CN112745305A - 一种三嗪酮类化合物及其用途 - Google Patents
一种三嗪酮类化合物及其用途 Download PDFInfo
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- CN112745305A CN112745305A CN201911038131.8A CN201911038131A CN112745305A CN 112745305 A CN112745305 A CN 112745305A CN 201911038131 A CN201911038131 A CN 201911038131A CN 112745305 A CN112745305 A CN 112745305A
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- Prior art keywords
- alkyl
- group
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- hydrogen
- methyl
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- -1 Triazinone compound Chemical class 0.000 title claims abstract description 148
- 150000001875 compounds Chemical class 0.000 claims abstract description 116
- 230000002363 herbicidal effect Effects 0.000 claims abstract description 114
- 239000004009 herbicide Substances 0.000 claims abstract description 107
- 241000196324 Embryophyta Species 0.000 claims abstract description 46
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 46
- 230000003287 optical effect Effects 0.000 claims abstract description 16
- 150000003839 salts Chemical class 0.000 claims description 111
- 229910052739 hydrogen Inorganic materials 0.000 claims description 94
- 239000001257 hydrogen Substances 0.000 claims description 94
- 239000003112 inhibitor Substances 0.000 claims description 94
- 239000000203 mixture Substances 0.000 claims description 83
- 150000002431 hydrogen Chemical class 0.000 claims description 70
- 150000003254 radicals Chemical class 0.000 claims description 65
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 59
- 229910052736 halogen Inorganic materials 0.000 claims description 36
- 150000002367 halogens Chemical class 0.000 claims description 36
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 35
- 229910052799 carbon Inorganic materials 0.000 claims description 34
- 125000001424 substituent group Chemical group 0.000 claims description 34
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 30
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 28
- 239000004480 active ingredient Substances 0.000 claims description 25
- 230000015572 biosynthetic process Effects 0.000 claims description 25
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 24
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 21
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 19
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 19
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 18
- 238000002360 preparation method Methods 0.000 claims description 18
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 16
- 125000000217 alkyl group Chemical group 0.000 claims description 16
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 claims description 15
- 108020001991 Protoporphyrinogen Oxidase Proteins 0.000 claims description 13
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 13
- 125000004438 haloalkoxy group Chemical group 0.000 claims description 13
- 229910052717 sulfur Inorganic materials 0.000 claims description 13
- QWWHRELOCZEQNZ-UHFFFAOYSA-N 2,2-dichloro-1-(1-oxa-4-azaspiro[4.5]decan-4-yl)ethanone Chemical compound ClC(Cl)C(=O)N1CCOC11CCCCC1 QWWHRELOCZEQNZ-UHFFFAOYSA-N 0.000 claims description 12
- 125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 12
- 229910052760 oxygen Inorganic materials 0.000 claims description 12
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 12
- YNQSILKYZQZHFJ-UHFFFAOYSA-N R-29148 Chemical compound CC1CN(C(=O)C(Cl)Cl)C(C)(C)O1 YNQSILKYZQZHFJ-UHFFFAOYSA-N 0.000 claims description 11
- 125000001188 haloalkyl group Chemical group 0.000 claims description 11
