CN1052308A - 异唑啉,其制备方法以及作为植物保护剂的应用 - Google Patents
异唑啉,其制备方法以及作为植物保护剂的应用 Download PDFInfo
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- CN1052308A CN1052308A CN90109402A CN90109402A CN1052308A CN 1052308 A CN1052308 A CN 1052308A CN 90109402 A CN90109402 A CN 90109402A CN 90109402 A CN90109402 A CN 90109402A CN 1052308 A CN1052308 A CN 1052308A
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- 238000002360 preparation method Methods 0.000 title claims description 27
- 239000004476 plant protection product Substances 0.000 title claims description 4
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 title description 7
- 150000003851 azoles Chemical class 0.000 title description 3
- 150000001875 compounds Chemical class 0.000 claims abstract description 58
- 230000001473 noxious effect Effects 0.000 claims abstract description 3
- 231100000419 toxicity Toxicity 0.000 claims abstract description 3
- 230000001988 toxicity Effects 0.000 claims abstract description 3
- 125000000217 alkyl group Chemical group 0.000 claims description 31
- -1 substituted-phenyl Chemical group 0.000 claims description 31
- 125000003545 alkoxy group Chemical group 0.000 claims description 26
- 239000013543 active substance Substances 0.000 claims description 25
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 22
- 150000003839 salts Chemical class 0.000 claims description 19
- 125000004414 alkyl thio group Chemical group 0.000 claims description 17
- 229910052736 halogen Inorganic materials 0.000 claims description 17
- 150000002367 halogens Chemical class 0.000 claims description 17
- 239000001301 oxygen Substances 0.000 claims description 14
- 229910052760 oxygen Inorganic materials 0.000 claims description 14
- 239000001257 hydrogen Substances 0.000 claims description 13
- 229910052739 hydrogen Inorganic materials 0.000 claims description 13
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 12
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 11
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 10
- 230000000694 effects Effects 0.000 claims description 10
- 125000003282 alkyl amino group Chemical group 0.000 claims description 9
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 9
- 239000000460 chlorine Substances 0.000 claims description 9
- 238000000034 method Methods 0.000 claims description 9
- 239000011737 fluorine Substances 0.000 claims description 8
- 229910052731 fluorine Inorganic materials 0.000 claims description 8
- 125000002757 morpholinyl group Chemical group 0.000 claims description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 8
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 7
- 229910052801 chlorine Inorganic materials 0.000 claims description 7
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 7
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 6
- 125000003368 amide group Chemical group 0.000 claims description 6
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 6
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 6
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 6
- 125000005843 halogen group Chemical group 0.000 claims description 5
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 4
- 150000001336 alkenes Chemical class 0.000 claims description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 4
- 125000000000 cycloalkoxy group Chemical group 0.000 claims description 4
- 125000001188 haloalkyl group Chemical group 0.000 claims description 4
- 230000002363 herbicidal effect Effects 0.000 claims description 4
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 3
- OILAIQUEIWYQPH-UHFFFAOYSA-N cyclohexane-1,2-dione Chemical class O=C1CCCCC1=O OILAIQUEIWYQPH-UHFFFAOYSA-N 0.000 claims description 3
- 239000004009 herbicide Substances 0.000 claims description 3
- 150000002825 nitriles Chemical class 0.000 claims description 3
- 125000006766 (C2-C6) alkynyloxy group Chemical group 0.000 claims description 2
- 125000005133 alkynyloxy group Chemical group 0.000 claims description 2
- 125000006310 cycloalkyl amino group Chemical group 0.000 claims description 2
- 239000000945 filler Substances 0.000 claims description 2
- 125000000717 hydrazino group Chemical group [H]N([*])N([H])[H] 0.000 claims description 2
- 125000004356 hydroxy functional group Chemical group O* 0.000 claims description 2
