CN1315376C - 农药制剂 - Google Patents
农药制剂 Download PDFInfo
- Publication number
- CN1315376C CN1315376C CNB028052870A CN02805287A CN1315376C CN 1315376 C CN1315376 C CN 1315376C CN B028052870 A CNB028052870 A CN B028052870A CN 02805287 A CN02805287 A CN 02805287A CN 1315376 C CN1315376 C CN 1315376C
- Authority
- CN
- China
- Prior art keywords
- alkyl
- weight
- acid
- methyl
- replace
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
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- 239000000203 mixture Substances 0.000 title claims description 78
- 238000009472 formulation Methods 0.000 title claims description 11
- 238000002360 preparation method Methods 0.000 claims abstract description 80
- 239000003112 inhibitor Substances 0.000 claims abstract description 34
- 239000003905 agrochemical Substances 0.000 claims abstract description 13
- 150000001875 compounds Chemical class 0.000 claims description 72
- -1 carboxylic acid alkyl esters compound Chemical class 0.000 claims description 71
- 239000007788 liquid Substances 0.000 claims description 32
- 229940100389 Sulfonylurea Drugs 0.000 claims description 31
- 150000003839 salts Chemical class 0.000 claims description 30
- 239000004094 surface-active agent Substances 0.000 claims description 27
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 claims description 15
- 239000012752 auxiliary agent Substances 0.000 claims description 14
- 230000000361 pesticidal effect Effects 0.000 claims description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 11
- 239000003960 organic solvent Substances 0.000 claims description 10
- 239000006185 dispersion Substances 0.000 claims description 8
- 229920000642 polymer Polymers 0.000 claims description 8
- 238000000034 method Methods 0.000 claims description 5
- 238000002156 mixing Methods 0.000 claims description 2
- 239000002253 acid Substances 0.000 abstract description 13
- 239000000126 substance Substances 0.000 abstract description 6
- 150000007513 acids Chemical class 0.000 abstract description 2
- 125000005907 alkyl ester group Chemical group 0.000 abstract 1
- 239000012669 liquid formulation Substances 0.000 abstract 1
- 239000002585 base Substances 0.000 description 42
- 239000004009 herbicide Substances 0.000 description 36
- 229910052760 oxygen Inorganic materials 0.000 description 31
- 239000001301 oxygen Substances 0.000 description 29
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 26
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 26
- 125000000217 alkyl group Chemical group 0.000 description 24
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 22
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 21
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 21
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 17
- YZHUMGUJCQRKBT-UHFFFAOYSA-M sodium chlorate Chemical compound [Na+].[O-]Cl(=O)=O YZHUMGUJCQRKBT-UHFFFAOYSA-M 0.000 description 17
- 125000003545 alkoxy group Chemical group 0.000 description 16
- 230000002363 herbicidal effect Effects 0.000 description 15
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 14
- UDSFAEKRVUSQDD-UHFFFAOYSA-N Dimethyl adipate Chemical compound COC(=O)CCCCC(=O)OC UDSFAEKRVUSQDD-UHFFFAOYSA-N 0.000 description 14
- 125000002947 alkylene group Chemical group 0.000 description 14
- 229910052799 carbon Inorganic materials 0.000 description 14
- 150000002148 esters Chemical class 0.000 description 14
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 14
- 235000013877 carbamide Nutrition 0.000 description 12
- 150000001721 carbon Chemical group 0.000 description 12
- 229910052740 iodine Inorganic materials 0.000 description 12
- 239000011630 iodine Substances 0.000 description 12
- 239000005584 Metsulfuron-methyl Substances 0.000 description 11
- SMWDFEZZVXVKRB-UHFFFAOYSA-N anhydrous quinoline Natural products N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 11
- 239000004202 carbamide Substances 0.000 description 11
- 125000004494 ethyl ester group Chemical group 0.000 description 11
- 229910052736 halogen Inorganic materials 0.000 description 11
- 150000002367 halogens Chemical class 0.000 description 11
- 150000002500 ions Chemical group 0.000 description 11
- 159000000000 sodium salts Chemical group 0.000 description 11
- JUJFQMPKBJPSFZ-UHFFFAOYSA-M Iodosulfuron-methyl-sodium Chemical compound [Na+].COC(=O)C1=CC=C(I)C=C1S(=O)(=O)[N-]C(=O)NC1=NC(C)=NC(OC)=N1 JUJFQMPKBJPSFZ-UHFFFAOYSA-M 0.000 description 10
- RJUFJBKOKNCXHH-UHFFFAOYSA-N Methyl propionate Chemical compound CCC(=O)OC RJUFJBKOKNCXHH-UHFFFAOYSA-N 0.000 description 10
- 150000003851 azoles Chemical class 0.000 description 10
- 229940017219 methyl propionate Drugs 0.000 description 10
- 241000196324 Embryophyta Species 0.000 description 9
- 125000000304 alkynyl group Chemical group 0.000 description 9
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 8
- LTMRRSWNXVJMBA-UHFFFAOYSA-L 2,2-diethylpropanedioate Chemical compound CCC(CC)(C([O-])=O)C([O-])=O LTMRRSWNXVJMBA-UHFFFAOYSA-L 0.000 description 8
- LIRDIZPKBSSVBK-UHFFFAOYSA-N 3-o-ethyl 1-o-methyl propanedioate Chemical compound CCOC(=O)CC(=O)OC LIRDIZPKBSSVBK-UHFFFAOYSA-N 0.000 description 8
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 8
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 8
- 239000003795 chemical substances by application Substances 0.000 description 8
- 239000000460 chlorine Substances 0.000 description 8
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 8
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 8
- 229910052739 hydrogen Inorganic materials 0.000 description 8
- 239000004615 ingredient Substances 0.000 description 8
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 8
