CN1007952B - 控制不希望的檀物生长的方法 - Google Patents
控制不希望的檀物生长的方法Info
- Publication number
- CN1007952B CN1007952B CN85109235A CN85109235A CN1007952B CN 1007952 B CN1007952 B CN 1007952B CN 85109235 A CN85109235 A CN 85109235A CN 85109235 A CN85109235 A CN 85109235A CN 1007952 B CN1007952 B CN 1007952B
- Authority
- CN
- China
- Prior art keywords
- compound
- alkyl
- isopropyl
- control
- methyl
- 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
Links
- 238000000034 method Methods 0.000 title claims abstract description 17
- 150000001875 compounds Chemical class 0.000 claims abstract description 28
- 239000000203 mixture Substances 0.000 claims abstract description 16
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims abstract 2
- -1 sec-amyl Chemical group 0.000 claims description 12
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 241000196324 Embryophyta Species 0.000 description 21
- 239000003814 drug Substances 0.000 description 16
- 239000002689 soil Substances 0.000 description 13
- 239000002270 dispersing agent Substances 0.000 description 10
- 230000002363 herbicidal effect Effects 0.000 description 9
- 238000012360 testing method Methods 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 230000000694 effects Effects 0.000 description 7
- 238000009472 formulation Methods 0.000 description 7
- 239000003921 oil Substances 0.000 description 7
- 235000019198 oils Nutrition 0.000 description 7
- 239000000843 powder Substances 0.000 description 7
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 6
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
- 125000000217 alkyl group Chemical group 0.000 description 6
- 239000003995 emulsifying agent Substances 0.000 description 6
- 239000004009 herbicide Substances 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 238000009736 wetting Methods 0.000 description 6
- 241000209764 Avena fatua Species 0.000 description 5
- 235000007320 Avena fatua Nutrition 0.000 description 5
- 244000207667 Rumex vesicarius Species 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 238000005507 spraying Methods 0.000 description 5
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 4
- 235000004535 Avena sterilis Nutrition 0.000 description 4
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 4
- 235000015422 Rumex crispus ssp. crispus Nutrition 0.000 description 4
- 235000015426 Rumex crispus ssp. fauriei Nutrition 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 239000008187 granular material Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- RSJKGSCJYJTIGS-UHFFFAOYSA-N undecane Chemical compound CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 description 4