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 10
- NDUPDOJHUQKPAG-UHFFFAOYSA-N Dalapon Chemical compound CC(Cl)(Cl)C(O)=O NDUPDOJHUQKPAG-UHFFFAOYSA-N 0.000 claims description 10
- GZUXJHMPEANEGY-UHFFFAOYSA-N bromomethane Chemical compound BrC GZUXJHMPEANEGY-UHFFFAOYSA-N 0.000 claims description 10
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 claims description 9
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 9
- VYNOULHXXDFBLU-UHFFFAOYSA-N Cumyluron Chemical compound C=1C=CC=CC=1C(C)(C)NC(=O)NCC1=CC=CC=C1Cl VYNOULHXXDFBLU-UHFFFAOYSA-N 0.000 claims description 9
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 9
- 125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 9
- 239000000460 chlorine Substances 0.000 claims description 9
- 229910052801 chlorine Inorganic materials 0.000 claims description 9
- ICJSJAJWTWPSBD-UHFFFAOYSA-N cloquintocet Chemical compound C1=CN=C2C(OCC(=O)O)=CC=C(Cl)C2=C1 ICJSJAJWTWPSBD-UHFFFAOYSA-N 0.000 claims description 9
- QMTNOLKHSWIQBE-FGTMMUONSA-N exo-(+)-cinmethylin Chemical compound O([C@H]1[C@]2(C)CC[C@@](O2)(C1)C(C)C)CC1=CC=CC=C1C QMTNOLKHSWIQBE-FGTMMUONSA-N 0.000 claims description 9
- 229910052731 fluorine Inorganic materials 0.000 claims description 9
- 239000011737 fluorine Substances 0.000 claims description 9
- 150000004669 very long chain fatty acids Chemical class 0.000 claims description 9
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 8
- 125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 8
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 8
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 8
- NRFQZTCQAYEXEE-UHFFFAOYSA-N Fenclorim Chemical compound ClC1=CC(Cl)=NC(C=2C=CC=CC=2)=N1 NRFQZTCQAYEXEE-UHFFFAOYSA-N 0.000 claims description 8
- GRSMWKLPSNHDHA-UHFFFAOYSA-N Naphthalic anhydride Chemical compound C1=CC(C(=O)OC2=O)=C3C2=CC=CC3=C1 GRSMWKLPSNHDHA-UHFFFAOYSA-N 0.000 claims description 8
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 claims description 8
- 150000002632 lipids Chemical class 0.000 claims description 8
- VTRWMTJQBQJKQH-UHFFFAOYSA-N pyributicarb Chemical compound COC1=CC=CC(N(C)C(=S)OC=2C=C(C=CC=2)C(C)(C)C)=N1 VTRWMTJQBQJKQH-UHFFFAOYSA-N 0.000 claims description 8
- 238000003786 synthesis reaction Methods 0.000 claims description 8
- HKELWJONQIFBPO-UHFFFAOYSA-N 1-(2,4-dichlorophenyl)-5-(trichloromethyl)-1,2,4-triazole-3-carboxylic acid Chemical compound N1=C(C(=O)O)N=C(C(Cl)(Cl)Cl)N1C1=CC=C(Cl)C=C1Cl HKELWJONQIFBPO-UHFFFAOYSA-N 0.000 claims description 7
- YOYAIZYFCNQIRF-UHFFFAOYSA-N 2,6-dichlorobenzonitrile Chemical compound ClC1=CC=CC(Cl)=C1C#N YOYAIZYFCNQIRF-UHFFFAOYSA-N 0.000 claims description 7
- 108010020183 3-phosphoshikimate 1-carboxyvinyltransferase Proteins 0.000 claims description 7
- OPEJGICLTMWFNQ-UHFFFAOYSA-N 5-[(2,6-difluorophenyl)methoxymethyl]-5-methyl-3-(3-methylthiophen-2-yl)-4h-1,2-oxazole Chemical compound C1=CSC(C=2CC(C)(COCC=3C(=CC=CC=3F)F)ON=2)=C1C OPEJGICLTMWFNQ-UHFFFAOYSA-N 0.000 claims description 7
- YRMLFORXOOIJDR-UHFFFAOYSA-N Dichlormid Chemical compound ClC(Cl)C(=O)N(CC=C)CC=C YRMLFORXOOIJDR-UHFFFAOYSA-N 0.000 claims description 7
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 7
- 230000008166 cellulose biosynthesis Effects 0.000 claims description 7
- 238000009472 formulation Methods 0.000 claims description 7
- 102000005396 glutamine synthetase Human genes 0.000 claims description 7
- 108020002326 glutamine synthetase Proteins 0.000 claims description 7
- 239000005556 hormone Substances 0.000 claims description 7
- 229940088597 hormone Drugs 0.000 claims description 7
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 claims description 7