- WRHHVVPVKLLPFT-UHFFFAOYSA-N 2-o-ethyl 1-o-methyl oxalate Chemical compound CCOC(=O)C(=O)OC WRHHVVPVKLLPFT-UHFFFAOYSA-N 0.000 description 7
- HBTAOSGHCXUEKI-UHFFFAOYSA-N 4-chloro-n,n-dimethyl-3-nitrobenzenesulfonamide Chemical compound CN(C)S(=O)(=O)C1=CC=C(Cl)C([N+]([O-])=O)=C1 HBTAOSGHCXUEKI-UHFFFAOYSA-N 0.000 description 7
- YHRUNAIXGSNSTP-UHFFFAOYSA-N 5-o-ethyl 1-o-methyl pentanedioate Chemical compound CCOC(=O)CCCC(=O)OC YHRUNAIXGSNSTP-UHFFFAOYSA-N 0.000 description 7
- CWOVOJUKEQPFBA-UHFFFAOYSA-N 6-o-ethyl 1-o-methyl hexanedioate Chemical compound CCOC(=O)CCCCC(=O)OC CWOVOJUKEQPFBA-UHFFFAOYSA-N 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 7
- DKMROQRQHGEIOW-UHFFFAOYSA-N Diethyl succinate Chemical compound CCOC(=O)CCC(=O)OCC DKMROQRQHGEIOW-UHFFFAOYSA-N 0.000 description 7
- ZDQWESQEGGJUCH-UHFFFAOYSA-N Diisopropyl adipate Chemical compound CC(C)OC(=O)CCCCC(=O)OC(C)C ZDQWESQEGGJUCH-UHFFFAOYSA-N 0.000 description 7
- MUXOBHXGJLMRAB-UHFFFAOYSA-N Dimethyl succinate Chemical compound COC(=O)CCC(=O)OC MUXOBHXGJLMRAB-UHFFFAOYSA-N 0.000 description 7
- NKOUWLLFHNBUDW-UHFFFAOYSA-N Dipropyl hexanedioate Chemical compound CCCOC(=O)CCCCC(=O)OCCC NKOUWLLFHNBUDW-UHFFFAOYSA-N 0.000 description 7
- HXXRQBBSGZDQNP-UHFFFAOYSA-N Ethyl methyl_succinate Chemical compound CCOC(=O)CCC(=O)OC HXXRQBBSGZDQNP-UHFFFAOYSA-N 0.000 description 7
- 239000005560 Foramsulfuron Substances 0.000 description 7
- LOMVENUNSWAXEN-UHFFFAOYSA-N Methyl oxalate Chemical compound COC(=O)C(=O)OC LOMVENUNSWAXEN-UHFFFAOYSA-N 0.000 description 7
- 241000209094 Oryza Species 0.000 description 7
- 235000007164 Oryza sativa Nutrition 0.000 description 7
- OUWSNHWQZPEFEX-UHFFFAOYSA-N diethyl glutarate Chemical compound CCOC(=O)CCCC(=O)OCC OUWSNHWQZPEFEX-UHFFFAOYSA-N 0.000 description 7
- 229940031578 diisopropyl adipate Drugs 0.000 description 7
- XTDYIOOONNVFMA-UHFFFAOYSA-N dimethyl pentanedioate Chemical compound COC(=O)CCCC(=O)OC XTDYIOOONNVFMA-UHFFFAOYSA-N 0.000 description 7
- ITHNIFCFNUZYLQ-UHFFFAOYSA-N dipropan-2-yl oxalate Chemical compound CC(C)OC(=O)C(=O)OC(C)C ITHNIFCFNUZYLQ-UHFFFAOYSA-N 0.000 description 7
- MSQKMFXJFBXZNQ-UHFFFAOYSA-N dipropan-2-yl pentanedioate Chemical compound CC(C)OC(=O)CCCC(=O)OC(C)C MSQKMFXJFBXZNQ-UHFFFAOYSA-N 0.000 description 7
- QRVSDVDFJFKYKA-UHFFFAOYSA-N dipropan-2-yl propanedioate Chemical compound CC(C)OC(=O)CC(=O)OC(C)C QRVSDVDFJFKYKA-UHFFFAOYSA-N 0.000 description 7
- SZHZCPHKDJWHNG-UHFFFAOYSA-N dipropyl butanedioate Chemical compound CCCOC(=O)CCC(=O)OCCC SZHZCPHKDJWHNG-UHFFFAOYSA-N 0.000 description 7
- HZHMMLIMOUNKCK-UHFFFAOYSA-N dipropyl oxalate Chemical compound CCCOC(=O)C(=O)OCCC HZHMMLIMOUNKCK-UHFFFAOYSA-N 0.000 description 7
- IXAVSISAEGUDSL-UHFFFAOYSA-N dipropyl pentanedioate Chemical compound CCCOC(=O)CCCC(=O)OCCC IXAVSISAEGUDSL-UHFFFAOYSA-N 0.000 description 7
- LWIWFCDNJNZEKB-UHFFFAOYSA-N dipropyl propanedioate Chemical compound CCCOC(=O)CC(=O)OCCC LWIWFCDNJNZEKB-UHFFFAOYSA-N 0.000 description 7
- XHEDLZYGAQSNTR-UHFFFAOYSA-N ethene;hexanedioic acid Chemical compound C=C.C=C.OC(=O)CCCCC(O)=O XHEDLZYGAQSNTR-UHFFFAOYSA-N 0.000 description 7
- 229910052731 fluorine Inorganic materials 0.000 description 7
- 125000001072 heteroaryl group Chemical group 0.000 description 7
- 239000001257 hydrogen Substances 0.000 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 7
- 235000009566 rice Nutrition 0.000 description 7
- 125000002769 thiazolinyl group Chemical group 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
- DKGAVHZHDRPRBM-UHFFFAOYSA-N Tert-Butanol Chemical compound CC(C)(C)O DKGAVHZHDRPRBM-UHFFFAOYSA-N 0.000 description 6
- 125000003282 alkyl amino group Chemical group 0.000 description 6
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 6
- 125000003118 aryl group Chemical group 0.000 description 6
- 150000001768 cations Chemical class 0.000 description 6
- 229910052801 chlorine Inorganic materials 0.000 description 6
- 239000008187 granular material Substances 0.000 description 6
- 125000001188 haloalkyl group Chemical group 0.000 description 6
- NIFKBBMCXCMCAO-UHFFFAOYSA-N methyl 2-[(4,6-dimethoxypyrimidin-2-yl)carbamoylsulfamoyl]-4-(methanesulfonamidomethyl)benzoate Chemical group COC(=O)C1=CC=C(CNS(C)(=O)=O)C=C1S(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 NIFKBBMCXCMCAO-UHFFFAOYSA-N 0.000 description 6
- 239000003921 oil Substances 0.000 description 6
- 235000019198 oils Nutrition 0.000 description 6
- QQVIHTHCMHWDBS-UHFFFAOYSA-N perisophthalic acid Natural products OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 6
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 6
- 150000003217 pyrazoles Chemical class 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 5
- LCGLNKUTAGEVQW-UHFFFAOYSA-N Dimethyl ether Chemical compound COC LCGLNKUTAGEVQW-UHFFFAOYSA-N 0.000 description 5
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 5
- 239000000839 emulsion Substances 0.000 description 5
- 238000005516 engineering process Methods 0.000 description 5
- 239000003337 fertilizer Substances 0.000 description 5
- 239000011737 fluorine Substances 0.000 description 5
- PXDNXJSDGQBLKS-UHFFFAOYSA-N foramsulfuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=C(NC=O)C=2)C(=O)N(C)C)=N1 PXDNXJSDGQBLKS-UHFFFAOYSA-N 0.000 description 5
- 125000005842 heteroatom Chemical group 0.000 description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 5
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 5
- BACHBFVBHLGWSL-JTQLQIEISA-N rac-diclofop methyl Natural products C1=CC(O[C@@H](C)C(=O)OC)=CC=C1OC1=CC=C(Cl)C=C1Cl BACHBFVBHLGWSL-JTQLQIEISA-N 0.000 description 5
- 229920006395 saturated elastomer Polymers 0.000 description 5
- 239000000243 solution Substances 0.000 description 5
