHFFFAOYSA-N propazine Chemical compound CC(C)NC1=NC(Cl)=NC(NC(C)C)=N1 WJNRPILHGGKWCK-UHFFFAOYSA-N 0.000 description 2
- 230000009467 reduction Effects 0.000 description 2
- MGLWZSOBALDPEK-UHFFFAOYSA-N simetryn Chemical compound CCNC1=NC(NCC)=NC(SC)=N1 MGLWZSOBALDPEK-UHFFFAOYSA-N 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 238000009331 sowing Methods 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000004546 suspension concentrate Substances 0.000 description 2
- FZXISNSWEXTPMF-UHFFFAOYSA-N terbutylazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)(C)C)=N1 FZXISNSWEXTPMF-UHFFFAOYSA-N 0.000 description 2
- 230000000007 visual effect Effects 0.000 description 2
- 239000004562 water dispersible granule Substances 0.000 description 2
- 239000000080 wetting agent Substances 0.000 description 2
- MTQKMPGBALVEDL-ZPCKWCKBSA-N (z,12r)-12-hydroxy-2-sulfooctadec-9-enoic acid Chemical class CCCCCC[C@@H](O)C\C=C/CCCCCCC(C(O)=O)S(O)(=O)=O MTQKMPGBALVEDL-ZPCKWCKBSA-N 0.000 description 1
- FYADHXFMURLYQI-UHFFFAOYSA-N 1,2,4-triazine Chemical compound C1=CN=NC=N1 FYADHXFMURLYQI-UHFFFAOYSA-N 0.000 description 1
- IUVCFHHAEHNCFT-INIZCTEOSA-N 2-[(1s)-1-[4-amino-3-(3-fluoro-4-propan-2-yloxyphenyl)pyrazolo[3,4-d]pyrimidin-1-yl]ethyl]-6-fluoro-3-(3-fluorophenyl)chromen-4-one Chemical compound C1=C(F)C(OC(C)C)=CC=C1C(C1=C(N)N=CN=C11)=NN1[C@@H](C)C1=C(C=2C=C(F)C=CC=2)C(=O)C2=CC(F)=CC=C2O1 IUVCFHHAEHNCFT-INIZCTEOSA-N 0.000 description 1
- WHDPHCMQLDWVTN-UHFFFAOYSA-N 2-n-tert-butyl-2-n-ethyl-6-methylsulfanyl-1,3,5-triazine-2,4-diamine Chemical compound CCN(C(C)(C)C)C1=NC(N)=NC(SC)=N1 WHDPHCMQLDWVTN-UHFFFAOYSA-N 0.000 description 1
- NWHRPZPSBCFTQX-UHFFFAOYSA-N 2-n-tert-butyl-6-chloro-2-n-ethyl-1,3,5-triazine-2,4-diamine Chemical compound CCN(C(C)(C)C)C1=NC(N)=NC(Cl)=N1 NWHRPZPSBCFTQX-UHFFFAOYSA-N 0.000 description 1
- UBPQITZLYDWRFS-UHFFFAOYSA-N 3,4-dihydro-1H-triazine-2,4-diamine Chemical compound NC1NN(N)NC=C1 UBPQITZLYDWRFS-UHFFFAOYSA-N 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 239000005909 Kieselgur Substances 0.000 description 1
- CPLXHLVBOLITMK-UHFFFAOYSA-N Magnesium oxide Chemical compound [Mg]=O CPLXHLVBOLITMK-UHFFFAOYSA-N 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 235000005775 Setaria Nutrition 0.000 description 1
- 235000017016 Setaria faberi Nutrition 0.000 description 1
- 241001355178 Setaria faberi Species 0.000 description 1
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical class OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- HFBWPRKWDIRYNX-UHFFFAOYSA-N Trietazine Chemical compound CCNC1=NC(Cl)=NC(N(CC)CC)=N1 HFBWPRKWDIRYNX-UHFFFAOYSA-N 0.000 description 1
- 239000002250 absorbent Substances 0.000 description 1
- 230000002745 absorbent Effects 0.000 description 1
- PZZYQPZGQPZBDN-UHFFFAOYSA-N aluminium silicate Chemical compound O=[Al]O[Si](=O)O[Al]=O PZZYQPZGQPZBDN-UHFFFAOYSA-N 0.000 description 1
- 229910000323 aluminium silicate Inorganic materials 0.000 description 1
- 239000010775 animal oil Substances 0.000 description 1
- 230000008485 antagonism Effects 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 229920005551 calcium lignosulfonate Polymers 0.000 description 1
- 239000001506 calcium phosphate Substances 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000007942 carboxylates Chemical class 0.000 description 1
- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 239000002738 chelating agent Substances 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 239000007799 cork Substances 0.000 description 1
