CN114213420A - 一种含氯代吡啶结构的化合物或其作为农药可接受的盐、组合物及其用途 - Google Patents
一种含氯代吡啶结构的化合物或其作为农药可接受的盐、组合物及其用途 Download PDFInfo
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- CN114213420A CN114213420A CN202111666387.0A CN202111666387A CN114213420A CN 114213420 A CN114213420 A CN 114213420A CN 202111666387 A CN202111666387 A CN 202111666387A CN 114213420 A CN114213420 A CN 114213420A
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- Prior art keywords
- radical
- alkyl
- chloropyridine
- formula
- compound containing
- Prior art date
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- 150000001875 compounds Chemical class 0.000 title claims abstract description 78
- 150000003839 salts Chemical class 0.000 title claims abstract description 25
- OKDGRDCXVWSXDC-UHFFFAOYSA-N 2-chloropyridine Chemical group ClC1=CC=CC=N1 OKDGRDCXVWSXDC-UHFFFAOYSA-N 0.000 title claims abstract description 24
- 239000000203 mixture Substances 0.000 title claims abstract description 20
- 239000000575 pesticide Substances 0.000 title claims abstract description 15
- -1 C1-C6Alkylthio radical Chemical class 0.000 claims description 72
- 150000003254 radicals Chemical class 0.000 claims description 24
- 125000005843 halogen group Chemical group 0.000 claims description 16
- 230000002363 herbicidal effect Effects 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 238000000034 method Methods 0.000 claims description 11
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 10
- 238000002360 preparation method Methods 0.000 claims description 9
- 125000004850 cyclobutylmethyl group Chemical group C1(CCC1)C* 0.000 claims description 8
- 229910052736 halogen Inorganic materials 0.000 claims description 8
- 150000002367 halogens Chemical class 0.000 claims description 8
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 5
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 5
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 4
- 125000003118 aryl group Chemical group 0.000 claims description 4
- 125000004186 cyclopropylmethyl group Chemical group [H]C([H])(*)C1([H])C([H])([H])C1([H])[H] 0.000 claims description 4
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 4
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 3
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 3
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 3
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 3
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 3
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 2
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 2
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 2
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 2
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 2
- JNCMHMUGTWEVOZ-UHFFFAOYSA-N F[CH]F Chemical compound F[CH]F JNCMHMUGTWEVOZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000004414 alkyl thio group Chemical group 0.000 claims description 2
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 claims description 2
- 239000012752 auxiliary agent Substances 0.000 claims description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 2
- AOJDZKCUAATBGE-UHFFFAOYSA-N bromomethane Chemical compound Br[CH2] AOJDZKCUAATBGE-UHFFFAOYSA-N 0.000 claims description 2
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 2
- HFPGRVHMFSJMOL-UHFFFAOYSA-N dibromomethane Chemical compound Br[CH]Br HFPGRVHMFSJMOL-UHFFFAOYSA-N 0.000 claims description 2
- ZJULYDCRWUEPTK-UHFFFAOYSA-N dichloromethyl Chemical compound Cl[CH]Cl ZJULYDCRWUEPTK-UHFFFAOYSA-N 0.000 claims description 2
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 claims description 2
