DD282687A5 - Verfahren zur herstellung eines phenoxyphthalididderivates, herbizide zusammensetzung und verfahren und verwendung fuer die bekaempfung von unerwuenschtem pflanzenwuchs - Google Patents

Verfahren zur herstellung eines phenoxyphthalididderivates, herbizide zusammensetzung und verfahren und verwendung fuer die bekaempfung von unerwuenschtem pflanzenwuchs Download PDF

Info

Publication number: DD282687A5
Authority: DD; German Democratic Republic
Prior art keywords: group; compound; formula; atom; halogen atom
Prior art date: 1986-10-20

Application number

DD87308076A

Other languages

German (de)

English (en)

Inventor

Michael T Clark

Ian I Gilmore

Clive A Raven

Original Assignee

��@��@��@��@�K@�K@��@��@��@��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.)

1986-10-20

Filing date

1987-10-19

Publication date

1990-09-19

1987-10-19 Application filed by ��@��@��@��@�K@�K@��@��@��@��k�� filed Critical ��@��@��@��@�K@�K@��@��@��@��k��

1990-09-19 Publication of DD282687A5 publication Critical patent/DD282687A5/de

Links

239000000203 mixture Substances 0.000 title claims abstract description 37
230000002363 herbicidal effect Effects 0.000 title claims abstract description 19
238000000034 method Methods 0.000 title claims abstract description 18
238000002360 preparation method Methods 0.000 title claims abstract description 9
230000008635 plant growth Effects 0.000 title claims abstract description 6
-1 PHENOXYPHTHALIDIDE DERIVATIVE Chemical class 0.000 title description 16
150000001875 compounds Chemical class 0.000 claims abstract description 48
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 18
125000005843 halogen group Chemical group 0.000 claims abstract description 17
239000001257 hydrogen Substances 0.000 claims abstract description 13
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 11
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims abstract description 11
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 9
125000000217 alkyl group Chemical group 0.000 claims abstract description 8
229910052717 sulfur Inorganic materials 0.000 claims abstract description 8
125000001188 haloalkyl group Chemical group 0.000 claims abstract description 6
125000004434 sulfur atom Chemical group 0.000 claims abstract description 6
125000003342 alkenyl group Chemical group 0.000 claims abstract description 5
125000004093 cyano group Chemical group *C#N 0.000 claims abstract description 5
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims abstract description 4
125000000304 alkynyl group Chemical group 0.000 claims abstract description 4
229910052760 oxygen Inorganic materials 0.000 claims abstract description 4
239000001301 oxygen Substances 0.000 claims abstract description 4
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 7
229910052783 alkali metal Inorganic materials 0.000 claims description 6
150000001340 alkali metals Chemical group 0.000 claims description 5
125000004429 atom Chemical group 0.000 claims description 5
239000004009 herbicide Substances 0.000 claims description 5
125000004430 oxygen atom Chemical group O* 0.000 claims description 4
125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 3
125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
229910052751 metal Inorganic materials 0.000 claims description 2
239000002184 metal Substances 0.000 claims description 2
125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
125000001424 substituent group Chemical group 0.000 claims 3
229930194542 Keto Natural products 0.000 claims 1
125000000468 ketone group Chemical group 0.000 claims 1
BGOZIOZETMDSAQ-UHFFFAOYSA-N 3-phenoxy-3h-2-benzofuran-1-one Chemical class C12=CC=CC=C2C(=O)OC1OC1=CC=CC=C1 BGOZIOZETMDSAQ-UHFFFAOYSA-N 0.000 abstract 2
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 18
238000012360 testing method Methods 0.000 description 18
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
239000004480 active ingredient Substances 0.000 description 12
239000002689 soil Substances 0.000 description 12
241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 11
235000021536 Sugar beet Nutrition 0.000 description 11
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
241000196324 Embryophyta Species 0.000 description 9
238000006243 chemical reaction Methods 0.000 description 9
239000007787 solid Substances 0.000 description 8
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
241000209140 Triticum Species 0.000 description 7
235000021307 Triticum Nutrition 0.000 description 7
239000000243 solution Substances 0.000 description 7