- 230000008878 coupling Effects 0.000 description 1
- 238000010168 coupling process Methods 0.000 description 1
- 238000005859 coupling reaction Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000006266 etherification reaction Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 230000008014 freezing Effects 0.000 description 1
- 238000007710 freezing Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000000227 grinding Methods 0.000 description 1
- 238000003306 harvesting Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 230000005764 inhibitory process Effects 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 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 description 1
- 239000000123 paper Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000001681 protective effect Effects 0.000 description 1
- 125000001453 quaternary ammonium group Chemical group 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920005552 sodium lignosulfonate Polymers 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- 150000003458 sulfonic acid derivatives Chemical class 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 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
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 239000013008 thixotropic agent Substances 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 229940078499 tricalcium phosphate Drugs 0.000 description 1
- 229910000391 tricalcium phosphate Inorganic materials 0.000 description 1
- 235000019731 tricalcium phosphate Nutrition 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Preparation Of Compounds By Using Micro-Organisms (AREA)
Claims (22)
1. Verfahren zur Bekämpfung des Wachstums von Unkräutern auf
einer Örtlichkeit, bei dem auf die Örtlichkeit ausgebracht
wird:
(a) ein 4-Benzoylisoxazol-Derivat der Formel I:
in der
R Wasserstoff oder -CO&sub2;R³ ist,
R¹ Cyclopropyl ist,
R² unter Halogen, -S (O) pMe und C&sub1;&submin;&sub6;-Alkyl oder
Halogenalkyl ausgewählt ist,
n 2 oder 3, p 0, 1 oder 2 und
R³ C&sub1;&submin;&sub4;-Alkyl ist, und
(b) ein Triazin-Herbicid
2. Verfahren nach Anspruch 1, wobei das Triazin-Herbicid eine
Verbindung der Formel II ist:
in der bedeuten:
R¹¹ Chlor oder geradkettiges oder verzweigtes Alkylthio
oder Alkoxy mit 1 bis 6 Kohlenstoffatomen, R¹² Azido,
Monoalkylamino, Dialkylamino oder Cycloalkylamino, wobei
die Alkyl- oder Cycloalkylreste gegebenenfalls mit einem
oder mehreren unter Cyano und Alkoxy ausgewählten
Substituenten substituiert sein können, und R¹³ geradkettiges
oder verzweigtes N-Alkylamino mit 1 bis 6
Kohlenstoffatomen,
oder eine Verbindung der Formel III ist:
in der R¹¹ das oben definierte und R¹&sup4; geradkettiges oder
verzweigtes Alkyl mit 1 bis 6 Kohlenstoffatomen bedeuetet.
3. Verfahren nach Anspruch 2, wobei in Formel II R¹² Azido,
geradkettiges oder verzweigtes N-Alkylamino mit 1 bis 4
Kohlenstoffatomen (wobei der Alkylrest gegebenenfalls mit
Cyano oder Methoxy substituiert ist) bedeutet.
4. Verfahren nach Anspruch 1 oder 2, wobei das
Triazin-Herbicid ausgewählt ist unter:
Simazin, nämlich 6-Chlor-N²,N&sup4;-diethyl-1,3,5-triazin-2,4-
diamin,
Cyanazin, nämlich 2-(4-Chlor-6-ethylamino-1,3,5-triazin-2-
ylamino)-2-methylpropionitril, oder
Atrazin, nämlich
6-Chlor-N²-ethyl-N&sup4;-isopropyl-1,3,5-triazin-2,4-diamin.
5. Verfahren nach Anspruch 4, wobei das Triazin-Herbicid
Cyanazin oder Atrazin ist.
6. Verfahren nach Anspruch 1 oder 2, wobei das
Triazin-Herbicid Metribuzin, nämlich
4-Amino-6-tert.-butyl-3-methylthio-1,2,4-triazin 5(4H)-on, ist.
