IL44031A - Synergistic herbicidal preparations containing an alpha-phenoxyalkanoic acid oxime ester - Google Patents
Synergistic herbicidal preparations containing an alpha-phenoxyalkanoic acid oxime esterInfo
- Publication number
- IL44031A IL44031A IL44031A IL4403174A IL44031A IL 44031 A IL44031 A IL 44031A IL 44031 A IL44031 A IL 44031A IL 4403174 A IL4403174 A IL 4403174A IL 44031 A IL44031 A IL 44031A
- Authority
- IL
- Israel
- Prior art keywords
- ester
- methyl
- phenyl
- preparation
- oxime
- Prior art date
Links
- -1 oxime ester Chemical class 0.000 title claims abstract description 66
- 238000002360 preparation method Methods 0.000 title claims abstract description 56
- 230000002363 herbicidal effect Effects 0.000 title claims abstract description 34
- 239000002253 acid Substances 0.000 title claims description 33
- 230000002195 synergetic effect Effects 0.000 title abstract description 10
- 150000001875 compounds Chemical class 0.000 claims abstract description 49
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 claims abstract description 30
- 241000196324 Embryophyta Species 0.000 claims abstract description 16
- 239000004094 surface-active agent Substances 0.000 claims abstract description 8
- JUUJGJKBAHKKSW-UHFFFAOYSA-N (2-cyanophenyl) hydrogen carbonate Chemical class OC(=O)OC1=CC=CC=C1C#N JUUJGJKBAHKKSW-UHFFFAOYSA-N 0.000 claims abstract description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 42
- 125000000217 alkyl group Chemical group 0.000 claims description 37
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims description 34
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 claims description 21
- 239000004202 carbamide Substances 0.000 claims description 21
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims description 20
- 238000000034 method Methods 0.000 claims description 20
- 125000004432 carbon atom Chemical group C* 0.000 claims description 15
- 125000003545 alkoxy group Chemical group 0.000 claims description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
- 125000005843 halogen group Chemical group 0.000 claims description 12
- 125000001424 substituent group Chemical group 0.000 claims description 11
- 125000003118 aryl group Chemical group 0.000 claims description 8
- 229910052799 carbon Inorganic materials 0.000 claims description 7
- 239000000839 emulsion Substances 0.000 claims description 7
- MZHCENGPTKEIGP-UHFFFAOYSA-N 2-(2,4-dichlorophenoxy)propanoic acid Chemical compound OC(=O)C(C)OC1=CC=C(Cl)C=C1Cl MZHCENGPTKEIGP-UHFFFAOYSA-N 0.000 claims description 6
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Substances CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 claims description 6
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 6
- 125000001931 aliphatic group Chemical group 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 6
- 125000001188 haloalkyl group Chemical group 0.000 claims description 6
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- 229910052736 halogen Inorganic materials 0.000 claims description 5
- 150000002367 halogens Chemical class 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- 125000004429 atom Chemical group 0.000 claims description 4
- 150000002923 oximes Chemical class 0.000 claims description 4
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 125000004414 alkyl thio group Chemical group 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- WWXKYLIBOBFNSP-UHFFFAOYSA-N CC(=O)C.ClC1=C(OCC(=O)O)C=CC(=C1)Cl Chemical compound CC(=O)C.ClC1=C(OCC(=O)O)C=CC(=C1)Cl WWXKYLIBOBFNSP-UHFFFAOYSA-N 0.000 claims description 2
- WHKUVVPPKQRRBV-UHFFFAOYSA-N Trasan Chemical compound CC1=CC(Cl)=CC=C1OCC(O)=O WHKUVVPPKQRRBV-UHFFFAOYSA-N 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 claims description 2
- 239000012965 benzophenone Substances 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 4
- NMGFRGWSRHOQOP-UHFFFAOYSA-N carbamic acid;urea Chemical compound NC(N)=O.NC(O)=O NMGFRGWSRHOQOP-UHFFFAOYSA-N 0.000 claims 2
- CLDLHEOVBBBZAF-UHFFFAOYSA-N cyano phenyl carbonate Chemical compound N#COC(=O)OC1=CC=CC=C1 CLDLHEOVBBBZAF-UHFFFAOYSA-N 0.000 claims 2
- SUBDBMMJDZJVOS-UHFFFAOYSA-N 5-methoxy-2-{[(4-methoxy-3,5-dimethylpyridin-2-yl)methyl]sulfinyl}-1H-benzimidazole Chemical compound N=1C2=CC(OC)=CC=C2NC=1S(=O)CC1=NC=C(C)C(OC)=C1C SUBDBMMJDZJVOS-UHFFFAOYSA-N 0.000 claims 1
- OOYGSFOGFJDDHP-KMCOLRRFSA-N kanamycin A sulfate Chemical group OS(O)(=O)=O.O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CN)O[C@@H]1O[C@H]1[C@H](O)[C@@H](O[C@@H]2[C@@H]([C@@H](N)[C@H](O)[C@@H](CO)O2)O)[C@H](N)C[C@@H]1N OOYGSFOGFJDDHP-KMCOLRRFSA-N 0.000 claims 1
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 claims 1
- 239000004009 herbicide Substances 0.000 abstract description 8
- 239000003795 chemical substances by application Substances 0.000 abstract description 7
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 30
- 239000000203 mixture Substances 0.000 description 14
- 239000005631 2,4-Dichlorophenoxyacetic acid Substances 0.000 description 10
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 10
- 239000013543 active substance Substances 0.000 description 9
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 9
- 150000002430 hydrocarbons Chemical group 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 229920000151 polyglycol Polymers 0.000 description 7
- 239000010695 polyglycol Substances 0.000 description 7
- 239000003559 2,4,5-trichlorophenoxyacetic acid Substances 0.000 description 6
- 150000002170 ethers Chemical class 0.000 description 6
- 125000000066 S-methyl group Chemical group [H]C([H])([H])S* 0.000 description 5
- GNVMUORYQLCPJZ-UHFFFAOYSA-M Thiocarbamate Chemical compound NC([S-])=O GNVMUORYQLCPJZ-UHFFFAOYSA-M 0.000 description 5
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 244000042664 Matricaria chamomilla Species 0.000 description 4
- 235000007232 Matricaria chamomilla Nutrition 0.000 description 4
- 239000012141 concentrate Substances 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 4
- ALSTYHKOOCGGFT-KTKRTIGZSA-N (9Z)-octadecen-1-ol Chemical compound CCCCCCCC\C=C/CCCCCCCCO ALSTYHKOOCGGFT-KTKRTIGZSA-N 0.000 description 3
- GQMMRLBWXCGBEV-VMPITWQZSA-N (ne)-n-[(3-nitrophenyl)methylidene]hydroxylamine Chemical compound O\N=C\C1=CC=CC([N+]([O-])=O)=C1 GQMMRLBWXCGBEV-VMPITWQZSA-N 0.000 description 3
- WNTGYJSOUMFZEP-UHFFFAOYSA-N 2-(4-chloro-2-methylphenoxy)propanoic acid Chemical compound OC(=O)C(C)OC1=CC=C(Cl)C=C1C WNTGYJSOUMFZEP-UHFFFAOYSA-N 0.000 description 3
- YRBHEEAQCPNPLY-UHFFFAOYSA-N 3,5-dibromo-4-(cyanomethoxy)benzonitrile Chemical compound BrC1=C(OCC#N)C(=CC(=C1)C#N)Br YRBHEEAQCPNPLY-UHFFFAOYSA-N 0.000 description 3
- YBFUKQVFDHVUHT-UHFFFAOYSA-N 4-(cyanomethoxy)-3,5-diiodobenzonitrile Chemical compound IC1=C(OCC#N)C(=CC(=C1)C#N)I YBFUKQVFDHVUHT-UHFFFAOYSA-N 0.000 description 3
- 240000004385 Centaurea cyanus Species 0.000 description 3
- 235000005940 Centaurea cyanus Nutrition 0.000 description 3
- 240000005702 Galium aparine Species 0.000 description 3
- 235000014820 Galium aparine Nutrition 0.000 description 3
- 235000017945 Matricaria Nutrition 0.000 description 3
- 101150052863 THY1 gene Proteins 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical group CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 125000001624 naphthyl group Chemical group 0.000 description 3
- 229940055577 oleyl alcohol Drugs 0.000 description 3
- XMLQWXUVTXCDDL-UHFFFAOYSA-N oleyl alcohol Natural products CCCCCCC=CCCCCCCCCCCO XMLQWXUVTXCDDL-UHFFFAOYSA-N 0.000 description 3
- TZIOBLYECXMHEQ-UHFFFAOYSA-N 2-(4-chloro-2-methylphenoxy)acetic acid propan-2-one Chemical compound CC(=O)C.CC1=C(OCC(=O)O)C=CC(=C1)Cl TZIOBLYECXMHEQ-UHFFFAOYSA-N 0.000 description 2
- JTUQIFYDYLLACG-UHFFFAOYSA-N 3,5-dichloro-4-(cyanomethoxy)benzonitrile Chemical compound ClC1=C(OCC#N)C(=CC(=C1)C#N)Cl JTUQIFYDYLLACG-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
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- NXEUKTBNIFLUJN-UHFFFAOYSA-N CC(=O)C.CC1=C(OC(C(=O)O)C)C=CC(=C1)Cl Chemical compound CC(=O)C.CC1=C(OC(C(=O)O)C)C=CC(=C1)Cl NXEUKTBNIFLUJN-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 244000058871 Echinochloa crus-galli Species 0.000 description 2
- 240000006694 Stellaria media Species 0.000 description 2
- 125000002029 aromatic hydrocarbon group Chemical group 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 125000000640 cyclooctyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])C1([H])[H] 0.000 description 2
- 238000000354 decomposition reaction Methods 0.000 description 2
- 125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 description 2
- UWNADWZGEHDQAB-UHFFFAOYSA-N i-Pr2C2H4i-Pr2 Natural products CC(C)CCC(C)C UWNADWZGEHDQAB-UHFFFAOYSA-N 0.000 description 2
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 2
- 125000000286 phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 2
- JMHQRDKVJHCIQK-UHFFFAOYSA-N (4-cyano-2,6-diiodophenyl) hydrogen carbonate Chemical compound C1=C(C=C(C(=C1I)OC(=O)O)I)C#N JMHQRDKVJHCIQK-UHFFFAOYSA-N 0.000 description 1
- 125000006204 1-benzoyl ethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(=O)C([H])(*)C([H])([H])[H] 0.000 description 1
- RMSGQZDGSZOJMU-UHFFFAOYSA-N 1-butyl-2-phenylbenzene Chemical group CCCCC1=CC=CC=C1C1=CC=CC=C1 RMSGQZDGSZOJMU-UHFFFAOYSA-N 0.000 description 1
- FKKAGFLIPSSCHT-UHFFFAOYSA-N 1-dodecoxydodecane;sulfuric acid Chemical class OS(O)(=O)=O.CCCCCCCCCCCCOCCCCCCCCCCCC FKKAGFLIPSSCHT-UHFFFAOYSA-N 0.000 description 1
- QWAVNXZAQASOML-UHFFFAOYSA-N 1-phenoxypropan-2-one Chemical compound CC(=O)COC1=CC=CC=C1 QWAVNXZAQASOML-UHFFFAOYSA-N 0.000 description 1
- XUJLWPFSUCHPQL-UHFFFAOYSA-N 11-methyldodecan-1-ol Chemical compound CC(C)CCCCCCCCCCO XUJLWPFSUCHPQL-UHFFFAOYSA-N 0.000 description 1
- ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 2,3-dimethylbutane Chemical group CC(C)C(C)C ZFFMLCVRJBZUDZ-UHFFFAOYSA-N 0.000 description 1