239000004094 surface-active agent Substances 0.000 description 7
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 6
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
229910052799 carbon Inorganic materials 0.000 description 6
125000004432 carbon atom Chemical group C* 0.000 description 6
239000007818 Grignard reagent Substances 0.000 description 5
229910052801 chlorine Inorganic materials 0.000 description 5
238000002474 experimental method Methods 0.000 description 5
150000004795 grignard reagents Chemical class 0.000 description 5
229910052736 halogen Inorganic materials 0.000 description 5
150000002367 halogens Chemical class 0.000 description 5
239000007788 liquid Substances 0.000 description 5
229910052757 nitrogen Inorganic materials 0.000 description 5
239000003921 oil Substances 0.000 description 5
239000000843 powder Substances 0.000 description 5
239000002904 solvent Substances 0.000 description 5
WNZQDUSMALZDQF-UHFFFAOYSA-N 2-benzofuran-1(3H)-one Chemical compound C1=CC=C2C(=O)OCC2=C1 WNZQDUSMALZDQF-UHFFFAOYSA-N 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
239000000654 additive Substances 0.000 description 4
238000004458 analytical method Methods 0.000 description 4
239000000969 carrier Substances 0.000 description 4
239000002270 dispersing agent Substances 0.000 description 4
239000000839 emulsion Substances 0.000 description 4
238000009472 formulation Methods 0.000 description 4
239000008187 granular material Substances 0.000 description 4
239000000047 product Substances 0.000 description 4
239000007921 spray Substances 0.000 description 4
239000003381 stabilizer Substances 0.000 description 4
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 4
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
FYYHWMGAXLPEAU-UHFFFAOYSA-N Magnesium Chemical compound [Mg] FYYHWMGAXLPEAU-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 3
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 3
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
244000225942 Viola tricolor Species 0.000 description 3
125000003545 alkoxy group Chemical group 0.000 description 3
125000003118 aryl group Chemical group 0.000 description 3
235000013339 cereals Nutrition 0.000 description 3
125000001309 chloro group Chemical group Cl* 0.000 description 3
238000004587 chromatography analysis Methods 0.000 description 3
239000003480 eluent Substances 0.000 description 3
239000000377 silicon dioxide Substances 0.000 description 3
239000011734 sodium Substances 0.000 description 3
229910052708 sodium Inorganic materials 0.000 description 3
229910052938 sodium sulfate Inorganic materials 0.000 description 3
235000011152 sodium sulphate Nutrition 0.000 description 3
239000000126 substance Substances 0.000 description 3
125000000547 substituted alkyl group Chemical group 0.000 description 3
244000075850 Avena orientalis Species 0.000 description 2
235000007319 Avena orientalis Nutrition 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
244000068988 Glycine max Species 0.000 description 2
235000010469 Glycine max Nutrition 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
240000006240 Linum usitatissimum Species 0.000 description 2
235000004431 Linum usitatissimum Nutrition 0.000 description 2
240000007594 Oryza sativa Species 0.000 description 2
235000007164 Oryza sativa Nutrition 0.000 description 2
LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 2
PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
125000002252 acyl group Chemical group 0.000 description 2
239000000853 adhesive Substances 0.000 description 2
230000001070 adhesive effect Effects 0.000 description 2
229910052784 alkaline earth metal Inorganic materials 0.000 description 2
125000004453 alkoxycarbonyl group Chemical group 0.000 description 2
HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 2
229910052782 aluminium Inorganic materials 0.000 description 2
125000003277 amino group Chemical group 0.000 description 2
125000003710 aryl alkyl group Chemical group 0.000 description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 2
YKYOUMDCQGMQQO-UHFFFAOYSA-L cadmium dichloride Chemical compound Cl[Cd]Cl YKYOUMDCQGMQQO-UHFFFAOYSA-L 0.000 description 2
OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 2
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
239000000460 chlorine Substances 0.000 description 2
239000004927 clay Substances 0.000 description 2
239000012141 concentrate Substances 0.000 description 2
239000007859 condensation product Substances 0.000 description 2
229920001577 copolymer Polymers 0.000 description 2
238000005260 corrosion Methods 0.000 description 2