- 125000005186 naphthyloxy group Chemical group C1(=CC=CC2=CC=CC=C12)O* 0.000 claims description 2
- 125000005936 piperidyl group Chemical group 0.000 claims description 2
- 125000004076 pyridyl group Chemical group 0.000 claims description 2
- 231100000331 toxic Toxicity 0.000 claims description 2
- 230000002588 toxic effect Effects 0.000 claims description 2
- 125000004665 trialkylsilyl group Chemical group 0.000 claims description 2
- FZERHIULMFGESH-UHFFFAOYSA-N N-phenylacetamide Chemical compound CC(=O)NC1=CC=CC=C1 FZERHIULMFGESH-UHFFFAOYSA-N 0.000 claims 2
- 244000038559 crop plants Species 0.000 claims 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 claims 1
- GNVMUORYQLCPJZ-UHFFFAOYSA-M Thiocarbamate Chemical compound NC([S-])=O GNVMUORYQLCPJZ-UHFFFAOYSA-M 0.000 claims 1
- 229960001413 acetanilide Drugs 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 239000000729 antidote Substances 0.000 abstract 1
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 21
- 239000000203 mixture Substances 0.000 description 17
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- 241000196324 Embryophyta Species 0.000 description 12
- 239000003921 oil Substances 0.000 description 12
- 239000011734 sodium Substances 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 229940017219 methyl propionate Drugs 0.000 description 10
- 239000003795 chemical substances by application Substances 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- 239000002904 solvent Substances 0.000 description 7
- 239000004562 water dispersible granule Substances 0.000 description 7
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- 238000009472 formulation Methods 0.000 description 6
- 239000004563 wettable powder Substances 0.000 description 6
- 230000006378 damage Effects 0.000 description 5
- 239000005995 Aluminium silicate Substances 0.000 description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
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- 150000002148 esters Chemical class 0.000 description 4
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- 229910052740 iodine Inorganic materials 0.000 description 4
- 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 4
- 239000007788 liquid Substances 0.000 description 4
- 240000005979 Hordeum vulgare Species 0.000 description 3
- 235000007340 Hordeum vulgare Nutrition 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 241000209140 Triticum Species 0.000 description 3
- 235000021307 Triticum Nutrition 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
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- 150000001721 carbon Chemical group 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 125000004494 ethyl ester group Chemical group 0.000 description 3
- FKRCODPIKNYEAC-UHFFFAOYSA-N ethyl propionate Chemical compound CCOC(=O)CC FKRCODPIKNYEAC-UHFFFAOYSA-N 0.000 description 3
- 150000002191 fatty alcohols Chemical class 0.000 description 3
- 239000003337 fertilizer Substances 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000007921 spray Substances 0.000 description 3
- 238000005507 spraying Methods 0.000 description 3
- 239000000080 wetting agent Substances 0.000 description 3
- WEQPBCSPRXFQQS-UHFFFAOYSA-N 4,5-dihydro-1,2-oxazole Chemical compound C1CC=NO1 WEQPBCSPRXFQQS-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 231100000674 Phytotoxicity Toxicity 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- 230000000996 additive effect Effects 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 125000000304 alkynyl group Chemical group 0.000 description 2
- 150000003863 ammonium salts Chemical class 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
- 235000013339 cereals Nutrition 0.000 description 2
- 239000004927 clay Substances 0.000 description 2
- 239000000084 colloidal system Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
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- 238000005469 granulation Methods 0.000 description 2
- 230000003179 granulation Effects 0.000 description 2
- 125000003971 isoxazolinyl group Chemical group 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 239000002480 mineral oil Substances 0.000 description 2
- 235000010446 mineral oil Nutrition 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