- 240000001592 Amaranthus caudatus Species 0.000 description 3
- 235000009328 Amaranthus caudatus Nutrition 0.000 description 3
- 241000219198 Brassica Species 0.000 description 3
- 235000003351 Brassica cretica Nutrition 0.000 description 3
- 235000003343 Brassica rupestris Nutrition 0.000 description 3
- 244000025254 Cannabis sativa Species 0.000 description 3
- 235000010086 Setaria viridis var. viridis Nutrition 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 238000007796 conventional method Methods 0.000 description 3
- 235000010460 mustard Nutrition 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 description 3
- 230000002265 prevention Effects 0.000 description 3
- 238000012545 processing Methods 0.000 description 3
- 239000004094 surface-active agent Substances 0.000 description 3
- 239000000080 wetting agent Substances 0.000 description 3
- 240000006995 Abutilon theophrasti Species 0.000 description 2
- 244000178993 Brassica juncea Species 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- 238000004061 bleaching Methods 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000004202 carbamide Substances 0.000 description 2
- 239000000969 carrier Substances 0.000 description 2
- 239000012141 concentrate Substances 0.000 description 2
- 239000010949 copper Substances 0.000 description 2
- 229910052802 copper Inorganic materials 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 229940079593 drug Drugs 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000003337 fertilizer Substances 0.000 description 2
- 244000304962 green bristle grass Species 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 150000002431 hydrogen Chemical class 0.000 description 2
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- HWZRUVUGGXYRSY-UHFFFAOYSA-N propan-2-yl 2-bromo-5-methyl-1-propan-2-ylimidazole-4-carboxylate Chemical compound CC(C)OC(=O)C=1N=C(Br)N(C(C)C)C=1C HWZRUVUGGXYRSY-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 239000004576 sand Substances 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- 239000000341 volatile oil Substances 0.000 description 2
- SMYMJHWAQXWPDB-UHFFFAOYSA-N (2,4,5-trichlorophenoxy)acetic acid Chemical class OC(=O)COC1=CC(Cl)=C(Cl)C=C1Cl SMYMJHWAQXWPDB-UHFFFAOYSA-N 0.000 description 1
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 description 1
- 239000003559 2,4,5-trichlorophenoxyacetic acid Substances 0.000 description 1
- FFRBMBIXVSCUFS-UHFFFAOYSA-N 2,4-dinitro-1-naphthol Chemical compound C1=CC=C2C(O)=C([N+]([O-])=O)C=C([N+]([O-])=O)C2=C1 FFRBMBIXVSCUFS-UHFFFAOYSA-N 0.000 description 1