- 239000000375 suspending agent Substances 0.000 description 5
- 239000003666 Amidosulfuron Substances 0.000 description 4
- CTTHWASMBLQOFR-UHFFFAOYSA-N Amidosulfuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)N(C)S(C)(=O)=O)=N1 CTTHWASMBLQOFR-UHFFFAOYSA-N 0.000 description 4
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- 125000003368 amide group Chemical group 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 4
- WCGGWVOVFQNRRS-UHFFFAOYSA-N dichloroacetamide Chemical compound NC(=O)C(Cl)Cl WCGGWVOVFQNRRS-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000001704 evaporation Methods 0.000 description 4
- 230000008020 evaporation Effects 0.000 description 4
- 125000005553 heteroaryloxy group Chemical group 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 4
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 239000003755 preservative agent Substances 0.000 description 4
- 230000002335 preservative effect Effects 0.000 description 4
- 235000019260 propionic acid Nutrition 0.000 description 4
- 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 4
- 239000002904 solvent Substances 0.000 description 4
- URAYPUMNDPQOKB-UHFFFAOYSA-N triacetin Chemical compound CC(=O)OCC(OC(C)=O)COC(C)=O URAYPUMNDPQOKB-UHFFFAOYSA-N 0.000 description 4
- 125000006526 (C1-C2) alkyl group Chemical group 0.000 description 3
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 description 3
- VONWPEXRCLHKRJ-UHFFFAOYSA-N 2-chloro-n-phenylacetamide Chemical class ClCC(=O)NC1=CC=CC=C1 VONWPEXRCLHKRJ-UHFFFAOYSA-N 0.000 description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- UWVKRNOCDUPIDM-UHFFFAOYSA-N Ethoxysulfuron Chemical compound CCOC1=CC=CC=C1OS(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 UWVKRNOCDUPIDM-UHFFFAOYSA-N 0.000 description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
- 239000005586 Nicosulfuron Substances 0.000 description 3
- 239000005616 Rimsulfuron Substances 0.000 description 3
- 239000005864 Sulphur Substances 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 230000000996 additive effect Effects 0.000 description 3
- 229910052783 alkali metal Inorganic materials 0.000 description 3
- 150000001345 alkine derivatives Chemical class 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 3
- 125000004429 atom Chemical group 0.000 description 3
- JFDZBHWFFUWGJE-UHFFFAOYSA-N benzonitrile Chemical compound N#CC1=CC=CC=C1 JFDZBHWFFUWGJE-UHFFFAOYSA-N 0.000 description 3
- 238000009835 boiling Methods 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 235000013339 cereals Nutrition 0.000 description 3
- NSWAMPCUPHPTTC-UHFFFAOYSA-N chlorimuron-ethyl Chemical compound CCOC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(Cl)=CC(OC)=N1 NSWAMPCUPHPTTC-UHFFFAOYSA-N 0.000 description 3
- 238000004040 coloring Methods 0.000 description 3
- 125000004093 cyano group Chemical group *C#N 0.000 description 3
- 239000013530 defoamer Substances 0.000 description 3
- 239000002274 desiccant Substances 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- QEWYKACRFQMRMB-UHFFFAOYSA-N fluoroacetic acid Chemical compound OC(=O)CF QEWYKACRFQMRMB-UHFFFAOYSA-N 0.000 description 3
- 239000003205 fragrance Substances 0.000 description 3
- 230000000855 fungicidal effect Effects 0.000 description 3
- 239000000417 fungicide Substances 0.000 description 3
- 239000002917 insecticide Substances 0.000 description 3
- 239000012948 isocyanate Substances 0.000 description 3
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 3
- 239000011976 maleic acid Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- ZTYVMAQSHCZXLF-UHFFFAOYSA-N methyl 2-[[4,6-bis(difluoromethoxy)pyrimidin-2-yl]carbamoylsulfamoyl]benzoate Chemical group COC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(OC(F)F)=CC(OC(F)F)=N1 ZTYVMAQSHCZXLF-UHFFFAOYSA-N 0.000 description 3
- 150000004702 methyl esters Chemical class 0.000 description 3
- RSMUVYRMZCOLBH-UHFFFAOYSA-N metsulfuron methyl Chemical group COC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(C)=NC(OC)=N1 RSMUVYRMZCOLBH-UHFFFAOYSA-N 0.000 description 3
- RTCOGUMHFFWOJV-UHFFFAOYSA-N nicosulfuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CN=2)C(=O)N(C)C)=N1 RTCOGUMHFFWOJV-UHFFFAOYSA-N 0.000 description 3
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- 125000003831 tetrazolyl group Chemical group 0.000 description 1
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- 125000001544 thienyl group Chemical group 0.000 description 1
- 229930192474 thiophene Natural products 0.000 description 1
- DQFPEYARZIQXRM-LTGZKZEYSA-N tralkoxydim Chemical compound C1C(=O)C(C(/CC)=N/OCC)=C(O)CC1C1=C(C)C=C(C)C=C1C DQFPEYARZIQXRM-LTGZKZEYSA-N 0.000 description 1
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Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N61/00—Biocides, pest repellants or attractants, or plant growth regulators containing substances of unknown or undetermined composition, e.g. substances characterised only by the mode of action
-
- 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
- A01N25/00—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests
- A01N25/02—Biocides, pest repellants or attractants, or plant growth regulators, characterised by their forms, or by their non-active ingredients or by their methods of application, e.g. seed treatment or sequential application; Substances for reducing the noxious effect of the active ingredients to organisms other than pests containing liquids as carriers, diluents or solvents
-
- 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<
- A01N47/36—Ureas or thioureas containing the groups >N—CO—N< or >N—CS—N< containing the group >N—CO—N< directly attached to at least one heterocyclic ring; Thio analogues thereof