- VUWZPRWSIVNGKG-UHFFFAOYSA-N fluoromethane Chemical compound F[CH2] VUWZPRWSIVNGKG-UHFFFAOYSA-N 0.000 claims description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- ROWMQJJMCWDJDT-UHFFFAOYSA-N tribromomethane Chemical compound Br[C](Br)Br ROWMQJJMCWDJDT-UHFFFAOYSA-N 0.000 claims description 2
- ZBZJXHCVGLJWFG-UHFFFAOYSA-N trichloromethyl(.) Chemical compound Cl[C](Cl)Cl ZBZJXHCVGLJWFG-UHFFFAOYSA-N 0.000 claims description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 2
- 229920002554 vinyl polymer Polymers 0.000 claims description 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 claims 1
- 241000196324 Embryophyta Species 0.000 abstract description 32
- 239000004009 herbicide Substances 0.000 abstract description 11
- 230000000694 effects Effects 0.000 abstract description 7
- 239000005556 hormone Substances 0.000 abstract description 4
- 229940088597 hormone Drugs 0.000 abstract description 4
- 230000004071 biological effect Effects 0.000 abstract description 3
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 13
- 239000000243 solution Substances 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 231100000674 Phytotoxicity Toxicity 0.000 description 10
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 10
- 238000002156 mixing Methods 0.000 description 9
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 8
- 125000004432 carbon atom Chemical group C* 0.000 description 8
- 239000011541 reaction mixture Substances 0.000 description 8
- 239000013543 active substance Substances 0.000 description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 7
- 239000000843 powder Substances 0.000 description 7
- 239000002689 soil Substances 0.000 description 7
- MZZBPDKVEFVLFF-UHFFFAOYSA-N cyanazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)(C)C#N)=N1 MZZBPDKVEFVLFF-UHFFFAOYSA-N 0.000 description 6
- 230000012010 growth Effects 0.000 description 6
- 239000000126 substance Substances 0.000 description 6
- 238000012360 testing method Methods 0.000 description 6
- 238000005160 1H NMR spectroscopy Methods 0.000 description 5
- 244000098338 Triticum aestivum Species 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 230000001276 controlling effect Effects 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- 229910000027 potassium carbonate Inorganic materials 0.000 description 5
- 235000011181 potassium carbonates Nutrition 0.000 description 5
- 238000003786 synthesis reaction Methods 0.000 description 5
- 238000005303 weighing Methods 0.000 description 5
- RXCPQSJAVKGONC-UHFFFAOYSA-N Flumetsulam Chemical compound N1=C2N=C(C)C=CN2N=C1S(=O)(=O)NC1=C(F)C=CC=C1F RXCPQSJAVKGONC-UHFFFAOYSA-N 0.000 description 4
- 239000005602 Propyzamide Substances 0.000 description 4
- 239000005627 Triclopyr Substances 0.000 description 4
- 235000021307 Triticum Nutrition 0.000 description 4
- 239000000460 chlorine Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 244000038559 crop plants Species 0.000 description 4
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 238000004895 liquid chromatography mass spectrometry Methods 0.000 description 4
- DSRNRYQBBJQVCW-UHFFFAOYSA-N metoxuron Chemical compound COC1=CC=C(NC(=O)N(C)C)C=C1Cl DSRNRYQBBJQVCW-UHFFFAOYSA-N 0.000 description 4
- 238000012544 monitoring process Methods 0.000 description 4
- 239000012074 organic phase Substances 0.000 description 4
- 238000010898 silica gel chromatography Methods 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 238000009331 sowing Methods 0.000 description 4
- 239000007921 spray Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- REEQLXCGVXDJSQ-UHFFFAOYSA-N trichlopyr Chemical compound OC(=O)COC1=NC(Cl)=C(Cl)C=C1Cl REEQLXCGVXDJSQ-UHFFFAOYSA-N 0.000 description 4
- 239000004562 water dispersible granule Substances 0.000 description 4
- 125000004191 (C1-C6) alkoxy group Chemical group 0.000 description 3