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- 239000000178 monomer Substances 0.000 description 2
- 238000010899 nucleation Methods 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
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- 239000010695 polyglycol Substances 0.000 description 2
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- BGRYSGVIVVUJHH-UHFFFAOYSA-N prop-2-ynyl propanoate Chemical compound CCC(=O)OCC#C BGRYSGVIVVUJHH-UHFFFAOYSA-N 0.000 description 2
- 230000001681 protective effect Effects 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
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- 239000002689 soil Substances 0.000 description 2
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- 150000003558 thiocarbamic acid derivatives Chemical class 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- TXTWXQXDMWILOF-UHFFFAOYSA-N (2-ethoxy-2-oxoethyl)azanium;chloride Chemical compound [Cl-].CCOC(=O)C[NH3+] TXTWXQXDMWILOF-UHFFFAOYSA-N 0.000 description 1
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 description 1
- QFBDCSDDHUBEGG-UHFFFAOYSA-N 1,2-dibutylnaphthalene;sodium Chemical compound [Na].C1=CC=CC2=C(CCCC)C(CCCC)=CC=C21 QFBDCSDDHUBEGG-UHFFFAOYSA-N 0.000 description 1
- XFRVVPUIAFSTFO-UHFFFAOYSA-N 1-Tridecanol Chemical compound CCCCCCCCCCCCCO XFRVVPUIAFSTFO-UHFFFAOYSA-N 0.000 description 1
- VONWPEXRCLHKRJ-UHFFFAOYSA-N 2-chloro-n-phenylacetamide Chemical class ClCC(=O)NC1=CC=CC=C1 VONWPEXRCLHKRJ-UHFFFAOYSA-N 0.000 description 1
- MSBVBOUOMVTWKE-UHFFFAOYSA-N 2-naphthalen-2-ylnaphthalene Chemical group C1=CC=CC2=CC(C3=CC4=CC=CC=C4C=C3)=CC=C21 MSBVBOUOMVTWKE-UHFFFAOYSA-N 0.000 description 1
- FOGYNLXERPKEGN-UHFFFAOYSA-N 3-(2-hydroxy-3-methoxyphenyl)-2-[2-methoxy-4-(3-sulfopropyl)phenoxy]propane-1-sulfonic acid Chemical compound COC1=CC=CC(CC(CS(O)(=O)=O)OC=2C(=CC(CCCS(O)(=O)=O)=CC=2)OC)=C1O FOGYNLXERPKEGN-UHFFFAOYSA-N 0.000 description 1
- NOBPWDYRGXWVRL-UHFFFAOYSA-N 5-[(2,4-dichlorophenyl)methyl]-4,5-dihydro-1,2-oxazole-3-carboxylic acid Chemical compound C1C(C(=O)O)=NOC1CC1=CC=C(Cl)C=C1Cl NOBPWDYRGXWVRL-UHFFFAOYSA-N 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 1
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- BMTAFVWTTFSTOG-UHFFFAOYSA-N Butylate Chemical compound CCSC(=O)N(CC(C)C)CC(C)C BMTAFVWTTFSTOG-UHFFFAOYSA-N 0.000 description 1
- 125000004399 C1-C4 alkenyl group Chemical group 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
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- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
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- DBMJMQXJHONAFJ-UHFFFAOYSA-M Sodium laurylsulphate Chemical compound [Na+].CCCCCCCCCCCCOS([O-])(=O)=O DBMJMQXJHONAFJ-UHFFFAOYSA-M 0.000 description 1
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- 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
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Abstract
式(I)所示化合物可用作许多除草剂的植物毒性
解毒剂,而除草剂对有害植物的有效性不受影响。式
(I)中的Z、X和n如权利要求1所述。
Description
本发明涉及安全剂或解毒剂,它与除草剂联合使用时能够降低除草剂对作物的植物毒性。
本发明的目的是提供通式(Ⅰ)所示的具有保护植物作用的异唑啉或其盐:
式中Z分别代表卤素,硝基,氰基或烷基,烷氧基,烷硫基或环烷基(其中最后四种基团未被取代或被烷氧基,羟基或卤素取代一次或多次),氨基,一或二烷基氨基,苯基或苯氧基(其中苯基和苯氧基未被取代或已被卤素或卤代烷基取代一次或多次),或者两个相邻的Z取代基共同代表一个未被取代的或被烷基取代的二价基团:-OCH2O-,-S-CH2-O-或-S-CH2-S-
n代表0-5的整数,
X代表羟基或烷氧基,烯氧基,炔氧基,烷硫基或环烷氧基(其中最后五个基团未被取代或被基团烷氧基,烷硫基,一和二烷基氨基,苯基,取代苯基,氰基和卤素取代一次或多次),苯氧基或取代苯氧基,三烷基甲硅烷基甲氧基,下式所示的基团:
(上式中R各代表氢或烷基,Z1与Z无关,具有上面Z中所述的含义,n1代表0-5的整数),
氨基,一或二烷基氨基,环烷基氨基,肼基,烷基肼基或二烷基肼基,吡啶基,吗啉基,二甲基吗啉基,下式的基团:
(上式中R1和R2分别代表烷基,或者R1和R2与连结它们的碳原子一起形成一个环烷基),此外,X还代表下式的基团:
(上式中R3和R4分别代表氢或烷基)。
式(Ⅰ)中的烷基,烷氧基,卤代烷基,烷氨基和烷硫基以及相应的不饱和的和/或被取代的基团可以是直链的或支链的。烷基以及复合基团如烷氧基,卤代烷基等中的烷基代表甲基,乙基,正-和异-丙基,正-、异-、叔和2-丁基,同分异构的戊基,己基,庚基,辛基,壬基,癸基,十一烷基和十二烷基以及带有至多24个碳原子的长链脂族烷基;优选的是C1-C12烷基。烯基和炔基具有与烷基相应的不饱和基团的意义,优选的为(C2-C12)烯基和炔基。卤素代表氟,氯,溴或碘,较好的为氟,氯或溴,最好为氟或氯。
在X=OH的情况下,式(Ⅰ)化合物可以形成盐。本发明使用的盐可以是可应用于农业上的盐类。例如这种盐包括金属盐如碱金属或碱土金属盐尤其是钠盐或钾盐,铵盐或被最好有至多4个碳原子的烷基和/或醇基取代一至四次的取代铵盐。
式(Ⅰ)化合物还包括所有的立体异构体和它们的混合物,尤其是纯对映体和它们的混合物(例如外消旋体)。若式(Ⅰ)中存在不对称碳原子或适当的取代双键,则主要产生立体异构体。不对称碳原子是在异噁唑啉环上与氧原子键合的碳原子。
本发明尤为感兴趣的是式(Ⅰ)所示的有保护植物作用的化合物,式中:
Z分别代表卤素,硝基,氰基,(C1-C4)烷基,(C1-C4)烷氧基,(C1-C4)烷硫基(其中烷基、烷氧基和烷硫基未被取代或被卤原子尤其是被氟或氯取代一次或多次),未被取代的或被(C1-C4)烷基取代的(C3-C6)烷基,氨基,(C1-C4)烷氨基,二(C1-C4)烷氨基,羟甲基,(C1-C4)烷氧基甲基,苯基或苯氧基(其中苯基或苯氧基未被取代或已被卤素取代一次或多次,或被三氟甲基取代一次,或被一个或几个卤原子和一个三氟甲基取代一次),或者,两个相邻的Z取代基代表二价基团:-O-CH2-O-,-S-CH2-O-或-S-CH2-S-,以及
n代表0,1,2或3。