7. Verfahren nach einem der vorhergehenden Ansprüche, wobei
in Formel I eine der Gruppen R² - S(O)p Me bedeutet und p
wie in Anspruch 1 definiert ist.
8. Verfahren nach einem der vorhergehenden Ansprüche, wobei
in Formel I n 3 ist und die Gruppen (R²)n die Stellungen
2, 3 und 4 des Benzoylrings besetzen oder n 2 ist und die
Gruppen (R²)n die Stellungen 2 und 4 des Benzoylrings
besetzen.
9. Verfahren nach einem der vorhergehenden Ansprüche, wobei
in Formel I (R²) n 2-SO&sub2;Me-4-CF&sub3;, 2-CF&sub3;-4-SO&sub2;Me,
2-Cl-4-SO&sub2;Me, 2-SO&sub2;Me-4-Br, 2-SO&sub2;Me-4-Cl oder
2-SMe-3,4-dichlor bedeutet.
10. Verfahren nach einem der vorhergehenden Ansprüche, wobei
die Verbindung der Formel I
5-Cyclopropyl-4-(2-methylsulfonyl-4-trifluormethyl)benzoylisoxazol ist.
11. Verfahren nach einem der Ansprüche 1 bis 9, wobei die
Verbindung der Formel I 3-[5-Cyclopropyl-4-(3,4-dichlor-2-
methylsulfenyl)benzoylisoxazol]carbonsäureethylester ist.
12. Verfahren nach einem der vorhergehenden Ansprüche, wobei
die Ausbringmenge des 4-Benzoylisoxazols 5 g bis 500 g pro
Hektar und die Ausbringmenge des Triazin-Herbicides 250 g
bis 5000 g pro Hektar beträgt.
13. Verfahren nach einem der vorhergehenden Ansprüche, wobei
die Ausbringmenge des 4-Benzoylisoxazols 25 g bis 150 g
pro Hektar und die Ausbringmenge des Triazin-Herbicids 500
g bis 1500 g pro Hektar beträgt.
14. Verfahren nach einem der vorhergehenden Ansprüche zur
Bekämpfung von Grasunkräutern in Mais.
15. Verfahren nach einem der vorhergehenden Ansprüche, wobei
die Verbindungen vor dem Auflaufen der Unkräuter
ausgebracht werden.
16. Verfahren nach Anspruche 6, wobei die Verbindungen nach
dem Auflaufen der Unkräuter ausgebracht werden.
17. Herbicide Zusammensetzung, die enthält:
(a) ein 4-Benzoylisoxazol-Derivat der in Anspruch 1
definierten Formel I und
(b) ein Triazin-Herbicid
in Verbindung mit einem für Herbicide verträglichen Ver_
dünnungsmittel oder Träger und/oder grenzflächenaktiven
Stoff.
18. Herbicide Zusammensetzung nach Anspruch 17, wobei das
Verhältnis (a) : (b) 2 : 1 bis 1 : 1000 G/G beträgt.
19. Herbicide Zusammensetzung nach Anspruch 17 oder 18, wobei
das Verhältnis (a) : (b) 1 : 3, 3 bis 1 : 60 G/G beträgt.
20. Produkt, das (a) ein 4-Benzoylisoxazol der in Anspruch 1
definierten Formel I und (b) ein Triazin-Herbicid in Form
eines Kombinationspräparates zur gleichzeitigen,
getrennten oder aufeinanderfolgenden Verwendung zur Bekämpfung
des Wachstums von Unkräutern auf einer Örtlichkeit
enthält.
21. Herbicide Zusammensetzung, die enthält:
(a) 5-Cyclopropyl-4-(2-methylsulfonyl-4-trifluormethyl)-
benzoylisoxazol und
(b) Atrazin, nämlich 6-Chlor-N²-ethyl-N&sup4;-isopropyl-1,3,5-
triazin-2,4-diamin,
in Verbindung mit einem für Herbicide verträglichen Ver-
dünnungsmittel oder Träger und/oder grenzflächenaktiven
Stoff.
22. Herbicide Zusammensetzung, die enthält:
(a) 5-Cyclopropyl-4-(2-methylsulfonyl-4-trifluormethyl)-
benzoylisoxazol und
(b) Metribuzin, nämlich
4-Amino-6-tert.-butyl-4,5-dihydro-3-methylthio-1,2,4-triazin-5(4H)-on,
in Verbindung mit einem für Herbicide verträglichen
Verdünnungsmittel oder Träger und/oder grenzflächenaktiven
Stoff.