230000007797 corrosion Effects 0.000 description 2
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
235000014113 dietary fatty acids Nutrition 0.000 description 2
230000000694 effects Effects 0.000 description 2
239000004495 emulsifiable concentrate Substances 0.000 description 2
239000000194 fatty acid Substances 0.000 description 2
229930195729 fatty acid Natural products 0.000 description 2
235000004426 flaxseed Nutrition 0.000 description 2
230000012010 growth Effects 0.000 description 2
238000003898 horticulture Methods 0.000 description 2
150000002430 hydrocarbons Chemical group 0.000 description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
238000005470 impregnation Methods 0.000 description 2
239000003112 inhibitor Substances 0.000 description 2
239000012669 liquid formulation Substances 0.000 description 2
229920000642 polymer Polymers 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
150000004760 silicates Chemical class 0.000 description 2
159000000000 sodium salts Chemical class 0.000 description 2
238000005507 spraying Methods 0.000 description 2
239000007858 starting material Substances 0.000 description 2
239000011593 sulfur Substances 0.000 description 2
239000004546 suspension concentrate Substances 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
KQZLRWGGWXJPOS-NLFPWZOASA-N 1-[(1R)-1-(2,4-dichlorophenyl)ethyl]-6-[(4S,5R)-4-[(2S)-2-(hydroxymethyl)pyrrolidin-1-yl]-5-methylcyclohexen-1-yl]pyrazolo[3,4-b]pyrazine-3-carbonitrile Chemical compound ClC1=C(C=CC(=C1)Cl)[C@@H](C)N1N=C(C=2C1=NC(=CN=2)C1=CC[C@@H]([C@@H](C1)C)N1[C@@H](CCC1)CO)C#N KQZLRWGGWXJPOS-NLFPWZOASA-N 0.000 description 1
HRMCXDSWURAYFR-UHFFFAOYSA-N 3-phenoxyphthalic acid Chemical class OC(=O)C1=CC=CC(OC=2C=CC=CC=2)=C1C(O)=O HRMCXDSWURAYFR-UHFFFAOYSA-N 0.000 description 1
OOOJECGTOMCHON-UHFFFAOYSA-N 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-benzofuran-1,3-dione Chemical compound ClC1=CC(C(F)(F)F)=CC=C1OC1=CC=C(C(=O)OC2=O)C2=C1 OOOJECGTOMCHON-UHFFFAOYSA-N 0.000 description 1
GGHPJWBRCUWCLV-UHFFFAOYSA-N 5-[2-chloro-4-(trifluoromethyl)phenoxy]-3,3-diethyl-2-benzofuran-1-one Chemical compound C1=C2C(CC)(CC)OC(=O)C2=CC=C1OC1=CC=C(C(F)(F)F)C=C1Cl GGHPJWBRCUWCLV-UHFFFAOYSA-N 0.000 description 1
GUVVEYJOVRMQDU-UHFFFAOYSA-N 5-[2-chloro-4-(trifluoromethyl)phenoxy]-3h-2-benzofuran-1-one Chemical compound ClC1=CC(C(F)(F)F)=CC=C1OC1=CC=C(C(=O)OC2)C2=C1 GUVVEYJOVRMQDU-UHFFFAOYSA-N 0.000 description 1
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
241000335053 Beta vulgaris Species 0.000 description 1
235000021533 Beta vulgaris Nutrition 0.000 description 1
244000056139 Brassica cretica Species 0.000 description 1
235000003351 Brassica cretica Nutrition 0.000 description 1
240000002791 Brassica napus Species 0.000 description 1
235000006008 Brassica napus var napus Nutrition 0.000 description 1
235000003343 Brassica rupestris Nutrition 0.000 description 1
OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
235000007866 Chamaemelum nobile Nutrition 0.000 description 1
239000004971 Cross linker Substances 0.000 description 1
FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
240000003173 Drymaria cordata Species 0.000 description 1
OTMSDBZUPAUEDD-UHFFFAOYSA-N Ethane Chemical compound CC OTMSDBZUPAUEDD-UHFFFAOYSA-N 0.000 description 1
241000287828 Gallus gallus Species 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
244000042664 Matricaria chamomilla Species 0.000 description 1
235000007232 Matricaria chamomilla Nutrition 0.000 description 1
NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
240000001307 Myosotis scorpioides Species 0.000 description 1
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
231100000674 Phytotoxicity Toxicity 0.000 description 1
244000292697 Polygonum aviculare Species 0.000 description 1
235000006386 Polygonum aviculare Nutrition 0.000 description 1
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
229930006000 Sucrose Natural products 0.000 description 1
240000008042 Zea mays Species 0.000 description 1
235000007244 Zea mays Nutrition 0.000 description 1
239000002253 acid Substances 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
239000013543 active substance Substances 0.000 description 1
125000004423 acyloxy group Chemical group 0.000 description 1
238000005054 agglomeration Methods 0.000 description 1
230000002776 aggregation Effects 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
150000001335 aliphatic alkanes Chemical class 0.000 description 1
125000001931 aliphatic group Chemical group 0.000 description 1
239000003513 alkali Substances 0.000 description 1