含有式(Ⅰ)化合物的本发明制剂尤其受到关注,式中:
X代表羟基,-OCH2Si(CH3)3,(C3-C6)环烷氧基,苯基(C1-C6)烷氧基,苯氧基,(C2-C6)烯氧基,(C2-C6)炔氧基,(C1-C6)烷氧基,(C1-C6)烷硫基(其中烷氧基或烷硫基未被取代或已被(C1-C2)烷氧基,一或二(C2-C6)烷基氨基,(C1-C2)烷硫基,氰基取代一次或两次,或者被卤素取代一次或多次),一个下式的基团:
(上式中,R各代表氢或(C1-C4)烷基,Z1具有在Z中所述含义以及n1为0,1,2或3),氨基,一或二(C1-C4)烷基氨基,(C5-C6)环烷基氨基,肼基,哌啶基,吗啉基或2,6-二甲基吗啉基,一个下式的基团:
(上式中,R1和R2分别代表(C1-C4)烷基,或者R1和R2与连结它们的碳原子共同形成一个5-、6-或7元环烷基),
或者一个下式的基团:
(上式中,R3和R4分别代表氢或(C1-C4)烷基)。
优先选用的是式(Ⅰ)所示的本发明化合物或其盐,式中:
Z分别代表卤素尤其是氟或氯,硝基,(C1-C4)烷基,(C1-C4)烷氧基或三氟甲基,以及n代表0,1或2,以及优先选用的是式(Ⅰ)所示的这样一些化合物,在这些化合物中,
X代表羟基,(C1-C4)烷氧基或一个下式所示的基团:
(上式中,R3代表氢或CH3,R4代表氢或(C1-C4)烷基)。
特别优选的是式(Ⅰ)所示的本发明化合物,式中Z、n和X分别代表上述含义。
本发明的任务还提供一种制备式(Ⅰ)化合物及其盐的方法,其特征在于,使式(Ⅱ)化合物与式(Ⅲ)氧化腈反应:
(上式中,(Z)n具有其在式(Ⅰ)中的含义),
(上式中,X具有其在式(Ⅰ)K的含义)。
适宜的溶剂为非极性有机溶剂,例如醚类如乙醚或THF。
式(Ⅱ)和式(Ⅲ)的原料在文献中是已知的(参见,J.Org.Chem.25,1160(1960);J.Med.Chem.17(1974),549-552;J.Chem.Soc.Chem.Commun.1984,968-969;以及其中所给出的引文),或者按照制备已知化合物的类似方法制备。式(Ⅲ)氧化腈通常是自2-卤代-2-氢亚氨基乙酸(衍生物)出发,在碱的作用下就地制备并直接与在反应混合物中含有的式(Ⅱ)化合物反应。反应最好在-15℃至溶剂沸点范围内的某一温度下进行,尤其是在室温下进行。
式(Ⅰ)化合物含有一个不对称碳原子,该不对称碳原子在异噁唑啉环中与氧原子键合。相应的对映异构体可按常规方法例如按外消旋化方法来获得。通常情况下,用旋光的碱经过式(Ⅰ)化合物(其中X=OH)的非对映异构的盐分离外消旋体是可能的。
式(Ⅰ)化合物可以减轻或消除在作物种植中由于使用除草剂而带来的不必要的植物中毒副作用。
式(Ⅰ)化合物和除草有效物质可以一起或以任意顺序施用。式(Ⅰ)化合物可以避免或完全消除除草剂对作物的有害副作用,而不损害除草剂对有害植物的有效性。
因此,可以大大扩展传统植物保护剂的使用范围。具有能够保护作物免受除草剂植物毒性损害的特性的这样一些化合物,称之为“解毒剂”或“安全剂”。
能借助于式(Ⅰ)化合物减轻其对植物的毒性副作用的除草剂例如有:氨基甲酸酯类,硫代氨基甲酸酯类,卤代乙腈类,被取代了的苯氧基-、萘氧基-、苯氧苯氧基-、苄氧苯氧基-和杂芳氧苯氧基-羟酸衍生物以及环己二酮衍生物。杂芳氧基-苯氧基羧酸衍生物例如有喹啉氧基-、喹噁啉氧-、吡啶氧基-、苯并噁唑氧基-、苯并噻唑氧基-苯氧基-羧酸酯。优选的是苯氧苯氧基-和杂芳氧苯氧基羧酸酯。作为酯类特别合适的是低级烷基-、烯基-和炔基酯。
以下举出除草剂的实例,但不限于此。
A)苯氧苯氧基-、苄基苯氧基和杂芳氧基-苯氧基羧酸的(C1-C4)烷基酯,(C2-C4)烯基酯和(C3-C4)炔基酯类型的除草剂,例如:
2-(4-(2,4-二氯苯氧基)-苯氧基)-丙酸甲酯
2-(4-(4-溴-2-氯苯氧基)-苯氧基)-丙酸甲酯,
2-(4-(4-三氟甲基苯氧基)-苯氧基)-丙酸甲酯,
2-(4-(2-氯-4-三氟甲基苯氧基)-苯氧基)-丙酸甲酯,
2-(4-(2,4-二氯苄基)-苯氧基)-丙酸甲酯,
4-(4-(4-三氟甲基苯氧基)-苯氧基)-戊-2-烯酸乙酯,
2-(4-(3,5-二氯吡啶基-2-氧基)-苯氧基)丙酸乙酯,
2-(4-(3,5-二氯吡啶基-2-氧基)-苯氧基)丙酸炔丙基酯,
2-(4-(6-氯苯并噁唑-2-基-氧基)苯氧基)丙酸乙酯
2-(4-(3-氯-5-三氟甲基-2-吡啶氧基)苯氧基)-丙酸甲酯
2-(4-(5-三氟甲基-2-吡啶氧基)苯氧基)丙酸丁酯
2-(4-(3-氟-5-氯吡啶-2-氧基)苯氧基)丙酸甲酯
2-(4-(3-氟-5-氯吡啶-2-氧基)-苯氧基)丙酸炔丙基酯,
2-(4-(6-氯-2-喹噁啉氧基)苯氧基)丙酸甲酯,
2-(4-(6-氟-2-喹噁啉氧基)苯氧基)丙酸甲酯,
2-(4-(6-氯-2-喹啉氧基)苯氧基)-丙酸甲酯,
2-(4-(5-氯-3-氟吡啶-2-基氧基)苯氧基)硫代丙酸(5-甲氧羰基甲酯),
B)氯代乙酰替苯胺类除草剂,例如:
N-甲氧甲基-2,6-二乙基-氯代乙酰替苯胺,
N-(3′-甲氧-丙-2′-基)-甲基-6-乙基-氯代乙酰替苯胺,
N-(3-甲基-1,2,4-噁二唑-5-基-甲基)-氯代醋酸-2,6-二甲基苯胺。
C)硫代氨基甲酸酯类,例如:
S-乙基-N,N二丙基硫代氨基甲酸酯或S-乙基-N,N-二异丁基硫代氨基甲酸酯,
D)环己二酮衍生物类,例如:
3-(1-烯丙氧基氨基)丁基-4-羟基-6,6-二甲基-2-氧代环己-3-烯羧酸甲酯,
2-(N-乙氧丁基亚氨酰基)-5-(2-乙基硫代丙基)-3-羟基-2-环己烯-1-酮
2-(N-乙氧丁基亚氨酰基)-5-(2-苯基硫代丙基)-3-羟基-2-环己烯-1-酮,
2-(1-烯丙氧基亚氨基丁基)-4-甲氧羰基-5,5-二甲基-3-氧代环己醇,
2-(1-(3-氯烯丙氧基)-亚氨丁基)-5-(2-乙硫基)丙基)-3-羟基-环己-2-烯酮,
2-(1-(乙氧亚氨基)-丁基)-3-羟基-5-(thian-3-基)-环己-2-烯酮或者
2-(1-乙氧亚氨丙基)-5-(2,4,6-三甲基苯基)-3-羟基-2-环己烯-1-酮
安全剂的含量:除草剂可以在较宽的范围内,较好是在1∶10和10∶1范围内,尤其是在2∶1和1∶10范围内。除草剂和安全剂的最佳用量取决于所应用的除草剂或安全剂的种类以及待处理的植物种类,并可按照具体情况由相应的试验确定。
安全剂的主要应用对象是谷类作物(小麦,黑麦,大麦,燕麦)、水稻、玉米和高梁,但也可以应用于棉花、甜菜、糖甘蔗和大豆。
式(Ⅰ)安全剂可根据其特性在作物种子的预处理中应用(种子的浸渍),或者在播种前放入犁沟中,或者在作物发芽前或发芽后与除草剂一同使用。芽前处理不仅包括在播种前对耕地的处理,也包括已播种但尚未被幼苗覆盖的耕地的处理。最好与除草剂共同使用。为此可以使用罐装混合物或现成的制剂。
所需的式(Ⅰ)化合物用量视其特征和所用的除草剂而定,可在宽范围内变动,通常每公顷的有效物质用量在0.01和10kg之间。
本发明的对象还有保护作物免受除草剂植物毒性副作用的方法,其特征在于在应用除草剂之前、之后或同时,向植物、植物种子或耕地,施用有效量的式(Ⅰ)化合物。
此外,本发明化合物对作物还具有调节生长的特性。这些化合物以调节方式影响作物本身的新陈代谢,从而可用它们例如通过避免枯萎、落叶和生长不良来达到容易获得收成的目的。此外,这些化合物还适用于控制和抑制不需要的植物的生长而不损害作物。抑制植物生长在许多单子叶和双子叶植物中起很大作用,因为借此可以减少或完全防止倒伏。
按预先规定了哪些生物和/或化学物理的参数而定,可将式(Ⅰ)化合物或它们与上述一种或几种除草剂或除草剂类的混合物配制成不同形式的制剂。可能的制剂形式例如有:
可湿性粉剂(WP),乳油(EC),水溶性粉剂,水溶性乳剂(SL),乳剂(EW),可喷洒液,胶囊悬浮液(CS),油基或水基分散液,悬浮乳剂,悬浮浓缩液(SC),粉剂(DP),油剂(OL),媒染剂,以微粒形、喷雾粒形、包衣粒形和吸附粒形存在的粒剂(GR),土壤用的粒剂和撒布用粒剂,水溶性粒剂(SG),水分散性粒剂(WG),微量喷雾剂,微囊剂以及蜡剂。
上述制剂形式原则是已知的,例如在以下文献中有叙述:
Winnacker-Küchler,“Chemische Technologie”,Band 7,C.Hauser Verlag München,4.Aufl.1986;van Valkenburg,“Pesticides Formulations”,Marcel Dekker N.Y.,2nd Ed.1972-73;K.Martens,“Spray Drying Handbook”,3rd Ed.1979,G.Goodwin Ltd.London.
必要的制剂助剂如惰性物质,表面活性剂、溶剂和其他添加剂同样是已知的,例如见诸以下文献:
Watkins,“Handbook of Insecticide Dust Diluents and Carriers”,2nd Ed.,Darland Books,Caldwell N.J.;H.v.Olphen,“Intruduction to Clay Colloid Chemistry”;2nd Ed.,J.Wiley & Sons,N.Y.,Marsden,“Solvents Guide”,2nd Ed.,Interscience,N.Y.1950;McCutcheon′s,“Detergents and Emulsifiers Annual”,MC Publ.Corp.,Ridgewood N.J.;Sisley and Wood,“Encyclopedia of Surface Active Agents”,Chem.Publ.Co.Inc.,N.Y.1964;Schoenfeldt,“Grenzflaechenaktive Aethylenoxidaddukte”,Wiss.Verlagsgesell.,Stuttgart 1976;Winnacker-Küchler,“Chemische Technolgie”,Band 7,C.Hauser Verlag Muenchen,4.Aufl.1986.