- RBSXHDIPCIWOMG-UHFFFAOYSA-N 1-(4,6-dimethoxypyrimidin-2-yl)-3-(2-ethylsulfonylimidazo[1,2-a]pyridin-3-yl)sulfonylurea Chemical compound CCS(=O)(=O)C=1N=C2C=CC=CN2C=1S(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 RBSXHDIPCIWOMG-UHFFFAOYSA-N 0.000 description 3
- JLYFCTQDENRSOL-UHFFFAOYSA-N 2-chloro-N-(2,4-dimethylthiophen-3-yl)-N-(1-methoxypropan-2-yl)acetamide Chemical compound COCC(C)N(C(=O)CCl)C=1C(C)=CSC=1C JLYFCTQDENRSOL-UHFFFAOYSA-N 0.000 description 3
- WVQBLGZPHOPPFO-UHFFFAOYSA-N 2-chloro-N-(2-ethyl-6-methylphenyl)-N-(1-methoxypropan-2-yl)acetamide Chemical compound CCC1=CC=CC(C)=C1N(C(C)COC)C(=O)CCl WVQBLGZPHOPPFO-UHFFFAOYSA-N 0.000 description 3
- XJFIKRXIJXAJGH-UHFFFAOYSA-N 5-chloro-1,3-dihydroimidazo[4,5-b]pyridin-2-one Chemical group ClC1=CC=C2NC(=O)NC2=N1 XJFIKRXIJXAJGH-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
- 239000005995 Aluminium silicate Substances 0.000 description 3
- 239000005472 Bensulfuron methyl Substances 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 239000005944 Chlorpyrifos Substances 0.000 description 3
- 239000005945 Chlorpyrifos-methyl Substances 0.000 description 3
- 239000005496 Chlorsulfuron Substances 0.000 description 3
- 239000005504 Dicamba Substances 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 208000030036 Hypertelorism-preauricular sinus-punctual pits-deafness syndrome Diseases 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000005619 Sulfosulfuron Substances 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 101100339555 Zymoseptoria tritici HPPD gene Proteins 0.000 description 3
- 235000012211 aluminium silicate Nutrition 0.000 description 3
- WQRCEBAZAUAUQC-UHFFFAOYSA-N benazolin-ethyl Chemical group C1=CC=C2SC(=O)N(CC(=O)OCC)C2=C1Cl WQRCEBAZAUAUQC-UHFFFAOYSA-N 0.000 description 3
- XMQFTWRPUQYINF-UHFFFAOYSA-N bensulfuron-methyl Chemical group COC(=O)C1=CC=CC=C1CS(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 XMQFTWRPUQYINF-UHFFFAOYSA-N 0.000 description 3
- SBPBAQFWLVIOKP-UHFFFAOYSA-N chlorpyrifos Chemical compound CCOP(=S)(OCC)OC1=NC(Cl)=C(Cl)C=C1Cl SBPBAQFWLVIOKP-UHFFFAOYSA-N 0.000 description 3
- VJYIFXVZLXQVHO-UHFFFAOYSA-N chlorsulfuron Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)Cl)=N1 VJYIFXVZLXQVHO-UHFFFAOYSA-N 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 238000011161 development Methods 0.000 description 3
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- IWEDIXLBFLAXBO-UHFFFAOYSA-N dicamba Chemical compound COC1=C(Cl)C=CC(Cl)=C1C(O)=O IWEDIXLBFLAXBO-UHFFFAOYSA-N 0.000 description 3
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- 230000035784 germination Effects 0.000 description 3
- 229910052740 iodine Inorganic materials 0.000 description 3
- 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 3
- NDNKHWUXXOFHTD-UHFFFAOYSA-N metizoline Chemical compound CC=1SC2=CC=CC=C2C=1CC1=NCCN1 NDNKHWUXXOFHTD-UHFFFAOYSA-N 0.000 description 3
- 229960002939 metizoline Drugs 0.000 description 3
- 235000015097 nutrients Nutrition 0.000 description 3
- AAEVYOVXGOFMJO-UHFFFAOYSA-N prometryn Chemical compound CSC1=NC(NC(C)C)=NC(NC(C)C)=N1 AAEVYOVXGOFMJO-UHFFFAOYSA-N 0.000 description 3
- PHNUZKMIPFFYSO-UHFFFAOYSA-N propyzamide Chemical compound C#CC(C)(C)NC(=O)C1=CC(Cl)=CC(Cl)=C1 PHNUZKMIPFFYSO-UHFFFAOYSA-N 0.000 description 3
- 239000007858 starting material Substances 0.000 description 3
- IPPAUTOBDWNELX-UHFFFAOYSA-N (2-ethoxy-2-oxoethyl) 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitrobenzoate Chemical group C1=C([N+]([O-])=O)C(C(=O)OCC(=O)OCC)=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 IPPAUTOBDWNELX-UHFFFAOYSA-N 0.000 description 2
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 2