150000001342 alkaline earth metals Chemical class 0.000 description 1
150000001336 alkenes Chemical class 0.000 description 1
125000003302 alkenyloxy group Chemical group 0.000 description 1
150000001345 alkine derivatives Chemical class 0.000 description 1
150000004703 alkoxides Chemical class 0.000 description 1
125000005085 alkoxycarbonylalkoxy group Chemical group 0.000 description 1
125000005078 alkoxycarbonylalkyl group Chemical group 0.000 description 1
125000002877 alkyl aryl group Chemical group 0.000 description 1
150000008051 alkyl sulfates Chemical class 0.000 description 1
125000004414 alkyl thio group Chemical group 0.000 description 1
125000005133 alkynyloxy group Chemical group 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
BFNBIHQBYMNNAN-UHFFFAOYSA-N ammonium sulfate Chemical compound N.N.OS(O)(=O)=O BFNBIHQBYMNNAN-UHFFFAOYSA-N 0.000 description 1
229910052921 ammonium sulfate Inorganic materials 0.000 description 1
235000011130 ammonium sulphate Nutrition 0.000 description 1
230000002528 anti-freeze Effects 0.000 description 1
239000002518 antifoaming agent Substances 0.000 description 1
239000010426 asphalt Substances 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
238000012925 biological evaluation Methods 0.000 description 1
230000015572 biosynthetic process Effects 0.000 description 1
235000010290 biphenyl Nutrition 0.000 description 1
239000004305 biphenyl Substances 0.000 description 1
125000006267 biphenyl group Chemical group 0.000 description 1
QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
RDHPKYGYEGBMSE-UHFFFAOYSA-N bromoethane Chemical compound CCBr RDHPKYGYEGBMSE-UHFFFAOYSA-N 0.000 description 1
239000006227 byproduct Substances 0.000 description 1
239000011575 calcium Substances 0.000 description 1
229910052791 calcium Inorganic materials 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
YYRMJZQKEFZXMX-UHFFFAOYSA-N calcium;phosphoric acid Chemical class [Ca+2].OP(O)(O)=O.OP(O)(O)=O YYRMJZQKEFZXMX-UHFFFAOYSA-N 0.000 description 1
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
239000004359 castor oil Substances 0.000 description 1
235000019438 castor oil Nutrition 0.000 description 1
239000003153 chemical reaction reagent Substances 0.000 description 1
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
239000000084 colloidal system Substances 0.000 description 1
229940125877 compound 31 Drugs 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
239000006184 cosolvent Substances 0.000 description 1
125000000000 cycloalkoxy group Chemical group 0.000 description 1
125000000753 cycloalkyl group Chemical group 0.000 description 1
229930007927 cymene Natural products 0.000 description 1
230000034994 death Effects 0.000 description 1
231100000517 death Toxicity 0.000 description 1
238000007865 diluting Methods 0.000 description 1
238000003113 dilution method Methods 0.000 description 1
USIUVYZYUHIAEV-UHFFFAOYSA-N diphenyl ether Chemical class C=1C=CC=CC=1OC1=CC=CC=C1 USIUVYZYUHIAEV-UHFFFAOYSA-N 0.000 description 1
POLCUAVZOMRGSN-UHFFFAOYSA-N dipropyl ether Chemical compound CCCOCCC POLCUAVZOMRGSN-UHFFFAOYSA-N 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
YRIUSKIDOIARQF-UHFFFAOYSA-N dodecyl benzenesulfonate Chemical compound CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 YRIUSKIDOIARQF-UHFFFAOYSA-N 0.000 description 1
MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical compound CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 description 1
229940043264 dodecyl sulfate Drugs 0.000 description 1
229940071161 dodecylbenzenesulfonate Drugs 0.000 description 1
239000000428 dust Substances 0.000 description 1
239000003995 emulsifying agent Substances 0.000 description 1
230000001804 emulsifying effect Effects 0.000 description 1
239000012259 ether extract Substances 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000000284 extract Substances 0.000 description 1
239000004744 fabric Substances 0.000 description 1
150000004665 fatty acids Chemical class 0.000 description 1
150000002191 fatty alcohols Chemical class 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
239000003337 fertilizer Substances 0.000 description 1
230000009969 flowable effect Effects 0.000 description 1
230000000855 fungicidal effect Effects 0.000 description 1
239000007789 gas Substances 0.000 description 1
ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
125000000623 heterocyclic group Chemical group 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
238000010348 incorporation Methods 0.000 description 1
239000004615 ingredient Substances 0.000 description 1