- 230000029553 photosynthesis Effects 0.000 claims description 7
- 238000010672 photosynthesis Methods 0.000 claims description 7
- 239000000049 pigment Substances 0.000 claims description 7
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 7
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 6
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 6
- 239000005644 Dazomet Substances 0.000 claims description 6
- 229940121849 Mitotic inhibitor Drugs 0.000 claims description 6
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 claims description 6
- BIWJNBZANLAXMG-YQELWRJZSA-N chloordaan Chemical compound ClC1=C(Cl)[C@@]2(Cl)C3CC(Cl)C(Cl)C3[C@]1(Cl)C2(Cl)Cl BIWJNBZANLAXMG-YQELWRJZSA-N 0.000 claims description 6
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 6
- QAYICIQNSGETAS-UHFFFAOYSA-N dazomet Chemical compound CN1CSC(=S)N(C)C1 QAYICIQNSGETAS-UHFFFAOYSA-N 0.000 claims description 6
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 6
- 125000004441 haloalkylsulfonyl group Chemical group 0.000 claims description 6
- ITGSCCPVERXFGN-UHFFFAOYSA-N isoxadifen Chemical compound C1C(C(=O)O)=NOC1(C=1C=CC=CC=1)C1=CC=CC=C1 ITGSCCPVERXFGN-UHFFFAOYSA-N 0.000 claims description 6
- JCHMGYRXQDASJE-UHFFFAOYSA-N metcamifen Chemical compound C1=CC(NC(=O)NC)=CC=C1S(=O)(=O)NC(=O)C1=CC=CC=C1OC JCHMGYRXQDASJE-UHFFFAOYSA-N 0.000 claims description 6
- 230000026683 transduction Effects 0.000 claims description 6
- 238000010361 transduction Methods 0.000 claims description 6
- 125000004205 trifluoroethyl group Chemical group [H]C([H])(*)C(F)(F)F 0.000 claims description 6
- QHXDTLYEHWXDSO-UHFFFAOYSA-N 6-chloro-2-n,2-n,4-n,4-n-tetraethyl-1,3,5-triazine-2,4-diamine Chemical compound CCN(CC)C1=NC(Cl)=NC(N(CC)CC)=N1 QHXDTLYEHWXDSO-UHFFFAOYSA-N 0.000 claims description 5
- PFJJMJDEVDLPNE-UHFFFAOYSA-N Benoxacor Chemical compound C1=CC=C2N(C(=O)C(Cl)Cl)C(C)COC2=C1 PFJJMJDEVDLPNE-UHFFFAOYSA-N 0.000 claims description 5
- IUFUITYPUYMIHI-UHFFFAOYSA-N N-[1-(3,5-dimethylphenoxy)propan-2-yl]-6-(2-fluoropropan-2-yl)-1,3,5-triazine-2,4-diamine Chemical compound N=1C(N)=NC(C(C)(C)F)=NC=1NC(C)COC1=CC(C)=CC(C)=C1 IUFUITYPUYMIHI-UHFFFAOYSA-N 0.000 claims description 5
- FCOHEOSCARXMMS-UHFFFAOYSA-N Oxaziclomefone Chemical compound C1OC(C)=C(C=2C=CC=CC=2)C(=O)N1C(C)(C)C1=CC(Cl)=CC(Cl)=C1 FCOHEOSCARXMMS-UHFFFAOYSA-N 0.000 claims description 5
- MKQSWTQPLLCSOB-UHFFFAOYSA-N benzyl 2-chloro-4-(trifluoromethyl)-1,3-thiazole-5-carboxylate Chemical compound N1=C(Cl)SC(C(=O)OCC=2C=CC=CC=2)=C1C(F)(F)F MKQSWTQPLLCSOB-UHFFFAOYSA-N 0.000 claims description 5
- 125000001028 difluoromethyl group Chemical group [H]C(F)(F)* 0.000 claims description 5
- PBTHJVDBCFJQGG-UHFFFAOYSA-N methyl azide Chemical compound CN=[N+]=[N-] PBTHJVDBCFJQGG-UHFFFAOYSA-N 0.000 claims description 5
- 229940102396 methyl bromide Drugs 0.000 claims description 5
- XSCHRSMBECNVNS-UHFFFAOYSA-N quinoxaline Chemical compound N1=CC=NC2=CC=CC=C21 XSCHRSMBECNVNS-UHFFFAOYSA-N 0.000 claims description 5
- 125000004454 (C1-C6) alkoxycarbonyl group Chemical group 0.000 claims description 4
- 125000004750 (C1-C6) alkylaminosulfonyl group Chemical group 0.000 claims description 4
- 125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims description 4
- YAQLSKVCTLCIIE-UHFFFAOYSA-N 2-bromobutyric acid Chemical compound CCC(Br)C(O)=O YAQLSKVCTLCIIE-UHFFFAOYSA-N 0.000 claims description 4
- WFVUIONFJOAYPK-KAMYIIQDSA-N Oxabetrinil Chemical compound C=1C=CC=CC=1C(/C#N)=N\OCC1OCCO1 WFVUIONFJOAYPK-KAMYIIQDSA-N 0.000 claims description 4