- JIGPTDXPKKMNCN-UHFFFAOYSA-N 1-(5-butylsulfonyl-1,3,4-thiadiazol-2-yl)-1,3-dimethylurea Chemical compound CCCCS(=O)(=O)C1=NN=C(N(C)C(=O)NC)S1 JIGPTDXPKKMNCN-UHFFFAOYSA-N 0.000 description 2
- KZNDFYDURHAESM-UHFFFAOYSA-N 2-chloro-n-(2-ethyl-6-methylphenyl)-n-(propan-2-yloxymethyl)acetamide Chemical compound CCC1=CC=CC(C)=C1N(COC(C)C)C(=O)CCl KZNDFYDURHAESM-UHFFFAOYSA-N 0.000 description 2
- XMTQQYYKAHVGBJ-UHFFFAOYSA-N 3-(3,4-DICHLOROPHENYL)-1,1-DIMETHYLUREA Chemical compound CN(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 XMTQQYYKAHVGBJ-UHFFFAOYSA-N 0.000 description 2
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- XEFQLINVKFYRCS-UHFFFAOYSA-N Triclosan Chemical compound OC1=CC(Cl)=CC=C1OC1=CC=C(Cl)C=C1Cl XEFQLINVKFYRCS-UHFFFAOYSA-N 0.000 description 2
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- DMSMPAJRVJJAGA-UHFFFAOYSA-N benzo[d]isothiazol-3-one Chemical compound C1=CC=C2C(=O)NSC2=C1 DMSMPAJRVJJAGA-UHFFFAOYSA-N 0.000 description 2
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- BAXLBXFAUKGCDY-UHFFFAOYSA-N mebendazole Chemical compound [CH]1C2=NC(NC(=O)OC)=NC2=CC=C1C(=O)C1=CC=CC=C1 BAXLBXFAUKGCDY-UHFFFAOYSA-N 0.000 description 1
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- 239000011780 sodium chloride Substances 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M sodium chloride Inorganic materials [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
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- 229920005552 sodium lignosulfonate Polymers 0.000 description 1
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- IUQAXCIUEPFPSF-UHFFFAOYSA-N tembotrione Chemical compound ClC1=C(COCC(F)(F)F)C(S(=O)(=O)C)=CC=C1C(=O)C1C(=O)CCCC1=O IUQAXCIUEPFPSF-UHFFFAOYSA-N 0.000 description 1
- IROINLKCQGIITA-UHFFFAOYSA-N terbutryn Chemical compound CCNC1=NC(NC(C)(C)C)=NC(SC)=N1 IROINLKCQGIITA-UHFFFAOYSA-N 0.000 description 1
- FZXISNSWEXTPMF-UHFFFAOYSA-N terbutylazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)(C)C)=N1 FZXISNSWEXTPMF-UHFFFAOYSA-N 0.000 description 1
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- IYMLUHWAJFXAQP-UHFFFAOYSA-N topramezone Chemical compound CC1=C(C(=O)C2=C(N(C)N=C2)O)C=CC(S(C)(=O)=O)=C1C1=NOCC1 IYMLUHWAJFXAQP-UHFFFAOYSA-N 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
- AMFGTOFWMRQMEM-UHFFFAOYSA-N triazophos Chemical compound N1=C(OP(=S)(OCC)OCC)N=CN1C1=CC=CC=C1 AMFGTOFWMRQMEM-UHFFFAOYSA-N 0.000 description 1
- BQZXUHDXIARLEO-UHFFFAOYSA-N tribenuron Chemical compound COC1=NC(C)=NC(N(C)C(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(O)=O)=N1 BQZXUHDXIARLEO-UHFFFAOYSA-N 0.000 description 1
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- IMEVJVISCHQJRM-UHFFFAOYSA-N triflusulfuron-methyl Chemical group COC(=O)C1=CC=CC(C)=C1S(=O)(=O)NC(=O)NC1=NC(OCC(F)(F)F)=NC(N(C)C)=N1 IMEVJVISCHQJRM-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
- C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
- C07D487/04—Ortho-condensed systems
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/90—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having two or more relevant hetero rings, condensed among themselves or with a common carbocyclic ring system
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
- C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
- C07D471/04—Ortho-condensed systems
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
本发明属于农药领域,具体涉及一种含氯代吡啶结构的化合物或其作为农药可接受的盐、组合物及其用途,所述化合物具有式(I)结构:
Description
技术领域
本发明属于农药技术领域,具体涉及一种具有除草活性的含氯代吡啶结构的化合物或其作为农药可接受的盐、组合物,并涉及这些化合物或其作为农药可接受的盐、组合物作为除草剂的用途。
背景技术
植物体内含有多种植物激素,对协调植物的生长、发育、开花与结果具有重要的作用,植物激素在植物的不同组织中的含量与比例都有严格的要求。激素型除草剂是人工合成的具有天然植物激素作用的物质,例如苯氧羧酸类(如2,4-D与2甲4氯等)、苯甲酸类(如麦草畏等)和氨氯吡啶酸等。随着除草剂的大量使用,杂草抗性越来越严重,如何解决抗性杂草的问题逐渐成为科研工作者们关注的研发热点。而轮换使用激素型除草剂与HPPD类除草剂可能会是较佳的解决方案。目前关注度较高的激素类除草剂在例如CN101360713B、CN102731381B、CN102731382B中均有描述,但其中所公开的化合物的速效性和杀草谱等并不足以令人满意。