229910052740 iodine Inorganic materials 0.000 description 1
239000003350 kerosene Substances 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000011777 magnesium Substances 0.000 description 1
229910052749 magnesium Inorganic materials 0.000 description 1
239000000391 magnesium silicate Substances 0.000 description 1
235000012243 magnesium silicates Nutrition 0.000 description 1
RMGJCSHZTFKPNO-UHFFFAOYSA-M magnesium;ethene;bromide Chemical compound [Mg+2].[Br-].[CH-]=C RMGJCSHZTFKPNO-UHFFFAOYSA-M 0.000 description 1
DQEUYIQDSMINEY-UHFFFAOYSA-M magnesium;prop-1-ene;bromide Chemical compound [Mg+2].[Br-].[CH2-]C=C DQEUYIQDSMINEY-UHFFFAOYSA-M 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
239000010445 mica Substances 0.000 description 1
229910052618 mica group Inorganic materials 0.000 description 1
239000003607 modifier Substances 0.000 description 1
VYQNWZOUAUKGHI-UHFFFAOYSA-N monobenzone Chemical compound C1=CC(O)=CC=C1OCC1=CC=CC=C1 VYQNWZOUAUKGHI-UHFFFAOYSA-N 0.000 description 1
229910052901 montmorillonite Inorganic materials 0.000 description 1
235000010460 mustard Nutrition 0.000 description 1
239000000025 natural resin Substances 0.000 description 1
229920002113 octoxynol Polymers 0.000 description 1
239000003960 organic solvent Substances 0.000 description 1
150000002901 organomagnesium compounds Chemical class 0.000 description 1
125000002734 organomagnesium group Chemical group 0.000 description 1
125000002524 organometallic group Chemical group 0.000 description 1
150000002926 oxygen Chemical class 0.000 description 1
HFPZCAJZSCWRBC-UHFFFAOYSA-N p-cymene Chemical compound CC(C)C1=CC=C(C)C=C1 HFPZCAJZSCWRBC-UHFFFAOYSA-N 0.000 description 1
230000035515 penetration Effects 0.000 description 1
WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
239000003208 petroleum Substances 0.000 description 1
ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
229910052698 phosphorus Inorganic materials 0.000 description 1
239000011574 phosphorus Substances 0.000 description 1
239000004800 polyvinyl chloride Substances 0.000 description 1
229920000915 polyvinyl chloride Polymers 0.000 description 1
238000001556 precipitation Methods 0.000 description 1
230000001681 protective effect Effects 0.000 description 1
238000010992 reflux Methods 0.000 description 1
239000011347 resin Substances 0.000 description 1
229920005989 resin Polymers 0.000 description 1
235000009566 rice Nutrition 0.000 description 1
239000011435 rock Substances 0.000 description 1
LIVNPJMFVYWSIS-UHFFFAOYSA-N silicon monoxide Chemical class [Si-]#[O+] LIVNPJMFVYWSIS-UHFFFAOYSA-N 0.000 description 1
229910052814 silicon oxide Inorganic materials 0.000 description 1
238000002791 soaking Methods 0.000 description 1
239000000600 sorbitol Substances 0.000 description 1
241000894007 species Species 0.000 description 1
238000003756 stirring Methods 0.000 description 1
238000003860 storage Methods 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical class [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 1
150000003871 sulfonates Chemical class 0.000 description 1
150000003459 sulfonic acid esters Chemical class 0.000 description 1
150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
239000002426 superphosphate Substances 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
239000000725 suspension Substances 0.000 description 1
229920003002 synthetic resin Polymers 0.000 description 1
239000000057 synthetic resin Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
229950011008 tetrachloroethylene Drugs 0.000 description 1
239000013008 thixotropic agent Substances 0.000 description 1
GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 1
238000007514 turning Methods 0.000 description 1
229920002554 vinyl polymer Polymers 0.000 description 1
239000001993 wax Substances 0.000 description 1
230000003442 weekly effect Effects 0.000 description 1
239000000080 wetting agent Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/87—Benzo [c] furans; Hydrogenated benzo [c] furans
- 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
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
- A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
- A01N43/12—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings condensed with a carbocyclic ring
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
- C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
- C07D307/87—Benzo [c] furans; Hydrogenated benzo [c] furans
- C07D307/88—Benzo [c] furans; Hydrogenated benzo [c] furans with one oxygen atom directly attached in position 1 or 3