在上述制剂的基础上,还可以与其他杀虫有效物质、肥料和/或生长调节剂制备混合制剂例如成品制剂或罐装混合物。
因此,本发明对象还有含有式(Ⅰ)所示的本发明化合物的制剂。这些制剂主要是一方面含有式(Ⅰ)所示的一种或多种化合物和适合于各种制剂类型的通用惰性助剂的植物保护剂,另一方面含有式(Ⅰ)所示化合物的混合物和一种或多种除草剂以及适合于各种制剂类型的通用助剂的除草制剂。
可湿性粉剂是在水中可均匀分散的制剂,它除了含有有效物质以外还含有稀释剂或惰性物质以及润湿剂如聚氧乙基化烷基酚,聚氧乙基化脂肪醇和脂肪胺,脂肪醇聚乙二醇醚硫酸酯,烷基磺酸盐或烷基酚磺酸盐,以及分散剂如木质素磺酸钠,2,2′-二萘基甲烷-6,6′-二磺酸钠,二丁基萘-磺酸钠或油酰基甲基牛磺酸钠。乳油是通过将有效物质溶解于一种有机溶剂如丁醇,环己酮,二甲基甲酰胺,二甲苯或高沸点芳烃或烃中,并加入一种或多种乳化剂制成的。作为乳化剂例如可以使用:烷基芳基磺酸钙盐,例如十二烷基苯磺酸钙或非离子乳化剂如聚乙二醇脂肪酸酯、聚乙二醇甲基芳基醚、聚乙二醇脂肪醇醚,环氧丙烷-环氧乙烷缩合物,聚烷基醚,山梨糖醇脂肪酸酯,聚氧乙烯山梨糖醇脂肪酸酯或聚氧乙烯山梨酸酯。
粉剂通过将有效物质与细分散的固体物质如滑石、天然粘土如高岭土、澎润土、绿坡缕石或硅藻土研磨而获得。
粒剂或者通过将有效物质喷洒在有吸附能力的粒状惰性物质上来制备,或者通过借助粘合剂如聚乙烯醇、聚丙烯酸钠或矿物油将有效物质浓缩物涂覆在载体表面如涂覆在砂子、高岭土或粒状惰性物质表面上来制备。合适的有效物质也可按制备肥料颗粒的通用方法,(必要时与肥料混合)进行造粒。
农业化学制剂通常含有0.1-99%(重量),尤其是0.1-95%(重量)的式(Ⅰ)有效物质或解毒剂有效物质混合物/除草剂,1-99.9%(重量),尤其是5-99.8%(重量)的固体或液体添加剂以及0-25%(重量),尤其是0.1-25%(重量)的表面活性剂。
可湿性粉剂的有效物质浓度例如约为10-90%(重量),其余(达100%(重量))由普通的制剂组分组成。乳油中有效物质的浓度约为1-80%(重量),最好是5-80%(重量)。粉剂中通常含有1-25%(重量),最好为5-20%(重量)的有效物质。喷洒溶液含有约0.2-25%(重量),最好为2-20%(重量)的有效物质。粒剂如水分散性粒剂中的有效物质的含量部分取决于有效物质是液态还是固态。一般情况下,水分散性粒剂的有效物质的含量在10和90%(重量)之间。
此外,上述有效物质制剂还可含有普通的粘合剂、润湿剂、分散剂、乳化剂、渗透剂、溶剂、填料或载体。
应用时,以商品形式存在的制剂在必要时可用普通方法稀释,例如,对于可湿性粉剂,乳油,分散溶剂和水分散性粒剂可用水稀释。粉剂,土壤用的和撒布用粒剂以及喷洒溶液在应用前一般不再用其它惰性物质稀释。
式(Ⅰ)化合物的须用量还随其他外部条件如温度、湿度以及使用的除草剂种类而变化。用量可以在宽范围内变化,例如有效物质用量在0.005和10.0千克/公顷之间,或更多些,最好在0.01和5千克/公顷之间。
以下实施例用以说明本发明:
A.制剂实施例
a)粉剂的制备:将10重量份式(Ⅰ)化合物和90重量份滑石或惰性物质混合并在一锤式磨粹机中粉碎。
b)在水中易分散的可湿性粉剂的制备:将25重量份式(Ⅰ)化合物,64重量份作为惰性物质的含高岭土石英,10重量份作为润湿剂和分散剂的木质素磺酸钾和1重量份油酰基甲基牛磺酸钠混合并在棒磨机中磨碎。
c)在水中易分散的浓分散液的制备:将20重量份的式(Ⅰ)化合物与6重量份的烷基酚聚乙二醇醚(TritonX 207),3重量份异十三烷醇聚乙二醇醚(8EO)和71重量份石蜡矿物油(沸程约255至277℃以上)混合,并在研磨机中磨碎至细度为5微米以下。
d)乳油的制备:由15重量份式(Ⅰ)化合物,75重量份作为溶剂的环己酮和10重量份作为乳化剂的氧乙基化的壬基酚制成。
e)水分散性粒剂的制备:将
75重量份式(Ⅰ)化合物
10重量份木质素磺酸钙
5重量份月桂基硫酸钠
3重量份聚乙烯醇,和
7重量份高岭土
混合,在棒磨机中磨碎,并将粉末在流化床中用水作为成粒液体通过喷洒来造粒。
f)水分散性粒剂的制备:将
25重量份式(Ⅰ)化合物
5重量份2,2′-二萘基甲烷-6,6′-二磺酸钠,
2重量份油酰基甲基牛磺酸钠,
1重量份聚乙烯醇,
17重量份碳酸钙和
50重量份水
在一胶体磨中均匀化并预粉碎,接着在球磨机中磨粹,所得悬浮体在一喷雾式洗涤塔中借助单级喷嘴喷雾并干燥。
B)化学实施例
5-(2,4-二氯苄基)-2-异噁唑啉-3-羧酸乙酯(实施例号93)
将18.8ml三乙胺滴加到其中有10.7g2,4-二氯-1-烯丙基的270ml乙醚中。接着在5小时内慢慢地滴加由20.55g2-氯-2-羟亚氨基醋酸乙酯和270ml乙醚组成的溶液。然后搅拌24小时,用水萃取,干燥乙醚相并蒸除乙醚。如此获得35.5g(98%理论量)标题化合物,折射率
=1.534。
2-氯-2-羟亚氨基-醋酸乙酯(实施例号93的原料)
将69.8g甘氨酸乙酯盐酸盐加到120ml水和41ml浓盐酸中。然后在-10℃,在1小时内向上述溶液中滴加于60ml水中的38gNaNO。半小时后另加入42.5ml浓盐酸并在1小时内再加入38g于60ml水中的NaNO。在-10℃下搅拌1小时。之后用乙醚萃取,乙醚相用水洗涤多次,蒸除乙醚并干燥晶体。如此获得38g(50%理论量)熔点为81-82℃的2-氯-2-羟亚氨基-醛酸乙酯。
下表Ⅰ中列出了该实施例化合物以及按类的方法制备的其他化合物。
原则上可按已知方法由相应的酯制备类似的异噁唑啉酸,或有选择地由相应的羧酸制备异噁唑啉酸酯。
表1
序号 (Z)nX 熔点 (n20 D)
1 n=O -O-C2H5油
2 ″ -OCH375-77℃
3 ″ -OH 128℃
4 ″ -OC3H7(1,5199)
5 ″ -OCH(CH3)2
6 ″ -OC4H9
7 ″ -OCH2CH(CH3)2
8 ″ -OCH2CO2CH3
9 ″ -OCH2CO2C2H5
10 ″ -OCH(CH3)CO2C2H5(1,5091)
11 ″ -NH-NH2
12 ″ -OCH2-C6H5
13 ″ -N(CH3)2
14 ″ -NH2
15 ″ -OCH(CH3)CO2CH3
16 ″ -NHC6H5
17 ″ -OCH2CH=CH2
18 ″ -OCH2C≡CH
19 ″ -O-K+
20 ″ -O-Na+
21 ″ -O-NH4
22 ″ -OCH2Si(CH3)3
23 ″ -OC6H5
表1(续)
序号 (Z)nX 熔点 (n20 D)
24 4-F -O-C2H5油
25 ″ -OCH3
26 ″ -OH 138-140℃
27 ″ -OC3H7
28 ″ -OCH(CH3)2
29 ″ -OC4H9
30 ″ -OCH2CH(CH3)2
31 ″ -OCH2CO2CH3
32 ″ -OCH2CO2C2H5
33 ″ -OCH(CH3)CO2C2H5
34 ″ -NH-NH2油