- HXKWSTRRCHTUEC-UHFFFAOYSA-N 2,4-Dichlorophenoxyaceticacid Chemical compound OC(=O)C(Cl)OC1=CC=C(Cl)C=C1 HXKWSTRRCHTUEC-UHFFFAOYSA-N 0.000 description 1
- XSBUXVWJQVTYLC-UHFFFAOYSA-N 2-(3-chlorophenoxy)acetic acid Chemical compound OC(=O)COC1=CC=CC(Cl)=C1 XSBUXVWJQVTYLC-UHFFFAOYSA-N 0.000 description 1
- 125000004182 2-chlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(*)C([H])=C1[H] 0.000 description 1
- DUIOKRXOKLLURE-UHFFFAOYSA-N 2-octylphenol Chemical class CCCCCCCCC1=CC=CC=C1O DUIOKRXOKLLURE-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 1
- AOKRXIIIYJGNNU-UHFFFAOYSA-N 3-methylcyclopentan-1-one Chemical compound CC1CCC(=O)C1 AOKRXIIIYJGNNU-UHFFFAOYSA-N 0.000 description 1
- QOWBBBGCACYSHD-UHFFFAOYSA-N 4-(cyanomethoxy)benzonitrile Chemical compound N#CCOC1=CC=C(C#N)C=C1 QOWBBBGCACYSHD-UHFFFAOYSA-N 0.000 description 1
- 125000004800 4-bromophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Br 0.000 description 1
- 125000004801 4-cyanophenyl group Chemical group [H]C1=C([H])C(C#N)=C([H])C([H])=C1* 0.000 description 1
- 125000001255 4-fluorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1F 0.000 description 1
- 125000004172 4-methoxyphenyl group Chemical group [H]C1=C([H])C(OC([H])([H])[H])=C([H])C([H])=C1* 0.000 description 1
- TUTJEXCMMKJPLL-UHFFFAOYSA-N CNC(=S)NC1=CC(=CC=C1)OC(NC1=CC=CC=C1)=O Chemical compound CNC(=S)NC1=CC(=CC=C1)OC(NC1=CC=CC=C1)=O TUTJEXCMMKJPLL-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- RENMDAKOXSCIGH-UHFFFAOYSA-N Chloroacetonitrile Chemical compound ClCC#N RENMDAKOXSCIGH-UHFFFAOYSA-N 0.000 description 1
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- 235000005470 Chrysanthemum segetum Nutrition 0.000 description 1
- OHMMXTBCDRFLJQ-UHFFFAOYSA-N ClC1=CC(=C(OC(C(=O)O)C)C=C1)CC Chemical compound ClC1=CC(=C(OC(C(=O)O)C)C=C1)CC OHMMXTBCDRFLJQ-UHFFFAOYSA-N 0.000 description 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical class OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 244000303225 Lamium amplexicaule Species 0.000 description 1
- 235000009198 Lamium amplexicaule Nutrition 0.000 description 1
- YNPNZTXNASCQKK-UHFFFAOYSA-N Phenanthrene Natural products C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 241000207763 Solanum Species 0.000 description 1
- 235000002634 Solanum Nutrition 0.000 description 1
- 235000019892 Stellar Nutrition 0.000 description 1
- WBCKRXPVFGFXGQ-UHFFFAOYSA-N [3-(methoxycarbonylamino)phenyl] n-hexylcarbamate Chemical compound CCCCCCNC(=O)OC1=CC=CC(NC(=O)OC)=C1 WBCKRXPVFGFXGQ-UHFFFAOYSA-N 0.000 description 1
- GLPBTXKJZBWNBN-UHFFFAOYSA-N [3-(methoxycarbonylamino)phenyl] n-propan-2-ylcarbamate Chemical compound COC(=O)NC1=CC=CC(OC(=O)NC(C)C)=C1 GLPBTXKJZBWNBN-UHFFFAOYSA-N 0.000 description 1
- QSUXYJUTJWUTLD-UHFFFAOYSA-N [4-cyano-2,6-diiodo-3-(propan-2-ylideneamino)phenyl] hydrogen carbonate Chemical compound CC(=NC1=C(C(=C(C=C1C#N)I)OC(=O)O)I)C QSUXYJUTJWUTLD-UHFFFAOYSA-N 0.000 description 1
- DHKHKXVYLBGOIT-UHFFFAOYSA-N acetaldehyde Diethyl Acetal Natural products CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 1
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- 230000000996 additive effect Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 150000004996 alkyl benzenes Chemical class 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 230000003042 antagnostic effect Effects 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 210000001217 buttock Anatomy 0.000 description 1
- FFSAXUULYPJSKH-UHFFFAOYSA-N butyrophenone Chemical compound CCCC(=O)C1=CC=CC=C1 FFSAXUULYPJSKH-UHFFFAOYSA-N 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- RNWGYDIGXJHCHP-UHFFFAOYSA-L calcium;dodecane-1-sulfonate Chemical compound [Ca+2].CCCCCCCCCCCCS([O-])(=O)=O.CCCCCCCCCCCCS([O-])(=O)=O RNWGYDIGXJHCHP-UHFFFAOYSA-L 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 229940125782 compound 2 Drugs 0.000 description 1
- 238000011109 contamination Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- 125000004802 cyanophenyl group Chemical group 0.000 description 1
- FWFSEYBSWVRWGL-UHFFFAOYSA-N cyclohex-2-enone Chemical compound O=C1CCCC=C1 FWFSEYBSWVRWGL-UHFFFAOYSA-N 0.000 description 1
- VVABQUXVKWMMHF-UHFFFAOYSA-N cyclohexanone 2-(2,4-dichlorophenoxy)propanoic acid Chemical compound C1(CCCCC1)=O.ClC1=C(OC(C(=O)O)C)C=CC(=C1)Cl VVABQUXVKWMMHF-UHFFFAOYSA-N 0.000 description 1
- FNIATMYXUPOJRW-UHFFFAOYSA-N cyclohexylidene Chemical group [C]1CCCCC1 FNIATMYXUPOJRW-UHFFFAOYSA-N 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 125000004177 diethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- LQZZUXJYWNFBMV-UHFFFAOYSA-N dodecan-1-ol Chemical compound CCCCCCCCCCCCO LQZZUXJYWNFBMV-UHFFFAOYSA-N 0.000 description 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 150000002191 fatty alcohols Chemical class 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 238000009472 formulation Methods 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
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- YGNXYFLJZILPEK-UHFFFAOYSA-N n-cyclopentylidenehydroxylamine Chemical compound ON=C1CCCC1 YGNXYFLJZILPEK-UHFFFAOYSA-N 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical class CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 125000003261 o-tolyl group Chemical group [H]C1=C([H])C(*)=C(C([H])=C1[H])C([H])([H])[H] 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 description 1
- 125000003538 pentan-3-yl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])C([H])([H])[H] 0.000 description 1
- BSCCSDNZEIHXOK-UHFFFAOYSA-N phenyl carbamate Chemical compound NC(=O)OC1=CC=CC=C1 BSCCSDNZEIHXOK-UHFFFAOYSA-N 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- GKBJOVPKZMJZOQ-UHFFFAOYSA-N propanoic acid;propan-2-one Chemical compound CC(C)=O.CCC(O)=O GKBJOVPKZMJZOQ-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 150000003467 sulfuric acid derivatives Chemical class 0.000 description 1
Classifications
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- 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
- A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
- A01N31/06—Oxygen or sulfur directly attached to a cycloaliphatic ring system
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/34—Nitriles
-
- 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
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/36—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids
- A01N37/38—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing at least one carboxylic group or a thio analogue, or a derivative thereof, and a singly bound oxygen or sulfur atom attached to the same carbon skeleton, this oxygen or sulfur atom not being a member of a carboxylic group or of a thio analogue, or of a derivative thereof, e.g. hydroxy-carboxylic acids having at least one oxygen or sulfur atom attached to an aromatic ring system
-
- 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
- A01N39/00—Biocides, pest repellants or attractants, or plant growth regulators containing aryloxy- or arylthio-aliphatic or cycloaliphatic compounds, containing the group or, e.g. phenoxyethylamine, phenylthio-acetonitrile, phenoxyacetone
- A01N39/02—Aryloxy-carboxylic acids; Derivatives thereof
-
- 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
- A01N39/00—Biocides, pest repellants or attractants, or plant growth regulators containing aryloxy- or arylthio-aliphatic or cycloaliphatic compounds, containing the group or, e.g. phenoxyethylamine, phenylthio-acetonitrile, phenoxyacetone
- A01N39/02—Aryloxy-carboxylic acids; Derivatives thereof
- A01N39/04—Aryloxy-acetic acids; Derivatives thereof
-
- 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
-
- 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
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/02—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom
- A01N47/06—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having no bond to a nitrogen atom containing —O—CO—O— groups; Thio analogues thereof
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/28—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N<
- A01N47/30—Derivatives containing the group >N—CO—N aryl or >N—CS—N—aryl
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- 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
- A01N53/00—Biocides, pest repellants or attractants, or plant growth regulators containing cyclopropane carboxylic acids or derivatives thereof
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- 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
- A01N2300/00—Combinations or mixtures of active ingredients covered by classes A01N27/00 - A01N65/48 with other active or formulation relevant ingredients, e.g. specific carrier materials or surfactants, covered by classes A01N25/00 - A01N65/48
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- General Health & Medical Sciences (AREA)
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Abstract
1460663 Synergistic herbicide preparations SCHERING AG 21 Jan 1974 [20 Jan 1973] 02726/74 Heading A5E A herbicidal preparation comprises a phenoxy-carboxylic acid oxime ester of formula: X, n, R 1 , R 2 and R 3 being defined, and a second compound selected from herbicidally active cyanophenyl carbonates, cyanophenoxyacetonitriles, diurethanes and carbamate-ureas. The preparations may be made up with isophorone and surface active agents into concentrated emulsifiable solutions, and find particular application in combating weeds in grain crop areas.
[GB1460663A]
Description
44031/3 Synergistic herbicidal preparations containing an a-phenoxyalkanoic acid oxime ester Dp TK >T. naottA' x T J "? x > D p 133-a The present invention is concerned with herbicidal preparations -j a- alkanoic f containing/phenoxy-e-arb©xyHe acid oxime-esters and cyanophenyl carbo- ! nates, cyanophenoxy-acetonitriles, diurethanes or carbamate-ureas, a- alkanoic especially concentrated solutions of /phenoxy-carboxyHe acid oxime-esters in admixture with the aforesaid compounds, and with their use for combating weeds, especially in grain crops.