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- WZDDLAZXUYIVMU-UHFFFAOYSA-N bromobutide Chemical compound CC(C)(C)C(Br)C(=O)NC(C)(C)C1=CC=CC=C1 WZDDLAZXUYIVMU-UHFFFAOYSA-N 0.000 claims description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 4
- 125000006255 cyclopropyl carbonyl group Chemical group [H]C1([H])C([H])([H])C1([H])C(*)=O 0.000 claims description 4
- 125000004741 (C1-C6) haloalkylsulfonyl group Chemical group 0.000 claims description 3
- WBFYVDCHGVNRBH-UHFFFAOYSA-N 7,8-dihydropteroic acid Chemical compound N=1C=2C(=O)NC(N)=NC=2NCC=1CNC1=CC=C(C(O)=O)C=C1 WBFYVDCHGVNRBH-UHFFFAOYSA-N 0.000 claims description 3
- 108010000700 Acetolactate synthase Proteins 0.000 claims description 3
- OBLNWSCLAYSJJR-UHFFFAOYSA-N Quinoclamin Chemical compound C1=CC=C2C(=O)C(N)=C(Cl)C(=O)C2=C1 OBLNWSCLAYSJJR-UHFFFAOYSA-N 0.000 claims description 3
- 239000002167 Quinoclamine Substances 0.000 claims description 3
- 208000014347 autosomal dominant hyaline body myopathy Diseases 0.000 claims description 3
- CWFOCCVIPCEQCK-UHFFFAOYSA-N chlorfenapyr Chemical compound BrC1=C(C(F)(F)F)N(COCC)C(C=2C=CC(Cl)=CC=2)=C1C#N CWFOCCVIPCEQCK-UHFFFAOYSA-N 0.000 claims description 3
- OAWUUPVZMNKZRY-UHFFFAOYSA-N cyprosulfamide Chemical compound COC1=CC=CC=C1C(=O)NS(=O)(=O)C1=CC=C(C(=O)NC2CC2)C=C1 OAWUUPVZMNKZRY-UHFFFAOYSA-N 0.000 claims description 3
- JITOKQVGRJSHHA-UHFFFAOYSA-M monosodium methyl arsenate Chemical compound [Na+].C[As](O)([O-])=O JITOKQVGRJSHHA-UHFFFAOYSA-M 0.000 claims description 3
- BMQNWLUEXNQIGL-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O.CCCCCCCCC(O)=O BMQNWLUEXNQIGL-UHFFFAOYSA-N 0.000 claims description 3
- WMMQJAQJAPXWDO-UHFFFAOYSA-N (4-chlorophenyl) n-methylcarbamate Chemical compound CNC(=O)OC1=CC=C(Cl)C=C1 WMMQJAQJAPXWDO-UHFFFAOYSA-N 0.000 claims description 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims description 2
- YZAZXIUFBCPZGB-QZOPMXJLSA-N (z)-octadec-9-enoic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O.CCCCCCCC\C=C/CCCCCCCC(O)=O YZAZXIUFBCPZGB-QZOPMXJLSA-N 0.000 claims description 2
- MHULQDZDXMHODA-UHFFFAOYSA-N 1-(2,2-dichloroacetyl)-3,3,8a-trimethyl-2,4,7,8-tetrahydropyrrolo[1,2-a]pyrimidin-6-one Chemical compound C1C(C)(C)CN(C(=O)C(Cl)Cl)C2(C)N1C(=O)CC2 MHULQDZDXMHODA-UHFFFAOYSA-N 0.000 claims description 2
- QUTYKIXIUDQOLK-PRJMDXOYSA-N 5-O-(1-carboxyvinyl)-3-phosphoshikimic acid Chemical compound O[C@H]1[C@H](OC(=C)C(O)=O)CC(C(O)=O)=C[C@H]1OP(O)(O)=O QUTYKIXIUDQOLK-PRJMDXOYSA-N 0.000 claims description 2
- LBGPXIPGGRQBJW-UHFFFAOYSA-N Difenzoquat Chemical compound C[N+]=1N(C)C(C=2C=CC=CC=2)=CC=1C1=CC=CC=C1 LBGPXIPGGRQBJW-UHFFFAOYSA-N 0.000 claims description 2
- PHVNLLCAQHGNKU-UHFFFAOYSA-N Dimethipin Chemical compound CC1=C(C)S(=O)(=O)CCS1(=O)=O PHVNLLCAQHGNKU-UHFFFAOYSA-N 0.000 claims description 2
- ICWUMLXQKFTJMH-UHFFFAOYSA-N Etobenzanid Chemical compound C1=CC(OCOCC)=CC=C1C(=O)NC1=CC=CC(Cl)=C1Cl ICWUMLXQKFTJMH-UHFFFAOYSA-N 0.000 claims description 2
- FMINYZXVCTYSNY-UHFFFAOYSA-N Methyldymron Chemical compound C=1C=CC=CC=1N(C)C(=O)NC(C)(C)C1=CC=CC=C1 FMINYZXVCTYSNY-UHFFFAOYSA-N 0.000 claims description 2
- 239000002671 adjuvant Substances 0.000 claims description 2
- XXWNKVBJDWSYBN-UHFFFAOYSA-N diethoxy-phenoxy-sulfanylidene-$l^{5}-phosphane Chemical compound CCOP(=S)(OCC)OC1=CC=CC=C1 XXWNKVBJDWSYBN-UHFFFAOYSA-N 0.000 claims description 2
- KKIJNRQIKXXGPF-UHFFFAOYSA-N dimethylarsanylsodium Chemical compound C[As](C)[Na] KKIJNRQIKXXGPF-UHFFFAOYSA-N 0.000 claims description 2
- 239000003188 fatty acid synthesis inhibitor Substances 0.000 claims description 2
- 125000001072 heteroaryl group Chemical group 0.000 claims description 2
- 125000005223 heteroarylcarbonyl group Chemical group 0.000 claims description 2