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB939325284A GB9325284D0 (en) | 1993-12-10 | 1993-12-10 | Herbicidal compositions |
| PCT/EP1994/004052 WO1995015691A1 (en) | 1993-12-10 | 1994-12-06 | Herbicidal compositions |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69413059D1 DE69413059D1 (de) | 1998-10-08 |
| DE69413059T2 true DE69413059T2 (de) | 1999-02-18 |
Family
ID=10746392
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69413059T Expired - Fee Related DE69413059T2 (de) | 1993-12-10 | 1994-12-06 | Herbizide zusammensetzungen |
Country Status (19)
| Country | Link |
|---|---|
| EP (1) | EP0732876B1 (de) |
| CN (1) | CN1069488C (de) |
| AT (1) | ATE170364T1 (de) |
| AU (1) | AU678670B2 (de) |
| BG (1) | BG62592B1 (de) |
| BR (1) | BR9408196A (de) |
| CA (1) | CA2178214A1 (de) |
| CZ (1) | CZ286785B6 (de) |
| DE (1) | DE69413059T2 (de) |
| DK (1) | DK0732876T3 (de) |
| ES (1) | ES2120718T3 (de) |
| GB (2) | GB9325284D0 (de) |
| HU (1) | HU221269B1 (de) |
| PL (1) | PL178690B1 (de) |
| RO (1) | RO114938B1 (de) |
| RU (1) | RU2134966C1 (de) |
| SK (1) | SK282251B6 (de) |
| UA (1) | UA45329C2 (de) |
| WO (1) | WO1995015691A1 (de) |
Families Citing this family (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5962370A (en) * | 1993-12-10 | 1999-10-05 | Rhone-Poulenc Agriculture Ltd | Herbicidal compositions comprising a 4-benzoylisoxazole and a triazine herbicide |
| GB9523724D0 (en) * | 1995-11-20 | 1996-01-24 | Rhone Poulenc Agrochimie | New herbicidal compositions |
| ZA9610348B (en) * | 1995-12-20 | 1997-07-11 | Rhone Poulenc Agriculture | Herbicidal compositions |
| DE19614856A1 (de) * | 1996-04-16 | 1997-10-23 | Basf Ag | Herbizide heterocyclisch anellierte Benzoylisothiazole |
| DE19614858A1 (de) * | 1996-04-16 | 1997-10-23 | Basf Ag | Herbizide heterocyclisch substituierte Benzoylisothiazole |
| DE19614859A1 (de) * | 1996-04-16 | 1997-10-23 | Basf Ag | Herbizide Benzoylisothiazole |
| US6297198B1 (en) | 1996-05-14 | 2001-10-02 | Syngenta Participations Ag | Isoxazole derivatives and their use as herbicides |
| ZA984938B (en) * | 1997-06-10 | 1999-01-04 | Rhone Poulenc Agrochimie | Herbicidal mixtures |
| DE19950943A1 (de) | 1999-10-22 | 2001-05-17 | Aventis Cropscience Gmbh | Synergistische herbizide Mittel enthaltend Herbizide aus der Gruppe der Hemmstoffe der Hydroxyphenylpyruvat-Dioxygenase |
| TW200508221A (en) | 2003-06-13 | 2005-03-01 | Astrazeneca Ab | New azetidine compounds |
| WO2005053407A1 (en) * | 2003-12-01 | 2005-06-16 | Syngenta Participations Ag | Pesticidally active combinations |
| UA117816C2 (uk) * | 2012-11-06 | 2018-10-10 | Байєр Кропсайєнс Акцієнгезелльшафт | Гербіцидна комбінація для толерантних соєвих культур |
| CN108849954A (zh) * | 2018-07-31 | 2018-11-23 | 广西壮族自治区农业科学院植物保护研究所 | 一种三元除草组合物及其应用 |
Family Cites Families (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA1158058A (en) * | 1980-03-31 | 1983-12-06 | Eli Lilly And Company | Herbicidal composition formulation and method |
| GB9025469D0 (en) * | 1990-11-22 | 1991-01-09 | Rhone Poulenc Agriculture | New compositions of matter |