技术问题
为解决现有技术中存在的上述问题,本发明提供了一种含氯代吡啶结构的化合物或其作为农药可接受的盐、组合物及其用途。令人惊喜的是本发明的含氯代吡啶结构的化合物具有比已知化合物更高的除草活性和效率,特别是对于已经对传统除草剂如HPPD类、PPO类产生抗性的杂草具有极佳的防治效果。
技术解决方案
本发明为实现上述目的采用的技术方案是:一种含氯代吡啶结构的化合物或其作为农药可接受的盐,其结构式如式(I)所示:
式(I)中,
R1选自H、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、C1-C6烷硫基、C1-C6烷胺基、C3-C6环烷基、C2-C6烯基、C2-C6烯氧基、C2-C6烯硫基、C2-C4炔基、C1-C6烷基羰基、C1-C6烷氧基羰基、C1-C6烷胺基羰基、C1-C6烷氧基取代的C1-C6烷氧基、C3-C6环烷基取代的C1-C6烷基、氨基羰基取代的C1-C6烷基、CN、卤素、NO2、COOR1、巯基、羧基、醛基、羟基或氨基;
R2和R3相同或不同,分别独立地选自H、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基或卤代C1-C6烷硫基;
或者,R2和R3一起形成基团-(CH2)m-,m表示1-6;
R4选自H、C1-C6烷基、卤代C1-C6烷基、芳基取代的C1-C6烷基或芳基。
进一步地,式(I)中,R1选自H、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、C2-C6烯基、C2-C6烯氧基、C2-C6炔基、C3-C6环烷基或C3-C6环烷基取代的C1-C6烷基。
进一步地,式(I)中,R2和R3一起形成基团-(CH2)m-,m表示2-5。
进一步地,式(I)中,R4选自H、C1-C6烷基、卤代C1-C6烷基、苯基取代的C1-C6烷基或苯基。
进一步地,式(I)中,R1选自H、C1-C4烷基、卤代C1-C4烷基、C1-C4烷氧基、C2-C4烯基、C2-C4烯氧基、C2-C4炔基、C3-C6环烷基或C3-C6环烷基取代的C1-C4烷基;
R2和R3一起形成基团-(CH2)m-,m表示3-5;
R4选自H、C1-C4烷基、苯基或苯基取代的C1-C4烷基。
进一步地,式(I)中,R1选自Me、Et、n-Pr、i-Pr、n-Bu、i-Bu、s-Bu、t-Bu、乙烯基、烯丙基、乙炔基、炔丙基、OMe、OEt、n-PrO、i-PrO、n-BuO、i-BuO、s-BuO、t-BuO、环丙烷基、环丁烷基、环戊烷基、环己烷基、环丙烷甲基、环丁烷甲基、CH2Cl、CHCl2、CCl3、CH2F、CHF2、CF3、CH2Br、CHBr2、CBr3、CH2CF3或CH2CH2Cl;
R2和R3一起形成基团-(CH2)m-,m表示3-5;
R4选自H、Me、Et、n-Pr、i-Pr、苯基或苄基。
进一步地,式(I)结构化合物选自:
所述的农药可接受的盐可以为本发明的含氯代吡啶结构的化合物与化学上可接受的酸进行反应制得的盐,其中化学上可接受的酸可以是无机酸(如盐酸、硫酸、磷酸或氢溴酸等)或有机酸(如草酸、马来酸、富马酸、苹果酸、酒石酸、柠檬酸或苯甲酸等);所述的农药可接受的盐也可以为本发明的含氯代吡啶结构的化合物与化学上可接受的碱进行反应制得的盐,其中化学上可接受的碱可以是无机碱(如氢氧化钠、氢氧化钾、氢氧化钙、碳酸钠、碳酸钾、碳酸氢钠或碳酸氢钾)或有机碱(如三甲胺、三乙胺等)。
进一步地,所述的农药可接受的盐可以为钾盐、钠盐、铵盐、钙盐、吡啶盐或胆碱盐。
本发明还公开了一种除草组合物,包括除草有效量的如上所述的含氯代吡啶结构的化合物或其作为农药可接受的盐中的至少一种。
优选的,还包括制剂载体或制剂助剂。
本发明还公开了一种控制不想要的植物的方法,包括将除草有效量的如上所述的含氯代吡啶结构的化合物或其作为农药可接受的盐中的至少一种或如上所述的除草组合物使用在不想要的植物上。
本发明还公开了如上所述的含氯代吡啶结构的化合物或其作为农药可接受的盐中的至少一种或如上所述的除草组合物在控制不想要的植物上的用途。
在上述化合物结构式的定义中,所使用的专业术语均具有如下含义:
C1-C6烷基:碳原子数为1-6的直链或支链烷基,例如甲基、乙基、丙基、异丙基或正丁基、异丁基、仲丁基、叔丁基等。
卤代C1-C6烷基:碳原子数为1-6的直链或支链烷基,在这些烷基上的氢原子可部分或全部被卤素所取代,例如,氯甲基、二氯甲基、三氯甲基、氟甲基、二氟甲基、三氟甲基等。
卤或卤素:指氟、氯、溴或碘。
C1-C6烷氧基:碳原子数为1-6的直链或支链烷基,经氧原子键连接到结构上。
卤代C1-C6烷氧基:碳原子数为1-6的直链或支链烷氧基,在这些烷氧基上的氢原子可部分或全部被卤素所取代,例如,氯甲氧基、二氯甲氧基、三氯甲氧基、氟甲氧基、二氟甲氧基、三氟甲氧基、氯氟甲氧基、三氟乙氧基等。
C1-C6烷硫基:碳原子数为1-6的直链或支链烷基,经硫原子键连接到结构上。
C1-C6烷氧基取代的C1-C6烷氧基:由碳原子数为1-6的烷氧基作为取代基对碳原子数为1-6的烷
式Ⅰ所述化合物的合成方法,具体是将式Ⅱ所示中间体化合物制备成羧酸盐后与式Ⅲ中间体化合物在碱和溶剂存在下进行反应后得到(在下列列举的化学式中,只要未另外进行定义,取代基和符号与式Ⅰ中定义的取代基和符号具有相同的意义)。式Ⅱ所代表的化合物可参考专利CN104788364A所述方法合成,式Ⅲ、IV所代表的化合物可通过市售获得:
进一步地,式(III)中,LG为氟、氯、溴或碘。
进一步地,溶剂选自乙腈、N,N-二甲基甲酰胺、N,N-二甲基乙酰胺、二甲亚砜、四氢呋喃、二氯甲烷、苯、甲苯、二甲苯、二氯乙烷、乙酸乙酯中的一种或多种溶剂。
对于许多一年生的单子叶和双子叶有害植物,本发明的式I化合物具有突出的除草活性。本发明的活性物质也对于多年生杂草有效,这些杂草从根茎、根状茎、或其它的多年生的器官上生长出来。至于本发明的活性物质的使用时机,可以是在播种前、萌发前或萌发后。特别提及本发明化合物可以控制的单子叶和双子叶杂草群的代表例,本发明的活性物质能起到有效作用的杂草物种代表例包括单子叶植物:一年生燕麦属、黑麦草属、看麦娘属、稗属、马唐属、狗尾草属和莎草属,和多年生的冰草属、狗牙根属、白茅属和高粱属、以及多年生的莎草属。
关于双子叶杂草物种,其作用可以扩展到的物种例如一年生的猪殃殃属、堇菜属、婆婆纳属、野芝麻属、繁缕属、苋属、白芥属、番薯属、黄花稔属、母菊属和苘麻属,和多年生杂草旋花属、蓟属、酸模属和艾属。本发明活性物质在水稻播种这种特定条件下依然能有效控制有害植物,例如稗属、慈姑属、泽泻属、荸荠属、蔗草和莎草属。如果将本发明化合物在萌芽前施用于土壤表面,可以在杂草长出前完全预防杂草的秧苗,或在杂草长出子叶时就停止生长,最后在三到四星期之后完全死亡。虽然本发明化合物对于单子叶和双子叶的杂草具有优良的除草活性,但对于重要的经济类作物植物,例如小麦、大麦、黑麦、稻子、玉米、甜菜、棉花和大豆却没有损害,或者是损害非常微小。因此,本发明化合物非常适于有选择地控制在农用作物或观赏植物中的无用植物。另外本发明化合物可以明显调节作物植物的生长。通过调节参与植物代谢,使用这些化合物定向控制植物的组分和促进收获,例如使植物干化和矮化生长。而且它们也适于调节和抑制不希望的植物生长,而不破坏作物的生长。抑制植物的生长在许多单子叶植物和双子叶植物作物中起着非常重要的作用,因为这样可以减少或完全预防倒伏。
可以使用一般的制剂来应用本发明的化合物,可使用可湿性粉剂、可溶性粉剂、乳油、水乳剂、悬浮剂、可分散油悬浮剂、粉剂、微囊悬浮剂、水分散粒剂、水溶性粒剂等。这样本发明也提供了包括式I化合物的除草剂组合物。根据通常的生物学和/或化学的物理参数,可以用多种方式配制式I化合物。适合的制剂选择实例为:可湿性粉剂(WP)、可湿性液剂(SL)、可溶性粉剂(SP)、可分散液剂(DC)、水剂(AS)、微乳剂(ME)、乳油(EC)、水乳剂(EW)、可喷洒溶液、悬浮剂(SC)、可分散油悬浮剂(OD)、粉剂(DP)、微囊悬浮剂(CS)、水分散粒剂(WG)、水溶性粒剂(SG)、大粒剂(GG)、用于撒播和土壤施药的颗粒剂(GR)、气雾剂(AE)、超低容量剂(ULV)和蜡制品。必要的制剂助剂,例如惰性物质、表面活性剂、溶剂及其它添加剂。