- OVSKIKFHRZPJSS-DOMIDYPGSA-N 2-(2,4-dichlorophenoxy)acetic acid Chemical compound OC(=O)[14CH2]OC1=CC=C(Cl)C=C1Cl OVSKIKFHRZPJSS-DOMIDYPGSA-N 0.000 description 1
- PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 description 1
- NCBRFNJSIVSEIW-UHFFFAOYSA-N 2-bromo-5-methyl-1h-imidazole-4-carboxylic acid Chemical compound CC=1N=C(Br)NC=1C(O)=O NCBRFNJSIVSEIW-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 1
- 235000011332 Brassica juncea Nutrition 0.000 description 1
- 235000007539 Brassica juncea var juncea Nutrition 0.000 description 1
- 235000014700 Brassica juncea var napiformis Nutrition 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- XVDWALQQOIVLEB-UHFFFAOYSA-N C(N)(O)=O.C(CNC(S)=S)NC(SC1CCCCC1)=S Chemical compound C(N)(O)=O.C(CNC(S)=S)NC(SC1CCCCC1)=S XVDWALQQOIVLEB-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- 229920000858 Cyclodextrin Polymers 0.000 description 1
- 241000234653 Cyperus Species 0.000 description 1
- 244000285774 Cyperus esculentus Species 0.000 description 1
- 235000005853 Cyperus esculentus Nutrition 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 240000001549 Ipomoea eriocarpa Species 0.000 description 1
- 235000005146 Ipomoea eriocarpa Nutrition 0.000 description 1
- 241000032989 Ipomoea lacunosa Species 0.000 description 1
- 239000005574 MCPA Chemical class 0.000 description 1
- 238000003820 Medium-pressure liquid chromatography Methods 0.000 description 1
- 241001465754 Metazoa Species 0.000 description 1
- 244000088461 Panicum crus-galli Species 0.000 description 1
- 235000011999 Panicum crusgalli Nutrition 0.000 description 1
- 229920001213 Polysorbate 20 Polymers 0.000 description 1
- 235000021501 Rumex crispus Nutrition 0.000 description 1
- OKUGPJPKMAEJOE-UHFFFAOYSA-N S-propyl dipropylcarbamothioate Chemical compound CCCSC(=O)N(CCC)CCC OKUGPJPKMAEJOE-UHFFFAOYSA-N 0.000 description 1
- 235000005775 Setaria Nutrition 0.000 description 1
- 241000232088 Setaria <nematode> Species 0.000 description 1
- 240000003461 Setaria viridis Species 0.000 description 1
- 235000002248 Setaria viridis Nutrition 0.000 description 1
- WHKUVVPPKQRRBV-UHFFFAOYSA-N Trasan Chemical class CC1=CC(Cl)=CC=C1OCC(O)=O WHKUVVPPKQRRBV-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 239000000443 aerosol Substances 0.000 description 1
- 125000002877 alkyl aryl group Chemical group 0.000 description 1