35 ″ -OCH2-C6H5
36 ″ -N(CH3)2
37 ″ -NH2
38 ″ -OCH(CH3)CO2CH3
39 ″ -NHC6H5
40 ″ -OCH2CH=CH2
41 ″ -OCH2C≡CH
42 ″ -O-K+
43 ″ -O-Na+
44 ″ -O-NH4
45 ″ -OCH2Si(CH3)3
46 ″ -OC6H5
表1(续)
序号 (Z)nX 熔点 (n20 D)
47 4-Cl -O-C2H5油
48 ″ -OCH392℃
49 ″ -OH 140℃
50 ″ -OC3H7(1,5075)
51 ″ -OCH(CH3)2
52 ″ -OC4H9
53 ″ -OCH2CH(CH3)2
54 ″ -OCH2CO2CH3
55 ″ -OCH2CO2C2H5
56 ″ -OCH(CH3)CO2C2H5(1,514)
57 ″ -NH-NH2
58 ″ -OCH2-C6H5
59 ″ -N(CH3)2
60 ″ -NH2
61 ″ -OCH(CH3)CO2CH3
62 ″ -NHC6H5
63 ″ -OCH2CH=CH2
64 ″ -OCH2C≡CH
65 ″ -O-K+
66 ″ -O-Na+
67 ″ -O-NH4
68 ″ -OCH2Si(CH3)3
69 ″ -OC6H5
表1(续)
序号 (Z)nX 熔点 (n20 D)
70 2-Cl -O-C2H5(1,526)
71 ″ -OCH3(1,547)
72 ″ -OH 80℃
73 ″ -OC3H7(1,533)
74 ″ -OCH(CH3)2
75 ″ -OC4H9
76 ″ -OCH2CH(CH3)2
77 ″ -OCH2CO2CH3
78 ″ -OCH2CO2C2H5
79 ″ -OCH(CH3)CO2C2H5
80 ″ -NH-NH2
81 ″ -OCH2-C6H5
82 ″ -N(CH3)2
83 ″ -NH2
84 ″ -OCH(CH3)CO2CH3
85 ″ -NHC6H5
86 ″ -OCH2CH=CH2
87 ″ -OCH2C≡CH
88 ″ -O-K+
89 ″ -O-Na+
90 ″ -O-NH4
91 ″ -OCH2Si(CH3)3
92 ″ -OC6H5
表1(续)
序号 (Z)nX 熔点 (n20 D)
93 2,4-Cl2-O-C2H5(1,534)
94 ″ -OCH3(1,544)
95 ″ -OH 40℃
96 ″ -OC3H7
97 ″ -OCH(CH3)2
98 ″ -OC4H9
99 ″ -OCH2CH(CH3)2
100 ″ -OCH2CO2CH3
101 ″ -OCH2CO2C2H5
102 ″ -OCH(CH3)CO2C2H5
103 ″ -NH-NH2油
104 ″ -OCH2-C6H5
105 ″ -N(CH3)2
106 ″ -NH2
107 ″ -OCH(CH3)CO2CH3
108 ″ -NHC6H5
109 ″ -OCH2CH=CH2
110 ″ -OCH2C≡CH
111 ″ -O-K+
112 ″ -O-Na+
113 ″ -O-NH4
114 ″ -OCH2Si(CH3)3
115 ″ -OC6H5
表1(续)
序号 (Z)nX 熔点 (n20 D)
215 2-OCHF2-OCH3
216 ″ -OC2H5
217 ″ -OCH2CO2CH3
218 4-OCHF2-OCH(CH3)CO2C2H5
219 ″ -OCH3
220 ″ -OC2H5
221 3-CF3-OCH3
222 3-F -OCH3
223 3-Cl -OC2H5
224 3,5-Cl2-OH
225 3,5-F2-OCH3
226 2-OCF3-OCH3
227 ″ -OC2H5
228 ″ -OCH2CO2CH3
229 4-OCF3-OCH3
230 ″ -OC2H5
231 ″ -OC4H9
232 3-OCF3-OCH3
233 2-SCH3-OCH3
234 3-SCH3-OCH3
235 4-SCH3-OCH3
236 2-SC2H5-OCH3
237 3-SC2H5-OCH3
238 4-SC2H5-OCH3
239 2-CH2CH2OH -OCH3
240 4-CH2CH2OH -OCH3
241 2-CH2CH2OH -OCH3
242 2-OCH2CH2OH -OCH3
243 3-OCH2CH2OH -OCH3
244 4-OCH2CH2OH -OCH3
245 2-OCH2CH2OCH3-OCH3
表1(续)
序号 (Z)nX 熔点 (n20 D)
246 4-OCH2CH2OCH3-OCH3
247 2-N(CH3)2-OCH3
248 3-N(C2H5)2-OCH3
249 4-N(CH3)2-OCH3
250 4-NO2-OCH3
251 ″ -OC2H5
252 2,4-(NO2)2-OCH3
253 2-NO2-OCH3
254 3-NO2-OCH3
255 2-CN -OCH3
256 3-CN -OCH3
257 4-CN -OCH3
258 2-CN,4-Cl -OCH3
259 2-Cl,4-CN -OCH3
260 2-CH3,4-CN -OCH3
261 4-Cyclo-C6H11-OCH3
262 4-Cyclo-C5H9-OCH3
263 4-C6H5-OCH3
264 4-OC6H5-OCH3
265 4-(2,4-C6H3Cl2) -OCH3
266 4-OC6H3Cl2(2,4) -OCH3
267 4-(2-CF3-C6H4) -OCH3
268 4-(4-CF3-C6H4) -OCH3
269 4-(2-CF3-C6H4-O-) -OCH3
270 4-(4-CF3-C6H4-O-) -OCH3
271 4-CH3-OC2H5(1,505)
表1(续)
序号 (Z)nX 熔点 (n20 D)
116 2-OCH3-O-C2H5油
117 ″ -OCH3
118 ″ -OH
119 ″ -OC3H7
120 ″ -OCH(CH3)2
121 ″ -OC4H9
122 ″ -OCH2CH(CH3)2
123 ″ -OCH2CO2CH3
124 ″ -OCH2CO2C2H5
125 ″ -OCH(CH3)CO2C2H5
126 ″ -NH-NH2
127 ″ -OCH2-C6H5
128 ″ -N(CH3)2
129 ″ -NH2
130 ″ -OCH(CH3)CO2CH3
131 ″ -NHC6H5
132 ″ -OCH2CH=CH2
133 ″ -OCH2C≡CH
134 ″ -O-K+
135 ″ -O-Na+
136 ″ -O-NH4
137 ″ -OCH2Si(CH3)3
138 ″ -OC6H5
表1(续)
序号 (Z)nX 熔点 (n20 D)
139 2-CH3,4-Cl -O-C2H5
140 ″ -OCH3
141 ″ -OH
142 ″ -OC3H7
143 ″ -OCH(CH3)2
144 ″ -OC4H9