在混配制剂或桶混制剂中,可以和本发明的活性物质混合的合适的活性物质为,例如《世界农药新品种技术大全》(中国农业科学技术出版社,2010.9)中的已知物质。例如以下提到的除草剂活性物质可以和式I混合物混合,(备注:化合物的名称,或者为根据国际标准化组织(ISO)的普通名称,或者为化学名称,适当的时候有代号):乙草胺、丁草胺、甲草胺、异丙草胺、异丙甲草胺、精异丙甲草胺、丙草胺、毒草胺、克草胺、萘丙酰草胺、R-左旋萘丙酰草胺、敌稗、苯噻酰草胺、双苯酰草胺、吡氟酰草胺、杀草胺、氟丁酰草胺、溴丁酰草胺、二甲噻草胺、高效二甲噻草胺、乙氧苯草胺、氟噻草胺、甲氧噻草胺、吡草胺、异噁草胺、高效麦草氟甲酯、高效麦草氟丙酯、二丙烯草胺、烯草胺、丁酰草胺、环丙草胺、氟磺酰草胺、庚酰草胺、异丁草胺、丙炔草胺、特丁草胺、二甲苯草胺、二甲草胺、落草胺、三甲环草胺、氯甲酰草胺、炔苯酰草胺、戊酰苯草胺、卡草胺、新燕灵、三环噻草胺、丁烯草胺、牧草胺、苄草胺、醌萍胺、苯氟磺胺、萘丙胺、乙酰甲草胺、萘草胺、噻草胺、吡氰草胺、苯草多克死、草克乐、氯酞亚胺、丁脒胺、氟吡草胺、莠去津、西玛津、扑草净、氰草净、西草净、莠灭净、扑灭津、异丙净、氟草净、特丁净、特丁津、三嗪氟草胺、环丙津、甘扑津、草达津、扑灭通、西玛通、叠氮净、敌草净、异戊乙净、灭莠津、另丁津、仲丁通、特丁通、甲氧丙净、氰草净、抑草津、可乐津、莠去通、灭草通、甘草津、三聚氰酸、Indaziflam、绿磺隆、甲磺隆、苄嘧磺隆、氯嘧磺隆、苯磺隆、噻磺隆、吡嘧磺隆、甲基二磺隆、甲基碘磺隆钠盐、甲酰氨基嘧磺隆、醚磺隆、醚苯磺隆、甲嘧磺隆、烟嘧磺隆、胺苯磺隆、酰嘧磺隆、乙氧嘧磺隆、环丙嘧磺隆、砜嘧磺隆、四唑嘧磺隆、啶嘧黄隆、单嘧磺隆、单嘧磺酯、氟唑磺隆、氟啶嘧磺隆、氟吡嘧磺隆、环氧嘧磺隆、唑吡嘧磺隆、氟嘧磺隆、丙苯磺隆、三氟丙磺隆、磺酰磺隆、三氟啶磺隆、氟胺磺隆、三氟甲磺隆、甲磺隆钠盐、氟吡磺隆、甲硫嘧磺隆、嘧苯胺磺隆、Propyrisulfuron(丙嗪嘧磺隆)、嗪吡嘧磺隆、三氟羧草醚、氟磺胺草醚、乳氟禾草灵、乙羧氟草醚、乙氧氟草醚、草枯醚、苯草醚、氯氟草醚乙酯、甲羧除草醚、三氟甲草醚、甲氧除草醚、三氟硝草醚、氟化除草醚、氟呋草醚、除草醚、甲草醚、二甲草醚、氟酯肟草醚、氟草醚酯、Halosafen、绿麦隆、异丙隆、利谷隆、敌草隆、莎扑隆、氟草隆、苯噻隆、甲基苯噻隆、苄草隆、磺噻隆、异噁隆、特丁噻草隆、炔草隆、氯溴隆、甲基杀草隆、酰草隆、甲氧杀草隆、溴谷隆、甲氧隆、绿谷隆、灭草隆、环草隆、非草隆、氟硫隆、草不隆、枯草隆、草完隆、异草完隆、环莠隆、噻氟隆、丁噻隆、枯莠隆、对氟隆、甲胺噻唑隆、隆草特、三甲异脲、噁唑隆、Monisouron、Anisuron、Methiuron、Chloreturon、四氟隆、甜菜宁、甜菜宁-乙酯、甜菜安、磺草灵、特草灵、燕麦灵、苯胺灵、氯苯胺灵、二氯苄草酯、灭草灵、氯炔灵、Carboxazole、Chlorprocarb、Fenasulam、BCPC、CPPC、Carbasulam、丁草特、禾草丹、灭草猛、禾草特、野麦畏、哌草丹、禾草畏、稗草丹、环草敌、燕麦敌、菌达灭、乙硫草特、坪草丹、克草猛、苄草丹、仲草丹、硫烯草丹、草灭散、Isopolinate、Methiobencarb、2,4-滴丁酯、2甲4氯钠、2,4-滴异辛酯、2甲4氯异辛酯、2,4-滴钠盐、2,4-滴二甲胺盐、2甲4氯乙硫酯、2甲4氯、2,4-滴丙酸、高2,4-滴丙酸盐、2,4-滴丁酸、2甲4氯丙酸、2甲4氯丙酸盐、2甲4氯丁酸、2,4,5-涕、2,4,5-涕丙酸、2,4,5-涕丁酸、2甲4氯胺盐、麦草畏、抑草蓬、伐草克、赛松、三氯苯酸、氨二氯苯酸、甲氧三氯苯酸、禾草灵、吡氟禾草灵、精吡氟禾草灵、氟吡甲禾灵、高效吡氟氯禾灵、喹禾灵、精喹禾灵、恶唑禾草灵、精恶唑禾草灵、喔草酯、氰氟草酯、恶唑酰草胺、炔草酯、噻唑禾草灵、炔禾灵、羟戊禾灵、三氟禾草肟、异恶草醚、百草枯、敌草快、安磺灵、乙丁烯氟灵、异丙乐灵、甲磺乐灵、环丙氟灵、氨基丙氟灵、乙丁氟灵、氯乙氟灵、氨基乙氟灵、地乐灵、氯乙地乐灵、Methalpropalin、丙硝酚、草甘膦、莎稗膦、草铵膦、甲基胺草磷、草硫膦、哌草膦、双丙氨膦、地散磷、抑草磷、蔓草磷、伐垅磷、双甲胺草磷、草特磷、咪唑烟酸、咪唑乙烟酸、咪唑喹啉酸、甲氧咪草烟、甲氧咪草烟铵盐、甲咪唑烟酸、咪草酯、氯氟吡氧乙酸、氯氟吡氧乙酸异辛酯、二氯吡啶酸、氨氯吡啶酸、三氯吡氧乙酸、氟硫草定、卤草定、三氯吡啶酚、噻草啶、氟啶草酮、氯氨吡啶酸、氟吡草腙、三氯吡氧乙酸丁氧基乙酯、Cliodinate、烯禾啶、烯草酮、噻草酮、禾草灭、环苯草酮、丁苯草酮、肟草酮、吡喃草酮、Buthidazole、嗪草酮、环嗪酮、苯嗪草酮、乙嗪草酮、Ametridione、Amibuzin、溴苯腈、辛酰溴苯腈、辛酰碘苯腈、碘苯腈、敌草腈、二苯乙腈、双唑草腈、羟敌草腈、Iodobonil、唑嘧磺草胺、双氟磺草胺、五氟磺草胺、磺草唑胺、氯酯磺草胺、双氯磺草胺、啶磺草胺、呋草黄、双草醚、嘧啶肟草醚、环酯草醚、嘧草醚、嘧硫草醚、双环磺草酮、硝磺草酮、磺草酮、Tembotrione、Tefuryltrione、Bicyclopyrone、Ketodpiradox、异噁唑草酮、异噁氯草酮、Fenoxasulfone、Methiozolin、异丙吡草酯、吡草醚、吡唑特、野燕枯、苄草唑、吡草酮、吡氯草胺、Pyrasulfotole、苯唑草酮、Pyroxasulfone、唑草胺、氟胺草唑、杀草强、胺唑草酮、唑啶草酮、氟唑草酮、甲磺草胺、Bencarbazone、双苯嘧草酮、氟丙嘧草酯、除草定、异草定、环草啶、特草定、Flupropacil、吲哚酮草酯、氟烯草酸、丙炔氟草胺、炔草胺、酞苄醚、Flumezin、五氯酚(钠)、地乐酚、特乐酚、特乐酯、戊硝酚、二硝酚、氯硝酚、地乐施、地乐特、丙炔噁草酮、噁草酮、环戊噁草酮、氟唑草胺、嗪草酸甲酯、四唑酰草胺、氟哒嗪草酯、杀草敏、溴莠敏、二甲达草伏、哒草醚、草哒酮、草哒松、哒草伏、Pyridafol、二氯喹啉酸、氯甲喹啉酸、苯达松、哒草特、噁嗪草酮、草除灵、异噁草酮、环庚草醚、异丙酯草醚、丙酯草醚、茚草酮、氯酸钠、茅草枯、三氯醋酸、一氯醋酸、六氯丙酮、四氟丙酸、牧草快、溴酚肟、三唑磺、灭杀唑、呋草酮、乙呋草磺、嘧草胺、氯酞酸、氟咯草酮、稗草稀、丙烯醛、苯草灭、灭草环、燕麦酯、噻二唑草胺、棉胺宁、羟草酮、甲氧苯酮、苯嘧磺草胺、氯酰草膦、三氯丙酸、Alorac、Diethamquat、Etnipromid、Iprymidam、Ipfencarbazone、Thiencarbazonemethyl、Pyrimisulfan、Chlorflurazole、Tripropindan、Sulglycapin、甲硫磺乐灵、Cambendichlor、环丙嘧啶酸、氟氯吡啶酯、氯氟吡啶酯。
有益效果
综上所述,由于采用了上述技术方案,本发明的有益效果是:
通过对具有氯代吡啶类结构的激素类除草剂化合物进行化学修饰和分子设计,引入了吡唑并环结构,得到了一系列更加高效、具有更好的选择性和安全性的可用于农业或林业除草用的具有除草活性的化合物,特别是对于已经对传统除草剂如HPPD类、PPO类产生抗性的杂草具有极佳的防治效果。
本发明的实施方式
下面将结合本发明实施例,对本发明实施例中的技术方案进行清楚、完整地描述。基于本发明中的实施例,本领域普通技术人员在没有做出创造性劳动前提下所获得的所有其他实施例,都属于本发明保护的范围。
通过对所合成的化合物的经济性、多样性以及生物活性进行综合考量,优选了部分化合物列于下表中。具体的化合物结构如表1所示、具体的化合物物性数据如表2所示。表1-2中的化合物只是为了更好的说明本发明,并不会对本发明产生限定,本领域的技术人员不应将此理解为本发明上述主题的范围仅限于以下化合物。
表1式I化合物结构
表2 1H NMR数据
制备本发明化合物的方法在以下技术方案和实施例中进行了说明。原料可以经市场购买到或者可以通过文献中已知的方法或者如详解所示进行制备。本领域技术人员应当理解,也可以利用其它合成路线合成本发明的化合物。尽管在下文中已经对合成路线中的具体原料和条件进行了说明,但是,可以很容易地将其替换为其它类似的原料及条件,这些对本发明制备方法的变型或者变体而产生的诸如化合物的各种异构体等都包括在本发明范围内。另外,如下所述制备方法可以按照本发明公开内容、使用本领域技术人员熟知的常规化学方法进行进一步修饰。例如,在反应过程中对适当的基团进行保护等等。
实施例1
化合物I-1的合成:
在100mL干燥的圆底烧瓶中,将中间体II(1.03g,3mmol)溶于20mL DMF中,向溶液中加入碳酸钾(0.83g,6mmol)。将中间体III-1(0.51g,3mmol)溶于10mL DMF,室温下滴入反应液中,加完将反应液移至75℃加热反应3小时。LC-MS监测,待反应结束后,冷却至室温。加入100mL水,用150mL的乙酸乙酯萃取三次,合并有机相,干燥,硅胶柱层析分离纯化,得白色固体I-1(0.65g,45.3%),1HNMR(500MHz,DMSO-d6)δ7.53–7.49(m,1H),7.37(d,J=8.7Hz,1H),7.21(s,1H),6.98(s,1H),4.29(d,J=5.6Hz,2H),4.15–4.12(m,2H),3.91(s,3H),3.88(s,3H),2.66(t,J=7.5Hz,2H),2.44–2.38(m,2H),2.14(s,3H).