- 150000001350 alkyl halides Chemical group 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 150000001448 anilines Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 238000000889 atomisation Methods 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- SMDHCQAYESWHAE-UHFFFAOYSA-N benfluralin Chemical compound CCCCN(CC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O SMDHCQAYESWHAE-UHFFFAOYSA-N 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- 235000012216 bentonite Nutrition 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- 150000001559 benzoic acids Chemical class 0.000 description 1
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
- 229910052794 bromium Inorganic materials 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 239000002361 compost Substances 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 239000000428 dust Substances 0.000 description 1
- 239000004495 emulsifiable concentrate Substances 0.000 description 1
- 239000004497 emulsifiable granule Substances 0.000 description 1
- 125000004494 ethyl ester group Chemical class 0.000 description 1
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 1
- 238000009313 farming Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 235000013312 flour Nutrition 0.000 description 1
- 238000002309 gasification Methods 0.000 description 1
- 230000035784 germination Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 239000004519 grease Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 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
- 239000003906 humectant Substances 0.000 description 1
- 239000003864 humus Substances 0.000 description 1
- 229910010272 inorganic material Inorganic materials 0.000 description 1
- 239000011147 inorganic material Substances 0.000 description 1
- 239000002917 insecticide Substances 0.000 description 1
- 229910052740 iodine Chemical group 0.000 description 1
- 239000011630 iodine Chemical group 0.000 description 1
- 239000003621 irrigation water Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002790 naphthalenes Chemical class 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000010451 perlite Substances 0.000 description 1
- 235000019362 perlite Nutrition 0.000 description 1
- 125000005342 perphosphate group Chemical group 0.000 description 1
- 239000003209 petroleum derivative Substances 0.000 description 1
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
- 238000002203 pretreatment Methods 0.000 description 1
- MMYIRYIEBITCJY-UHFFFAOYSA-N propan-2-yl 2-bromo-5-methyl-1h-imidazole-4-carboxylate Chemical compound CC(C)OC(=O)C=1NC(Br)=NC=1C MMYIRYIEBITCJY-UHFFFAOYSA-N 0.000 description 1