Landscapes
- Life Sciences & Earth Sciences (AREA)
- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Agronomy & Crop Science (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Toxicology (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
本发明涉及液体制剂，其中含a)一种或多种多元羧酸烷基酯和b)一种或多种属于ALS抑制剂的农药。
Description
本发明涉及农药制剂领域，特别是农药活性化合物如乙酰乳酸合成酶抑制剂(ALS抑制剂)，例如磺酰脲类及其盐的液体制剂。
在农业化学领域中，ALS抑制剂是主要用作除草剂的物质。由于其低用量和宽作用谱，ALS抑制剂被用于所有经济上重要的作物。
通常，农药活性化合物不以原药的形式使用，而是根据使用的区域和使用形式希望具有的物理性能结合某些助剂使用，即“配成制剂”。通常，活性化合物可根据其主要的生物和/或物化参数以各种方式配成制剂。下面是通常可能的制剂的实例：可湿性粉剂(WP)、水包油或油包水乳剂(分别是EW和EO)、悬浮剂(SC)、悬乳剂(SE)、乳油(EC)、水溶液(SL)或土施或撒施的颗粒剂，或水分散性粒剂(WG)。上述制剂类型是通常已知的并描述于例如：Winnacker-Kuchler，“ChemischeTechnologie”[化学工艺]，第7卷，C.Hauser-Verlag，慕尼黑，第4版，1986；van Valkenburg，“Pesticide Formulations”，Marcel-DekkerN.Y.，1973；K.Martens，“Spray Drying Handbook”，第3版，1979，G.Goodwin Ltd.伦敦。
如果要配制成制剂的农药活性化合物是通常在溶解状态或液体介质中易于化学降解的化合物，通常优选固体制剂如可湿性粉剂或颗粒剂。如US4599412和US5731264中所述，例如ALS抑制剂类除草活性化合物如甲磺隆、烟嘧磺隆或砜嘧磺隆、氟嘧磺隆、醚苯磺隆、氟磺隆、酰嘧磺隆或乙氧嘧磺隆就是这种情况。因此，如在WO9910857、WO9809516、WO9508265、US5441923、WO9423573、JP05017305、JP04297404、JP04297403或JP04066509中所述的这些除草剂的粉剂或颗粒剂是已知的。
当用水稀释上述粉剂或颗粒剂(为制备喷液)时，浓缩物中的不溶解成分常常不能完全溶解，即喷液是该浓缩物的悬浮液。然而，如果喷液是尽可能地细分散的，那么总是有利的，因为这会降低喷嘴被堵塞的风险并且因此通常可降低用于清除的费用。况且粉剂和颗粒剂只能在较高的能源输入和技术复杂的搅拌器的条件下制备，即，即使在其制备过程中也有相当多的缺点。
上述种类的除草剂的胶悬剂形式的液体悬浮剂是已知的(FR2576181、EP0205348、EP0237292或EP0246984)。然而就悬浮剂来说，活性化合物也是不溶解的，因此在该喷液的施用过程中会遇到与施用粉剂或颗粒剂相似的问题。况且胶悬剂(SC)和悬乳剂(SE)是热力学不稳定的制剂，其物理储藏稳定性有限。
磺酰脲类的无表面活性剂的水溶液描述于US4683000、US4671817和EP0245058中，无水乳油描述于DE3422824、US4632693、WO09608148和US5597778中。这些出版物均未提示如何增加所述制剂的储藏稳定性。
因此，本发明的目的是提供一种农药制剂，该制剂不易降解并且具有良好的操作性能。
令人惊讶的是现已发现通过某种液体活性化合物制剂可实现此目的，所述液体制剂含特定的多元羧酸酯和作为农药活性化合物的ALS抑制剂如磺酰脲类和/和其盐。
因此，本发明提供一种液体制剂，该制剂包含
a)一种或多种多元羧酸的烷基酯，优选一种或多种选自多元羧酸的C1-C20-烷基酯的化合物，和
b)一种或多种选自ALS抑制剂的农药活性化合物，特别是一种或多种磺酰脲类和/或其盐，例如与基于氮、硫或磷的有机阳离子和/或无机阳离子如金属阳离子形成的盐。
本发明的液体制剂优选除草剂制剂，例如乳油形式的制剂。所述制剂优选包含至少一种溶解形式的选自ALS抑制剂的活性化合物，用作溶剂的多元羧酸烷基酯a)。此外，还优选仅含一种多元羧酸烷基酯a)的制剂。
必要时，本发明的液体制剂除成分a)和b)以外，还包含一种或多种助剂和添加剂作为其他成分，例如：
(c)表面活性剂和/或非表面活性剂聚合物，
(d)不同于成分a)的有机溶剂，
(e)不同于ALS抑制剂的农药，如除草剂、杀虫剂、杀真菌剂、安全剂、生长调节剂或肥料，
(f)常规的制剂助剂，如消泡剂、蒸发抑制剂、添味剂、着色剂、防冻剂或防腐剂、稳定剂、干燥剂或增稠剂，
(g)桶混成分，和/或
(h)附加的水。
本发明的制剂中所含的作为成分a)的多元羧酸烷基酯可充当溶剂，并且是例如低分子量二羧酸、三羧酸、四羧酸或具有更高官能度的羧酸优选具有2-20个碳原子的羧酸的烷基酯。聚合的多元羧酸也适合，其中优选分子量至多2000g/mol的。多元羧酸的实例是草酸、丙二酸、琥珀酸、戊二酸、己二酸、庚二酸、癸二酸、壬二酸、辛二酸、马来酸、邻苯二甲酸、对苯二酸、苯六甲酸、苯偏三酸、聚马来酸、聚丙烯酸和聚甲基丙烯酸，以及还有含马来酸、丙烯酸和/或甲基丙烯酸单元的共聚物或三元共聚物。
合适的多元羧酸烷基酯a)的醇成分是例如烷基醇类，优选含1-20个碳原子的单官能的烷基醇。上述烷基醇的实例是甲醇、乙醇、正丙醇、异丙醇、正丁醇、仲丁醇、异丁醇和叔丁醇。
多元羧酸烷基酯a)优选具有下列通式(I)
Rγ-O-OC-(CRαRβ)x-CO-O-Rδ (I)
其中
Rα和Rβ是相同或不同的并且是H，取代或未取代的C1-C20-烃基，如C1-C10-烷基，或基团((CR′R″)y-CO-OR，其中R′和R″是相同或不同的并且是H或未取代或取代的C1-C20-烃基，如C1-C10-烷基，y是0-10的整数，R是未取代或取代的C1-C20-烃基，如C1-C10-烷基，
Rγ和Rδ是相同或不同的，并且是未取代或取代的C1-C20-烃基，如C1-C10-烷基，x是0-20的整数。
特别优选的多元羧酸烷基酯a)是下式(Ia)的二酯
Rγ-O-OC-(CH2)x-CO-O-Rδ (Ia)
其中x是0-20的整数和
Rγ和Rδ是彼此独立地相同或不同的C1-C6-烷基。
多元羧酸烷基酯a)的实例是草酸酯如草酸二甲酯、草酸二乙酯、草酸二正丙酯、草酸二异丙酯和草酸甲乙酯，丙二酸酯如丙二酸二甲酯、丙二酸二乙酯、丙二酸二正丙酯、丙二酸二异丙酯和丙二酸甲乙酯，丁二酸酯如丁二酸二甲酯、丁二酸二乙酯、丁二酸二正丙酯、丁二酸二异丙酯和丁二酸甲乙酯，戊二酸酯如戊二酸二甲酯、戊二酸二乙酯、戊二酸二正丙酯、戊二酸二异丙酯和戊二酸甲乙酯，和己二酸酯如己二酸二甲酯、己二酸二乙酯、己二酸二正丙酯、己二酸二异丙酯和己二酸甲乙酯。优选己二酸酯，特别是己二酸二甲酯。
多元羧酸烷基酯a)可通过例如游离羧酸与醇反应获得，例如可以通过“活化的”多元羧酸如多元羧酸酐或聚碳酰(多)氯化物与醇按照已知的酯化方法反应制备该酯。
本发明的制剂中作为成分b)存在的ALS抑制剂类活性化合物尤其是咪唑啉酮类、嘧啶氧基吡啶羧酸衍生物、嘧啶氧基苯甲酸衍生物、三唑并嘧啶磺酰胺衍生物或磺胺类，优选磺酰脲类，特别优选式(II)的磺酰脲和/或其盐：
Ra-SO2-NRb-CO-(NRc)x-Rd (II)
其中
Ra是烃基，优选未取代或取代的芳基如苯基，或取代或未取代的杂环基，优选杂芳基如吡啶基，其中的基团包括取代基在内含1-30个碳原子，优选1-20个碳原子，或Ra是吸电子基团如氨磺酰基，
Rb是氢原子或烃基，该烃基是未取代或取代的并且包括取代基在内含1-10个碳原子，例如未取代或取代的C1-C6-烷基，优选氢原子或甲基，
Rc是氢原子或烃基，该烃基是未取代或取代的并且包括取代基在内含1-10个碳原子，例如未取代或取代的C1-C6-烷基，优选氢原子或甲基，
x是0或1，和
Rd是杂环基。
为说明起见，烃基是直链、支链或环状的饱和或不饱和脂族或芳族烃基，例如烷基、烯基、炔基、环烷基、环烯基或芳基；芳基是单-、双-或多环芳族体系，例如苯基、萘基、四氢萘基、茚基、茚满基、并环戊二烯基、芴基等，优选苯基。除非另有说明，烃基优选含1-40个碳原子，更优选1-30个碳原子；特别优选烃基是含至多12个碳原子的烷基、烯基或炔基或含3、4、5、6或7个环原子的环烷基，或苯基。烃氧基是经由氧原子结合的如上所述的烃基。
为说明起见，杂环基或环(杂环)可以是饱和的、不饱和，或杂芳族的并且可以是未取代或取代的；优选环中含一个或多个杂原子，杂原子优选自N、O和S；优选含3-7个环原子的脂族杂环基或含5或6个环原子的杂芳基，并且其中含1、2或3个杂原子。例如杂环基可以是杂芳基或环(杂芳基)如单-、双-或多环芳族体系，其中至少一个环含有一个或多个杂原子，例如吡啶基、嘧啶基、哒嗪基、吡嗪基、三嗪基、噻吩基、噻唑基、唑基、呋喃基、吡咯基、吡唑基和咪唑基，或者是部分或全部氢化的基团，如环氧乙烷基、氧杂环丁烷基、吡咯烷基、氮杂环己基、哌嗪基、二氧戊环基、吗啉基、四氢呋喃基。取代的杂环基的适宜的取代基是下面提到的取代基，此外还有氧。氧基还可存在于杂环原子上，可能以不同的氧化态存在例如N和S。
为说明起见，被取代的基团如取代的烃基例如取代的烷基、烯基、炔基或芳基如苯基或苯甲基或取代的杂环基，是例如源自未取代的母体化合物的被取代基团，其中的取代基是例如一个或多个(优选1、2或3)选自下组的基团：卤素(氟、氯、溴、碘)，烷氧基，卤代烷氧基，烷硫基，羟基，氨基，硝基，羧基，氰基，叠氮基，烷氧基羰基，烷基羰基，甲酰基，氨甲酰基，单-和二-烷基氨基羰基，被取代的氨基如酰胺基、单-和二烷基氨基，和烷基亚磺酰基，卤代烷基亚磺酰基，烷基磺酰基，卤代烷基磺酰基，就环状基团来说还有烷基和卤代烷基，和与上述饱和的含烃基团对应的不饱和脂族基团如烯基、炔基、烯氧基、炔氧基等。在含碳原子的基团中，优选含1-4个碳原子的，特别是1-2个碳原子的。通常优选属于下组的取代基：卤素例如氟和氯，(C1-C4)烷基优选甲基或乙基，(C1-C4)卤代烷基优选三氟甲基，(C1-C4)烷氧基优选甲氧基或乙氧基，(C1-C4)卤代烷氧基，硝基和氰基。
为说明起见，在各种情况下，脂族基团如烷基、烷氧基、卤代烷氧基、烷基氨基和烷硫基以及相应的不饱和和/或饱和基团均可以是直链或在碳骨架中分枝的，并且对于碳原子数为3个或更多个的基团还可以是环状的。在这些基团中，除非另有说明优选低级碳骨架的，例如含1-6个碳原子的或就不饱和基团来说是含2-6个碳原子的。
烷基，以及复合含义如烷氧基、卤代烷基等中的烷基是例如甲基、乙基、正丙基、异丙基或环丙基、正丁基、异丁基、叔丁基、2-丁基或环丁基、戊烷基、己烷基如正己基、异己基和1，3-二甲基丁基、庚烷基如正庚基、1-甲基己基和1，4-二甲基戊基；烯基和炔基具有对应于烷基的可能不饱和的基团的含义；烯基是例如烯丙基、1-甲基丙-2-烯-1-基、2-甲基丙-2-烯-1-基、丁-2-烯-1-基、丁-3-烯-1-基、1-甲基-丁-3-烯-1-基和1-甲基-丁-2-烯-1-基；炔基是例如炔丙基、丁-2-炔-1-基、丁-3-炔-1-基、1-甲基-丁-3-炔-1-基。
卤素是例如氟、氯、溴或碘。卤代烷基、卤代烯基和卤代炔基分别是部分或完全被卤素取代的烷基、烯基和炔基，所述卤素优选氟、氯和/或溴，特别是氟或氯，例如CF3、CHF2、CH2F、CF3CF2、CH2FCHCl、CCl3、CHCl2、CH2CH2Cl；卤代烷氧基是例如OCF3、OCHF2、CCH2F、CF3CF2O、OCH2CF3和OCH2CH2Cl；这相应地适用于卤代烯基和其他卤代基团。
为本发明的目的起见，在所有情况下，本发明的液体制剂中所含作为成分b)的属于ALS抑制剂的活性化合物如磺酰脲类除了中性化合物外还包括其与无机和/或有机平衡离子形成的农业上适用的盐。
磺酰脲例如式(II)的磺酰脲可通过例如-SO2-NH-基团中的氢被农业上适宜的阳离子取代而成盐。这些盐是例如金属盐，特别是碱金属盐或碱土金属盐，油漆是钠盐和钾盐，或铵盐、锍盐或膦盐。成盐还可通过向碱性基团如氨基和烷基氨基加酸而发生。适用于此目的的酸是强无机酸和有机酸，例如HCl、HBr、H2SO4或HNO3。
含无机平衡离子的适宜的盐是例如含NH4 、SH3 或PH4 平衡离子的盐，或含例如碱金属或碱土金属平衡例子如Na、K、Mg2或Ca2的金属盐。与有机平衡离子形成的适宜的盐是例如有机铵盐、锍盐和膦盐。优选式[NR8R9R10R11]+、[SR12R13R14]+或[PR15R16R17R18]+的有机平衡离子，或季吡啶鎓离子[Py-R19]+，其中R8至R19彼此独立地相同或不同，并且是H或未取代或取代的烃基，如未取代或取代的(C1-C30)-烷基，未取代或取代的(C1-C10)-烷基芳基，未取代或取代的(C3-C30)-(低聚)烯基，未取代或取代的(C3-C10)-(低聚)烯基芳基，未取代或取代的(C3-C30)-(低聚)炔基，未取代或取代的(C3-C10)-(低聚)炔基，芳基或未取代或取代的芳基，或未取代或取代的杂环基，特别是杂芳基，如未取代或取代的(C1-C10)-烷基-杂芳基，未取代或取代的(C3-C10)-(低聚)烯基-杂芳基，未取代或取代的(C3-C10)-(低聚)炔基-杂芳基或未取代或取代的杂芳基，或两个基团R8/R9、R10/R11、R12/R13、R15/R16或R17/R18一起可形成未取代或取代的环，其中R8至R11基团中的至少一个和R12至R14基团中的至少一个和R15至R18基团中的至少一个不是氢。