Herbicidal mixtures containing various active substances are often used. They serve, for example, to destroy a larger number of species of plants with a single treatment more completely than is possible by using the separate components. However, most herbicides in the form of mixtures merely exhibit the action which they would exhibit if they were used ndividually. It is quite rare for such mixtures to exhibit an action which extends beyond or is different from that of the individual components, and this effect cannot be foreseen, owing to the peesent lack of knowledge of the mechanisms underlying such an effect.
Herbicidal preparations based on diurethanes (cf. German Offenle-gungsschrift No. 1,567,151) and carbamate-ureas (cf. German Offenlegungs-schrift No. 1,593,520) have already been proposed for use as weed combating agents. It has, however, been found that their herbicidal action does not always sufficiently fulfil the requirements of practice. A further disadvantage is their relatively sparing solubility, which makes it difficult or Impossible to prepare concentrates having a high concentration of active substance that are generally preferred 1n practice.
The present invention is therefore based on the problem of overcoming the disadvantages of the known herbicides and providing a weed-combating preparation which is capable of being formulated in a high concentration and exhibits an increased herbicidal action, which problem is solved by the herbicidal preparations of the present invention.
The present invention accordingly provides a herbicidal prepa- an - pheno^yal kanoi c ration which comprises a_pbeD0..y=earbexy44e acid oxime-ester of the general formula I (X) in which R- and R.^ each represents an aromatic, aliphatic, cycloaliphatic or araliphatic hydrocarbon group which groups may be unsubstituted or optionally mono-, di- or poly-substituted by alkyl, halogen, alkoxy, halogeno-alkyl and nitro groups and R-may also represent a hydrogen atom, or R. and together with the adjacent carbon atom represent a cycloaliphatic hydrocarbon group which may be unsubstituted or optionally mono-, di- or polysubstituted by alkyl, R^ represents a hydrogen atom or a lower alkyl group, n_ represents 0, 1 , 2 or 3 and each X represents a lower alkyl group, a lower alkoxy group, a halogenoalkyl group or a halogen atom, in admixture or conjunction with a second compound selected from herbici dally active cyanophenyl carbonates, cyanophenoxy-acetonitriles , diurethanes and carbamate-ureas, the relative proportion by weight of the -phenoxy-alkanoic acid oxime ester to the second compound being 10 to 75:1 to 50, preferably 50:5 to 10.
The herbici dal preparations of the present invention advantageously also contain isophorone of the formula II the relative proportions by weight of the -phenoxy alkanoic acid oxime ester: the second compound: the isophorone being 10 to 75:1 to 50:20 to 75, preferably 50:5 to 10: 35 to 45. of the /phenoxy-eai^x-y-Vte acid oxime-ester: the second compound : the surface-active agent being 10 to 75 : 1 to 50 : 2 to 25, preferably 50 : 1 5 to 10 : 4 to 5. a- alkanoic When two or more/phenoxy-o^Vk5- acid oxime-esters of the general formula I given above are used, the proportion of 10 to 75, preferably 50, refers of course to the total amount present of such compounds, and similarly for the proportions given above for the other components in the herbicide! preparations of the present invention.
The herbicidal preparations of the present invention are advantageously in the form of concentrated solutions containing (A)10 to 75 parts by weight preferably 50 parts by weight, of at least one compound of the general formula I in which R-j „ Rg5 R3, n and X have the meanings given above, (B) 20 to 75 parts by weight, preferably 35 to 45 parts by weight, of isophorone of the formula and, if desired, 2 to 25 parts by weight, preferably 4 to 5 parts by wiight, of a surface-active agent, in admixture with 1 to 50 parts by weight, preferably 5 to 10 parts by weight, of a herbicidal ly active compound selected from cyanophenyl carbonates (C), cyanophenoxy-acetoni-triles (D), dlurethanes (E) and carbamate-ureas(F) .
The herbicidal preparations of the present invention surprisingly exhibit a herbicidal action which, at the same rates of application, is constitutes a considerable technical advance. However, as has been further - discovered, these preparations can also be made up with isophorone Into the form of highly concentrated emulsifiable solutions having a content of active substance of up to about 80 percent by weight, which i t has not hitherto been possible to achieve andjis of supreme importance for the formulation of these herbicides .
In contradistinction to comparable preparations containing substituted a- al kanoi c /phenoxy-Gd*sboxy-Vte acid esters of known constitution dissolved in isophorone, the herbicidal preparations of the present invention containing isophorone also exhibit the unforeseeable advantage that they develop no vapour pressure.
In this way contamination of the air, and the risk of endangering sensitive crops present in the vicinity of treated areas , are avoided.
As especial ly suitable components fori the manufacture of the herbicidal preparations of the present invention there may be mentioned, for example, the following: ar al kanoi c A/Phenoxy-c-€H >o*yHc add oxlme-esters of the general formula (I ) In this formula there come into consideration for the meanings of R.| and as aromatic hydrocarbon groups , for example, a phenyl or naphthyl group, as aliphatic hydrocarbon groups , for example , those containing 1 to 12 carbon atoms , for example methyl , ethyl , propyl , isopropyl or butyl , as cycloal¾)hat1c hydrocarbon groups those containing 5 to 8 carbon atoms , for example cyclohexyl , and as aral iphatlc hydrocarbon groups , for example, benzyl or phenyl-ethyl , which groups may, for example, be identical ly or differently substituted by one or more' substi tuents selected from lower alkyl groups , for example methyl and ethyl , halogen atoms , for example chlorine and bromine, lower al koxy groups , for example methoxy and ethoxy, and other substi tuents . As lower alkyl groups represented by t¾3 and the other such groups mentioned above there come into consideration those containing 1 to 3 carbon atoms . and together with the adjacent carbon atom may also form a cycloal lphatic 5- to 8- membered ring, for example cyclohexylidene or cyclo-octyl idene, which may be mono- , di- or poly- for example methyl, and other substi tuents ,,-aad may -a†str~bc i nterrupted- -by — and/or O^-hel ru atoms, · a- alkanoic Preferred/ phenoxy-carboxylie acid oxime-esters are given in the following Table 1.
Table 1 Name of the compound Physical constant 2-(2,4-Dichlorophenoxy)-propionic acid 2Q acetone oxime-ester n^ = 1.5390 2-(2,4-D1chlorophenoxy)- rop1onic acid (3,5,5-tri- 2Q methyl -2-cyclohexenonejoxi me) -ester nQ = 1.5495 2-(2-Methyl-4-chlorophenoxy)-propionic acid 2Q acetone oxime-ester nQ = 1.5248 2- ( 2, 4-Dichlorophenoxy) -propionic acid methyl 2o isobutyl ketowime-ester n^ = 1.5245 2-(2,4-Dichlorophenoxy)-propionic acid benzophenone 2Q oxime-ester nQ - 1.6005 (2-Methyl-4-chlorophenoxy)-acetic acid cyclohexanone 2Q oxime-ester nQ = 1.5462 2,4-Dichlorophenoxy-acetic acid methyl ethyl 2Q ketoxime-ester nQ = 1.5461 20 2,4-Dichlorophenoxy-acetic acid diethyl ketoxime-ester nQ = 1.5411 2-(2,4-Dichlorophenoxy)-propionic acid methyl ethyl 20 ketoxime-ester nQ * 1.5324 2-(2,4-Dichlorophenoxy)-propionic acid diethyl 2Q ketoxime-ester ηβ = 1.5305 2- (2,4-D1chlorophenoxy)-propion1c acid methyl propyl 20 ketoxime-ester nD = 1.5292 20 3- Chlorophenoxy-acetic acid actone oxime-ester nQ β 1.5406 2,4-Didiorophenoxy-acetic acid methyl isobutyl ketoxime- 2n ester n^ = 1.5354 2,4-Dichlorophenoxy-acetic acid methyl Isopropyl keto- 2Q xime-ester D = 1.5383 (2-Methyl-4-chlorophenoxy)acetic acid methyl ethyl 2Q ketoxime-ester nQ = 1.5330 (2-Methyl-4-chlorophenoxi)-acet1c acid diethyl ketoxime- 9n ester n^u - 1.5297 2-(2,4-D1chlorophenoxy)-propionic acid butyrophenone 2Q oxime-ester nQ = 1.5666 Name of the compound Physical constant ( V 2,4-Dichlorophenoxy-acetic acid diisobutyl ketoxime- ester 'D 2,4-Dichlorophenoxy-acetic acid phenoxyacetone oxime- ester 1.5720 2-(2,4-Dichlorophenoxy)-propionic add phenoxyacetone 20 oxlme-ester nQ = 1 .5628 2- (2-Methyl-4-ch1orophenoxy) -propionic acid diethyl 2Q ketoxime-ester nD = 1 .5179 2-(2-Methyl-4-chlorophenoxy)-propionic acid methyl 2o ethyl ketoxime-ester ηβ = 1 .5223 2-(2-Methyl -4-chlorophenoxy)-prop1on1c add methyl 20 propyl ketoxime-ester nQ = 1 .5177 2-(2- ethyl-4-chlorophenoxy)-propionic acid methyl 2Q isobutyl ketoxime-ester ηβ = 1 .5125 2,4,5-Trichlorophenoxy-acetic acid methyl ethyl 2Q ketoxime-ester ηβ = 1.5581 2,4,5-Trichlorophenoxy-acetic aacid methyl propyl 2o ketoxime-ester nQ = 1.5450 2,4,5-Trichlorophenoxy-acetic acid methyl isobutyl 2Q ketoxime-ester - 1.5261 (2-Methyl-4-chlorophenoxy)-acet'ic acid dipropyl ketoxime-ester 1 .5210 2,4-Dichlorophenoxy-acetic add dipropyl ketoxime-ester 1.5319 2-(2,4-Dichlorophenoxy)-propionic add dipropyl Q ketoxime-ester nD = 1 .5210 