145 ″ -OCH2CH(CH3)2
146 ″ -OCH2CO2CH3
147 ″ -OCH2CO2C2H5
148 ″ -OCH(CH3)CO2C2H5
149 ″ -NH-NH2
150 ″ -OCH2-C6H5
151 ″ -N(CH3)2
152 ″ -NH2
153 ″ -OCH(CH3)CO2CH3
154 ″ -NHC6H5
155 ″ -OCH2CH=CH2
156 ″ -OCH2C≡CH
157 ″ -O-K+
158 ″ -O-Na+
159 ″ -O-NH4
160 ″ -OCH2Si(CH3)3
161 ″ -OC6H5
表1(续)
序号 (Z)nX 熔点 (n20 D)
162 2,3,4,5,6-F5-O-C2H589℃
163 ″ -OCH3121℃
164 ″ -OH
165 ″ -OC3H7
166 ″ -OCH(CH3)2
167 ″ -OC4H9
168 ″ -OCH2CH(CH3)2
169 ″ -OCH2CO2CH3
170 ″ -OCH2CO2C2H5
171 ″ -OCH(CH3)CO2C2H5
172 ″ -NH-NH2
173 ″ -OCH2-C6H5
174 ″ -N(CH3)2
175 ″ -NH2
176 ″ -OCH(CH3)CO2CH3
177 ″ -NHC6H5
178 ″ -OCH2CH=CH2
179 ″ -OCH2C≡CH
180 ″ -O-K+
181 ″ -O-Na+
182 ″ -O-NH4
183 ″ -OCH2Si(CH3)3
184 ″ -OC6H5
表1(续)
序号 (Z)nX 熔点 (n20 D)
185 3,4-O-CH2-O- -O-C2H5(1,541)
186 ″ -OCH3102℃
187 ″ -OH 147-149℃
188 ″ -OC3H7(1,516)
189 ″ -OCH(CH3)2
190 ″ -OC4H9(1,528)
191 ″ -OCH2CH(CH3)2
192 ″ -OCH2CO2CH3
193 ″ -OCH2CO2C2H5
194 ″ -OCH(CH3)CO2C2H5
195 ″ -NH-NH2
196 ″ -OCH2-C6H5
197 ″ -N(CH3)2
198 ″ -NH2
199 ″ -OCH(CH3)CO2CH3
200 ″ -NHC6H5
201 ″ -OCH2CH=CH2
202 ″ -OCH2C≡CH
203 ″ -O-K+
204 ″ -O-Na+
205 ″ -O-NH4
206 ″ -OCH2Si(CH3)3
207 ″ -OC6H5
208 4-CF3-OCH3
209 2-CF3-OCH3
210 4-CF3-OC2H5
211 2-CF3-OC2H5
213 4-CF3-OCH2CO-OCH3
214 2-CF3-OCH(CH3)COOC2H5
C.生物实施例
实施例1
在温室中用塑料盆培育小麦和大麦至3-4叶片阶段,然后用本发明化合物和除草剂进行芽后处理。除草剂和式(Ⅰ)化合物的水悬浮液或乳液,包括换算成的水用量施用量为800升/公顷。处理后3-4周,通过目测评定每种植物被施用的除草剂的损害程度,其中尤其注意连续抑制生长的程度。经与未处理的对照植物比较后,评定值以百分值计。
表Ⅱ结果说明,本发明化合物可以有效地降低除草剂对作物的损害。
甚至在除草剂剂量大大过量时也可明显降低作物上出现的严重损害并可完全消除微小的损伤。因此,由除草剂和本发明化合物组成的混合物非常适于有选择性地消灭谷物种植中的杂草。
表Ⅱ
本发明化合物的安全效果
剂量
除草剂(H)
有效物质/公顷 植物损害(%)
安全剂序号 kg TRAE HOVU
H 2,0 80 -
0,2 - 85-90
H+1 2,0+1,25 20 -
H+1 0,2+1,25 - 30
H+3 2,0+1,25 25 -
H+3 0,2+1,25 - 35
H+2 0,2+1,25 - 40
H+4 ″ - 40
H+10 ″ - 40
H+24 ″ - 50
H+47 ″ - 40
H+49 ″ - 50
H+26 ″ - 40
H+70 ″ - 18
H+71 ″ - 20
H+72 ″ - 20
H+73 ″ - 28
H+75 ″ - 20
H+94 ″ - 10
H+95 ″ - 50
缩写:
小麦=TRAE
大麦=HOVU
a.i=有效物质(即指纯有效物质)
H=2-(4-(6-氯苯并噁唑-2-基氧基)苯氧基-丙酸乙酯
(Fenoxaprop-ethyl)
安全剂序号=表Ⅰ中的制备实施例中的系列号。
Claims (11)
1、式(Ⅰ)所示化合物或其盐:
式中Z分别代表卤素,硝基,氰基或烷基,烷氧基,烷硫基或环烷基(其中上述最后四个基团未被取代或被烷氧基、羟基或卤素取代一次或多次),氨基,一或二烷基氨基,苯基或苯氧基(其中苯基和苯氧基基未被取代或分别被卤素或卤代烷基取代一次或多次),或者两个相邻的Z取代基共同代表一个未被取代的或被烷基取代的二价基团:-OCH2O-,-S-CH2-O-或-S-CH2-S-,
n代表0~5的整数,
x代表羟基或烷氧基,烯氧基,炔氧基,烷硫基或环烷氧基(其中上述最后五个基团未被取代或被烷氧基,烷硫基,一和二烷基氨基,苯基,取代苯基,氰基和卤素取代一次或多次),苯氧基或取代苯氧基,三烷基甲硅烷基甲氧基,下式所示基团:
(上式中,R分别代表氢或烷基,Z1与A无关,具有上面Z中所述的含义,n为0~5的整数)氨基,一或二烷基氨基,环烷基氨基,肼基,烷基肼基或二烷基肼基,吡啶基,吗啉基,二甲基吗啉基,下式所示的基团:
(上式中,R1和R2分别代表烷基,或者R1和R2与连结它们的碳原子共同形成一个环烷基),此外,X还代表下式所示的基团:
(上式中,R3和R4分别代表氢或烷基)。
2、按照权利要求1所述的化合物或其盐,其特征在于,在式(Ⅰ)中,
Z分别代表卤素,硝基,氰基,(C1-C4)烷基,(C1-C4)烷氧基,(C1-C4)烷硫基(其中烷基,烷氧基和烷硫基未被取代或被卤原子尤其是氟或氯取代一次或多次),未被取代的或被(C1-C4)烷基取代的(C3-C6)环烷基,氨基,(C1-C4)烷基氨基,二(C1-C4)烷基氨基,羟甲基,(C1-C4)烷氧甲基,苯基或苯氧基(其中苯基和苯氧基未被取代或被卤素取代一次或多次或被三氟甲基取代一次或被一个或几个卤素原子和三氟甲基取代一次),或者两个相邻的Z取代基代表二价基:-O-CH2-O-,-S-CH2-O-或-S-CH2-S-,以及
n代表0,1,2或3。
3、按照权利要求1或2所述的化合物或其盐,其特征在于,
X代表羟基,-OCH2Si(CH3)3,(C3-C6)环烷氧基,苯基(C1-C6)烷氧基,苯氧基,(C2-C6)烯氧基,(C2-C6)炔氧基,(C1-C6)烷氧基,(C1-C6)烷硫基(其中烷氧基或烷硫基未被取代或被(C1-C2)烷氧基,一或二(C2-C6)烷基氨基,(C1-C7)烷硫基,氰基取代一次或两次,或被卤素取代一次或多次),代表下式所示的基团:
(上式中R分别代表氢或(C1-C4)烷基,Z1具有上面Z中所述的含义,n1为0,1,2或3),此外,X还代表氨基,一或二(C1-C4)烷基氨基,(C5-C6)环烷基氨基,肼基,哌啶基,吗啉基或2,6-二甲基吗啉基,下式所示的基团:
(上式中,R1和R2分别代表(C1-C4)烷基,或者R1和R2与连结它们的碳原子形成一个5元、6元或7元环烷基),或者代表下式所示的基团:
(上式中,R3和R4分别代表氢或(C1-C4)烷基。)
6、植物保护剂,其特征在于,含有按权利要求1-4中之一项或多项所述的式(Ⅰ)化合物或其盐以及惰性填料。
7、选择性除草剂,其特征在于,含有除草剂以及权利要求1-4中的一项或多项所述的式(Ⅰ)化合物或其盐。
8、按照权利要求7所述的选择性除草剂,其特征在于,作为除草剂,它们含有来自以下这组化合物的有效物质,这组化合物有:氨基甲酸酯,硫代氨基甲酸酯,卤代乙酰替苯胺,被取代的苯氧基-、萘氧基-、苯氧基苯氧基-、苄氧基苯氧基和杂芳氧基苯氧基羧酸衍生物以及环己二酮衍生物。
9、在有用植物种植中除去有害植物的方法,其特征在于,将除草剂和按权利要求1-4中之一项或多项所述的式(Ⅰ)化合物或其盐混合,施用到植物上、植物种子上和耕地上。
10、保护有用植物免遭除草剂对植物的毒性副作用的方法,其特征在于,将除草剂和按权利要求1-4中之一项或多项所述的式(Ⅰ)化合物或其盐混合,施用到植物上、植物种子上和耕地上。
11、权利要求1-4中之一项或多项所述的式(Ⅰ)化合物或其盐在消除除草剂对植物毒性副作用方面的应用。
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Publication number | Priority date | Publication date | Assignee | Title |
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IT1174454B (it) * | 1984-01-06 | 1987-07-01 | Montedison Spa | Composti ad attivita'antidotica per la difesa di culture agrarie dall'azione di erbicidi non seletivi |
IE59813B1 (en) * | 1986-05-09 | 1994-04-06 | Warner Lambert Co | Styryl pyrazoles, isoxazoles and analogs thereof having activity as 5-lipoxy-genase inhibitors and pharmaceutical compositions containing them |
DE3809765A1 (de) * | 1988-03-23 | 1989-10-05 | Basf Ag | Isoxazoline, verfahren zu ihrer herstellung und ihre verwendung als herbizide |
-
1989
- 1989-11-25 DE DE3939010A patent/DE3939010A1/de not_active Withdrawn
-
1990
- 1990-11-17 EP EP19900916475 patent/EP0501986A1/de not_active Withdrawn
- 1990-11-17 AU AU67160/90A patent/AU654119B2/en not_active Ceased
- 1990-11-17 CA CA002069406A patent/CA2069406A1/en not_active Abandoned
- 1990-11-17 US US07/856,204 patent/US5314863A/en not_active Expired - Fee Related
- 1990-11-17 WO PCT/EP1990/001966 patent/WO1991008202A1/de not_active Application Discontinuation
- 1990-11-17 HU HU921711A patent/HUT61649A/hu unknown
- 1990-11-23 ZA ZA909410A patent/ZA909410B/xx unknown
- 1990-11-23 NZ NZ236199A patent/NZ236199A/en unknown
- 1990-11-23 IL IL9645890A patent/IL96458A/en not_active IP Right Cessation
- 1990-11-24 CN CN90109402A patent/CN1052308A/zh active Pending
-
1992
- 1992-05-22 HU HU9201711A patent/HU9201711D0/hu unknown
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN101785470B (zh) * | 1994-11-11 | 2012-12-12 | 赫彻斯特-舍林农业发展有限公司 | 苯基磺酰脲除草剂和安全剂的组合物 |
CN103917097A (zh) * | 2011-09-16 | 2014-07-09 | 拜耳知识产权有限责任公司 | 5-苯基-或5-苄基-2-异噁唑啉-3-甲酸酯用于改善植物产量的用途 |
Also Published As
Publication number | Publication date |
---|---|
US5314863A (en) | 1994-05-24 |
NZ236199A (en) | 1994-03-25 |
AU654119B2 (en) | 1994-10-27 |
EP0501986A1 (de) | 1992-09-09 |
AU6716090A (en) | 1991-06-26 |
HUT61649A (en) | 1993-03-01 |
DE3939010A1 (de) | 1991-05-29 |
WO1991008202A1 (de) | 1991-06-13 |
ZA909410B (en) | 1991-08-28 |
IL96458A (en) | 1994-08-26 |
HU9201711D0 (en) | 1992-09-28 |
IL96458A0 (en) | 1991-08-16 |
CA2069406A1 (en) | 1991-05-26 |
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