优选的ALS抑制剂源于磺酰脲类，例如嘧啶-或三嗪基氨基羰基[苯-、吡啶-、吡唑-、噻吩-和(烷基磺酰基)烷基氨基]磺酰胺。嘧啶环或三嗪环上优选的取代基是烷氧基，烷基，卤代烷氧基，卤代烷基，卤素或二甲基氨基，其中所有的取代基可彼此独立地组合。苯、吡啶、吡唑、噻吩或(烷基磺酰基)烷基氨基部分的优选取代基是烷基、烷氧基、卤素、氨基、烷基氨基、二烷基氨基、酰胺基、酰胺基甲基、硝基、烷氧基羰基、氨基羰基、烷基氨基羰基、二烷基氨基羰基、烷氧基氨基羰基、卤代烷氧基、卤代烷基、烷基羰基、烷氧基烷基、(烷基磺酰基)烷基氨基。所述适宜的磺酰脲是例如：
b1)苯基-和苯甲基磺酰脲类和相关化合物，例如
1-(2-氯苯基磺酰基)-3-(4-甲氧基-6-甲基-1，3，5-三嗪-2-基)脲(氯磺隆)，
1-(2-乙氧基羰基苯基磺酰基)-3-(4-氯-6-甲氧基嘧啶-2-基)脲(氯嘧磺隆)，
1-(2-甲氧基苯基磺酰基)-3-(4-甲氧基-6-甲基-1，3，5-三嗪-2-基)脲(甲磺隆)，
1-(2-氯乙氧基苯基磺酰基)-3-(4-甲氧基-6-甲基-1，3，5-三嗪-2-基)脲(醚苯磺隆)
1-(2-甲氧基羰基苯基磺酰基)-3-(4，6-二甲基嘧啶-2-基)脲(sulfumeturon-methyl)
1-(2-甲氧基羰基苯基磺酰基)-3-(4-甲氧基-6-甲基-1，3，5-三嗪-2-基)-3-甲基脲(苯磺隆)，
1-(2-甲氧基羰基苯甲基磺酰基)-3-(4，6-二甲氧基嘧啶-2-基)脲(苄嘧磺隆)，
1-(2-甲氧基羰基苯基磺酰基)-3-(4，6-双(二氟甲氧基)嘧啶-2-基)脲(氟嘧磺隆)，
3-(4-乙基-6-甲氧基-1，3，5-三嗪-2-基)-1-(2，3-二氢-1，1-二氧代-2-甲基苯并[b]噻吩-7-磺酰基)脲(EP-A079683)，
3-(4-乙氧基-6-乙基-1，3，5-三嗪-2-基)-1-(2，3-二氢-1，1-二氧代-2-甲基苯并[b]噻吩-7-磺酰基)脲(EP-A0079683)，
3-(4-甲氧基-6-甲基-1，3，5-三嗪-2-基)-1-(2-甲氧基羰基-5-碘代苯基-磺酰基)脲(碘甲磺隆及其盐如钠盐，WO92/13845)，
DPX-66037，氟胺磺隆(见 Brighton Crop Prot.Conf.-Weeds-1995，第853页)，
CGA-277476(见Brighton Crop Prot.Conf.-Weeds-1995，第79页)，
2-[3-(4，6-二甲氧基嘧啶-2-基)脲基磺酰基]-4-甲磺酰胺甲基苯甲酸甲酯(甲磺胺磺隆及其盐如钠盐，WO95/10507)，
N，N-二甲基-2-[3-(4，6-二甲氧基嘧啶-2-基)脲基磺酰基]-4-甲酰氨基苯甲酰胺(甲酰胺磺隆及其盐如钠盐，WO95/01344)；
b2)噻吩基磺酰脲类，例如
1-(2-甲氧基羰基噻吩-3-基)-3-(4-甲氧基-6-甲基-1，3，5-三嗪-2-基)脲(噻磺隆)；
b3)吡唑基磺酰脲类，例如
1-(4-乙氧基羰基-1-甲基吡唑-5-基磺酰基)-3-(4，6-二甲氧基嘧啶-2-基)脲(吡嘧磺隆)；
3-氯-5-(4，6-二甲氧基嘧啶-2-基氨基甲酰基氨磺酰基)-1-甲基-吡唑-4-甲酸甲酯(EP-A0282613)；
5-(4，6-二甲基嘧啶-2-基氨基甲酰基氨磺酰基)-1-(2-吡啶基)-吡唑-4-羧酸甲酯(NC-330，见Brighton Crop Prot.Conference “Weeds”1991，第1卷，第45页以后各页)，
DPX-A8947，四唑嘧磺隆，(见Brighton Crop Prot.Conf.“Weeds”1995，第65页)；
b4)磺二酰胺衍生物类，例如
3-(4，6-二甲氧基嘧啶-2-基)-1-(N-甲基-N-甲基磺酰基氨基磺酰基)脲(磺氨磺隆)及其结构类似物(EP-A0131258和Z.Plf.Krankh.Pfl.Schutz，专刊XII，489-497(1990))；
b5)吡啶基磺酰脲类，例如
1-(3-N，N-二甲基氨基羰基吡啶-2-基磺酰基)-3-(4，6-二甲氧基嘧啶-2-基)脲(烟嘧磺隆)，
1-(3-乙基磺酰基吡啶-2-基磺酰基)-3-(4，6-二甲氧基嘧啶-2-基)脲(砜嘧磺隆)，
2-[3-(4，6-二甲氧基嘧啶-2-基)脲基磺酰基]-6-三氟甲基-3-吡啶-羧酸甲酯，钠盐(DPX-KE459，氟啶磺隆，见Brighton Crop Prot.Conf.Weeds，1995，第49页)，
吡啶基磺酰脲类，例如DE-A4000503和DE-A4030577所述的，优选下式的那些化合物
其中
E是CH或N，优选CH，
R20是碘或NR25R26，
R21是氢，卤素，氰基，(C1-C3)-烷基，(C1-C3)-烷氧基，(C1-C3)-卤代烷基，(C1-C3)-卤代烷氧基，(C1-C3)-烷硫基，(C1-C3)-烷氧基-(C1-C3)-烷基，(C1-C3)-烷氧基-羰基，单-或二-((C1-C3)-烷基)氨基，(C1-C3)-烷基亚磺酰基或-磺酰基，SO2-NRxRy或CO-NRxRy，特别是氢，
Rx，Ry彼此独立地是氢，(C1-C3)-烷基，(C1-C3)-烯基，(C1-C3)-炔基或二者一起为-(CH2)4-，-(CH2)5-或-(CH2)2-O-(CH2)2-，
n是0、1、2或3，优选0或1，
R22是氢或CH3，
R23是卤素，(C1-C2)-烷基，(C1-C2)-烷氧基，(C1-C2)-卤代烷基，特别是CF3，(C1-C2)-卤代烷氧基，优选OCHF2或OCH2CF3，
R24是(C1-C2)-烷基，(C1-C2)-卤代烷氧基，优选OCHF2或(C1-C2)-烷氧基，
R25是(C1-C4)-烷基，
R26是(C1-C4)-烷基磺酰基或
R25和R26一起为式-(CH2)3SO2-或-(CH2)4SO2-链，例如3-(4，6-二甲氧基嘧啶-2-基)-1-(3-N-甲基磺酰基-N-甲基-氨基吡啶-2-基)磺酰脲或其盐；
b6)烷氧基苯氧基磺酰脲类，例如EP-A0342569中所述，优选下式的化合物
其中
E是CH或N，优选CH，
R27是乙氧基，丙氧基或异丙氧基，
R28是卤素，NO2，CF3，CN，(C1-C4)-烷基，(C1-C4)-烷氧基，(C1-C4)-烷硫基或(C1-C3)-烷氧基-羰基，优选位于苯环上的6-位，
n是0、1、2或3，优选0或1，
R29是氢，(C1-C4)-烷基或(C3-C4)-烯基，
R30、R31彼此独立地是卤素，(C1-C2)-烷基，(C1-C2)-烷氧基，(C1-C2)-卤代烷基，(C1-C2)-卤代烷氧基或(C1-C2)-烷氧基-(C1-C2)-烷基，优选OCH3或CH3，例如3-(4，6-二甲氧基嘧啶-2-基)-1-(2-乙氧基苯氧基)磺酰脲或其盐；
b7)咪唑基磺酰脲类，例如
MON 37500，乙黄磺隆(见Brighton Crop Prot.Conf.“Weeds”，1995，第57页)和其他相关磺酰脲衍生物及其混合物。
这些活性化合物的典型代表尤其是下列化合物：
磺氨磺隆，四唑黄隆，苄嘧磺隆，氯嘧磺隆，氯磺隆，醚磺隆，环丙嘧磺隆，胺苯磺隆，乙氧嘧磺隆，啶嘧磺隆，氟啶黄隆，氯吡嘧磺隆，唑吡嘧磺隆，甲磺隆，烟嘧磺隆，环丙氧黄隆，氟嘧磺隆，氟磺隆，吡嘧磺隆，砜嘧磺隆，甲嘧磺隆，乙黄黄隆，噻吩磺隆，醚苯磺隆，苯磺隆，氟胺磺隆，碘甲磺隆及其盐如钠盐(WO92/13845)，甲磺胺磺隆及其盐如钠盐(Agrow No.347，3月3日，2000年，第22页(PJB出版有限公司2000))和甲酰胺磺隆及其盐如钠盐(AgroW No.338，10月15日，1999，第26页(PJB出版有限公司2000))。
上述活性化合物已知于例如《农药手册》(The Pesticide Manual)，第12版(1999)，The British Crop Ptrotection Council或各活性化合物后所列的参考文献书目。
多元羧酸烷基酯a)和ALS抑制剂b)的优选组合是将上述优选的成分a)和b)组合到一起。特别优选的多元羧酸烷基酯a)和ALS抑制剂b)的组合是酰嘧磺隆与一种或多种，优选一种选自下组的多元羧酸烷基酯的组合物：草酸二甲酯，草酸二乙酯、草酸二正丙酯、草酸二异丙酯、草酸甲乙酯、丙二酸二甲酯、丙二酸二乙酯、丙二酸二正丙酯、丙二酸二异丙酯和丙二酸甲乙酯、丁二酸二甲酯、丁二酸二乙酯、丁二酸二正丙酯、丁二酸二异丙酯和丁二酸甲乙酯、戊二酸二甲酯、戊二酸二乙酯、戊二酸二正丙酯、戊二酸二异丙酯、戊二酸甲乙酯、己二酸二甲酯、己二酸二乙酯、己二酸二正丙酯、己二酸二异丙酯和己二酸甲乙酯，是乙氧嘧磺隆与一种或多种，优选一种选自下组的多元羧酸烷基酯的组合物：草酸二甲酯，草酸二乙酯、草酸二正丙酯、草酸二异丙酯、草酸甲乙酯、丙二酸二甲酯、丙二酸二乙酯、丙二酸二正丙酯、丙二酸二异丙酯和丙二酸甲乙酯、丁二酸二甲酯、丁二酸二乙酯、丁二酸二正丙酯、丁二酸二异丙酯和丁二酸甲乙酯、戊二酸二甲酯、戊二酸二乙酯、戊二酸二正丙酯、戊二酸二异丙酯、戊二酸甲乙酯、己二酸二甲酯、己二酸二乙酯、己二酸二正丙酯、己二酸二异丙酯和己二酸甲乙酯，是碘甲磺隆和/或其钠盐与一种或多种，优选一种选自下组的多元羧酸烷基酯的组合物：草酸二甲酯，草酸二乙酯、草酸二正丙酯、草酸二异丙酯、草酸甲乙酯、丙二酸二甲酯、丙二酸二乙酯、丙二酸二正丙酯、丙二酸二异丙酯和丙二酸甲乙酯、丁二酸二甲酯、丁二酸二乙酯、丁二酸二正丙酯、丁二酸二异丙酯和丁二酸甲乙酯、戊二酸二甲酯、戊二酸二乙酯、戊二酸二正丙酯、戊二酸二异丙酯、戊二酸甲乙酯、己二酸二甲酯、己二酸二乙酯、己二酸二正丙酯、己二酸二异丙酯和己二酸甲乙酯，是甲酰胺磺隆和/或其钠盐与一种或多种，优选一种选自下组的多元羧酸烷基酯的组合物：草酸二甲酯，草酸二乙酯、草酸二正丙酯、草酸二异丙酯、草酸甲乙酯、丙二酸二甲酯、丙二酸二乙酯、丙二酸二正丙酯、丙二酸二异丙酯和丙二酸甲乙酯、丁二酸二甲酯、丁二酸二乙酯、丁二酸二正丙酯、丁二酸二异丙酯和丁二酸甲乙酯、戊二酸二甲酯、戊二酸二乙酯、戊二酸二正丙酯、戊二酸二异丙酯、戊二酸甲乙酯、己二酸二甲酯、己二酸二乙酯、己二酸二正丙酯、己二酸二异丙酯和己二酸甲乙酯，和甲磺胺磺隆和/或其钠盐与一种或多种，优选一种选自下组的多元羧酸烷基酯的组合物：草酸二甲酯，草酸二乙酯、草酸二正丙酯、草酸二异丙酯、草酸甲乙酯、丙二酸二甲酯、丙二酸二乙酯、丙二酸二正丙酯、丙二酸二异丙酯和丙二酸甲乙酯、丁二酸二甲酯、丁二酸二乙酯、丁二酸二正丙酯、丁二酸二异丙酯和丁二酸甲乙酯、戊二酸二甲酯、戊二酸二乙酯、戊二酸二正丙酯、戊二酸二异丙酯、戊二酸甲乙酯、己二酸二甲酯、己二酸二乙酯、己二酸二正丙酯、己二酸二异丙酯和己二酸甲乙酯。
在另一优选实施方案种，本发明的液体制剂含一种或多种，优选一种选自下组的多元羧酸烷基酯作为成分a)：草酸二甲酯，草酸二乙酯、草酸二正丙酯、草酸二异丙酯、草酸甲乙酯、丙二酸二甲酯、丙二酸二乙酯、丙二酸二正丙酯、丙二酸二异丙酯和丙二酸甲乙酯、丁二酸二甲酯、丁二酸二乙酯、丁二酸二正丙酯、丁二酸二异丙酯和丁二酸甲乙酯、戊二酸二甲酯、戊二酸二乙酯、戊二酸二正丙酯、戊二酸二异丙酯、戊二酸甲乙酯、己二酸二甲酯、己二酸二乙酯、己二酸二正丙酯、己二酸二异丙酯和己二酸甲乙酯，优选己二酸二甲酯，和两种或多种磺酰脲的混合物作为成分b)，例如酰嘧磺隆/碘甲磺隆、酰嘧磺隆/碘甲磺隆钠盐、甲酰胺磺隆/碘甲磺隆、甲酰胺磺隆/碘甲磺隆钠盐、甲酰胺磺隆钠盐/碘甲磺隆、甲酰胺磺隆钠盐/碘甲磺隆钠盐、甲磺胺磺隆/碘甲磺隆、甲磺胺磺隆/碘甲磺隆钠盐、甲磺胺磺隆钠盐/碘甲磺隆和甲磺胺磺隆钠盐/碘甲磺隆钠盐。制剂还可含安全剂，例如吡唑解草酸二乙酯(mefenpyr-diethyl)、双苯唑酸乙酯或喹氧乙酸异庚酯(cloquintocet-mexyl)。
如果合适的话，本发明的液体制剂除成分a)和b)外还可含有一种或多种助剂和添加剂作为其他成分，例如：
(c)表面活性剂如分散剂和乳化剂和/或非表面活性剂聚合物，
(d)不同于成分a)的有机溶剂，
(e)不同于ALS抑制剂的农药，如除草剂、杀虫剂、杀真菌剂、安全剂、生长调节剂或肥料，
(f)常规的制剂助剂，如消泡剂、防冻剂、蒸发抑制剂、防腐剂、添味剂、着色剂、稳定剂、干燥剂或增稠剂，
(g)桶混成分，和/或
(h)附加的水。
因此，本发明的液体制剂可包含例如一种或多种表面活性剂例如离子、非离子或内铵盐表面活性剂作为成分c)。所述表面活性剂可以是单体的或聚合的(例如接枝聚合物)。成分c)的实例是基于硅酮的表面活性剂，例如trisiloxane表面活性剂，聚二甲基硅氧烷的衍生物和/或硅油，或糖基表面活性剂如Atplus309F(Uniqema)。成分c)的其他实例是(C4-C30)-(聚)环氧烷加合物，可以是分枝的、线形的、饱和或不饱和的，特别是脂肪醇和/或脂肪酸和/或脂肪酸酯。(聚)环氧烷加合物的实例是Soprophor CY8(Rhodia)，Genapol X-060，GenapolX-080，Genapol X-150，Genapol X-200，Sapogenat T300，Sapogenat T500，GenapolT200，GenapolT800和GenagenMEE(甲基酯乙氧基化物，Clariant)和具有甲基、乙基、正丙基、异丙基、正丁基、叔丁基、异丁基、仲丁基或乙酰基作为端基的其他末端封端表面活性剂，例如GenapolX-060甲基醚或GenapolX-150甲基醚。