- 230000010627 oxidative phosphorylation Effects 0.000 claims description 2
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- 125000004737 (C1-C6) haloalkoxy group Chemical group 0.000 claims 1
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- SDIXRDNYIMOKSG-UHFFFAOYSA-L disodium methyl arsenate Chemical compound [Na+].[Na+].C[As]([O-])([O-])=O SDIXRDNYIMOKSG-UHFFFAOYSA-L 0.000 claims 1
- OFPXSFXSNFPTHF-UHFFFAOYSA-N oxaprozin Chemical compound O1C(CCC(=O)O)=NC(C=2C=CC=CC=2)=C1C1=CC=CC=C1 OFPXSFXSNFPTHF-UHFFFAOYSA-N 0.000 claims 1
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- 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 33
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- 229910052708 sodium Inorganic materials 0.000 description 26
- MEFQWPUMEMWTJP-UHFFFAOYSA-N fluroxypyr Chemical compound NC1=C(Cl)C(F)=NC(OCC(O)=O)=C1Cl MEFQWPUMEMWTJP-UHFFFAOYSA-N 0.000 description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 23
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- WJCNZQLZVWNLKY-UHFFFAOYSA-N thiabendazole Chemical compound S1C=NC(C=2NC3=CC=CC=C3N=2)=C1 WJCNZQLZVWNLKY-UHFFFAOYSA-N 0.000 description 1
- 229960004546 thiabendazole Drugs 0.000 description 1
- 229910052723 transition metal Inorganic materials 0.000 description 1
- 150000003624 transition metals Chemical class 0.000 description 1
- PHLBKPHSAVXXEF-UHFFFAOYSA-N trazodone Chemical compound ClC1=CC=CC(N2CCN(CCCN3C(N4C=CC=CC4=N3)=O)CC2)=C1 PHLBKPHSAVXXEF-UHFFFAOYSA-N 0.000 description 1
- 229960003991 trazodone Drugs 0.000 description 1
- YWBFPKPWMSWWEA-UHFFFAOYSA-O triazolopyrimidine Chemical compound BrC1=CC=CC(C=2N=C3N=CN[N+]3=C(NCC=3C=CN=CC=3)C=2)=C1 YWBFPKPWMSWWEA-UHFFFAOYSA-O 0.000 description 1
- YMXOXAPKZDWXLY-QWRGUYRKSA-N tribenuron methyl Chemical group COC(=O)[C@H]1CCCC[C@@H]1S(=O)(=O)NC(=O)N(C)C1=NC(C)=NC(OC)=N1 YMXOXAPKZDWXLY-QWRGUYRKSA-N 0.000 description 1
- 125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-O triethanolammonium Chemical compound OCC[NH+](CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-O 0.000 description 1
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- RKBCYCFRFCNLTO-UHFFFAOYSA-N triisopropylamine Chemical compound CC(C)N(C(C)C)C(C)C RKBCYCFRFCNLTO-UHFFFAOYSA-N 0.000 description 1
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 1
- NRZWQKGABZFFKE-UHFFFAOYSA-N trimethylsulfonium Chemical compound C[S+](C)C NRZWQKGABZFFKE-UHFFFAOYSA-N 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000004565 water dispersible tablet Substances 0.000 description 1
- 239000003021 water soluble solvent Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
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- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings
- C07D413/10—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing two hetero rings linked by a carbon chain containing aromatic rings
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- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- C07D413/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms containing three or more hetero rings
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Abstract
本发明属于农用除草剂领域,具体涉及一种三嗪酮类化合物及其旋光异构体及其用途。三嗪酮类化合物如通式(I)所示,R5、R6所连接的碳原子或R7、R8所连接的碳原子为不对称碳原子时,两处碳原子处构型可分别为R或者S。通式(I)化合物具有很好的除草活性,可以有效地控制稗草、狗尾草、异型莎草、水莎草、马唐、荩草、苘麻、百日草、反枝苋、马齿苋、苍耳、龙葵、决明、野西瓜苗、野大豆等杂草,在低剂量下就可以获得很好的除草效果,且对作物如玉米、小麦、水稻等具有较好的安全性,在农业上可作为选择性除草剂用作作物,亦可作为灭生性除草剂用于非耕地\休闲地、林地、果园、田埂等。
Description
技术领域
本发明属于农用除草剂领域,具体涉及一种三嗪酮类化合物及其用途。
背景技术
Trifludimoxazin为巴斯夫公司开发的具有三嗪酮结构的原卟啉原氧化酶(PPO)抑制剂类除草剂,颇为独特的是,既为PPO抑制剂,又能防除PPO抗性杂草,包括苋属(Amaranthus spp.)、豚草属(Ambrosia spp.)杂草等。