2 ,4,5-Trichlorophenoxy-acetic acid diisobutyl ketoxime- 2Q ester n^ = - 1. ..5287 2-(2-Methyl-4-chlorophenoxy)-propionic acid dipropyl 2Q ketoxime-ester ηβ e 1 .5090 (2-Methyl-4-chlorophenoxy)-acetic acid methyl isopropyl 2Q ketoxime-ester nQ = 1 .5282 2- (2-Methyl-4-chbrophenoxy) -propionic add methyl 2Q isopropyl ketoxime-ester nQ s 1.5163 2-(2,4-Dichlorophenoxy)propionic acid methyl isopropyl 2Q ketoxime-ester nD = 1.5283 ( 2-i$ethyl-4-chlorophenoxy)-acetic acid methyl hexyl 2Q ketoxime-ester nD = 2,4-Dichlorophenoxy-acetic add methyl hexyl ketoxime- 2Q ester nQ = 1 .5255 2- (2- ethyl~4-chlorophenoxy) -propionic acid methyl 2Q hexyl ketoxime-ester nD = 1.5080 Name of the compound Physical constant 2- (2 ,4-Dichlorophenoxy) -propionic acid methyl hexyl ketoxime-ester „20= nD 1 .5182 2,4,5-Trichlorophenoxy-acetic acid methyl hexyl ketoxime-ester nD - 1 .5328 2- (2-Methyl-4-chlorophenoxy)-propionic acid (3,5 ,5- tr i methyl - 2-cycl ohexenone oxi me ) -es ter nD - 1.5418 2- (2,4-Dichlorophenoxy)-propionic acid',(3,5-dimethyl~ 2-cycl ohexenone oxime)-ester « n2D0- - 1.5571 2,4,5-Trichlorophenoxy-acetic acidj(3,5 ,5-trimethyl -2- cycl ohexenone oxime)-ester 4°- 1.5678 2 , 4-Dichlo¾pphenyl -acetic acid cyclohexanone oxime-ester η20Β 1 .5569 D 2-(2,4-Dichlorophenoxy)-propionic acid cyclohexanone oxime-ester n20- nD - 1.5489 2- (2-Methyl-4-chlorophenoxy) -propionic acid cyclohexanone oxime-ester n20= nD 1.5372 2,4-Dichlorophenoxy-acetic acid methyl 2-methoxyethyl ketoxime-ester n n2D0= 1.5412 2-(2 ,4-D1chlorophenoxy ^propionic add methyl 2- methoxyethyl ketoxime-estar nD - 1 .5311 (2- ethyl-4-chlorophenoxy)-acetic acid ethyl butyl ketoxime-ester n20- nD " 1.5200 2,4-Dichlorophenoxy-acetic acid ethyl butyl ketoxime- ester n20« nD 1.5292 2-(2-Methyl -4-chlorophenoxy)-propionic acid ethyl butyl 20 ketoxime-ester nD = 1 .5122 2- (2,4-Dichlorophenoxy)-propionic acid ethyl butyl ketoxime-ester n20- nD " 1 .5218 2,4,5-Trichlorophenoxy-acetic acid ethyl butyl ketoxime- ester n20- nD * 1 .5375 2,4-Dichlorophenoxy-acetic acid (3-methyl-cyclopentanone 20_ oximejoester nD - 1 .5485 2- ( 2-Methyl -4-chl orophenoxy ) -propi oni c aci d!( 3-Methy 1 - 20 cyclopentanone oxime)-ester 8D = 1 .5272 2-(2,4-Dichlorophenoxy)-propionic aci dp-methyl - cyc¾pentanone oxime) -ester n20- nD - 1.5418 2,4-Dichlorophenoxy-acetic acid ethyl propyl ketoxime-ester n20- nD * 1.5232 2-(2,4-Dichlorophenoxy)-propionic acid ethyl propyl ketoxime-ester n20- nD " 1.5240 2- (2-Methyl -4-chl orophenoxy) -propionic acid ethyl propyl ketoxime-ester nD - 1 .5133 2,4,5-Trichlorophenoxy-acetic acid ethyl propyl 20 ketoxime-ester nD e 1 .5440 ( 2-Methyl -4-chl orophenoxy acet1c acid di lsopropyl ketoxime-ester n20- nD - 1 .5173 2,4-Dichlorophenoxy-acetic acid diisopropyl ketoxime- ester n20- nD - 1.5271 Name of the compound Physical constant 2-(2-Methyl-4-chlorophenoxy)-propion1c ac-jd diisopropyl ketosime-ester n .2Q0. = 1.5092 2- (2,4-Dichlorophenoxy)-propionic acid diisopropyl 2n ketoxime-ester nD - 1 .5190 2,4-Dichlorophenoxy-acetic acid methyl (1 -methyl - 2n propyl )ketox1me-ester nQ = 1 .5360 (2-Methyl-4-chlorophenoxy}acetic acid (3 ,5,5-trimethyl - 2-cyclohexanone-ox1me) -ester 2-(2,4-Dichlorophenoxy)-propionic acid acetophenone oxime-ester 2-(2,4-Dichlorophenoxy)propionic acidj(3-nitrobenzaldehyde- oxime)-ester 2,4,5-Trichlorophenoxy-acetic acid acetone oxime-ester (2-Methyl-4-chlorophenoxy)-acetic acid acetone oxime-ester 2-(2,4,5-Trfch!orophenoxy)~propion1c acid acetone oxime-ester These compounds may be prepared by methods known per se, for example, a? al kanoic by reacting the corresponding oximes witn/phenoxyeaf^x-yHe acid chlorides or anhydrides , if desired in the presence of acid-binding agents and a solvent. The compounds mentioned may be used either alone or as mixtures of two or more such compounds .
B ISOPHORONE OF the FORMULA (II) This known compound may also be prepared by known methods .
As surface-active agents there may be used, for example, calcium octyl dodecyl sulphonate , oleyl alcohol polyglycol ethers , ethoxylated iso-^-t -l- phenol , ethoxylated octyl-phenol , ethoxylated nonyl -phenol , alky! -phenol polyglycol ethers , tr1 butyl -phenyl polyglycol ethers , alkyl -ary ulphonates , alkyl -aryl polyether alcohols , isotridecyl alcohol , al kyl sulphates , lauryl- ether sulphates , fatty alcohol ethylene oxide-condensates , ethoxylated castor oil , polyoxyethylene alkyl ethers , ethoxylated polyoxypropylene , sorbitol esters and lauryl alcohol polyglycol ether acetal .
C CYAN0PHENYL CARBONATES of the general formula III (HI) 1n which R, and R„ each represents an aromatic, aliphatic, cycloallphatic or araliphatic hydrocarbon group which groups may be unsubstituted or optional ty mon-, di- or poly-substituted by alkyl, halogen, or alkoxy groups and may also represent a hydrogen atom, or and R2 together with the adjacent carbon atom represent a cycloallphatic hydrocarbon group, which may be unsubstituted or optionally mon-, di- or polysubstituted by alkyl, and X and Y each represent a halogen atom.
In this formula there come into consideration for the meanings of R.J and as aromatic hydrocarbon groups, for example, a phenyl or naphthyl group, as aliphatic hydrocarbon groups, for example, those containing 1 to 12 carbon atoms, for example methyl, ethyl, propyl, isopropyl or butyl, as cycloallphatic hydrocarbon groups, those containing 5 to 8 carbon atoms, for example cyclohexyl , and as araliphatic hydrocarbon groups, for example, benzyl or phenylethyl, which groups may, for example, be identically or differently substituted by one or more substituents selected from lower alkyl groups, for example methyl and ethyl, halogen atoms, for example and chlorine and bromine lower alkoxy groups, for example methoxy and ethoxy, and other substituents. and R2 together with the adjacent carbon atom may also form a cycloallphatic 5- to 8-membered ring, for example cyclohexyl or cyclo-octyl exty4, which may be mono-, di- or poly-substituted by one or more substituents selected from lower alkyl groups, for example methyl, and other substituents.
Preferred cyanophenyl carbonates are given in the following Table 2.
Table 2 Name of the compound Physical constant 3 ,3 ,5-Trimethyl cycl ohexen- (5 ) -yl i dene-ami no (2,6-diiodo-4-cyanophenyl )carbonate M.p.: 151-152°C 1 -Ethyl -propyl i dene-ami no- (2 ,6-d1 i odo-4-cyanophenyl ) carbonate M.p.: 102-104°C Name of the compound Physical constant l-sec.-Butyl-ethyl1dene-amino-(2,6-diiodo-4-cyanophenyl ) ?π Γ carbonate n^ = 1.5620 1 1 -rv-Propyl -ethyl i dene-ami no- ( 2 ,6-Di i odo-4-cy anopheny 1 ) -carbonate M.p.: 92-94°C 1 - Isopropyl -ethyl i dene-ami no- (2 ,6-di i odo-4-cyanophenyl )carbonate M.p. :115-117°C (w th decomposition) 1 -Methyl -propyl dene-ami no- ( 2 ,6-di bromo-4-cyano-phenyl )carbonate W.p.: 82-83°C l-Mathyl-propylidene-amino-(2,6-dichloro-4-cyanophenyl ) carbonate M.p.: 96-70°C 1 -Ethyl -ethyl dene-ami no- (2 ,6-di i odo-4-cyanophenyl )-carbonate M.p.: 107-108°C (with decomposition) Isopropyl i dene-ami no- ( ,6-di i odo-4-cyanophenyl ) carbonate M.p.: 167-168°C (with decomposit on) Isopropyl idene-ami no- (2, 6-dibromo-4-cyanophenyl ) carbonate M.p.: 145-146°C Isopropyl idene-ami no-(2,6-dichloro-4-cyanophenyl ) carbonate M.p.: 96-98°C 1 -Benzoyl -ethyl idBne-ami no- (2 ,6-di iodo-4-cyanophenyl ) carbonate M.p.: 110-111°C These compounds may be prepared, for example, in a manner known per se o-by reacting corresponding hydroxy-benzonitrlles with/halogeno-formyl ¾ oximes, if desired with the addition of a base.
D Cyanophenoxy-acetonitriles of the general formula IV in which -j and have identical or different rmeanings and each represents a halogen atom.
Preferred cyanophenoxy-acetonitriles are given in the following Table 3.
- - Table 3 Name of the compound Physical constant 2,6-Dibromo-4-cyanophenoxy-acetonitrile M.p.: 126 - 129eC 2,6-Diiodo-4-cyanophenoxy-acetonitrile M.p.: 153 - 154eC 2,6-Dichloro~4-cyanophenoxy-acetonitrile M.p.: Ill - 112°C These compounds may be prepared in a manner known per se by reacting the corresponding hydroxy-benzonitriles with chloracetonitrile with the use of an organic solvent and if desired in the presence of an acid-binding agent.
E Diurethanes of the general formula V in which R-j represents an alkyl, cycloalkyl or alkenyl group, or an aryl group which may be substituted by one or more substituents selected from halogen atoms and alkyl, trifluoromethyl, alkoxy and alkylthio groups, g represents a hydrogen atom or an alkyl group, R^ represents an alkyl group, and X represents an oxygen or sulphur atom.
In this formula, for example, R^ represents an alkyl group containing 1 to 18 carbon atoms, an allyl group, a cycloalkyl group containing 3 to 8 carbon atoms, a phenyl group, or a phenyl or naphthyl group mono-, di- or poly-substituted by halogen and/or alkyl containing Ί to 3 carbon atoms and/or methoxy and/or trifluoromethyl and/or methyl -mercapto, 2 represents a hydrogen atom or an alkyl group containing 1 to 4 carbon atoms, Rg represents a methyl or ethyl group, and X represents an oxygen or sulphur atom.
- - Preferred diurethanes are given in the following Table 4.