- QZCUILGAOGOQMV-UHFFFAOYSA-N propan-2-yl 2-bromo-5-methyl-3-propan-2-ylimidazole-4-carboxylate Chemical compound CC(C)OC(=O)C1=C(C)N=C(Br)N1C(C)C QZCUILGAOGOQMV-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000003921 pyrrolotriazines Chemical class 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
- 239000000376 reactant Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- HFHDHCJBZVLPGP-UHFFFAOYSA-N schardinger α-dextrin Chemical compound O1C(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC(C(O)C2O)C(CO)OC2OC(C(C2O)O)C(CO)OC2OC2C(O)C(O)C1OC2CO HFHDHCJBZVLPGP-UHFFFAOYSA-N 0.000 description 1
- 238000012216 screening Methods 0.000 description 1
- 239000000741 silica gel Substances 0.000 description 1
- 229910002027 silica gel Inorganic materials 0.000 description 1
- 238000010898 silica gel chromatography Methods 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 150000003558 thiocarbamic acid derivatives Chemical class 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N titanium dioxide Inorganic materials O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- VXUYXOFXAQZZMF-UHFFFAOYSA-N titanium(IV) isopropoxide Chemical compound CC(C)O[Ti](OC(C)C)(OC(C)C)OC(C)C VXUYXOFXAQZZMF-UHFFFAOYSA-N 0.000 description 1
- 238000005809 transesterification reaction Methods 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000010455 vermiculite Substances 0.000 description 1
- 229910052902 vermiculite Inorganic materials 0.000 description 1
- 235000019354 vermiculite Nutrition 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/90—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)
- Catalysts (AREA)
Abstract
控制不希望的植物生长的为法,该方法包括施用有效除莠量的一种具有以下结构的化合物到需要控制的地域上,此化合物是以与农业上常用的惰性载体的混合物的形式施用的
式中R为C1-C6烷基;Y为环丙基甲基、C1-C3烷基或烯丙基。
Description
控制不希望的植物生长的方法具有结构式为:
的化合物在美国3,501,286号专利中作为除莠剂而被描述,式中R为氢、烷基或取代的烷基,Y为氢、烷基、取代的烷基、卤素、氰基或硝基。
Pyman和Timmis在1923年的《英国化学会志》第494-498页中进述了一种式为
的化合物,但是除了用做制备药物的中间体之外,没有谈到其它用途。
本发明讲的是作为除莠剂的2-溴-4-甲基咪唑-5-羧酸酯。本发明的新化合物具有如下结构式:
式中,R为C1-C10烷基,较为满意的是C2-C5烷基,异丙基、仲丁基或仲戊基则更好。而Y是C3-C6环烷基烷基(其中烷基有1-6个碳原子),更为满意的是环丙甲基;C1-C6烷基,更好是C1-C3烷基,最好是甲基或异丙基;或者是C3-C6烯烃基,更好是烯丙基。
以上所描述的本发明的化合物中,烷基包括直链和支链构型,例如甲基、乙基、正丙基、异丙基、正丁基、仲丁基、异丁基和叔丁基,以及各种戊基、各种己基、各种庚基、各种壬基及各种癸基。
本发明的化合物是一般类型的活性除莠剂。也就是说它们对大范围种类的植物有除莠剂效果。本发明的控制所不希望的植物生长的方法包括在需要控制的地域内施以有效除莠量的上述化合物。
本发明的化合物可按下述一般方法制备:
反应式中R为已定义的,TEC为酯基转移催化剂,如Ti(O-烷基)4,更满意的是四异丙氧基钛。
式中R为已定义的,Y-X为卤代烷或卤代烯烃,其中Y为已定义的,X为氯、溴或碘。
通常,对于步骤1)至少要用一摩尔该醇与该乙酯反应以制备咪唑类化合物。最好是用稍稍过量的醇。将反应混合物回流至反应完全。除去挥发物来回收反应产物。大气压下、低于一大气压的或超过一大气压的压力都能用,这取决于所用溶剂的沸点,乙醇在升温和减压条件下易于除尽。
反应步骤2)是在象苯或甲苯这样的溶剂中进行的,反应温度约为25-100℃,回流温度更好,用等摩尔量的两种反应物和叔胺碱。该叔胺碱最好是二氮杂二环十一烷。
反应产物为(1)异构体
的混合物,是用常规技术加工得到的。
(1)和(3)异构体可用硅胶色谱法分开。属于本发明的(3)异构体是所希望的产物,具有良好的除莠活性。(1)异构体有较小的除莠活性。
以下诸例讲述了本发明的代表性化合物的合成。
实例Ⅰ
2-溴-3-异丙基-4-甲基-5-咪唑羧酸异丙酯