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
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)
Indole Compounds (AREA)
Organic Insulating Materials (AREA)
Acyclic And Carbocyclic Compounds In Medicinal Compositions (AREA)
Furan Compounds (AREA)

DD87308076A 1986-10-20 1987-10-19 Verfahren zur herstellung eines phenoxyphthalididderivates, herbizide zusammensetzung und verfahren und verwendung fuer die bekaempfung von unerwuenschtem pflanzenwuchs DD282687A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
GB868625106A GB8625106D0 (en)	1986-10-20	1986-10-20	Diphenyl ether herbicides

Publications (1)

Publication Number	Publication Date
DD282687A5 true DD282687A5 (de)	1990-09-19

Family

ID=10606033

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD87308076A DD282687A5 (de)	1986-10-20	1987-10-19	Verfahren zur herstellung eines phenoxyphthalididderivates, herbizide zusammensetzung und verfahren und verwendung fuer die bekaempfung von unerwuenschtem pflanzenwuchs

Country Status (26)

Country	Link
EP (1)	EP0265020B1 (fr)
JP (1)	JPS63104972A (fr)
KR (1)	KR880005115A (fr)
CN (1)	CN1017997B (fr)
AT (1)	ATE56003T1 (fr)
AU (1)	AU606890B2 (fr)
BR (1)	BR8705577A (fr)
CA (1)	CA1327809C (fr)
DD (1)	DD282687A5 (fr)
DE (1)	DE3764603D1 (fr)
DK (1)	DK166495B1 (fr)
ES (1)	ES2017493B3 (fr)
FI (1)	FI874585L (fr)
GB (1)	GB8625106D0 (fr)
GR (1)	GR3000959T3 (fr)
HU (1)	HUT45042A (fr)
IE (1)	IE872806L (fr)
IL (1)	IL84200A0 (fr)
MA (1)	MA21087A1 (fr)
NZ (1)	NZ222208A (fr)
OA (1)	OA08767A (fr)
PH (1)	PH24996A (fr)
PT (1)	PT85945A (fr)
TR (1)	TR23097A (fr)
ZA (1)	ZA877827B (fr)
ZW (1)	ZW18987A1 (fr)

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB8522528D0 (en) *	1985-09-11	1985-10-16	Shell Int Research	Diphenyl ether herbicides
GB8720509D0 (en) *	1987-09-01	1987-10-07	Shell Int Research	Diphenyl ether herbicides
GB8722968D0 (en) *	1987-09-30	1987-11-04	Shell Int Research	Preparing diphenyl ethers
IT202000021232A1 (it) *	2020-09-08	2022-03-08	Lamberti Spa	Metodo per migliorare le prestazioni di sostanze attive sistemiche e di inoculanti microbici