实施例2
化合物I-2的合成:
在100mL干燥的圆底烧瓶中,将中间体II(1.03g,3mmol)溶于20mLDMF中,向溶液中加入碳酸钾(0.83g,6mmol)。将中间体III-2(0.55g,3mmol)溶于10mLDMF,室温下滴入反应液中,加完将反应液移至75℃加热反应3小时。LC-MS监测,待反应结束后,冷却至室温。加入100mL水,用150mL的乙酸乙酯萃取三次,合并有机相,干燥,硅胶柱层析分离纯化,得白色固体I-2(0.71g,48.1%),1HNMR(500MHz,DMSO-d6)δ7.53–7.48(m,1H),7.37(d,J=8.7Hz,1H),7.20(s,1H),6.97(s,1H),4.29(d,J=5.6Hz,2H),4.14–4.09(m,2H),3.91(s,3H),3.88(s,3H),2.65(t,J=7.5Hz,2H),2.58–2.54(m,2H),2.43–2.38(m,2H),1.22(s,3H).
实施例3
化合物I-16的合成:
在100mL干燥的圆底烧瓶中,将中间体II(1.03g,3mmol)溶于20mLDMF中,向溶液中加入碳酸钾(0.83g,6mmol)。将中间体III-16(0.55g,3mmol)溶于10mLDMF,室温下滴入反应液中,加完将反应液移至75℃加热反应3小时。LC-MS监测,待反应结束后,冷却至室温。加入100mL水,用150mL的乙酸乙酯萃取三次,合并有机相,干燥,硅胶柱层析分离纯化,得白色固体I-16(0.66g,44.7%),1HNMR(500MHz,DMSO-d6)δ7.53–7.49(m,1H),7.37(d,J=8.7Hz,1H),7.21(s,1H),6.98(s,1H),4.29(d,J=5.6Hz,2H),3.91(s,3H),3.87(s,3H),3.83–3.78(m,2H),2.78–2.67(m,2H),2.19(s,3H),1.95–1.79(m,4H).
实施例4
化合物I-17的合成:
在100mL干燥的圆底烧瓶中,将中间体II(1.03g,3mmol)溶于20mLDMF中,向溶液中加入碳酸钾(0.83g,6mmol)。将中间体III-17(0.60g,3mmol)溶于10mLDMF,室温下滴入反应液中,加完将反应液移至75℃加热反应3小时。LC-MS监测,待反应结束后,冷却至室温。加入100mL水,用150mL的乙酸乙酯萃取三次,合并有机相,干燥,硅胶柱层析分离纯化,得白色固体I-17(0.73g,48.1%),1HNMR(500MHz,DMSO-d6)δ7.53–7.47(m,1H),7.38(d,J=8.7Hz,1H),7.20(s,1H),6.97(s,1H),4.28(d,J=5.6Hz,2H),3.91(s,3H),3.88(s,3H),3.84–3.77(m,2H),2.78–2.70(m,2H),2.66(d,J=7.0Hz,2H),1.95–1.79(m,4H),1.25–1.18(m,3H).
实施例5
制剂的制备:
1、粉剂:称取30%的式(Ⅰ)化合物,70%的高岭土混合均匀,经粉碎而得到产品。
2、可湿性粉剂:称取30%的式(Ⅰ)化合物、5%的木质素磺酸钙、2%十二烷硫酸钠、3%白炭黑、高岭土加至100%。混合均匀,经气流粉碎后得到产品。
3、水分散粒剂:称取70%的式(Ⅰ)化合物、5%木质素磺酸钠、5%NNO(烷基萘磺酸盐甲醛缩合物)、2%拉开粉BX(二丁基萘磺酸钠)、3%K-12(十二烷基硫酸钠)、5%羧甲基(乙基)纤维素、5%硅藻土、高岭土加至100%。混合均匀,经气流粉碎后,称量好粉剂加入水混合,在造粒机中进行造粒,然后干燥、筛分,即得到颗粒状产品。
4、乳油:称取20%的式(Ⅰ)化合物、5%农乳700#、5%农乳500#、5%农乳1601#、10%环已酮、3%N-甲基吡咯烷酮、溶剂油加至100%,经溶解完全并混合均匀,得到产品。
5、悬浮剂:称取20%的式(Ⅰ)化合物、4%FS3000(磷酸酯型阴离子表面活性剂)、2%NS-500LQ(非离子型羟基聚环氧乙烷嵌段共聚物)、0.2%黄原胶、1%硅酸镁铝、5%乙二醇、0.1%BIT(1,2-苯并异噻唑啉-3-酮)、0.3%有机改性硅氧烷消泡剂,去离子水加至100%,制成浆料,进行砂磨后得到产品。
以上均为重量百分比。
实施例6
生物活性评价(苗后):
待测化合物原药用DMF溶解配制成2.5%母液,再用0.1%吐温-80的水稀释备用。准备营养土装至盆口直径10cm、高9cm的塑料盆中,将靶标种子撒入其中,播后覆土0.5-1cm,底部吸水后置于温室内培养,按试验设计剂量用喷雾塔进行喷雾处理,试验设3次重复。待药液自然风干后,置于温室内按常规方法管理,定期观察试材的生长发育情况,根据农药室内生物测定试验准则第4部分,并依据实际情况,于处理后定期(7天、14天、21天)通过目测法调查供试药剂对杂草的防除效果。防除效果分级标准:
9级:相当于空白对照区杂草的67.6-100%;
8级:相当于空白对照区杂草的35.1-67.5%;
7级:相当于空白对照区杂草的25.1-35%;
6级:相当于空白对照区杂草的15.1-25%;
5级:相当于空白对照区杂草的10.1-15%;
4级:相当于空白对照区杂草的5.1-10%;
3级:相当于空白对照区杂草的2.6-5%;
2级:相当于空白对照区杂草的0-2.5%;
1级:全部死亡。
按照以上方法,选取部分化合物(化合物编号如表3所示)分别与如下化合物进行除草活性的平行测定:
表3防除效果