于一20毫升苯中溶有2克(8.1×10-3摩尔)2-溴-4-甲基-5-咪唑羧酸异丙酯的溶液中加热1.2毫升(8.2×10-3摩尔)二氮杂二环十一烷,再加入1.0克(8.1×10-3摩尔)2-溴丙烷。所得到的混合物加热回流过夜,然后冷至室温并过滤。真空下浓缩得到一金黄色油状物。此剩余物在硅胶上进行中压液相色谱提纯,得到1.6克(70%)黄色油状的1-异丙基-2-溴-4-甲基-5-咪唑羧酸异丙酯,以及466毫克(20%)预期产物,即也是一黄色油状物的2-溴-3-异丙基-4-甲基-5-咪唑羧酸异丙酯。
下表所列是一些挑选出的可按此处所述方法制备的化合物。化合物编号指定于每一化合物并一直用于本申请书的其余部分。
表Ⅰ在后面
如前所述,按照上面所述的方法生产的、此处描述的化合物都是阻止植物生长的化合物,在控制各种植物方面都是有用的和有价值的。所选出的化合物是作为除莠剂按下述方法进行试验的。
出芽前除莠剂试验:在前处理那一天,将八种不同的莠草种子分行种在肥沃的沙土中,每行一个品种,行的长度为苗床的宽度。所用种子为绿狐尾草(FT)(Setaria Vividis)、湿地草类(WG)(Echinochloa Crusgalli)、野燕麦(WO)(Avenafatua)、一年生牵牛花(AMG)(Ipomoealacunosa)、苘麻(VL)(Abutilon theophrasti)、印度芥(MD)(Brassica Juncea)、皱叶酸模(CD)(Rumex crispus)、和铁荸荠(YNG)
(Cyperus esulentus)的种子。要种下足够多的种子,使出芽后每行有20至40棵小苗,这取决于植物的大小。
用一张已知重量的半透明玻璃称量纸在分析天平上称出600毫克要试验的化合物。化合物与纸一起放入60毫升广口透明瓶中并溶于45毫升丙酮或代用溶剂中。将18毫升所得溶液转移到60毫升广口玻璃瓶中,并用22毫升含有足够的聚氧乙烯山梨聚糖单月桂酸酯乳化剂的水与丙酮的混合物(19∶1)冲稀,得到最终为0.5%(V/V)的溶液。然后将溶液用一校准到能按80加仑/英亩(748升/公顷)比例喷洒的线性喷洒台(Linearspray table)喷洒到播过种的苗床上,施用率为4磅/英亩(4.48公斤/公顷)。
处理后,将苗床放在温度为70-80°F的温室内,并以喷洒法浇水。二周后与同样年龄的未处理的核对植物相比较以确定损害或控制的程度,记录对每种植物的由零到100%的损害程度,作为控制百分率数据,以0%代表未损害的,以100%代表完全控制的。
试验结果示于表Ⅱ在后面。
出芽后除莠试验:本试验是以和出芽前除莠试验的试验步骤基本相同的方式进行的,只不过8种不同莠草的种子是在处理前10至12天种下的。另外,给已处理过的苗床浇水时也是限制在土壤表层,而不能浇到发芽植物的叶子上。
出芽后除莠试验的结果报告于表Ⅲ中在后面。
本发明的化合物可用做除莠剂,且可按不同方法、以各种浓度使用。在实践中,可将本发明的化合物按有效除莠量与通常用于促使农业上应用的各种活性成分分散的载体和辅剂相混合而配制成各种除莠组合物,但要认识到这样一个事实,即对于给定用途而言,药物的剂型(formulation)及其使用方式能够影响所用材料的活性。例如,可将这些有除莠活性的化合物配制成粒度相当大的颗粒剂、可湿性粉剂、乳油、粉剂、溶液或其它几种已知剂型,这取决于所希望的使用方式。用于出芽前除莠的较好剂型是可湿性粉剂、可乳化浓缩物和颗粒剂。这些剂型中活性成分的重量百分含量可以从小至约为0.5%到大至约为95%或更多些。有效剂量决定于所要控制的种子或植物的性质;施用率为约0.05-25磅/英亩,更好是约0.1-10磅/英亩。
可湿性粉剂是易于分散于水或其它分散剂中的细微颗粒形式。可湿性粉剂最终施用于土壤的形式既可以是干粉,也可以是在水或其它液体中的悬浮体。可湿性粉剂的典型载体有漂白土、高岭土、氧化硅和其它易湿的有机或无机稀释剂。可湿性粉剂通常配制成含有约5%到95%的活性成分的形式,并且一般还含有少量湿润剂、分散剂或乳化剂以促进湿润和分散。
乳油是分散在水或其它分散剂中的均相液体组合物,可以完全由活性化合物和一种液体或固体乳化剂所组成,或者还可以含有一种液体载体,象二甲苯、重芳香挥发油、异佛尔铜及其它非挥发性有机溶剂。除莠时,将这些浓缩物分散在水或其它液体载体中并且常以喷雾的形式施用到待处理的区域内。主要的活性成分的重量百分比可按照组合物的使用方式而改变,但通常活性成分的含量约为除莠组合物重量的0.5%到95%。
颗粒剂中药物是承载在相当粗的颗粒上的,通常可以不经稀释而施用到希望抑制植物生长的区域内。颗粒剂中的典型载体包括:沙子、漂白土、膨润土、蛭石、珍珠岩及其它吸收药物或能被药物覆盖的有机和无机材料。颗粒剂通常制成含有约5%到25%的活性成分的形式,其中可含有象湿润剂、分散剂或乳化剂等表面活性剂,象重芳香挥发油、煤油或其它石油馏分或植物油的油类,以及/或象环糊精、动物胶或合成树脂等粘着剂。
用于农业药剂的典型湿润剂、分散剂或乳化剂包括,例如:磺酸和硫酸的烷基酯、烷基芳基酯和钠盐,多羟基醇及其它类型的表面活性剂,其中许多都是能在商业上得到的。当使用表面活性剂时,其含量通常约为除莠剂重量的0.1%到15%。
活性成分与诸如滑石、粘土、面粉及其它对该成分起分散剂和载体作用的有机和无机固体的细微固体形成的自由流动混合物-粉剂,是与土壤掺和施用的有用剂型。
细微的固体药物在象水或油等液体载体中所成的均匀悬浮体的糊浆用于特殊目有。这类药剂中通常含有约5%-95%重量的活性成分,还可以含有少量湿润剂、分散剂或乳化剂以利于分散。施用时,一般将糊浆冲稀并以喷雾形式施用到植物生长的区域内。
其它有用的除莠制剂包括活性成分以所希望的
表1
化合物编号 R Y 熔点℃
1(a)异丙基 异丙基 黄色油
2 仲丁基 异丙基 ″
3 乙基 环丙甲基 ″
4 异丙基 乙基 ″
5 正丙基 异丙基 ″
6 异丙基 甲基 77~79
7 仲戊基 甲基 黑色油
8 仲丁基 甲基 ″
9 异丙基 烯丙基 黄色油
10 乙基 甲基 67~68
(a)实例Ⅱ中制备的。
除莠筛选试验
表Ⅱ
出芽前除莠活性,施用率:4.48公斤/公顷
化合物
编号 FT WG WO AMG VL MD CD YNG