现有技术中,公开的化合物虽与本发明化合物有一定的相似之处,但本发明通式所示的化合物与现有技术是有显著区别的,且均具有很好的除草活性。
发明内容
为了研制新型除草剂以解决日益严重的除草剂抗性问题,本发明提供一种三嗪酮类化合物及其用途。
为实现上述目的,本发明采用的技术方案如下:
本发明提供一种三嗪酮类化合物,如通式(I)所示:
式中:
R1、R2分别选自C1-C6烷基或C1-C6卤代烷基;
R3、R4分别选自氢、卤素、C1-C6烷基、C1-C6烷氧基、C1-C6卤代烷氧基、C1-C6烷硫基或C1-C6烷基磺酰基;
R5、R6分别选自氢、氰基、C1-C6烷基、CO2R9、CH2OR10、苯基或被1-4个独立选自以下基团取代的苯基:卤素、CN、NO2、C1-C8烷基、C1-C8卤代烷基、C1-C8烷氧基、C1-C8卤代烷氧基、C1-C8烷氧基羰基、C1-C8烷硫基或C1-C8烷基磺酰基;
R7、R8分别选自氢、氰基、C1-C6烷基、C1-C6卤代烷基、C1-C6烷基CO2R9、CO2R9、CH2OR10、CH2NR11R12、CONR11R12、苯基或被1-4个独立选自以下基团取代的苯基:卤素、CN、NO2、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基、C1-C4卤代烷氧基、C1-C4烷氧基羰基、C1-C4烷硫基、C1-C4烷基磺酰基;
R9选自氢、C1-C6烷基、C1-C6卤代烷基、C3-C6烯基、C3-C6炔基、C1-C6烷氧基C1-C6烷基、C1-C6烷羰基氧基C2-C4烷基,未取代或者被1-4个独立选自以下基团取代的苄基、呋喃亚甲基、噻唑亚甲基、四氢呋喃亚甲基或吡啶亚甲基:卤素、CN、NO2、C1-C8烷基、C1-C8卤代烷基、C1-C8烷氧基、C1-C8卤代烷氧基、C1-C8烷氧基羰基、C1-C8烷硫基、C1-C8烷基磺酰基;
R10选自氢、C1-C6烷基、C1-C6卤代烷基、C1-C6烷氧基羰基、C1-C6烷基羰基、C1-C6卤代烷基羰基、C3-C6环烷基羰基、C3-C6卤代环烷基羰基、C1-C6烷基磺酰基、C1-C6卤代烷基磺酰基、C1-C6烷基氨基磺酰基、二(C1-C6)烷基氨基磺酰基、C1-C6烷基氨基羰基、二(C1-C6)烷基氨基羰基、二(C1-C6)烷基氨基硫代羰基、C1-C6烷硫基C2-C6烷基羰基,未取代或者被1-4个独立选自以下基团取代的苯基、苯基C1-C2烷基、苯基C2-C4烯基、苯基羰基、苯基C1-C2烷基羰基、苯氧基C1-C2烷基羰基、苯基C2-C4烯基羰基、杂芳基、杂芳基C1-C2烷基、杂芳基羰基:卤素、CN、NO2、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基、C1-C4卤代烷氧基、C1-C4烷氧基羰基、C1-C4烷硫基、C1-C4烷基磺酰基或被1-4个卤素、CN、NO2、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基或C1-C4卤代烷氧基独立取代的苯氧基;
R11、R12分别选自氢、C1-C6烷基、C1-C6卤代烷基、C1-C6烷氧基羰基C1-C6烷基、SO2NH(C1-C6烷基)或SO2N(C1-C6烷基)(C1-C6烷基);
X选自O、S、NCH3、NN(CH3)2、NCN或NOCH3;
R5、R6选自不同时取代基所连接的碳原子为不对称碳原子,其构型为R或S;
R7、R8选自不同时取代基所连接的碳原子为不对称碳原子,其构型为R或S;
或,式(I)所示化合物、式(I)所示化合物的旋光异构体(当含羧基时)的可农用盐或衍生物。
本发明较为优选的化合物为,通式(I)中
R1、R2分别选自C1-C4烷基或C1-C4卤代烷基;
R3、R4分别选自氢、卤素、C1-C6烷基或C1-C6烷氧基;
R5选自氢或C1-C6烷基;
R6选自氢、C1-C6烷基、CO2R9或CH2OR10;
R7选自氢、氰基、C1-C6烷基、C1-C6卤代烷基、C1-C6烷基CO2R9、CO2R9、CH2OR10、CH2NR11R12或CONR11R12;
R8选自氢、C1-C6烷基、C1-C6卤代烷基、苯基或被1-4个独立选自以下基团取代的苯基:卤素、CN、NO2、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基、C1-C4卤代烷氧基、C1-C4烷氧基羰基、C1-C4烷硫基或C1-C4烷基磺酰基;
R9选自氢、C1-C6烷基、C3-C4烯基、C1-C6卤代烷基、C3-C4炔基、C1-C4烷氧基C1-C4烷基、C1-C4烷羰基氧基C2-C3烷基,未取代或者被1-4个独立选自以下基团取代的苄基、呋喃亚甲基或四氢呋喃亚甲基:卤素、CN、NO2、C1-C6烷基或C1-C6卤代烷基;
R10选自氢、C1-C6烷基、C1-C6卤代烷基、C1-C6烷氧基羰基、C1-C6烷基羰基、C1-C6卤代烷基羰基、C3-C6环烷基羰基、C3-C6卤代环烷基羰基、C1-C6烷基磺酰基、C1-C6卤代烷基磺酰基、C1-C6烷基氨基磺酰基、二(C1-C6)烷基氨基磺酰基、C1-C6烷基氨基羰基、二(C1-C6)烷基氨基羰基、二(C1-C6)烷基氨基硫代羰基、C1-C6烷硫基C2-C6烷基羰基,未取代或者被1-4个独立选自以下基团取代的苯基C1-C2烷基、苯基羰基、苯基C1-C2烷基羰基、苯基C2-C4烯基羰基、苯氧基C1-C2烷基羰基、噻吩羰基、吡唑羰基、喹啉羰基:卤素、CN、NO2、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基、C1-C4卤代烷氧基、C1-C4烷氧基羰基、C1-C4烷硫基、C1-C4烷基磺酰基或被1-4个卤素、CN、NO2、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基或C1-C4卤代烷氧基独立取代的苯氧基;
R11、R12分别选自氢、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基羰基C1-C4烷基、SO2NH(C1-C4烷基)或SO2N(C1-C4烷基)(C1-C4烷基);
X选自O、S、NCH3、NN(CH3)2、NCN或NOCH3;
R5、R6选自不同取代基时所连接的碳原子为不对称碳原子,其构型为R或S;
R7、R8选自不同取代基时所连接的碳原子为不对称碳原子,其构型为R或S;
或,式(I)所示化合物、式(I)所示化合物的旋光异构体的可农用盐或衍生物。
本发明进一步优选的化合物为:通式(I)中
R1、R2分别选自甲基、乙基、正丙基、正丁基、异丙基或叔丁基;
R3、R4分别选自氢、氟、氯或甲基;
R5选自氢;
R6选自氢;
R7选自氢、氰基、甲基、乙基、正丙基、正丁基、异丙基、异丁基、叔丁基、C1-C3烷基CO2R9、CO2R9、CH2OR10、CH2NR11R12或CONR11R12;
R8选自氢、C1-C4烷基、C1-C4卤代烷基、苯基或被1-4个独立选自以下基团取代的苯基:卤素、CN、NO2、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基或C1-C4卤代烷氧基;
R9选自氢、C1-C4烷基、C1-C4卤代烷基、烯丙基、炔丙基、C1-C3烷氧基C1-C3烷基、C1-C4烷羰基氧基C2-C3烷基,未取代或者被1-4个独立选自以下基团取代的苄基、呋喃亚甲基或四氢呋喃亚甲基:卤素、CN、NO2或C1-C4烷基;
R10选自氢、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基羰基、C1-C4烷基羰基、C1-C4卤代烷基羰基、C3-C6环烷基羰基、C1-C4烷基磺酰基、C1-C4卤代烷基磺酰基、二(C1-C3)烷基氨基磺酰基、C1-C3烷基氨基羰基、二(C1-C3)烷基氨基羰基、二(C1-C3)烷基氨基硫代羰基、C1-C2烷硫基C2-C4烷基羰基,未取代或者被1-4个独立选自以下基团的苯基羰基、苯基C1-C2烷基羰基或苯氧基C1-C2烷基羰基:卤素、CN、NO2、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基或C1-C4卤代烷氧基;
R11、R12分别选自氢、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基羰基C1-C2烷基、SO2NH(C1-C4烷基)或SO2N(C1-C2烷基)(C1-C4烷基);