Table 4 Name of the compound Physical constant Ethyl -N- [3- [ ' - (2 ' -chl orophenyl ) -carbamoyl oxy]-phenyl 1 carbamate ' M.p.: 117 - 119eC Methyl-N-|3-[N'-(3'-chlorophenyl ) -carbamoyl oxy] -phenyl \ carbamate^ ' M.p.: 153 - 155°C Ethyl -N-|3-[N ' - (3 ' -chl orophenyl )-carbamoyloxy]-phenyl j carbamate ' M.p.: 127 - 128°C Methyl ~N- ί 3-[ ' - (4 ' -chl orophenyl ) -carbamoyl oxy ]-phenylI carbamate1 ' M.p. : 178°C Ethyl-N- 3-[N'-(4'-chlorophenyl ) -carbamoyl oxy] -phenyl j carbamate ' M.p.: 150- 151°C Methyl -N- /3-[N ' - (2' -methyl -phenyl )-catbamoyl oxy]-phenyl carbamate M.p.: 158 - 160°C Ethyl -N- !s-[ ' -(2 ' -methyl -phenyl ) -carbamoyl oxy] -phenyl I ) carbamate M.p.: 126 - 127°C Ethyl -N- [3- ( ' ,N 1 -di ethyl -carbamoyl ox ) -phenyl ] -carbamate M.p.: 75 - 76°C Methyl -N-[3- (N ' -cycl ohexyl carbamoyl oxy ) -phenyl ] -carbamate M.p.: 159 - 161°C °C Name of the compound Physical constant Methyl -N-03- (N ' -ethyl -carbamoyl oxy -phenyl ] -carbamate M.p. 148 - 151°C Methyl - -[3- ( 1 -i sopropyl carbamoyl oxy )-phenyl ]-carbamate M.p. • 156 - 159.5°C Methyl -N-[3- ( ' -n_-propyl carbamoyl oxy) -phenyl ]carbamate M.p. 142 - 144°C Ethyl -N-[3-(N'-ethylcarbamoyloxy)-phenyl]-carbamate M.p. 146.5 - 149°C Ethyl-N-[3-(N'-isopropylGarbamoyloxy)-phenyl]carbamate M.p. 163 - 166°C Ethyl -N-[3-(N'-n_-propylearbam6yloxy:)-phenyl]carbamate M.p. 134 - 137°C Ethyl -N- [3- (N 1 - tert . -butyl carbamoyl oxy ) -phenyl ] -carbamate M.p. 159 - 160°C Me thyl-N-[3-(N'-tert. -butyl carbamoyloxy)-phenyl]-carbamate M.p. 165 - 166°C Ethyl -N- [3- (N 1 -sec . -butyl carbamoyl oxy ) -phenyl ]carbamate M.p. 173 - 174°C Ethyl -N-[3-(N' -i sobutyl carbamoyl oxy ) -phenyl ]carbamate M.p. 145 - 146°C Methyl -N-[3- (N * -al lyl -carbamoyl oxy ) -phenyl ]-carbamate M.p. 132 - 134°C Ethyl -N- [3- ( 1 -ally 1 -carbamoyl oxy ) -phenyl ]-carbamate M.p. 123 - 124°C Methyl -N-[3-(N'-sec. -butyl -carbamoyl oxy )-phenyl]-carbamate M.p. 137 - 138eC Methyl -N-[3- (N ' -1 sobutyl -carbamoyl oxy ) -phenyl ]carbamate M.p. 117 - 118°C Methyl -N- [3- ( 1 -n-hexyl -carbamoyl oxy ) -phenyl ]carbamate M.p." 112 - 113°C Ethyl - -[3- (N 1 -n-octyl -carbamoyl oxy )-phenyl jcarbamate M.p.: 90 - 91 °C Methyl -N- }3-[ ' - (4' -f 1 uorophenyl )-carbamo4iloxy]-phenyl carbamate M.p.: 161 - 162°C Methyl -N-j 3· - ( 41 - odopheny 1 ) -carbamoyl oxy ] - phen l carbamate M.p. : 174.5 - 176°C Methyl -N-S3- -bromophenyl ) -carbamo l ox ]-phen 1 0 carbamate M.p.: 176 - 177.5°C Ethyl -N- .( - [ ' - (4 ' -f 1 uorophenyl ) -carbamoyl oxy]-pheny 1 carbamate M.p.: 133 - 134°C Ethyl -N- (3- [N ' - (4 ' -i odopheny! ) -carbamoyl oxy ]-phenyl ! carbamate M . p . : 163.5-164.5°C Ethyl-N- )3-[N'-(4' -bromophenyl ) -carbamoyl oxy] -phenyl carbamate M.p.: 148 - 149°C Methyl-N- 3-[N'-(1 '-methyl -butyl )-carbamoyloxy]-phenyl '- ) carbamate M.p.: 149 - 149.5°C Ethyl -N- |3-[N * - (11 -methyl -butyl ) -carbamoyl oxy]-pheny 1 j Name of the compound Physical constant Methyl -N- 3-[ ' - (4 ' -bromo-2 ' ,5 ' -dimethyl -phenyl ) -carbamoyl oxy ]-phenyl jcarbamate M.p. 168-168.5°C Methyl -N-[3- (N ' ,N ' -dimethyl -carbamoyl oxy) -phenyl ]carbanaate M.p. 140 - 141 °C Ethyl -N-[3- (N' -methyl -carbamoyl oxy )ppenyl ] carbamate M.p. 131 - 132°C Ethyl -N-[3-(N' ,N"-dimethyl -carbamoyl oxy ) -phenyl ]-carbamate M. p. 118 - 119.5°C Methyl -N- [3- ( ' -n-butyl -carbamoyl oxy ) -phenyl carbamate M.p. 114 - 115°C Ethyl -N-[3- ( ' -n-butyl -carbamoyl oxy )phenyl ]carbamate M.p. 99.5°C Methyl -N-[3- ( ' ,N ' -diethyl -carbamoyl oxy ) -phenyl ]-carbamate M.p. 87 - 89°C Methyl -N-[3- ( 1 -cycl opropyl -carbamoyl oxy ) -phenyl 3-carbamate M.p. 152 - 153°C .5 °C carbamate M.p. : 113 - 115°C Ethyl -N-[3- (N ' -i sopropyl - ' -phenyl -carbamoyl oxy ) -phenyl 3 °C °C Ethyl -N-[3-(N' -octadecyl -carbamoyloxy ) -phenyl ] -carbamate M.p. : 100 - 101°C Ethyl -N- |3-[N' - (1 ' -methyl -hexyl )-carba>soy! oxy]-pheny 1 ) carbamate M.p. : 101 - 103eC Ethyl-N-js-CN'-O W ^' ,3' -tetramethyl-butyl )-carbamoyloxy]-phenyl jcarbamate M.p. : 138 - 139°C Ethyl -Ν-[3- (Ν' ,Ν' -diethyl -carbamoyl oxy )-phenyl ] carbamate M.p. : 62 - 68°C Methyl -N- [3- (N* -ethyl - 1 -cycl ohexyl -carbamoyloxy ) -phenyl ] carbamate rip = 1 .5245 Name of the compound Physical constant Ethyl -N-[3- (N ' -ethyl -N ' -cyclohexyl -carbamoyl oxy )- ^ phenyl] -carbamate M.p.: 106-107°C ^ Ethyl-N-j3-[N'-(3' ,4' , -dimethyl -phenyl ) -carbamoyl oxy ]-phenyl I carbamate M.p.: 143 -144°C Ethyl -N- j 3- [N ' - ( 2 * -ethyl -phenyl ) -carbamoyl oxy ] -phenyl j carbamate M.p.: 150-151 °C thiocarbamate M.P.: 159 - 160°C S-Methyl -N- 3-[ '- (3 ' -tri fl uoromethyl -phenyl ) -carbamoyl oxy] -phenyl jthi ocarbamate M.p.: 157 - 159°C S-Methyl -N-|3-[N ' - (3 * -f 1 uorophenyl )-carbamoyl oxy]-phenyl jthiocarbamate M.p. : 150 - 151 °C ) S-Methyl -N- 3-[N ' - (31 -bromophenyl )-carbamoyl oxy]-phenyl jthiocarbamate M.p.: 132 - 133°C S-Methyl -N- ( 3- [ ' - ( 3 ' -methoxy-phenyl ) -carbamoyl oxy ]- phenyl jthiocarbamate M.p.: 153 - 156°C S-Ethyl -N- j3-[N ' - (3 ' -chl orophenyl ) -carbamoyl oxy]-phenyl Jthiocarbamate M.p.: 144 - 145°C Name of the compound Physical constant S-Ethy 1 -N- 3- [ ' - (3 ' -methyl -phenyl )-carbamoyl oxy]-phenyl j thiocarbamate M.p.: 151-152°C S-Ethyl-N-|3-[N'-(3'-methoxy-phenyl)-carbamoyloxy]-phenyl j thiocarbamate M.p.: 152-153°C S-Ethy -N- |3-[ 1 - (31 - tri f 1 uorome thy 1 -phenyl ) -carbamoyl oxy]-phenyl I thiocarbamate M.p.: 167-168°C S-Methyl -N- |3-[ ' - (31 -methylmercapto-phenyl )-carbamoyl oxy]-phenyl I thiocarbamate M.p.: 162-163eC Methyl-N- 3-[N ' - (3 ' -methyl -butyl -2 ' )-carbamoyl oxy]-phenyl J carbamate These compounds are known or may be made by methods known per se.
F Carbamate-ureas of the general formula VI in which represents a hydrogen atom or an alkyl group, R2 represents an aryl or aralkyl group which may be mono-, di- or poly-substituted by one or more substituents selected from alkyl, halogenoalkyl, alkoxy and aikylmercapto groups and halogen atoms, represents a hydrogen atom or an alkyl group, R^, represents a hydrogen atom or an alkyl group, R5 represents an alkyl or alkoxy group and X represents an oxygen or sulphur atom.
In this formula, for example, R2 represents phenyl, 2-, 3- or 4-tolyl, 2, 3-dimethyl phenyl , 2 ,4-dimethyl phenyl , 2-, 3- or 4-chlorophenyl , 4-fluorophenyl , 4-bromophenyl , 4-1odophenyl , 3,4-dichlorophenyl , 2,5-dichlorophenyl , 3-chl oro-4-methyl phenyl , 3- tri fiuoromethyl -phenyl , 4-methoxy-phenyl, 4-methylmercapto-phenyl , a-naphthyl , benzyl or 4-ch orobenzyl , R3 and each represents a hydrogen atom or a lower alkyl group, for example methyl or ethyl, Rg represents a lower alkyl or alkoxy group, for example methyl, ethyl or methoxy, and X represents an oxygen or sulphur atom.