成分c)的其他实例是不溶于制剂的连续相的成分，例如阴离子表面活性剂如Hostapur OSB(Clariant)、Netzer IS(Clariant)、GalorylDT 201(CFPI)，Tamol(BASF)或Morwet D 425(Witco)。通过将不溶于连续相的成分或不溶的活性化合物掺入制剂中，可获得分散体。因此，本发明还包含分散体。
可能的成分c)包括磺基丁二酸酯，例如式(III)的化合物
其中
R1、R2彼此独立地相同或不同，并且是取代或未取代的C1-C30-烃基，如C1-C30-烷基，或(聚)环氧烷加合物，和
M是阳离子，例如金属阳离子如碱金属或碱土金属阳离子，铵阳离子如NH4，烷基-、烷芳基-或聚(芳烷基)苯基-铵阳离子或其(聚)环氧烷加合物，或氨基-封端的(聚)环氧烷加合物。
为说明起见，(聚)环氧烷加合物是可以被烷氧基化的起始物如醇类、胺类、羧酸类如脂肪酸、羟基-或氨基-官能的羧酸酯类(例如基于蓖麻油的甘油三酸酯)或羧酰胺类与烯化氧的反应产物，其中的(聚)环氧烷加合物含有至少一个烯化氧单元，但通常是聚合的，即含有2-200个、优选5-150个烯化氧单元。在烯化氧单元中，优选环氧乙烷、环氧丙烷和环氧丁烷单元，尤其是环氧乙烷单元。所述(聚)环氧烷加合物可由相同或不同的烯化氧构成，例如嵌段或无规排列的环氧丙烷和环氧乙烷单元，因此本申请也包括这种混合的烯化氧加合物。
可能的成分c)还有非表面活性剂聚合物，例如聚乙烯醇、聚丙烯酸酯或聚环氧乙烷。
作为成分c)存在的聚合物可以是无机的(例如硅酸盐、磷酸盐)或有机的，阳离子、阴离子或中性的，以及合成的或天然存在的。
此外，本发明的液体制剂还可包含不同于成分a)的各种有机溶剂作为成分d)，例如非极性溶剂、极性质子性溶剂或偶极非质子性溶剂和其混合物。有机溶剂d)的实例是
-脂族或芳族烃，例如矿物油，石蜡或甲苯，二甲苯和萘衍生物，特别是1-甲基萘，2-甲基萘，C6-C16-芳族化合物的混合物如Solvesso组(ESSO)，例如Solvesso100型(沸点162-177℃)，Solvesso150型(沸点187-207℃)和Solvesso200型(沸点219-282℃)和C6-C20-脂族化合物，其可以是线形或环状的如Shellsol组的产品，T型、K型或BP-n石蜡，
-卤代脂族或芳族烃，如二氯甲烷或氯苯，
-酯类如三醋精(甘油三乙酸酯)，丁内酯，碳酸丙二酯，柠檬酸三乙酯和邻苯二甲酸(C1-C22)烷基酯，特别是邻苯二甲酸(C1-C8)烷基酯，马来酸(C1-C13)烷基酯，
-线形、分枝的饱和或不饱和C1-C20-醇类如甲醇、乙醇、正丙醇和异丙醇、正丁醇、异丁醇、仲丁醇和叔丁醇、四氢糠基醇，以及戊醇、己醇、庚醇
-醚类如乙醚，四氢呋喃(THF)，二氧己环，烷撑二醇单烷基醚和二烷基醚例如丙二醇单甲基醚，特别是DowanolPM(丙二醇单甲基醚)，丙二醇单乙基醚，乙二醇单甲基醚或单乙基醚，二甘醇二甲醚和四甘醇二甲醚，
-酰胺类，如二甲基甲酰胺(DMF)，二甲基乙酰胺，二甲基辛酰胺/二甲基癸酰胺和N-烷基吡咯烷酮，
-酮类，如水溶性丙酮，还有水-不可混溶酮类例如环己酮或异佛尔酮，
-腈类，如乙腈，丙腈，丁腈和苄腈，
-亚砜类和砜类，如二甲基亚砜(DMSO)和环丁砜，还有
-通常所说的油类，如矿物油或植物油如玉米油、亚麻籽油和油菜籽油。
对本发明来说优选作为成分d)的有机溶剂是酯油如油菜籽油甲基酯，和脂族或芳族烃类，Solvesso型，例如Solvesso200或Solvesso150。
本发明的液体制剂可含有非ALS抑制剂的农药作为成分e)。例如非ALS抑制剂的除草剂，例如(杂)芳氧基苯氧基丙酸酯如禾草灵或喹禾灵酯类，杂芳氧基苯氧基丙酸酯类如唑禾草灵乙酯或炔草酯，或烷基嗪类，或安全剂、肥料、杀虫剂、杀真菌剂或杀螨剂。
非ALS抑制剂的除草剂是例如氨基甲酸酯类，硫代氨基甲酸酯类，卤代乙酰替苯胺类，取代的苯氧基-、萘氧基-和苯氧基苯氧基羧酸衍生物，以及还有杂芳氧基苯氧基烷羧酸衍生物如喹啉氧基-、喹喔啉氧基-、吡啶氧基-、苯并唑氧基-和苯并噻唑氧基-苯氧基烷羧酸酯，环己二酮衍生物，以及还有S-(N-芳基-N-烷基氨基甲酰基甲基)二硫代磷酸酯类的除草剂。优选苯氧基苯氧基-和杂芳氧基苯氧基除草剂和与ALS抑制剂(乙酰乳酸合成酶抑制剂)合并使用能拓宽作用谱的除草剂，例如灭草松、氰草津、莠去津、麦草畏、吡氟酰草胺或羟基苄腈类如溴苯腈和碘苯腈和其他叶面除草剂。
可以在本发明的制剂中作为成分e)存在的适宜除草剂是例如：
A)苯氧基苯氧基-和杂芳氧基苯氧基羧酸衍生物类除草剂，如
A1)苯氧基苯氧基-和苄氧基苯氧基羧酸衍生物，例如
2-(4-(2，4-二氯苯氧基)苯氧基)丙酸甲酯(禾草灵)，
2-(4-(4-溴-2-氯苯氧基)苯氧基)丙酸甲酯(DE-A2601548)，
2-(4-(4-溴-2-氟苯氧基)苯氧基)丙酸甲酯(US-A4808750)，
2-(4-(2-氯-4-三氟甲基苯氧基)苯氧基)丙酸甲酯(DE-A2433067)，
2-(4-(2-氟-4-三氟甲基苯氧基)苯氧基)丙酸甲酯(US-A4808750)，
2-(4-(2，4-二氯苯甲基)苯氧基)丙酸甲酯(DE-A2417487)，
4-(4-(4-三氟甲基苯氧基)苯氧基)戊-2-烯酸乙酯，
2-(4-(4-三氟甲基苯氧基)苯氧基)丙酸甲酯(DE-A2433067)；
A2)“单环的”杂芳氧基苯氧基烷羧酸衍生物，例如
2-(4-(3，5-二氯吡啶基-2-氧)苯氧基)丙酸乙酯(EP-A0002925)，
2-(4-(3，5-二氯吡啶基-2-氧)苯氧基)丙酸炔丙酯(EP-A0003114)，
2-(4-(3-氯-5-三氟甲基-2-吡啶氧基)苯氧基)丙酸甲酯(EP-A0003890)，
2-(4-(3-氯-5-三氟甲基-2-吡啶氧基)苯氧基)丙酸乙酯(EP-A0003890)，
2-(4-(5-氯-3-氟-2-吡啶氧基)苯氧基)丙酸炔丙酯(EP-A0191736)，
2-(4-(5-三氟甲基-2-吡啶氧基)苯氧基)丙酸丁酯(精吡氟禾草灵)；
A3)“双环的”杂芳氧基苯氧基烷羧酸衍生物，例如
2-(4-(6-氯-2-喹喔啉氧基)苯氧基)丙酸甲酯和乙酯(喹禾灵甲酯和喹禾灵乙酯)，
2-(4-(6-氟-2-喹喔啉氧基)苯氧基)丙酸甲酯(见J.Pest.Sci.第10卷61(1985))，
2-(4-(6-氟-2-喹喔啉氧基)苯氧基)丙酸2-异亚丙基氨基氧乙酯(喔草酯)，
2-(4-(6-氯苯并唑-2-基氧)苯氧基)丙酸乙酯(唑禾草灵乙酯)，其D(+)异构体(精唑禾草灵乙酯)和2-(4-(6-氯苯并噻唑-2-基氧)苯氧基)丙酸乙酯(DE-A2640730)，
2-(4-(6-氯喹喔啉氧基)苯氧基)丙酸四氢-2-呋喃基甲基酯(EP-A0323727)；
B)氯乙酰替苯胺类，例如
N-甲氧基甲基-2，6-二乙基-氯乙酰替苯胺(甲草胺)，
N-(3-甲氧基丙-2-基)-2-甲基-6-乙基氯乙酰替苯胺(异丙甲草胺)，
2，6-二甲基-N-(3-甲基-1，2，4-二唑-5-基甲基)氯乙酰替苯胺，
N-(2，6-二甲基苯基)-N-(1-吡唑基甲基)氯乙酰替苯胺(吡唑草胺)；
C)硫代氨基甲酸酯类，例如
N，N-二丙基硫代氨基甲酸S-乙基酯(EPTC)，
N，N-二异丁基硫代氨基甲酸S-乙基酯(丁草敌)；
D)环己二酮肟类，例如
3-(1-烯丙氧基亚胺基丁基)-4-羟基-6，6-二甲基-2-氧环己-3-烯甲酸甲酯(禾草灭)，
2-(1-乙氧基亚胺基丁基)-5-(2-乙基硫代丙基)-3-羟基环己-2-烯-1-酮(稀禾啶)，
2-(1-乙氧基亚胺基丁基)-5-(2-苯基硫代丙基)-3-羟基环己-2-烯-1-酮(环己烯草酮)，
2-(1-(3-氯烯丙氧基)亚胺基丁基)-5-(2-乙基硫代丙基)-3-羟基环己-2-烯-1-酮，
2-(1-(3-氯烯丙氧基)亚胺基丙基)-5-(2-乙基硫代丙基)-3-羟基环己-2-烯-1-酮(烯草酮)，
2-(1-乙氧基亚胺基丁基)-3-羟基-5-(四氢噻喃-3-基)环己-2-烯酮(噻草酮)，
2-(1-乙氧基亚胺基丁基)-5-(2，4，6-三甲基苯基)-3-羟基环己-2-烯-1-酮(肟草酮)；
E)苯甲酰环己二酮类，例如
2-(2-氯-4-甲基磺酰基苯甲酰基)环己烷-1.3-二酮(SC-0051，EP-A-0137963)，
2-(2-硝基苯甲酰基)-4，4-二甲基环己烷-1，3-二酮(EP-A0274634)，
2-(2-硝基-3-甲基磺酰基苯甲酰基)-4，4-二甲基环己烷-1，3-二酮(WO91/13548)；
F)S-(N-芳基-N-烷基氨基甲酰基甲基)二硫代磷酸酯类，如
S-[N-(4-氯苯基)-N-异丙基氨基甲酰基甲基]O，O-二甲基二硫代磷酸酯(莎稗磷)；
G)烷基嗪类，例如WO97/08156、WO-A-97/31904、DE-A-19826670、WO-A-98/15536、WO-A-8/15537、WO-A-98/15538、WO-A-98/15539和DE-A-19828519、WO-A-98/34925、WO-A-98/42684、WO-A-99/18100、W99/19309、WO-A-99/37627和WO-A-99/65882中所述，优选式(E)的化合物
其中
R1是(C1-C4)-烷基或(C1-C4)-卤代烷基；
R2是(C1-C4)-烷基，(C3-C6)-环烷基或(C3-C6)-环烷基-(C1-C4)-烷基和
A是-CH2、-CH2-CH2-、-CH2-CH2-CH2-、-O-、-CH2-CH2-O-、-CH2-CH2-CH2-O-，特别优选式E1-E7的化合物
组A至G的除草剂已知于例如上述公开文本和《农药手册》(“ThePesticide Manual”)，The British Crop Protection Council，第12版，2000(缩写成PM)，“Agricultural Chemicals Book II-Herbicides-”，W.T.Thompson，Thomposon Publications，Fresno CA，USA1990和“Farm Chemicals Handbook’90”，Meister Publishing Company，Willoughby OH，USA，1990。
下列各组化合物可以在本发明的制剂中例如作为安全剂存在，作为成分e)：
a)二氯苯基吡唑啉-3-羧酸(S1)类化合物，优选化合物1-(2，4-二氯苯基)-5-(乙氧基羰基)-5-甲基-2-吡唑啉-3-羧酸乙酯(S1-1)，和相关化合物(吡唑解草酸二(C1-C15-烷基)酯，如吡唑解草酸二乙酯)，如WO91/07874和PM第594-595页所述，
b)二氯苯基吡唑羧酸的衍生物，优选化合物如EP-A-333131和EP-A-269806中所述的
1-(2，4-二氯苯基)-5-甲基吡唑-3-羧酸乙酯(S1-2)，
1-(2，4-二氯苯基)-5-异丙基吡唑-3-羧酸乙酯(S1-3)，
1-(2，4-二氯苯基)-5-(1，1-二甲基乙基)吡唑-3-羧酸乙酯(S1-4)，
1-(2，4-二氯苯基)-5-苯基吡唑-3-羧酸乙酯(S1-5)和
相关化合物，
c)三唑羧酸(S1)类化合物，优选化合物如解草唑，即1-(2，4-二氯苯基)-5-三氯甲基-(1H)-1，2，4-三唑-3-羧酸乙酯(S1-6)和相关化合物(见EP-A-174562和EP-A-346620)；
d)5-苯甲基-或5-苯基-2-异唑啉-3-羧酸或5，5-二苯基-2-异唑啉-3-羧酸类化合物，优选化合物如WO91/08202所述的
5-(2，4-二氯苯甲基)-2-异唑啉-3-羧酸乙酯(S1-7)或
5-苯基-2-异唑啉-3-羧酸乙酯(S1-8)和相关化合物，或如德国专利申请(WO-A-95/07897)中所述的
5，5-二苯基-2-异唑啉羧酸乙酯(S1-9，双苯唑酸乙酯)或正丙酯(S1-10)或
5-(4-氟苯基)-5-苯基-2-异唑啉-3-羧酸乙酯(S1-11)，
e)8-喹啉氧乙酸(S2)类化合物，优选如EP-A-86750、EP-A-94349和EP-A-191736或EP-A-0492366中所述的(5-氯-8-喹啉氧)乙酸1-甲基己-1-基酯(S2-1，喹氧乙酸异庚酯，例如PM(第195-196页))，
(5-氯-8-喹啉氧)乙酸1，3-二甲基丁-1-基酯(S2-2)，
(5-氯-8-喹啉氧)乙酸4-烯丙氧基丁基酯(S2-3)，
(5-氯-8-喹啉氧)乙酸1-烯丙氧基丙-2-基酯(S2-4)，
(5-氯-8-喹啉氧)乙酸乙酯(S2-5)，
(5-氯-8-喹啉氧)乙酸甲酯(S2-6)，
(5-氯-8-喹啉氧)乙酸烯丙酯(S2-7)，
(5-氯-8-喹啉氧)乙酸2-(2-亚丙基亚氨氧基)-1-乙基酯(S2-8)，
(5-氯-8-喹啉氧)乙酸2-氧代丙-1-基酯(S2-9)和相关化合物，
f)(5-氯-8-喹啉氧)丙二酸类化合物，优选化合物如EP-A-0582198所述的
(5-氯-8-喹啉氧)丙二酸二乙酯，
(5-氯-8-喹啉氧)丙二酸二烯丙酯，
(5-氯-8-喹啉氧)丙二酸甲乙酯和相关化合物，
g)苯氧基乙酸或丙酸衍生物或芳族羧酸类活性化合物，例如