X选自O、S、NCH3、NN(CH3)2、NCN或NOCH3;
R7、R8选自不同取代基时所连接的碳原子为不对称碳原子,其构型为R或S;
或,式(I)所示化合物、式(I)所示化合物的旋光异构体的可农用盐或衍生物。
本发明更为优选的化合物为:通式(I)中
R1、R2分别选自甲基或乙基;
R3、R4分别选自氢、氟、氯或甲基;
R5选自氢;
R6选自氢;
R7选自氢、氰基、甲基、乙基、正丙基、正丁基、异丙基、异丁基、叔丁基、CH2CO2R9、CH2CH2CO2R9、CO2R9、CH2OR10或CONR11R12;
R8选自氢、甲基、乙基、三氟甲基、二氟甲基、苯基或被1-4个独立选自以下基团取代的苯基:卤素、CN、NO2、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基或C1-C4卤代烷氧基;
R9选自氢、甲基、乙基、正丙基、正丁基、异丙基、异丁基、叔丁基、三氟乙基、烯丙基、炔丙基、甲氧基乙基、乙氧基乙基、甲基羰基氧基乙基或四氢呋喃亚甲基;
R10选自氢、C1-C4烷氧基羰基、C1-C4烷基羰基、C1-C4卤代烷基羰基、C3-C6环烷基羰基、C1-C4烷基磺酰基、C1-C4卤代烷基磺酰基、二(C1-C2)烷基氨基磺酰基、C1-C2烷基氨基羰基、二(C1-C3)烷基氨基羰基、二(C1-C2)烷基氨基硫代羰基、C1-C2烷硫基C2-C4烷基羰基,未取代或者被1-4个独立选自以下基团的苯基羰基、苯基C1-C2烷基羰基或苯氧基C1-C2烷基羰基:卤素、CN、NO2、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基或C1-C4卤代烷氧基;
R11选自氢、C1-C4烷基或C1-C4卤代烷基;
R12选自氢、C1-C4烷基、C1-C4烷氧基羰基C1-C4烷基、SO2NH(C1-C4烷基)或SO2N(C1-C2烷基)(C1-C4烷基);
X选自O、S、NCH3、NN(CH3)2、NCN或NOCH3;
R7、R8选自不同取代基时所连接的碳原子为不对称碳原子,其构型为R或S;
或,式(I)所示化合物、式(I)所示化合物的旋光异构体的可农用盐或衍生物。
本发明再进一步较为优选的化合物为:通式(I)中
R1、R2分别选自甲基或乙基;
R3、R4分别选自氢、氟、氯或甲基;
R5选自氢;
R6选自氢;
R7选自氢、氰基、甲基、乙基、正丙基、正丁基、异丙基、异丁基、叔丁基、CH2CO2R9、CH2CH2CO2R9、CO2R9、CH2OR10或CONR11R12;
R8选自氢、甲基、乙基、三氟甲基、二氟甲基、正丙基、正丁基、异丙基、叔丁基、苯基或被1-4个独立选自以下基团取代的苯基:卤素、CN、NO2或C1-C4烷基;
R9选自氢、甲基、乙基、正丙基、正丁基、异丙基、异丁基、叔丁基、三氟乙基、烯丙基、炔丙基、甲氧基乙基、乙氧基乙基、甲基羰基氧基乙基或四氢呋喃亚甲基;
R10选自氢、C1-C4烷基羰基、C1-C4卤代烷基羰基、环丙甲酰基、C1-C4烷基磺酰基或C1-C4卤代烷基磺酰基;
R11选自氢、C1-C4烷基或C1-C4卤代烷基;
R12选自氢、C1-C4烷基、C1-C4烷氧基羰基C1-C4烷基、SO2NH(C1-C4烷基)或SO2N(C1-C2烷基)(C1-C4烷基);
X选自O或S;
R7、R8选自不同取代基时所连接的碳原子为不对称碳原子,其构型为R或S;
或,式(I)所示化合物、式(I)所示化合物的旋光异构体的可农用盐或衍生物。
本发明最优选的化合物为:通式(I)中
R1、R2分别选自甲基;
R3、R4分别选自氢、氟或氯;
R5选自氢;
R6选自氢;
R7选自氢、氰基、甲基、乙基、正丙基、正丁基、异丙基、异丁基、叔丁基、CH2CO2CH3、CH2CO2C2H5、CH2CH2CO2CH3、CH2CH2CO2C2H5、CO2R9或CH2OR10;
R8选自氢、甲基、乙基或三氟甲基;
R9选自氢、甲基、乙基、正丙基、正丁基、异丙基、异丁基、叔丁基、三氟乙基、烯丙基、炔丙基、甲氧基乙基、乙氧基乙基、甲基羰基氧基乙基或四氢呋喃亚甲基;
R10选自氢、C1-C4烷基羰基、C1-C4卤代烷基羰基、环丙甲酰基、C1-C4烷基磺酰基或C1-C4卤代烷基磺酰基。
X选自O或S;
R7、R8选自不同时所连接的碳原子为不对称碳原子,其构型为R或者S;
或,式(I)所示化合物、式(I)所示化合物的旋光异构体的可农用盐或衍生物。
上面给出的通式(I)化合物的定义中,汇集所用术语一般定义如下:
卤素:指氟、氯、溴或碘。烷基:直链或支链烷基,例如甲基、乙基、丙基、异丙基、正丁基或叔丁基。环烷基:取代或未取代的环状烷基,例如环丙基、环戊基或环己基。取代基如甲基、卤素等。卤代烷基: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原子所取代,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。烷氧基:直链或支链烷基,经氧原子键连接到结构上。卤代烷氧基: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原子所取代。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。烷硫基:直链或支链烷基,经硫原子键连接到结构上。卤代烷硫基:直链或支链烷硫基,在这些烷基上的氢原子可部分或全部被卤原子所取代。例如,氯甲硫基、二氯甲硫基、三氯甲硫基、氟甲硫基、二氟甲硫基、三氟甲硫基、氯氟甲硫基等。烯基:直链或支链烯类,例如乙烯基、1-丙烯基、2-丙烯基和不同的丁烯基、戊烯基和己烯基异构体。烯基还包括多烯类,如1,2-丙二烯基和2,4-己二烯基。烷基磺酰基:直链或支链烷基经磺酰基(-SO2-)连接到结构上,如甲基磺酰基。卤代烷基磺酰基:直链或支链烷基磺酰基,其烷基上的氢原子可部分或全部被卤原子所取代。烷基亚磺酰基:直链或支链烷基经磺酰基(-SO-)连接到结构上,如甲基亚磺酰基。卤代烷基磺酰基:直链或支链烷基亚磺酰基,其烷基上的氢原子可部分或全部被卤原子所取代。烷氧基羰基:烷氧基经羰基连接到结构上,如CH3OCO-或CH3CH2OCO-。烷氧基烷基:烷基-O-烷基-,如CH3OCH2-。烷羰基氧基烷氧基羰基:烷基-CO-O-烷基-OCO-,如CH3COOCH2OCO-、CH3COOCH2CH2OCO-或C2H5COOCH2CH2OCO-等。烷基羰基:烷基经羰基连接到结构上,如CH3CO-或CH3CH2CO-等。卤代烷基羰基:卤代烷基经羰基连接到结构上,如CF3CO-或CF2HCO-等。环烷基羰基:环烷基经羰基连接到结构上,如环丙甲酰基或环己基甲酰基等。卤代环烷基羰基:卤代环烷基经羰基连接到结构上,如1-氯环丙甲酰基等。烷基氨基磺酰基:烷基-NH-SO2-,如CH3NHSO2-或C2H5NHSO2-等。二烷基氨基磺酰基:二烷基-N-SO2-,如(CH3)2NSO2-或(C2H5)2NSO2-等。烷基氨基羰基:烷基-NH-CO-,如CH3NHCO-或C2H5NHCO-等。二烷基氨基羰基:二烷基-N-CO-,如(CH3)2NCO-或(C2H5)2NCO-等。二烷基氨基硫代羰基:二烷基-N-CS-,如(CH3)2NCS-或(C2H5)2NCS-等。烷硫基烷基羰基:烷基-S-烷基-CO,如CH3SCH2CO或CH3SCH2CH2CO等。SO2NH(C1-C4烷基):-SO2NHCH3或-SO2NHC2H5等。SO2N(C1-C2烷基)(C1-C4烷基):-SO2N(CH3)2或-SO2N(CH3)[CH(CH3)2]等。
一种所述的通式(I)化合物在用于防治杂草的应用。
一种除草制剂,制剂以所述的通式(I)化合物作为有效活性成分,与农业上可接受的载体和至少一种助剂混合;有效成分占制剂重量的1~99%。
一种所述除草制剂的应用,所述除草剂在防除农作物耕地、园林地或非耕地中的一年生及多年生杂草、抗性或耐性杂草的应用。
本发明还提供了一种除草组合物,组合物为活性成分A与活性成分B和/或活性成分C;其中,活性成分A为至少一种以权利要求1所述的通式(I)化合物、具有羧基的式(I)化合物的农用盐或其衍生物;活性成分B为至少一种除草剂化合物、其盐或其衍生物;活性成分C为至少一种安全剂化合物、其盐或其衍生物;活性成分A和活性成分B质量份数比为1:100-100:1;活性成分A和活性成分C质量份数比为1:100-100:1。
活性成分B)为至少一种除草剂B(b1)-b15)类除草剂):