Preferred carbamate-ureas are given in the following Table 5. , Table 5 Name of the compound Physical constant NjN-Dimethyl - ' - (3-[N"- (3 ' -methyl -phenyl ) -carbamoyl oxy]- ( phenylj-urea M.p.: 174 - 175.5 Ν,Ν-Dimethyl -N ' -methyl - ' - j3-[N"- (3 ' -methyl -phenyl )-carbamoyl oxy]-phenyl j-urea M.p.: 96 - 97°C N-Methyl - ' - - (3 ' -methyl -phenyl ) -carbamoyl oxy]-phenylj-urea M.p.: 151-152°C N , N-Di methyl - · -methyl - ' - j3-[N" - (31 -methyl -phenyl ) -carbamoyl oxy ]-phenyl I -urea M.p.: 96 - 97°C N-Methyl - '- (3-[N"-methyl -N"- (3 ' -methyl -phenyl ) -carbamoyl oxyj-phenyl j-thiourea Resinif ies N-Methyl - ' - j 3-[N" - ( 3 ' -methyl -phenyl ) -carbamoyl oxy ]-phenyl J-thiourea M.p.: 126 - 127°C N-Methyl-N'-[3-(N"-phenyl-carbamoyloxy)-phenyl]-thiourea M.p.: 142 - 144°C N-Ethyl-N' - 3-[N"-(3' -methyl -phenyl )-carbamoyToxy]-phenyl |-urea M.p.: 137 - 138eC NjN-Dimethyl - ' - j3-[N"- (3 ' - tri f 1 uoromethyl -phenyl )-carbamoyl oxy]-phenyl J-urea M.p.: 158 - 159°C N.N-Dimethyl-N'-js-EN S'-chlorophenylJ-carbamoyl oxy]-phenylj-urea M.p.: 164 - 166°C N,N-Dimethyl - ' - j3-[N" -methyl -N"- (3 ' -methyl -phenyl )-carbamoyl oxy]-phenyl -urea M.p.: 126eC N-Methyl - ' -methy -N -[3- (M" -methyl -N" -phenyl -carbamoyl oxy ) -phenyl ]-urea M.p.: 87 - 88°C N-Methyl - ' -methyl -N'-|3-[N" -ethyl -N"-(3 ' -methyl -phenyl ) -carbamoyl oxy] -phenyl )-urea M.p.: 119 - 120°C Ν,Ν-Dimethyl -N ' - j3-[N"-ethyl -N"- (4 ' -methyl -phenyl )-carbamoyl -oxyj-phenyl J-urea M.p.: 146 - 147°C N-Methyl -N'-[3- (N" -methyl -N"-phenyl -carbamoyl xy ) -phenyl ]-urea M.p.: 153 - 154eC N-Elhyl - ' -[3- (N" -methyl -N" -phenyl -carbamoyl oxy ) -phenyl ]-urea M.p.: 138 - 139°C N-Methyl - ' - j3-[N" -methyl -N" - (3 ' -methyl -phenyl ) -carbamoyl oxyQ-phenyl j-urea M.p.: 128 - Ί3θβ(Γ N-Methyl -N'-j3-[N"-ethyl-N"- 3' -methyl -phenyl) -carbamoyl oxy] -phenyl J-urea M.p.: 122 -123eC N-Methyl-N'-|3-[N"-(3'-methyl-phenyl)-carbamoyloxy]-phenyl J-urea M.p.: 151 - 152°C Name of the compound Physical constant N-Methyl - ' -[3- (N"-phenyl-carbamoyloxy)-phenyl]-thiourea M.p.: 142 - 144eC phenyl] -urea resinifies M.p.: 142 - 144°C phenyl ]-thiourea M.p. : 187 - 188°C NeN-Dimethyl-N'-[3-(N"-methyl-N"-phenyl-carbamoylox phenyl] -urea These compounds are also known and may be made by methods known per se.
The aforesaid components A to F9 which may be used in the herbicidai preparations of the present invention, are advantageously mixed together in the following proportions.
A 10 to 75 parts by weight, preferably 50 parts by weight, of or phenoxy-GiH^feoxy-Vve acid oxime-esters ; B 20 to 75 parts by weight, preferably 35 to 45 parts by weight, of isophorone, and if desi red al so 2 to 25 parts by weight , preferably 4 to 5 parts by weight, of a surface-active agent; C 1 to 50 parts by weight, preferably 5 to 10 parts by weight, of cyanophenyl carbonates ; D 1 to 50 parts by slight , preferably 5 to 10 arts by weight , of cyanophenoxy-aeetoni tri 1 es ; E 1 to 50 parts by weight, preferably 5 to 10 parts by weight, of diurethanes : F 1 to 50 parts by weight, preferably 5 to 10 parts by weight, of carbamate-ureas For this purpose the components are brought together and are intensively mixed together by a suitable sti rring or mixing method.
In this way there are formed the desired highly concentrated solutions of active substances , which do not tend to crystal l ize even at low temperatures and are extraordinari ly stable to storage.
When diluted with water these solutions form aqueous emulsions of excell ent quali ty.
Especial ly sui table are those mixtures in which the components C, D, E , or F are present in proportions of 5 to 25 parts by weight, and preferably 5 to 10 parts by weight.
The herbici dal preparations of the present invention are general ly used in the post-emergence method , the rates of appl ication being 0.5 to 2 kg of herbicidal ly active compounds per hectare depending on the compounds used.
For the same degree of action it is surprising that the rates of appl ication can be considerably reduced as compared with those of the i ndividual components of the herbicidal preparations .
The herbicidal preparations are applied in the usual manner, ^ or example, with water as carrier in quantities of spcray τ quor from 100 to 1,000 liters per hectare. For the total destruction of weeds it is also possible without difficulty to apply quantities of spray liquor exceeding 1,000 liters per hectare, which are sometimes used. It is also possible to apply the preparations by the so-called "ultra-low volume method".
The present invention accordingly also provides a method of protecting a living plant against weeds, wherein the area in the vicinity of the living plant is treated with a herbicidal preparation of the present invention.
The present invention further provides a method of protecting a crop area, especially a grain crop area, against weeds, wherein the crop area is treated with a herbicidal preparation of the present invention.
The following Examples illustrate the invention:-Example 1 50 parts by weight of the compound 2(2,4-dichlorophenoxy)~propionic acid acetone oxime-ester or 2-(2-methyl-4-chlorophenoxy)- propionic acid acetone oxime-ester, and 10 parts by weight of one of the components C, isopropyli dene-ami no- (2, 6-dibromo-4-cyanophenyl ) carbonate, 1 -sec . -butyl -ethyl 1 dene-ami no- (2 ,6-di i odo-4-cyanophenyl ) - carbonate , 1 -ethyl -ethyl i dene-ami no- (2 ,6-di 1 odo-4-cyanophenyl ) carbonate , 1 -i sopropyl -ethyl i dene-ami no- (2 ,6-di i odo-4-cyano- phenyl ) -carbonate , i soprop l i dene-ami no- (2 ,6-di i odo-4-cyanopheny 1 ) carbonate , 1 -methyl -propyl i dene-ami no- ( 2 ,6-di bromo-4-cyanophenyl ) carbonate, D, 2,6-dibromo-4-cyanoph noxy-acetonitrile, 2,6-di iodo-4- cyanophenoxy-acetoni tr i 1 e , 236-di chl oro-4-cyanophenoxy-acd toni tri 1 E , methyl -N-[3- ( ' -sec . -butyl -carbamoyl oxy) -phenyl J-carbamate , phenyl -carbamate " or F, N,N-di methyl - ' - [3- ( " -methyl - " -phenyl -carbamoyl oxy ) - phenyl ]-urea and also 36 parts by weight of isophorone , 2 parts by weight of al ky! -benzenes and ^ 2 parts by weight of and oleyl alcohol polyglycol ethers were mixed together.
The resulting product served as an emulsion concentrate and could be diluted with water to form an emulsion.
Example 2 50 parts by weightof the compound 2-(2 ,4-dichlorophenoxy)-propionic acid acetone oxime-ester or 2-(2-methyl -4-chlorophenoxy)~ propionic acid acetone oxime-ester, and 5 parts by weight of one of the components C , i sopropyl 1 dene-ami no- (2 ,6-di -bromo-4-cyanophenyl )carbonate , 1 -sec . -butyl -ethyl i dene-ami no- (2 ,6-di i odo-4-cyanophenyl ) carbonate , 1 -ethyl -ethyl i dene-ami no- (2 ,6-di i odo-4-cyanophenyl ) carbonate , 1 -1 sopropyl -ethyl idene-am1 no- (2 ,6-di iodo-4- cyanophenyl ) carbonate, isopropyl idene-amino-(2,6-di1odo-4- cyanophenyl ) -carbonate , 1 -methyl -propyl i dene-ami no- (2 ,6- di bromo-4-cyanophenyl ) carbonate , D, 2,6-dibromo-4-cyanophenoxy-acetonitri le, 2,6-di iodo-4- cyanophenoxy-acetoni tri 1 e , 2 ,6-di chl oro-4-cyanophenoxy- acetonitrile , E , methyl -N-[3- (N ' -sec . -butyl -carbamoyl oxy ) -phenyl ] -carbamate , methyl -N- |3-[ 1 - (2 ' ,2 ' -dimethyl propyl )-carbamoyl oxy]-phenyl j- carbamate , methyl -N-|3-[N' -(3 'methyl -butyl -21 ) -carbamoyl oxy] - phenyl | -carbamate or F , ,N-dimethyl -N ' -[3-(N" -methyl -N"-phenyl -carbamoyl oxy ) -phany 1 ] 40.5 parts by weight of Isophorone, ^ 2.25 parts by weight of alkyl -benzenes and 2.25 parts by weight of a mixture of calcium dodecyl-benzene3ulPnonate and oleyl alcohol polyglycol ethers were mixed together. The resulting product served as an emulstion concentrate and could be diluted with water to form an emulsion.
Example 3 10 parts by weight of the compound 2- (2, 4-dichlorophenoxy) -propionic acid acetone oxime-ester and 10 parts by weight of the compound 2-(2-methyl-4-chlorophenoxy)-propionic acid acetone oxime-ester, and- or 10 parts by weight of one of the components C , isopropyl 1 dene-ami no- (2 ,6-di -bromo-4-cyanophenyl )-carbonate , 1 -sec. -butyl -ethyl idene-ami no- (2 ,6-di iodo-4-cyanophenyl } carbonate , 1 -ethyl -ethyl i dene-ami no- ( 2 ,6-di i odo-4-cyanopheny 1 ) carbonate , 1 -isopropyl -ethyl 1 dene-ami no- (2 ,6-di i odo-4-cyano- phenyl) carbonate, isopropylidene-amino-(2,6-diiodo-4- cyanophenyl) carbonate, l-methyl-pt©pyl1dene-amino-(2,6- dibromo-4-cyanophenyl Jcarbonate, D, 2,6-Dibromo-4-cyanophenoxy-acetonitrile, 2,6-diiodo-4- cyanophenoxy-acetoni tri 1 e , 2 ,6-di chl oro-4-cyanophenoxy- acetonitrile, E , methyl -N-[3- ( ' -sec . -butyl -carbamoyl oxy) -phenyl ] -carbamate , methyl -N- 13- [N ' - ( 2 ' , 2 ' -dimethyl propyl ) -carbamoyl exy] -phenyl j carbamate , methyl -N- j3-[ ' - (3 -methyl -butyl -2 ' )-carbamo 1 oxy]- phenyl j -carbamate or F, NJN-dimethyl-N-[3-(N"-methyl-N"-phenyl-carbamoyloxy)-phenyl]- urea, and also 72 parts by weight of isophorone, 4 parts by weight of al kyl benzenes and 4 parts by weight of a mixture of calcium dodecyl sulphonate and alcohol polyglycol ethers were mixed together. The resulting product served as an emulsion concentrate capable of being di luted with water.