| GB8920519D0 (en) * | 1989-09-11 | 1989-10-25 | Rhone Poulenc Ltd | New compositions of matter |
| IL102674A (en) * | 1991-08-05 | 1996-11-14 | Rhone Poulenc Agriculture | History of 4-benzoyl isoxazole, the process for their preparation and herbicides containing the same |
| GB9116834D0 (en) * | 1991-08-05 | 1991-09-18 | Rhone Poulenc Agriculture | Compositions of new matter |
| US5334753A (en) * | 1992-03-12 | 1994-08-02 | Rhone-Poulenc Agriculture Ltd | Processes for preparing ortho-substituted benzoic acids |
-
1993
- 1993-12-10 GB GB939325284A patent/GB9325284D0/en active Pending
-
1994
- 1994-12-06 PL PL94314961A patent/PL178690B1/pl not_active IP Right Cessation
- 1994-12-06 BR BR9408196A patent/BR9408196A/pt not_active IP Right Cessation
- 1994-12-06 RU RU96115011A patent/RU2134966C1/ru not_active IP Right Cessation
- 1994-12-06 ES ES95904423T patent/ES2120718T3/es not_active Expired - Lifetime
- 1994-12-06 HU HU9601573A patent/HU221269B1/hu not_active IP Right Cessation
- 1994-12-06 UA UA96072763A patent/UA45329C2/uk unknown
- 1994-12-06 CA CA002178214A patent/CA2178214A1/en not_active Abandoned
- 1994-12-06 RO RO96-01192A patent/RO114938B1/ro unknown
- 1994-12-06 SK SK741-96A patent/SK282251B6/sk unknown
- 1994-12-06 DK DK95904423T patent/DK0732876T3/da active
- 1994-12-06 DE DE69413059T patent/DE69413059T2/de not_active Expired - Fee Related
- 1994-12-06 AT AT95904423T patent/ATE170364T1/de not_active IP Right Cessation
- 1994-12-06 AU AU13122/95A patent/AU678670B2/en not_active Ceased
- 1994-12-06 CN CN94194449A patent/CN1069488C/zh not_active Expired - Fee Related
- 1994-12-06 WO PCT/EP1994/004052 patent/WO1995015691A1/en active IP Right Grant
- 1994-12-06 EP EP95904423A patent/EP0732876B1/de not_active Expired - Lifetime
- 1994-12-06 CZ CZ19961674A patent/CZ286785B6/cs not_active IP Right Cessation
- 1994-12-09 GB GB9424851A patent/GB2284547B/en not_active Revoked
-
1996
- 1996-07-02 BG BG100691A patent/BG62592B1/bg unknown
Also Published As
| Publication number | Publication date |
|---|---|
| GB2284547B (en) | 1998-01-14 |
| DK0732876T3 (da) | 1998-11-16 |
| DE69413059D1 (de) | 1998-10-08 |
| GB9424851D0 (en) | 1995-02-08 |
| EP0732876B1 (de) | 1998-09-02 |
| CN1137221A (zh) | 1996-12-04 |
| BR9408196A (pt) | 1997-08-26 |
| GB2284547A (en) | 1995-06-14 |
| HU221269B1 (en) | 2002-09-28 |
| AU678670B2 (en) | 1997-06-05 |
| UA45329C2 (uk) | 2002-04-15 |
| WO1995015691A1 (en) | 1995-06-15 |
| RU2134966C1 (ru) | 1999-08-27 |
| PL314961A1 (en) | 1996-09-30 |
| EP0732876A1 (de) | 1996-09-25 |
| ATE170364T1 (de) | 1998-09-15 |
| AU1312295A (en) | 1995-06-27 |
| SK282251B6 (sk) | 2001-12-03 |
| RO114938B1 (ro) | 1999-09-30 |
| CA2178214A1 (en) | 1995-06-15 |
| CZ167496A3 (en) | 1996-10-16 |
| GB9325284D0 (en) | 1994-02-16 |
| CZ286785B6 (en) | 2000-07-12 |
| SK74196A3 (en) | 1996-11-06 |
| ES2120718T3 (es) | 1998-11-01 |
| PL178690B1 (pl) | 2000-06-30 |
| BG100691A (en) | 1997-09-30 |
| CN1069488C (zh) | 2001-08-15 |
| BG62592B1 (bg) | 2000-03-31 |
| HUT75583A (en) | 1997-05-28 |
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