通过上述实验,可以发现本发明所保护的化合物具有极佳的生物活性,具备较好的商业应用前景。
实施例7
作物安全性评价(苗后):
准备营养土装至直径为7cm的纸杯中,将定量的作物种子撒入纸杯中,播后覆土1.5cm,镇压、淋水后置于温室内培养,用含有0.1%吐温80的水稀释溶解有待测化合物原药的丙酮溶液至所需的浓度,按试验设计剂量用喷雾塔进行喷雾处理(每处理设3次重复),之后置于温室内按常规方法管理,定期观察试材的生长发育情况,根据农药室内生物测定试验准则第8部分,并依据实际情况,于处理后定期通过目测法调查供试药剂对作物的影响,同时描述药害症状,主要症状有:
1)颜色变化(黄化、白化、变紫等);
2)形态变化(新叶畸形、扭曲等);
3)生长变化(脱水、枯萎、矮化、簇生等)。
药害评价分级:
a级:无药害;
b级:药害程度为1-10%,无明显药害;
c级:药害程度为11-30%,轻微药害;
d级:药害程度为31-50%,中度药害;
e级:药害程度为51-100%,严重药害。
按照以上方法,选取部分化合物与市售的氟氯吡啶酯进行了作物安全性的平行测定。施药3周后的作物安全性实验效果如下表所示:
表4作物安全性试验
化合物编号 | 施药量(g/亩) | 小麦 |
I-16 | 32 | a |
I-1 | 32 | a |
I-17 | 32 | a |
I-2 | 32 | a |
氟氯吡啶酯 | 32 | b |
可见,在当前用药量下本发明所保护的化合物对于小麦经目测法观察基本为无药害,因此,在适合的剂量下对于作物尤其是小麦有很好的安全性。
上述实施例只是为了说明本发明的技术构思及特点,其目的是在于让本领域内的普通技术人员能够了解本发明的内容并据以实施,并不能以此限制本发明的保护范围。凡是根据本发明内容的实质所作出的等效的变化或修饰,都应涵盖在本发明的保护范围内。
Claims (10)
1.一种含氯代吡啶结构的化合物或其作为农药可接受的盐,其结构式如式(I)所示:
式(I)中,
R1选自H、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、C1-C6烷硫基、C1-C6烷胺基、C3-C6环烷基、C2-C6烯基、C2-C6烯氧基、C2-C6烯硫基、C2-C4炔基、C1-C6烷基羰基、C1-C6烷氧基羰基、C1-C6烷胺基羰基、C1-C6烷氧基取代的C1-C6烷氧基、C3-C6环烷基取代的C1-C6烷基、氨基羰基取代的C1-C6烷基、CN、卤素、NO2、COOR1、巯基、羧基、醛基、羟基或氨基;
R2和R3相同或不同,分别独立地选自H、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、卤代C1-C6烷氧基、C1-C6烷硫基或卤代C1-C6烷硫基;
或者,R2和R3一起形成基团-(CH2)m-,m表示1-6;
R4选自H、C1-C6烷基、卤代C1-C6烷基、芳基取代的C1-C6烷基或芳基。
2.如权利要求1所述的一种含氯代吡啶结构的化合物或其作为农药可接受的盐,其特征在于,式(I)中,R1选自H、C1-C6烷基、卤代C1-C6烷基、C1-C6烷氧基、C2-C6烯基、C2-C6烯氧基、C2-C6炔基、C3-C6环烷基或C3-C6环烷基取代的C1-C6烷基。
3.如权利要求1所述的一种含氯代吡啶结构的化合物或其作为农药可接受的盐,其特征在于,式(I)中,R2和R3一起形成基团-(CH2)m-,m表示2-5。
4.如权利要求1所述的一种含氯代吡啶结构的化合物或其作为农药可接受的盐,其特征在于,式(I)中,R4选自H、C1-C6烷基、卤代C1-C6烷基、苯基取代的C1-C6烷基或苯基。
5.如权利要求1所述的一种含氯代吡啶结构的化合物或其作为农药可接受的盐,其特征在于,式(I)中,R1选自H、C1-C4烷基、卤代C1-C4烷基、C1-C4烷氧基、C2-C4烯基、C2-C4烯氧基、C2-C4炔基、C3-C6环烷基或C3-C6环烷基取代的C1-C4烷基;
R2和R3一起形成基团-(CH2)m-,m表示3-5;
R4选自H、C1-C4烷基、苯基或苯基取代的C1-C4烷基。
6.如权利要求1所述的一种含氯代吡啶结构的化合物或其作为农药可接受的盐,其特征在于,式(I)中,R1选自Me、Et、n-Pr、i-Pr、n-Bu、i-Bu、s-Bu、t-Bu、乙烯基、烯丙基、乙炔基、炔丙基、OMe、OEt、n-PrO、i-PrO、n-BuO、i-BuO、s-BuO、t-BuO、环丙烷基、环丁烷基、环戊烷基、环己烷基、环丙烷甲基、环丁烷甲基、CH2Cl、CHCl2、CCl3、CH2F、CHF2、CF3、CH2Br、CHBr2、CBr3、CH2CF3或CH2CH2Cl;
R2和R3一起形成基团-(CH2)m-,m表示3-5;
R4选自H、Me、Et、n-Pr、i-Pr、苯基或苄基。
8.一种除草组合物,其特征在于,包括除草有效量的权利要求1-7任一项所述的含氯代吡啶结构的化合物或其作为农药可接受的盐中的至少一种;优选的,还包括制剂载体或制剂助剂。
9.一种控制不想要的植物的方法,其特征在于,包括将除草有效量的权利要求1-7任一项所述的含氯代吡啶结构的化合物或其作为农药可接受的盐中的至少一种或如权利要求8所述的除草组合物使用在不想要的植物上。
10.如权利要求1-7任一项所述的含氯代吡啶结构的化合物或其作为农药可接受的盐中的至少一种或如权利要求8所述的除草组合物在控制不想要的植物上的用途。
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