The herbicidal action of the mixtures descri bed in Examples 1 to 3 can be seen from the fol lowing Examples .
Example 4 In a series of tests Matricaria ehaffiomi l la . Lam um am lexicaule, Gal ium aparine and Echinochloa crus gal l i were treated in a green-house by the post-emergence method with preparations containing the agents given in the following Table and at the rates of appl ication given in the Table. The agents were sprayed uniformly on the plants in the form of aqueous emulsions using 500 l iters of water per hectare. 14 Days after the spraying the results of the treatment were eval uated according to a l inear scheme of cl assification extending from 0 to 100, in which 0 = totally destroyed and 190 = not damaged.
In order to evaluate the synergistic action the method described by S.R. COLBY was used (cf. S.R. COLBY "Calculating Synergistic and Antagonistic Responses of Herbicide Combinations" , Weeds 15, 1 , 1967) .
The calculation is carried out according to the fol lowing formula: x = Growth in relation to the control on treatment with herbicide X at the rate of p_ kg per hectare. Control equal to 100. y = Growth in relation to the control on treatment with herbicide Y at the rate of g_ kg per hectare. Control equal to 100.
E = Expected growth as a % in relation to the control after treatment with the herbicidal mixture (X+Y) at the rate of (p+g)kg per hectare.
If the observed value is lower than the expected value E, the mixture has a synergistic action.
The values for the activities obtained in this Example and the following Examples are always smaller than the additive activities calculated according to COLBY of the preparations according to the present invention, of which the synergistic action is thereby proved.
Active substance or mixture Rate of Matricaria Lamiu application chamomilla amplexi in the preparation in kg of active substance/ha 2-(2,4-Dichlorophenoxy)-propionic acici acetone oxime-ester (I) 0.5 90 70 Isoropyl dene-ami no- (2,6-di odo™ 4-cyanophenyl )carbonate (II) 0.1 30 30 1 -sec. -Butyl -ethyl i dene-ami no- (2.6 -di i odo-4 -cyanophenyl )carbonate( 111)0.1 30 40 1 -Ethyl -ethy i dene- ami no- (2 ,6-di i odo--4-cyanophenyl Jcarbonate (IV) 0.1 30 30 1 - Isopropyl - ethyl i dene-ami no- ( ,6-di iodo-4-cyanophenyl Jcarbonate (V) 0.1 30 40 1 - Me thy 1 - pr o py 1 i den e - am i n o - ( 2 , 6 -di romo-4-cyanophenyl Jcarbonate (VI) 0.1 50 70 I + II 0.5 + 0.1 10 (27) 10 ( I + III 0.5 + 0.1 10 (27) 10 ( I + IV 0.5 + 0.1 10 (27) 20 ( I + V 0.5 + o.l 10 (27) 20 ( I + VI 0.5 + 0.1 30 (45) 30 ( Untreated control 100 100 0 = totally destroyed 100 = not damaged ( ) = the values calculated according to COLCY Example 5 In a series of tests the agents mentioned in the following Table were sprayed onto the weeds Stellar a med a,, Centaurea cyanus , Galium aparine, Solanum ssp. and Setari italica. The treatment and evaluation were carried out as described in Example 4.
Also in this experiment the values were smaller than the calculated values according to the formula of COLBY.
The synergistic action of the preparations of the present invention is therefore l kewise proved.
- - Active substance or mixture in the preparation Rate of Stellaria C application in kg of media c active substance/ha Isopropyl idene-amino- (2,6-diiodo-4-cyanophenyl ) carbonate (VII) 0.1 50 4 2- (2, 4-Dichl orophenoxy}- propionic acid acetone oxime-ester (VIII) 0.5 - 3 2-Meth l-4-chlorophenoxy-acetic acid ( 3 s a , 5- tr i methyl -3-cycl ohexenone oxime ) -ester (IX) 0.5 80 5 2- (2, 4-Dichl orophenoxy) -propionic acid ( 3 , 5 , 5- trl me thy 1 -2-cycl ohexenone-oxime ) -ester (X) 0.5 80 5 2- (2 ,4-Di chl orophenoxy )-propi oni c aci d acetophenone oxime-ester (XI) 0.5 80 8 2-(2,4-Dichlorophenoxy)-propionic acid methyl isobutyl ketoxime-ester (XII) 0.5 80 5 2- (2,4-Dichlorophenoxy)spropionic acid (3-nitrobenzaldehyde-oxime)-ester (XIII) 0.5 80 8 2-(2,4-Dichlorophenoxy)-prop1onic acid benzophenone oxime-ester (XIV) 0.5 70 8 VII + VIII 0.1+0.5 - 0 VII + IX 0.1+0.5 9(40) 0 VII + X 0.1+0.5 10(40) 0 VII + XI 0.1+0.5 0(40) 0 VII + XII 0.1+0.5 30(40) 0 VII + XIII 0.1+0.5 10(40) 0 VII + XIV 0.1+0.5 10(35) 0( Untreated control 100 1 0 = totally destroyed 100 = not damated ( ) = the values calculated according to COLBY Example 6 In a series of tests Stel laria media , Senedo vulgaris , Matricaria chamomi 11a, Lami urn amplexicaule, Centaurea cyanus and Echinochloa crus gain were treated uniformly by the post-emergence method with preparations containing the agents l isted in the following Table and at the dosages given 1n the Table , using 500 l itres of water per hectare.
The values obtained in this experiment 14 days after the treatment were smaller than those calculated according to the formula of COLBY. Accordingly, a synergistic action was also obtained with thede mixtures. ct ve su stance or mx ure ae o app- e ara enec o lication of in the preparation active sub. media vulgaris stance in kg/ha Isopropylidene-amino-(2t6-diiodo-4-cyanophenyl ) carbonate (XV) 0.1 20 20 2-(2,4-Dichlorophenoxy)-prop1onic acid acetone oxlme-ester (XVI) 0.5 50 40 2-(2-Methyl-4-chlorophenoxy)-propion1c acid acetone oxlme-ester (XVII) 0.5 50 60 2,4-Dichlorophenoxy-acetic acid acetone oxime-ester (XVIII) 0.5 70 30 2,4,5-Trichlorophenoxy-acetic acid acetone oxime-ester (XIX)0.5 70 40 2-Methyl-4-chlorophenoxy-acetic acid acetone oxime-ester (XX) 0.5 40 20 2-(2,4,5-Trichlorophenoxy)-propionic acid acetone oxime-ester (XXI) 0.5 20 40 XV + XVI 0.1 + 0.5 0(10) 0(8) XV + XVII 0.1 + 0.5 •(10) 0(12) XV + XVIII 0.1 + 0.5 0(14) 0(6) XV + XIX 0.1 + 0.5 0(14) 0(8) XV + XX 0.1 + 0.5 0(8) 0(4) XV + XXI 0.1 +0.5 0(5) 0(6) Untreated control - 100 100 0 * totally destroyed 100 = not damaged ( ) » the values calculated according to COLBY Example 7 In a series of tests Ste "Maria media, Matricaria chamomilla, Lamium amplexicaule, Centaurea cyanus, Galium aparine and Chrysanthemum segetum were treated by the post-emergence method with preparations containing the agents listed 1n the following Table and at the dosages given in the Table, using 500 litres of water per hectare. 14 Days after the spraying the fresh (undrled) weight was determined and expressed as a percentage of the untreated controd.
The percentages determined in this experiment were smaller than the calculated values. The result of this experiment also validly proves the synergistic action of the preparations of the present invention. application med1a cham of active substance in kg/ha 2-(2,4-Dichlorophenoxy)-propion1c acid acetone oxime-ester (XXII) 0.5 28 100 2,6-Dibromo-4-cyanophenoxy-acetonitrile (XXIII)O 1 78 2,6-Diiodo-4-cyanophenoxy-acetonitrile (XXIV) 0.1 41 83 2,6-Dichloro-4-cyanophenoxy-acetonitrile (XXV) 0.1 -Methyl-N-[3-(N*-( ' -sec. -butyl -carbamoyl oxy)-phenyl] carbamate (XXVI) 0.1 57 100 Methy1 -N- j3-[N' - (2' ,2* -dimeth l propyl )-carbamoyloxy]-phenylj carbamate (XXVII) 0.1 11 71 Methyl - -j3-[N' - (3' -methy1 -butyl -2'}-carbamoy1oxy]-phenyl? carbamate (XXVIII) 0.1 12 73 N,N-Dimethyl -N'-[3- (N"-methyl -N"-phenyl -carbamoy1oxy)-phenyl ]-urea (XXIX) 0.1 4 16 XXII + XXIII 0.5 + 0.1 - 62( XXII + XXIV 0.5 + o.l 9(11) 81( XXII + XXV 0.5 + 0.1 - - XXII + XXVI 0.5 + 0.1 1(16) 79( XXII + XXVII 0.5 + 0.1 1(3) 52( XXII + XXVIII 0.5 + 0.1 1(3) 57( XXII + XXIX 0.5 + 0.1 0(1) 10( Untreated control - - 100 10 0 * totally destroyed 100 = not damaged ( ) s the values calculated according to COLBY
Claims (19)
1. 44037/2 What we claim 1s: 1. A herblddal preparation which comprises an a -phenoxyalkanolc add oxlme ester of the general formula 1n which R^ and each represents an aromatic, aliphatic, cycloallphatic or arallphatic hydrocarbon group which groups may be unsubstltuted or optionally mono- d1- or poly-subst tuted by alkyl, halogen, alkoxy, halogeno-alkyl and nltro groups, and may also represent a hydrogen atom, or and ^ together with the adjacent carbon atom represent a cycloallphatic hydrocarbon group, which may be unsubsti tuted or optionally mono-, d1- or poly-substl tuted by alkyl, R3 represents a hydrogen atom or a lower alkyl group, n. represents 0, 1, 2 or 3 and X represents a lower alkyl group, a lower alkoxy group, a halogenoalkyl group or a halogen atom, 1n admixture or conjunction with a second compound selected from a) herblci dally active cyanophenyl carbonates of the general formula 1n which R1 and R2 each represents an aromatic, aliphatic, cycloallphatic or arallphatic hydrocarbon group which groups may be unsubstltuted or optionally mono-, d1- or poly-substl tuted by alkyl, halogen, or alkoxy groups and R-j may also represent a hydrogen atom, or R-j and R2 together with the adjacent carbon atom represent a cycloallphatic hydrocarbon group, which may be unsubstltuted or optionally mono-, d - or poly-substituted by alkyl, and X and Y ^each represent a halogen atom; 44031/2 b) herblcldally active cyanophenoxy-acetonitriles of the general formula in which X-j and each represents a halogen atom; c) herbicidally active diurethanes of the general formula in which R-j represents an alkyl, cycloalkyl or alkenyl group, or an aryl group which may be substituted by one or more substituents selected from halogen atoms and alkyl, tri fl uoromethyl , alkoxy and alkylthio groups, R^ represents a nydrogen atom or an alkyl group, represents an alkyl group, and X represents an oxygen or sulphur atom; and d) herbicidally active carbamate-ureas of the general formula in which -j represents a hydrogen atom or an alkyl group, R^ represents an aryl or ara kyl group which may be substituted by one or more substituents selected from alkyl, halogenoal kyl , alkoxy and alkyl mercapto groups and halo en atoms and each re resents a h dro en atom or an alk l 44031 /2 sulphur atom; the relative proportion by weight of the a-phenoxy-al kano c acid oxime exter to the second compound being 10 to 75 : 1 to 50.