2，4-二氯苯氧基乙酸(酯)(2，4-D)，
4-氯-2-甲基苯氧基丙酸酯(2甲4氯丙酸)，MCPA或
3，6-二氯-2-甲氧基苯甲酸(酯)(麦草畏)，
h)嘧啶类活性化合物，被用作稻的土壤作用安全剂，例如
“解草啶”(PM，第386-387页)(＝4，6-二氯-2-苯基嘧啶)，已知在播种稻中作为丙草胺的安全剂，
i)二氯乙酰胺类活性化合物，经常被用作苗前安全剂(土壤作用安全剂)，例如
“烯丙酰草胺”(PM，第270-271页)(＝N，N-二烯丙基-2，2-二氯乙酰胺)，
“R-29148”(＝3-二氯乙酰基-2，2，5-三甲基-1，3-唑烷，来自Stauffer)，
“解草嗪”(PM，第74-75页)(＝4-二氯乙酰基-3，4-二氢-3-甲基-2H-1，4-苯并嗪)，
“PPG-1292”(＝N-烯丙基-N-[(1，3-二氧戊环-2-基)甲基]二氯乙酰胺，产自PPG Industries)，
“DK-24”(＝N-烯丙基-N-[(烯丙基氨基羰基)甲基]二氯乙酰胺，来自Sagro-Chem)，
“AD-67”或“MON 4660”(＝3-二氯乙酰基-1-氧杂-3-氮杂-螺[4，5]癸烷，产自Nitrokemia或Monsanto)，
“diclonon”或“BAS145138”或“LAB145138”(＝3-二氯乙酰基-2，5，5-三甲基-1，3-二氮杂双环[4.3.0]壬烷，来自BASF)和
“解草呋”或“MON13900”(见PM，482-483)(＝(RS)-3-二氯乙酰基-5-(2-呋喃基)-2，2-二甲基唑烷酮)，
j)二氯酮衍生物类活性化合物，例如
“MG191”(CAS-Reg.No.96420-72-3)(＝2-二氯甲基-2-甲基-1，3-二氧戊环，产自Nitrokemia)，已知可用作谷物的安全剂，
k)氧亚氨基化合物类活性化合物，该化合物已知可用作拌种，例如
“解草腈”(PM，第689页)(＝(Z)-1，3-二氧戊环-2-基甲氧基-亚氨基(苯基)乙腈)，该化合物已知可用作拌种安全剂保护作物不受异丙甲草胺的危害，
“肟草安”(PM，第467-468页)(＝1-(4-氯苯基)-2，2，2-三氟-1-乙酮O-(1，3-二氧戊环-2-基甲基)肟)，该化合物已知用作拌种安全剂保护作物不受异丙甲草胺的危害，和
“抑害腈”或“-CGA-43089”(PM，第983页)(＝(Z)-氰基甲氧基亚氨基(苯基)乙腈)，该化合物已知用作拌种安全剂保护作物不受异丙甲草胺的危害，
l)噻唑羧酸酯类活性化合物，该化合物已知用作拌种剂，例如
“解草胺”(PM，第450-451页)(＝2-氯-4-三氟甲基-1，3-噻唑-5-羧酸苯甲酯)，该化合物已知用作拌种安全剂保护作物不受甲草胺和异丙甲草胺的危害，
m)萘二羧酸衍生物类活性化合物，该化合物已知用作拌种剂，例如
“萘二甲酐”(PM，第1009-1010页)(＝1，8-萘二甲酸酐)，该化合物已知用作拌种安全剂保护谷物不受硫代氨基甲酸酯除草剂的危害，
n)苯并二氢吡喃乙酸衍生物类活性化合物，例如
“解草酸”(CAS-Reg.No.31541-57-8)(＝2-84-羧基苯并二氢吡喃-4-基)乙酸，产自American Cyanamid)，该化合物已知用作安全剂保护谷物不受咪唑啉酮的危害，
o)除对有害植物有除草活性外还对作物如稻有安全剂作用的活性化合物，例如
“哌草丹”或“MY-93”(PM，第302-303页)(＝S-1-甲基-1-苯基乙基哌啶-1-硫代羧酸酯)，该化合物已知用作安全剂保护稻不受除草剂草达灭的危害，
“香草隆”或“SK 23”(PM，第247页)(＝1-(1-甲基-1-苯基乙基)-3-对甲苯脲)，该化合物已知用作安全剂保护稻不受除草剂唑吡嘧磺隆的危害，
“苄草隆”＝“JC-940”(＝3-(2-氯苯基甲基)-1-(1-甲基-1-苯基乙基)脲，见JP-A-60087254)，该化合物已知用作安全剂保护稻不受一些除草剂的危害，
“去草酮”或“NK049”(＝3，3-二甲基-4-甲氧基二苯甲酮)，该化合物已知用作安全剂保护稻不受一些除草剂的危害，
“CSB”(＝1-溴-4-(氯甲基磺酰基)苯)(CAS-Reg.No.54091-06-4，来自Kumiai)。
优选的安全剂是吡唑解草酸二乙酯、双苯唑酸乙酯和喹氧乙酸异庚酯。
在本发明的液体制剂中，可含有常规的制剂助剂如消泡剂、防冻剂、蒸发抑制剂、防腐剂、添味剂、着色剂、稳定剂、干燥剂或增稠剂作为成分f)。优选的制剂助剂是防冻剂和蒸发抑制剂如甘油，例如2-10重量％含量，和防腐剂例如MergalK9N(Riedel)或CobateC。
本发明的制剂还可含有桶混成分作为成分g)。实例是桶混助剂如Telmion(Hoechst)或植物油如Actirob B(Novance)或Hasten(Victorian Chemicals)，无机化合物如肥料，例如硫酸铵、硝酸铵、硫酸氢铵、尿素或水溶助长剂(hydrotropics)。
本发明的制剂还可含有附加的水作为成分h)。
本发明的液体制剂可以例如溶液、乳油或分散体的形式存在，如乳剂或悬浮剂。本文优选至少一种属于ALS抑制剂的活性化合物，优选至少一种磺酰脲，以溶解的形式存在。在更优选的实施方案中，所有的活性化合物成分都是溶解的。
根据本发明可通过加水将含成分a)和b)和，如果合适的话，成分c)、d)、e)、f)和g)的溶液转化成微乳剂和/或粗乳剂或含水溶液。因此，除了溶于多元羧酸烷基酯a)和/或有机溶剂中的溶液外，本发明还包含含水制剂如微乳剂和粗乳剂(例如EW和EO制剂)。
通过将不溶于连续相的活性化合物或成分掺入制剂，可获得分散体。因此，本发明还包含所述分散体。当用水稀释时，本发明的制剂形成分散体或含水溶液，这同样包含在本发明范围内。
本发明的制剂中活性化合物的含量通常在0.001-60重量％，在个别的情况下可允许更高的含量，特别是当使用多种活性化合物时。由于ALS抑制剂是高效活性化合物，优选的用量通常是1-1000g，优选500g，优选1-100ga.i./ha。一般而言，根据本发明，多元羧酸衍生物的含量是0.01-99.9％，优选0.1-99％；然而在个别情况下可以更高或更低。
在本发明的液体制剂特别是乳油中成分a)∶b)的优选比例是0.1∶1-1000∶1，优选1∶1-500∶1，特别是1∶1至200∶1。特别优选的是成分a)的重量超过成分b)，例如约2∶1、3∶1、5∶1、6∶1、7∶1、10∶1、50∶1、100∶1、200∶1、300∶1、400∶1和500∶1。
可用于制备本发明的制剂的助剂和添加剂例如表面活性剂和溶剂是通常已知的并描述于例如：McCutcheon的“Detergents andEmulsifiers Annual”，MC Publ.Corp.，Ridgewood N.J.；Sisley andWood，“Encyclopedia of Surface Active Agents”，Chem.Publ.Co.Inc.，N.Y. 1964；Schnfeldt，“Grenzflchenaktivethylenoxidaddukte”[表面活性环氧乙烷加合物]，Wiss，Verlagsgesellschaft，Stuttgart 1976；Winnacker-Küchler，“ChemischeTechnologie”[化学工艺]，第7卷，C.Hauser-Verlag，慕尼黑，第4版1986。
本发明的液体制剂可通过常规已知的工艺制备，即例如通过借助搅拌器、振动器或(静电)混合器将不同的成分混合。必要时短暂的加热是有利的。就ALS抑制剂类盐来说，此简单工艺可以通过使用例如非离子表面活性剂原位制备相应的ALS抑制剂盐，优选其中未发生中和作用的那些非离子表面活性剂。
因此，本发明还包含用于制备本发明的液体制剂的所述工艺。这些工艺特别因产量相关的优点而突出。
在优选的实施方案中，所用的ALS抑制剂如磺酰脲类是带有具有相转移性能的平衡离子的抑制剂。所述平衡离子是例如有机平衡离子如有机铵、锍或膦离子。如果所述平衡离子存在于与另外的例如非离子的制剂成分的混合物中，那么它们可以以特别简单的方式掺入制剂中。因此，本发明还包括将平衡离子掺入制剂。
本发明的液体制剂优选包含
(a)0.01-99.9重量％，优选0.1-60重量％的多元羧酸烷基酯，
(b)0.001-50重量％，优选0.1-15重量％的属于ALS抑制剂的除草活性化合物，优选磺酰脲类和/或其盐，
(c)0-60重量％，优选0.1-50重量％的表面活性剂和/或非表面活性剂聚合物，
(d)0-90重量％，优选1-30重量％的不同于成分a)的有机溶剂，
(e)0-50重量％，优选0-30重量％的非ALS抑制剂的农药，
(f)0-20重量％，优选0-10重量％的常规制剂助剂，和
(g)0-50重量％，优选0-10重量％的额外的水。
特别优选的液体制剂包含：
(a)0.01-99重量％的二羧酸二烷基酯，例如具有下述结构：
(C1-C6)烷基-O-OC-(CH2)0-10-CO-O-(C1-C6)烷基的化合物
(b)0.001-30重量％的磺酰脲类和/或其盐，
(c1)任选的0.5-40重量％的非离子表面活性剂，例如下式
R-(EO)x(PO)y(EO)z-R’的那些表面活性剂
其中R是H或C1-C30-烃氧基如二-或三-苯乙烯基苯酚，单-、二-或三-(C1-C10)烷基-芳氧基或(C1-C20)烷基-(聚)烯氧基，优选(C8-C18)-烷氧基或单-、二-或三-(C1-C10)烷基苯氧基和
R’是H、COH、CO-(C1-C6)烷基、CO(C1-C6)烷氧基或(C1-C6)烷基，和
x、y和z是0-200的整数，其中4≤x+y+z≤200，优选6≤x+y+z≤100；特别优选x是6-200的整数，优选8-100，和y＝z＝0，和
(C2)任选的0.5-60重量％的式(IIIa)的磺酰丁二酸酯：
RIIIO2C-CH2-CH(SO3M)-CO2RIV (IIIa)
其中
RIII和RIV是相同或不同的(C1-C10)烷基，如2-乙基己基，和
M是金属阳离子，例如碱金属离子如Na或K离子。
这些特别优选的组合物自身就是制剂，或也能构成成品制剂的基础。
使用本发明的配方可获得储藏稳定的ALS抑制剂如磺酰脲和/或其盐的溶液，以及其中溶解了至少一种磺酰脲和/或其盐的液体制剂。
如果将磺酰脲和/或其衍生的盐溶解于成分a)，通过添加表面活性剂和，如果合适的话，其他助剂可以获得相应的液体制剂。
本发明的液体制剂可用于例如防治例如作物中的不想要的植物。为此，将有效量的本发明制剂(必要时用水稀释后)施用到种子、植物、植物部分或需处理的区域，例如栽培区。
本发明的制剂是物理和化学稳定的制剂，并且在用水稀释时得到具有良好的物理操作特性的喷液。此外，本发明的制剂具有良好的生物性能并且可被广泛用于例如防治不想要的植物。
实施例：
实施例1
将1.1g碘甲磺隆钠盐添加到98.9g己二酸二甲酯中，搅拌混合物直至活性化合物完全溶解。在40℃，该制剂稳定储藏超过2个月。
实施例2
将1.05g甲磺胺磺隆添加到98.95g己二酸二甲酯中，搅拌混合物直至活性化合物完全溶解。在40℃，该制剂稳定储藏超过2个月。
实施例3
搅拌条件下，将1.05g碘甲磺隆钠盐溶解于88.95g己二酸二甲酯中。一旦碘甲磺隆钠盐完全溶解，添加10g GenapolX-060甲基醚。搅拌混合物直至获得清澈制剂。在40℃，该制剂稳定储藏超过2个月。
实施例4
使用Ultraturax将5.38g碘甲磺隆钠盐、10g HostapurSAS 93G和84.62g己二酸二甲酯均匀混合。然后向混合物中加入玻璃珠，在珠磨中研磨直至获得均匀的分散体。在40℃，该制剂稳定储藏超过2个月。
实施例5
向58.46g己二酸二甲酯、15.00g TritonGR-7M E和3.0g EdenorME SU中添加1.54g碘甲磺隆钠盐、4.46g吡唑解草酸二乙酯和8.02g2-(1-环丁基-4-苯基丙基)氨基-4-氨基-6-(1-氟-1-甲基乙基)-1，3，5-三嗪(E1)。搅拌混合物直至活性化合物完全溶解。然后添加9.52gGenapolX-060甲基醚。搅拌混合物直至获得清澈的制剂。在40℃，该制剂稳定储藏超过2个月。
Claims (11)
1.一种液体制剂，包含a)一种或多种多元羧酸烷基酯类化合物和b)一种或多种选自磺酰脲类和/或其盐的农药活性化合物，其中至少一种活性化合物以溶解形式存在。
2.如权利要求1所述的液体制剂，包含一种或多种式(I)的化合物作为成分a)
Rγ-O-OC-(CRαRβ)x-CO-O-Rδ (I)
其中
Rα和Rβ是相同或不同的，并且是H，取代或未取代的C1-C20-烃基，或基团(CR′R″)y-CO-OR，其中R′和R″是相同或不同的，并且是H或未取代或取代的C1-C20-烃基，y是0-10的整数，R是未取代或取代的C1-C20-烃基，
Rγ和Rδ是相同或不同的，并且是未取代或取代的C1-C20-烃基，x是0-20的整数。
3.如权利要求2所述的液体制剂，其中所述C1-C20-烃基是C1-C10-烷基。
4.如权利要求1-3中任一项所述的液体制剂，包含一种或多种选自磺酰脲类和/或其盐的农药活性化合物结合一种或多种非ALS抑制剂的农药作为成分b)。
5.如权利要求1-4中任一项所述的液体制剂，包含
a)一种或多种多元羧酸烷基酯类化合物，和
b)一种或多种选自磺酰脲类和/或其盐的农药活性化合物，和
选自下组的一种或多种其他成分
(c)表面活性剂和/或非表面活性剂聚合物，