Family Cites Families (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0145078B1 (fr) *	1983-12-02	1988-10-12	Shell Internationale Researchmaatschappij B.V.	Diphényl éthers herbicides
GB8720509D0 (en) *	1987-09-01	1987-10-07	Shell Int Research	Diphenyl ether herbicides

1986
- 1986-10-20 GB GB868625106A patent/GB8625106D0/en active Pending
1987
- 1987-09-25 CA CA000547857A patent/CA1327809C/fr not_active Expired - Fee Related
- 1987-10-17 KR KR870011582A patent/KR880005115A/ko not_active Ceased
- 1987-10-19 ES ES87202009T patent/ES2017493B3/es not_active Expired - Lifetime
- 1987-10-19 IE IE872806A patent/IE872806L/xx unknown
- 1987-10-19 DE DE8787202009T patent/DE3764603D1/de not_active Expired - Lifetime
- 1987-10-19 AT AT87202009T patent/ATE56003T1/de not_active IP Right Cessation
- 1987-10-19 AU AU79883/87A patent/AU606890B2/en not_active Ceased
- 1987-10-19 NZ NZ222208A patent/NZ222208A/en unknown
- 1987-10-19 PH PH35954A patent/PH24996A/en unknown
- 1987-10-19 EP EP87202009A patent/EP0265020B1/fr not_active Expired - Lifetime
- 1987-10-19 FI FI874585A patent/FI874585L/fi not_active IP Right Cessation
- 1987-10-19 ZW ZW189/87A patent/ZW18987A1/xx unknown
- 1987-10-19 HU HU874682A patent/HUT45042A/hu unknown
- 1987-10-19 IL IL84200A patent/IL84200A0/xx unknown
- 1987-10-19 JP JP62261941A patent/JPS63104972A/ja active Pending
- 1987-10-19 MA MA21328A patent/MA21087A1/fr unknown
- 1987-10-19 CN CN87106953A patent/CN1017997B/zh not_active Expired
- 1987-10-19 DK DK546387A patent/DK166495B1/da not_active IP Right Cessation
- 1987-10-19 OA OA59212A patent/OA08767A/xx unknown
- 1987-10-19 ZA ZA877827A patent/ZA877827B/xx unknown
- 1987-10-19 TR TR706/87A patent/TR23097A/xx unknown
- 1987-10-19 PT PT85945A patent/PT85945A/pt unknown
- 1987-10-19 BR BR8705577A patent/BR8705577A/pt active Search and Examination
- 1987-10-19 DD DD87308076A patent/DD282687A5/de not_active IP Right Cessation
1990
- 1990-10-19 GR GR90400783T patent/GR3000959T3/el unknown

Also Published As

Publication number	Publication date
FI874585A7 (fi)	1988-04-21
CN87106953A (zh)	1988-05-04
FI874585L (fi)	1988-04-21
JPS63104972A (ja)	1988-05-10
IE872806L (en)	1988-04-20
CA1327809C (fr)	1994-03-15
HUT45042A (en)	1988-05-30
GR3000959T3 (en)	1991-12-10
IL84200A0 (en)	1988-03-31
KR880005115A (ko)	1988-06-28
MA21087A1 (fr)	1988-07-01
PT85945A (en)	1987-11-01
EP0265020B1 (fr)	1990-08-29
TR23097A (tr)	1989-03-15
NZ222208A (en)	1990-12-21
GB8625106D0 (en)	1986-11-26
BR8705577A (pt)	1988-05-24
AU606890B2 (en)	1991-02-21
OA08767A (en)	1989-03-31
ATE56003T1 (de)	1990-09-15
ZW18987A1 (en)	1988-01-20
DK166495B1 (da)	1993-06-01
ZA877827B (en)	1988-04-22
AU7988387A (en)	1988-04-21
CN1017997B (zh)	1992-08-26
DK546387A (da)	1988-04-21
FI874585A0 (fi)	1987-10-19
ES2017493B3 (es)	1991-02-16
EP0265020A1 (fr)	1988-04-27
DK546387D0 (da)	1987-10-19
PH24996A (en)	1990-12-26
DE3764603D1 (de)	1990-10-04