2. A preparation as claimed 1n claim 1 , wherein the relative proportion by weight of the ct-phenoxy-alkanolc add oxime ester to the second compound 1s 50 : 5 to 10.
3. A preparation as claimed in claim 1 or 2, which al so contains sophorone of the formula the relative proportions by weight of the phenoxy-carboxy 11 c acid oxime ester : the second compound: the Isophorone bei g 10 to 75 : 1 to 50 : 20 to 75.
4. A preparation as claimed 1n cl aim 3, wherein the relative proportions by weight of the a-pbenoxy-al kanolc add oxime ester : the second compound: the Isophorone 1s 50 : 5 to 10 : 35 to 45.
5. A preparation as claimed 1 n any one of claims 1 to 4, which also contains a surface-active agent, the relative proportions by weight of the a-phenoxy-al kanoic a d oxime ester : the second compound : the surface-active agent being 10 to 75 : 1 to 50 : 2 to 25.
6. A preparation as claimed In claim 5 , wherei n the rel ative proportions by weight of the a-phenoxy-alkano1 c add oxime-ester : the second compound: the surface-active agent 1s 50 : 5 to 10 : 4 to 5. 44031/2
7. A preparation as claimed in eny one of claims 1 to 6, wherein the cx-phenoxy-alkanoic acid oxime ester is 2-(2 ,4-dichlorophenoxy)-prop1onic acid acetone oxime-ester, (2-methyl-4-chlorophenoxy)-acetic acid (3,5,5-trimethyl -2-cycl ohexenone-oxime ) -ester , 2- (2 ,4-di chl orophenoxy ) -propi on c acid (3,5,5-trimethyl -2-cyc 1 ohexenone-oxime) -ester , 2- (2 ,4-di chl orophenox )-propionic acid acetophenonoe oxime-ester , 2-(2,4-dichlorophenoxy)-propion1c acid methyl isobutyl ketoxime-este , 2-(2,4-dichlorophenoxy)-propionic acid (3-ni trobenzaldehyde-oxime)-ester, 2- ( ,4-dichlorophenoxy )-propion1c add benzophenone oxime-ester, 2-(2-metnyl-4-chlorophenoxy)-propionic acid acetone oxime-ester, 2,4-dichlorophenoxy-acetic acid acetone oxime-ester, 2,4,5-trichlorophenoxy-acetic acid acetone oxime-ester, (2-methyl-4-chloro-phenoxy)-acetic acid acetone oxime ester or 2- (2 ,4 ,5-trichlorophenoxy) propionic acid acetone oxime ester.
8. A preparation as claimed in any one of claims 1 to 6, wherein the -phenoxy-alkanoic acid oxime ester is any one of the compounds listed in Table 1 herein.
9. A preparation as claimed in claim 1 , wherein the cyanophenyl carbonate is isopropylidene-amino-(2,5-diiodo-4-cyanophenyl ) carbonate, 1-sec. -butyl-ethyl idene-ami no- (2 ,6-di i odo-4-cyanophenyl ) carbonate , 1 -ethyl -ethyl 1dene-H ami no- ( ,6-di i odo-4-cyanophenyl ) carbonate , 1 -i sopropyl -ethyl i dene-ami no- ( ,6-di i odo-4-cyanophenyl ) -carbonate , 1 -methyl propyl i dene-ami no- (2 ,6-di bromo-4-cyanophenyl ); carbonate or i sopropyl i dene-ami no- ( 2 ,6-di bromo-4-cyanophenyl ) carbonate. 1
10. A preparation as claimed in claim # wherein the cyanophenyl carbonate is any one of the compounds listed in Table 2 herein.
11. A preparation as claimed in claim 1 wherein the diurethane is any one of the compounds listed in Table 4 herein.
12. A preparation as claimed in claim 1, wherein the diurethane is methyl -N- [3- (N' -sec. -butyl -carbamoyl oxy ) -phenyl ] carbamate , methyl -N-|3-[ ' -(21 ,2' -dimethyl ropyl }-?carbamoyloxy]-phenyl j carbamate or methyl-N- 3-[N'—(3' -methyl -butyl -2' )-carbamoyloxy]- henyl ) carbamate. 44031/3
13. A preparation as claimed 1n claim 1, wherein the carbamate-urea 1 s , N-di meth l - ' - [3- ( " -methyl -N " -phenyl -carbamoyl oxy ) -phenyl ] -urea .
14. A preparation as claimed 1n claim 1, wherein the carbamate-urea 1s any one of the compounds listed in Table 5 herein.
15. A preparation as claimed 1n any one of claims 1 to 14, which 1s in the form of an aqueous emulsion.
16. Any one of the herbicidal preparations substantially as described 1n Examples 1 to 3 herein.
17. Any one of the herbicidal preparations as claimed in claim 1 and substantially as described 1n Examples 4 to 7 herein.
18. A method of protecting a living plant against weeds, wherein the area in the vicinity of the living plant Is treated with a herbicidal preparation as claimed in claim 1.
19. A method as claimed in claim 18, wherein the area is treated with a preparation as claimed In any one of claims 2 to 17. i A method as claimed 1n claim 18 or 19, wherein the preparation 1s used in such an amount that a total amount of 0.5 to 2 kg per hectare of herbici dally active compounds 1s applied to the area. 21. A method of protecting a crop area against weeds, wherein the crop area is treated with a herbicidal preparation as claimed 1n claim 1. 22. A method as claimed in claim 21 wherein the crop area 1s treated with a preparation as claimed 1n any one of claims 2 to 17. 23. A method as claimed in claim 21 or 22, wherein the preparation is used 1n such an amount that a total amount of 0.5 to 2 kg per hectare of herbici dally active compounds 1s applied to the crop area. 24. A method as claimed in any one of claims 21 to 23 wherein the crop area is a grain crop area. For the applicants Wolff, Bregman and Goller
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2303336A DE2303336A1 (en) | 1973-01-20 | 1973-01-20 | HERBICIDAL MIXTURES |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IL44031A0 IL44031A0 (en) | 1974-05-16 |
| IL44031A true IL44031A (en) | 1977-03-31 |
Family
ID=5869802
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IL44031A IL44031A (en) | 1973-01-20 | 1974-01-20 | Synergistic herbicidal preparations containing an alpha-phenoxyalkanoic acid oxime ester |
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| Country | Link |
|---|---|
| JP (1) | JPS49102842A (en) |
| AR (1) | AR216883A1 (en) |
| AT (1) | AT331555B (en) |
| BE (1) | BE809928A (en) |
| BG (2) | BG21180A3 (en) |
| BR (1) | BR7400375D0 (en) |
| CA (1) | CA1013961A (en) |
| CH (1) | CH584505A5 (en) |
| CS (2) | CS178442B2 (en) |
| DD (1) | DD107571A5 (en) |
| DE (1) | DE2303336A1 (en) |
| DK (1) | DK137421C (en) |
| FI (1) | FI56472C (en) |
| FR (1) | FR2214407B1 (en) |
| GB (1) | GB1460663A (en) |
| HU (1) | HU170900B (en) |
| IE (1) | IE38761B1 (en) |
| IL (1) | IL44031A (en) |
| IT (1) | IT1049215B (en) |
| LU (1) | LU69116A1 (en) |
| NL (1) | NL7400739A (en) |
| NO (1) | NO141777C (en) |
| PL (2) | PL91646B1 (en) |
| RO (2) | RO69339A (en) |
| SE (1) | SE401075B (en) |
| SU (2) | SU580797A3 (en) |
| TR (1) | TR18484A (en) |
| ZA (1) | ZA74396B (en) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3426719A1 (en) * | 1984-07-20 | 1986-01-23 | Hoechst Ag, 6230 Frankfurt | PLANT PROTECTIVE AGENTS BASED ON OXIMESTERS |
-
1973
- 1973-01-20 DE DE2303336A patent/DE2303336A1/en not_active Withdrawn
- 1973-11-22 DK DK631173A patent/DK137421C/en active
- 1973-12-03 DD DD175058*A patent/DD107571A5/xx unknown
- 1973-12-10 CS CS5704A patent/CS178442B2/cs unknown
- 1973-12-10 CS CS8535A patent/CS178438B2/cs unknown
- 1973-12-12 TR TR18484A patent/TR18484A/en unknown
- 1973-12-14 NO NO4775/73A patent/NO141777C/en unknown
-
1974
- 1974-01-04 LU LU69116A patent/LU69116A1/xx unknown
- 1974-01-10 PL PL1974168032A patent/PL91646B1/pl unknown
- 1974-01-16 FI FI115/74A patent/FI56472C/en active
- 1974-01-17 IE IE99/74A patent/IE38761B1/en unknown
- 1974-01-17 AR AR251980A patent/AR216883A1/en active
- 1974-01-18 RO RO7484790A patent/RO69339A/en unknown
- 1974-01-18 SU SU7401991123A patent/SU580797A3/en active
- 1974-01-18 ZA ZA740396A patent/ZA74396B/en unknown
- 1974-01-18 BG BG28742A patent/BG21180A3/xx unknown
- 1974-01-18 IT IT19558/74A patent/IT1049215B/en active
- 1974-01-18 HU HU74SC00000459A patent/HU170900B/en unknown
- 1974-01-18 BR BR375/74A patent/BR7400375D0/en unknown
- 1974-01-18 RO RO7477325A patent/RO68496A/en unknown
- 1974-01-18 BG BG25536A patent/BG22055A3/xx unknown
- 1974-01-18 SE SE7400666A patent/SE401075B/en unknown
- 1974-01-18 NL NL7400739A patent/NL7400739A/xx not_active Application Discontinuation
- 1974-01-18 BE BE139973A patent/BE809928A/en unknown
- 1974-01-18 CH CH70774A patent/CH584505A5/xx not_active IP Right Cessation
- 1974-01-18 FR FR7401727A patent/FR2214407B1/fr not_active Expired
- 1974-01-20 IL IL44031A patent/IL44031A/en unknown
- 1974-01-21 AT AT46674*#A patent/AT331555B/en not_active IP Right Cessation
- 1974-01-21 CA CA190,523A patent/CA1013961A/en not_active Expired
- 1974-01-21 GB GB272674A patent/GB1460663A/en not_active Expired
- 1974-01-21 JP JP49009177A patent/JPS49102842A/ja active Pending
- 1974-08-10 PL PL1974184009A patent/PL92143B1/pl unknown
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1975
- 1975-04-18 SU SU752126029A patent/SU667094A3/en active
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