(d)不同于成分a)的有机溶剂，
(e)非ALS抑制剂的农药，
(f)常规的制剂助剂，
(g)桶混成分，和/或
(h)水。
6.如权利要求1-5中任一项所述的液体制剂，包含
(a)0.1-80重量％的一种或多种多元羧酸烷基酯类化合物，
(b)0.001-50重量％的一种或多种选自磺酰脲类和/或其盐的农药活性化合物，
(c)0-60重量％的表面活性剂和/或非表面活性剂聚合物，
(d)0-90重量％的不同于成分a)的有机溶剂，
(e)0-50重量％的非ALS抑制剂的农药，
(f)0-20重量％的常规制剂助剂，和/或
(g)0-50重量％的水。
7.如权利要求1-6中任一项所述的液体制剂，包含
(a)10-60重量％的一种或多种多元羧酸烷基酯类化合物，
(b)1-15重量％的一种或多种选自磺酰脲类和/或其盐的农药活性化合物，
(c)0-50重量％的表面活性剂和/或非表面活性剂聚合物，
(d)0-30重量％的不同于成分a)的有机溶剂，
(e)0-50重量％的非ALS抑制剂的农药，
(f)0-10重量％的常规制剂助剂。
8.溶液、分散体或乳油形式的如权利要求1-7中任一项所述的液体制剂。
9.一种制备权利要求1-8中任一项所述的液体制剂的方法，包括将各成分彼此混合。
10.如权利要求9所述的方法，其中各成分在混合后被研磨。
11.一种防治不想要的植物的方法，包括将有效量的如权利要求1-8中一项或多项所述的制剂施用到种子、植物、植物部分或需处理区。
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE10108472.2 | 2001-02-22 | ||
| DE10108472A DE10108472A1 (de) | 2001-02-22 | 2001-02-22 | Agrochemische Formulierungen |
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| Publication Number | Publication Date |
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| CN1529549A CN1529549A (zh) | 2004-09-15 |
| CN1315376C true CN1315376C (zh) | 2007-05-16 |
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| Application Number | Title | Priority Date | Filing Date |
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| CNB028052870A Expired - Lifetime CN1315376C (zh) | 2001-02-22 | 2002-01-19 | 农药制剂 |
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| Country | Link |
|---|---|
| US (1) | US7776792B2 (zh) |
| EP (1) | EP1363490B1 (zh) |
| JP (1) | JP2004518749A (zh) |
| CN (1) | CN1315376C (zh) |
| AP (1) | AP1696A (zh) |
| AR (1) | AR032813A1 (zh) |
| AT (1) | ATE404054T1 (zh) |
| AU (1) | AU2002225025B2 (zh) |
| BR (1) | BR0207440A (zh) |
| CA (1) | CA2438992A1 (zh) |
| CZ (1) | CZ20032243A3 (zh) |
| DE (2) | DE10108472A1 (zh) |
| DK (1) | DK1363490T3 (zh) |
| DZ (1) | DZ3495A1 (zh) |
| EA (1) | EA008006B1 (zh) |
| ES (1) | ES2310587T3 (zh) |
| HR (1) | HRP20030663A2 (zh) |
| HU (1) | HUP0303260A3 (zh) |
| MA (1) | MA26002A1 (zh) |
| MX (1) | MXPA03007579A (zh) |
| NZ (1) | NZ527671A (zh) |
| PL (1) | PL367280A1 (zh) |
| SK (1) | SK10312003A3 (zh) |
| UA (1) | UA82829C2 (zh) |
| WO (1) | WO2002067676A1 (zh) |
| YU (1) | YU65503A (zh) |
| ZA (1) | ZA200305991B (zh) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE10258216A1 (de) * | 2002-12-13 | 2004-07-08 | Bayer Cropscience Gmbh | Ölsuspensionskonzentrat |
| DE10258867A1 (de) * | 2002-12-17 | 2004-07-08 | Bayer Cropscience Gmbh | Mikroemulsionskonzentrate |
| DE10334301A1 (de) * | 2003-07-28 | 2005-03-03 | Bayer Cropscience Gmbh | Flüssige Formulierung |
| AU2006200731B2 (en) | 2005-03-31 | 2011-05-19 | Sumitomo Chemical Company, Limited | Emulsifiable concentrate |
| ZA200802442B (en) | 2005-09-01 | 2010-02-24 | Du Pont | Liquid sulfonylurea herbicide formulations |
| TW200816921A (en) * | 2006-07-24 | 2008-04-16 | Sumitomo Chemical Co | Pesticide emulsifiable concentrate |
| JP5066880B2 (ja) * | 2006-09-27 | 2012-11-07 | 住友化学株式会社 | 乳剤組成物 |
| DE102008058642A1 (de) * | 2008-11-22 | 2010-05-27 | Bayer Cropscience Ag | Herbizid-Kombinationen enthaltend Diflufenican und ALS-Inhibitoren |
| AR082963A1 (es) * | 2010-09-17 | 2013-01-23 | Sumitomo Chemical Co | Composicion para aerosol de control de plagas |
| AU2013265337B2 (en) * | 2012-05-25 | 2016-09-08 | Bayer Cropscience Ag | Chemical stabilization of iodosulfuron-methyl sodium salt by hydroxystearates |
| EP3081550A4 (en) * | 2013-12-11 | 2017-04-26 | Oxiteno S.A. Industria e Comercio | Polycarboxilic acid alkyl ester derived from branched and linear alcohol of plant origin, and use of an alkyl ester in agrochemical formulations |
| US11109588B2 (en) | 2019-02-19 | 2021-09-07 | Gowan Company, L.L.C. | Stable liquid formulations and methods of using the same |
| GB202014872D0 (en) * | 2020-09-21 | 2020-11-04 | Upl Corporation Ltd | A stable herbicidal composition |
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| DE10029169A1 (de) | 2000-06-19 | 2002-01-03 | Aventis Cropscience Gmbh | Herbizide Mittel |
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2001
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- 2002-01-19 EP EP02715454A patent/EP1363490B1/de not_active Expired - Lifetime
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| US4626274A (en) * | 1982-12-20 | 1986-12-02 | Bayer Aktiengesellschaft | Herbicidal agents |
| EP1023833A2 (en) * | 1999-01-29 | 2000-08-02 | American Cyanamid Company | Emulsifiable concentrate containing one or more pesticides and adjuvants |
Also Published As
| Publication number | Publication date |
|---|---|
| HUP0303260A3 (en) | 2004-06-28 |
| WO2002067676A1 (de) | 2002-09-06 |
| SK10312003A3 (sk) | 2004-05-04 |
| EA008006B1 (ru) | 2007-02-27 |
| MXPA03007579A (es) | 2003-12-08 |
| CN1529549A (zh) | 2004-09-15 |
| YU65503A (sh) | 2006-08-17 |
| US7776792B2 (en) | 2010-08-17 |
| ATE404054T1 (de) | 2008-08-15 |
| US20040097378A1 (en) | 2004-05-20 |
| ES2310587T3 (es) | 2009-01-16 |
| DZ3495A1 (fr) | 2002-09-06 |
| UA82829C2 (en) | 2008-05-26 |
| MA26002A1 (fr) | 2003-12-31 |
| JP2004518749A (ja) | 2004-06-24 |
| DE50212634D1 (de) | 2008-09-25 |
| ZA200305991B (en) | 2004-05-31 |
| EP1363490B1 (de) | 2008-08-13 |
| DK1363490T3 (da) | 2008-10-27 |
| BR0207440A (pt) | 2004-03-02 |
| AP1696A (en) | 2006-12-15 |
| AU2002225025B2 (en) | 2006-08-17 |
| AR032813A1 (es) | 2003-11-26 |
| HRP20030663A2 (en) | 2005-06-30 |
| HUP0303260A2 (hu) | 2004-01-28 |
| EA200300802A1 (ru) | 2004-02-26 |
| EP1363490A1 (de) | 2003-11-26 |
| NZ527671A (en) | 2005-06-24 |
| AP2003002861A0 (en) | 2003-09-30 |
| CA2438992A1 (en) | 2002-09-06 |
| DE10108472A1 (de) | 2002-09-05 |
| CZ20032243A3 (cs) | 2003-11-12 |
| PL367280A1 (en) | 2005-02-21 |
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