Legal Events

Date	Code	Title	Description
1995-02-16	ENJ	Ceased due to non-payment of renewal fee
1995-03-02	ENJ	Ceased due to non-payment of renewal fee

Publication	Publication Date	Title
DE2822304C3 (de)	1981-02-05	Substituierte Cyclohexan-13-dion-Derivate, Herstellungsverfahren und herbizides Mittel
CH644371A5 (de)	1984-07-31	In 2- und 4-stellung disubstituierte 5-thiazolcarbonsaeuren und deren funktionelle derivate.
DE3123018C2 (de)	1984-06-20	Substituierte Cyclohexan-1,3-dion-Derivate, Verfahren zu deren Herstellung und herbicide Mittel
DD148289A5 (de)	1981-05-20	Herbizide zusammensetzungen und verfahren zur bekaempfung unerwuenschten pflanzenwuchses
DE1039304B (de)	1958-09-18	Unkrautbekaempfungsmittel
DE2101938C2 (de)	1983-05-11	3-[2-Chlor-4-(3,3-dimethylureido)-phenyl]-5-tert.-butyl-1,3,4-oxadiazolon-(2), seine Herstellung und herbicide Zusammensetzungen, die es enthalten
DD149452A5 (de)	1981-07-15	Fungizide zusammensetzung
DD282687A5 (de)	1990-09-19	Verfahren zur herstellung eines phenoxyphthalididderivates, herbizide zusammensetzung und verfahren und verwendung fuer die bekaempfung von unerwuenschtem pflanzenwuchs
DE2732115A1 (de)	1978-01-19	Oxadiazinderivate, verfahren zu ihrer herstellung und solche verbindungen enthaltende insektizide
EP0153601B1 (fr)	1987-04-01	Dérivés d'alcoxyaminosulfonyle-2-benzènesulfonylurées
DE2155391A1 (de)	1972-05-10	l-Hydrocarbyldithio-3-arylharnstoffe und dieselben enthaltende Herbizide
CH619113A5 (en)	1980-09-15	Herbicidal composition
DE2524578A1 (de)	1975-12-11	Barbitursaeurederivate, verfahren zu ihrer herstellung und ihre verwendung als herbizide
DE1944525C3 (de)	1979-10-04	Anilinoalkanohydroxamsäureverbindungen, Verfahren zu ihrer Herstellung und ihre Verwendung als herbicide Mittel
EP0098972A2 (fr)	1984-01-25	Dérivés de 5-(4' ureido)-phénoxy benzisothiazole, procédé pour les préparer et leur utilisation comme herbicides
DE2323197C2 (de)	1984-02-02	Verfahren zur Herstellung von 2,5-Dimethyl-3-furancarboxamiden, bestimmte dieser 2,5-Dimethyl-3-furancarboxamide als solche und fungizide Mittel, die die letzteren enthalten
DE2302029C2 (de)	1985-07-18	N,N-disubstituierte &alpha;-Aminothiopropionsäureester, Verfahren zu ihrer Herstellung und ihre Verwendung
DD236868A5 (de)	1986-06-25	Mittel zum protahieren der wirkungsdauer und zur erhoehung der selektivitaet von herbiziden zusammensetzungen
DD262025A5 (de)	1988-11-16	Imidazol-derivate
DE2061051A1 (de)	1971-12-09	Thiocarbamidsaeureester und deren Verwendung als Pestizid
DE2556938C2 (de)	1985-05-30	N,N-disubstituierte Alaninderivate, Verfahren zu ihrer Herstellung und ihre Verwendung als herbicide Mittel
DD209566A5 (de)	1984-05-16	Fungizide zusammensetzungen
DE2008601A1 (de)	1970-11-12	Anilinoalkylthiocarboxamidverbindungen, Verfahren zu ihrer Herstellung und ihre Verwendung als herbicide Mittel
DE2548898A1 (de)	1976-05-06	Benzothiazolderivate, verfahren zu ihrer herstellung und ihre verwendung als herbizide
DD215001A5 (de)	1984-10-31	Pestizide zusammensetzung