1 60 60 30 60 60 60 60 0
2 100 100 30 60 90 100 100 0
3 0 0 0 0 0 0 0 0
4 0 0 0 0 0 0 0 0
5 0 0 0 20 20 100 15 0
6 100 100 100 100 100 100 100 0
7 0 0 0 0 0 0 0 0
8 30 0 25 20 90 100 90 0
9 60 80 30 100 100 100 85 -
10 0 30 20 100 100 100 75 0
表Ⅲ
出芽前除莠活性,施用率:4.48公斤/公顷
化合物
编号 FT WG WO AMG VL MD CD YNG
1 100 100 100 100 100 100 100 0
2 100 100 100 100 100 100 100 0
3 100 25 20 80 100 100 30 0
4 0 0 0 30 70 100 0 0
5 100 50 70 100 100 100 100 20
6 100 100 100 100 100 100 100 0
7 0 0 0 100 100 80 100 0
8 0 0 0 100 100 100 0 0
9 100 50 70 95 95 90 85 0
0 20 15 10 60 85 95 15 0
浓度完全溶解在分散剂中所形成的简单溶液,这些分散剂有丙酮、烷基化萘类、二甲苯及其它有机溶剂。也可以使用加压喷雾药,典型的是气溶胶,其中活性成分分散的程度很高,这是象佛利昂类的低沸点分散剂溶剂载体气化的结果。
本发明的阻止植物生长的药剂是以常规方式施用于植物的。例如,粉剂和液剂可用电动洒粉器、臂式和手提式喷雾器以及喷雾洒粉器施用于植物。因为有效剂量很低,所以这些药剂也可以在飞机上以粉尘或喷雾的形式施用,为了改进控制发芽种子或破土籽苗的生长-作为一个典型例子,可将粉剂或液剂按照常规方法施用于土壤并分布在土壤表面以下至少半英寸深度的土壤内。将阻止植物生长的药剂与土壤颗粒混合并不是必需的,因为这些药剂也可仅仅通过喷雾或喷洒于土壤表面来施用。本发明的阻止植物生长的药剂也可通过将其加到灌溉水中的方法施用到待处理的土地中。这种施用方法能使药剂象水被吸收一样渗入土壤。已施用到土壤表面的粉剂、粒剂或液体制剂(formulation),可用常规方法分布到土壤表面下,如用圆盘耙耕作、耙地或混合操作。
本发明的阻止植物生长的药剂中也可以含有其它附加物,例如:作为辅剂使用或与前面所述的辅剂中的任一种联合使用的肥料及其它除莠剂、杀虫剂以及类似物。与前述化合物联合使用的其它阻止植物成长的化合物包括,例如:2,4-二氯苯氧乙酸、2,4,5-三氯苯氧乙酸、2-甲基-4-氯苯氧乙酸及其盐类、酯类和酰胺类;三嗪衍生物,如2,4-双(3-甲氧丙胺基)-6-甲硫基均三嗪、2-氯-4-乙胺基-6-异丙胺基均三嗪及2-乙胺基-4-异丙胺基-6-甲硫基均三嗪;脲衍生物,如1-(3,4-二氯苯基)-1,1-二甲基脲和3-(对氯苯基)-1,1-二甲基脲;乙酰胺类,如N,N-二烯丙基-a-氯乙酰胺和类似物;苯甲酸类,如3-氨基-2,5-二氯代苯甲酸;硫代氨基甲酸酯类,如N,N-二丙基硫代氨基甲酸S-丙酯、N,N-二丙基硫代氨基甲酸S-乙酯、环己基乙基硫代氨基甲酸S-乙酯、六氢-1H-氮杂卓-1-硫代羧酸S-乙酯以及类似物;苯胺类,如4-(甲磺酰)-2,6-二硝基-N,N-取代的苯胺、4-三氟甲基-2,6-二硝基-N,N-二正丙基苯胺、4-三氟甲基-2,6-二硝基-N-乙基-N-丁基苯胺;2-[4-(2,4-二氯苯氧基)苯氧基]丙酸;2-[1-(乙氧亚胺基)丁基)]-5-[2-(乙硫基)丙基]-3-羟基-2-环己烯-1-铜;(±)-丁基-2-[4-[(5-三氟甲基)-2-吡啶基]氧基]苯氧基]丙酸酯;5-[2-氯-4-(三氟甲基)苯氧基]-2-硝基苯甲酸钠;2,2-二氧化3-异丙基-1H-2,1,3-苯并噻二嗪-4(3H)-酮及4-氨基-6-叔丁基-3-(甲硫基)-1,2,4-三嗪-5(4H)-酮或(4-氨基-6-(1,1-二甲基乙基)-3-(甲硫基)-1,2,4-三嗪-5(4H)-酮。与活性成分联合使用的肥料包括,例如:硝酸铵、尿素和过磷酸盐。其它有用的附加物包括植物组织可在其中生根和生长的材料,例如堆肥、腐殖质、沙子等等。
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US5211737A (en) * | 1989-01-31 | 1993-05-18 | Basf Aktiengesellschaft | 4-arryl-2-haloimidazole-5-carboxylic esters, the preparation and use thereof |
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NZ213864A (en) | 1988-11-29 |
IL76698A (en) | 1989-01-31 |
RO92794A (ro) | 1987-11-30 |
HU198607B (en) | 1989-11-28 |
ZA857970B (en) | 1987-01-28 |
EP0180787B1 (en) | 1988-04-20 |
AR240170A1 (es) | 1990-02-28 |
JPS6197269A (ja) | 1986-05-15 |
ATE33643T1 (de) | 1988-05-15 |
HUT39324A (en) | 1986-09-29 |
US4595400A (en) | 1986-06-17 |
CA1258861A (en) | 1989-08-29 |
CN85109235A (zh) | 1986-12-17 |
AU573911B2 (en) | 1988-06-23 |
EP0180787A1 (en) | 1986-05-14 |
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