b1)类脂生物合成抑制剂;
b2)乙酰乳酸合成酶抑制剂(ALS抑制剂);
b3)光合成抑制剂;
b4)原卟啉原氧化酶抑制剂(PPO抑制剂);
b5)色素合成抑制剂;
b6)5-烯醇丙酮莽草酸-3-磷酸合成酶抑制剂(EPSP抑制剂);
b7)谷氨酰胺合成酶抑制剂(GST抑制剂);
b8)7,8-二氢蝶酸合成酶抑制剂(DHP抑制剂);
b9)有丝分裂抑制剂;
b10)极长链脂肪酸合成抑制剂(VLCFA抑制剂);
b11)纤维素生物合成抑制剂;
b12)氧化磷酸化解偶联剂除草剂;
b13)激素合成类除草剂;
b14)激素传导抑制剂;以及
b15)选自由如下组成的组的其他除草剂:溴丁酰草胺(bromobutide)、氯甲丹(chlorflurenol)、氯甲丹(chlorflurenol-methyl)、环庚草醚(cinmethylin)、苄草隆(cumyluron)、茅草枯(dalapon)、棉隆(dazomet)、野燕枯(difenzoquat)、野燕枯硫酸盐(difenzoquat-metilsulfate)、噻节因(dimethipin)、甲胂钠(DSMA)、香草隆(dymron)、敌草腈(endothal)及其盐、乙苯酰草(etobenzanid)、氟燕灵(flamprop)、氟燕灵(flampropisopropyl)、甲氟燕灵(flamprop-methyl)、强氟燕灵(flamprop-M-isopropyl)、麦草伏(flamprop-M-methyl)、抑草丁酸(flurenol)、抑草丁(flurenol-butyl)、调嘧醇(flurprimidol)、调节膦(fosamine)、调节膦铵盐(fosamine-ammonium)、茚草酮(indanofan)、茚嗪氟草胺(indaziflam)、抑芽丹(maleic hydrazide)、氟草磺(mefluidide)、威百亩(metam)、叠氮甲烷(methyl azide)、溴甲烷(methyl bromide)、苯丙隆(methyl-dymron)、碘甲烷(methyl iodide)、甲胂一钠(MSMA)、油酸(oleic acid)、氯嗪草(oxaziclomefone)、壬酸(pelargonicacid)、稗草畏(pyributicarb)、灭藻醌(quinoclamine)、苯氧丙胺津(triaziflam)、灭草环(tridiphane)、methiozolin和tetflupyrolimet;
包括其可农用盐或衍生物。
活性成分C为安全剂,可选自(喹啉-8-氧基)乙酸类、1-苯基-5-卤代烷基-1H-1,2,4-三唑-3-甲酸、1-苯基-4,5-二氢-5-烷基-1H-吡唑-3,5-二甲酸、4,5-二氢-5,5-二芳基-3-异唑甲酸、二氯乙酰胺类、α-肟基苯基乙腈、苯乙酮肟类、4,6-二卤代-2-苯基嘧啶类、N-[[4-(氨基羰基)苯基]磺酰基]-2-苯甲酰胺类、1,8-萘二甲酸酐、2-卤代-4-卤代烷基-5-噻唑羧酸、硫代磷酸酯类和N-烷基-O-苯基氨基甲酸酯类及其可农用盐和其可农用衍生物如酰胺、酯和硫酯,条件是它们具有酸基。包括其盐或衍生物。
本发明活性成分A的部分化合物可以用表1-6中列出的具体化合物来说明,但本发明并不仅限于这些化合物。
表1中的化合物R1=CH3,R2=CH3,R5、R6=H,X=S,其他基团如表1所示。
表1
表2:R1=CH3,R2=CH3,R5、R6=H,X=S,R7、R8所连接碳原子为不对称碳原子,其构型为R,其他基团如表2所示。
表2
表3:R1=CH3,R2=CH3,R5、R6=H,X=S,R7、R8所连接碳原子为不对称碳原子,其构型为S,其他基团R3、R4、R7或R8取代基与表2中所列一致,相应的组合物编号为3-1~3-77。
表4:R1=CH3,R2=CH3,R5、R6=H,X=O,R7、R8所连接碳原子为不对称碳原子,其构型为消旋体,其他基团R3、R4、R7或R8取代基与表1中所列一致,相应的组合物编号为4-1~4-351。
表5:R1=CH3,R2=CH3,R5、R6=H,X=O,R7、R8所连接碳原子为不对称碳原子,其构型为R,其他基团R3、R4、R7或R8取代基与表2中所列一致,相应的组合物编号为5-1~5-77。
表6:R1=CH3,R2=CH3,R5、R6=H,X=O,R7、R8所连接碳原子为不对称碳原子,其构型为S,其他基团R3、R4、R7或R8取代基与表2中所列一致,相应的组合物编号为6-1~6-77。
所述除草剂B可选自一种类脂生物合成抑制剂(除草剂b1)。这类化合物为抑制类脂生物合成的化合物。可以通过抑制乙酰CoA羧化酶(下文称为ACC除草剂)或通过不同作用模式(下文称为非ACC除草剂)而进行类脂生物合成的抑制。ACC除草剂属于HRAC分类体系的A类,而非ACC除草剂属于HRAC分类的N类。
所述除草剂B可选自一种ALS抑制剂(除草剂b2)。这类化合物的除草活性基于乙酰乳酸合成酶的抑制并因此基于支链氨基酸生物合成的抑制。这些抑制剂属于HRAC分类体系的B类。
所述除草剂B可选自一种光合成抑制剂(除草剂b3)。这类化合物的除草活性基于植物中光合系统II的抑制(所谓的PSII抑制剂,HRAC分类的C1、C2和C3类)或基于使植物中光合系统I中的电子转移转向(所谓的PSI抑制剂,HRAC分类的D类)并因此基于光合成的抑制。其中优选PSII抑制剂。
所述除草剂B可选自一种原卟啉原氧化酶抑制剂(除草剂b4)。这类化合物的除草活性基于原卟啉原氧化酶的抑制。这些抑制剂属于HRAC分类体系的E类。
所述除草剂B可选自一种色素合成抑制剂除草剂(除草剂b5)。这类化合物的除草活性基于类胡萝卜素生物合成的抑制。这些包括通过抑制八氢番茄红素脱氢酶而抑制类胡萝卜素生物合成的化合物(所谓的PDS抑制剂,HRAC分类的F1类),抑制4-羟基苯基丙酮酸双氧化酶的化合物(HPPD抑制剂,HRAC分类的F2类),抑制DOX合成酶的化合物(HRAC分类的F4类)和通过未知作用方式抑制类胡萝卜素生物合成的化合物(色素合成抑制剂—未知目标,HRAC分类的F3类)。
所述除草剂B可选自一种EPSP合成酶抑制剂(除草剂b6)。这类化合物的除草活性基于5-烯醇丙酮莽草酸-3-磷酸合成酶的抑制并且因此基于植物中氨基酸生物合成的抑制。这些抑制剂属于HRAC分类体系的G类。
所述除草剂B可选自一种谷氨酰胺合成酶抑制剂(除草剂b7)。这类化合物的除草活性基于谷氨酰胺合成酶的抑制并且因此基于植物中氨基酸生物合成的抑制。这些抑制剂属于HRAC分类体系的H类。
所述除草剂B可选自一种DHP合成酶抑制剂(除草剂b8)。这类化合物的除草活性基于7,8-二氢蝶酸合成酶的抑制。这些抑制剂属于HRAC分类体系的I类。
所述除草剂B可选自一种有丝分裂抑制剂(除草剂b9)。这些化合物的除草活性基于微管形成或组织化的扰乱或抑制并且因此基于有丝分裂的抑制。这些抑制剂属于HRAC分类体系的K1和K2类。其中优选K1类化合物,尤其是二硝基苯胺类。
所述除草剂B可选自一种VLCFA抑制剂(除草剂b10)。这类化合物的除草活性基于非常长链脂肪酸合成的抑制并且因此基于植物中细胞分裂的扰乱或抑制。这些抑制剂属于HRAC分类体系的K3类。
所述除草剂B可选自一种纤维素生物合成抑制剂(除草剂b11)。这类化合物的除草活性基于纤维素生物合成的抑制并且因此基于植物中细胞壁合成的抑制。这些抑制剂属于HRAC分类体系的L类。
所述除草剂B可选自一种氧化膦酸化解偶联剂除草剂(除草剂b12)。这类化合物的除草活性基于细胞膜的干扰。这些抑制剂属于HRAC分类体系的M类。
所述除草剂B可选自一种激素合成类除草剂(除草剂b13)。这类包括模拟植物生长素,即植物激素并影响植物生长的化合物。这些化合物属于HRAC分类体系的O类。
所述除草剂B可选自一种激素传导抑制剂(除草剂b14)。这类化合物的除草活性基于植物中植物生长素输送的抑制。这些化合物属于HRAC分类体系的P类。
所述除草剂B可选自其他未知作用机理(除草剂b15)。该类化合物属于HRAC分类体系的Z类。对于活性物质的给定作用机理和分类,例如参见“HRAC,根据作用模式的除草剂分类”,http://www.plantprotection.org/hrac/MOA.html)。
具体上述记载除草剂b1-b15具体为:
b1)选自如下的类脂生物合成抑制剂:ACC除草剂如枯杀达(alloxydim)、枯杀达钠(alloxydim-sodium)、丁氧环酮(butroxydim)、烯草酮(clethodim)、炔草酯(clodinafop)、炔草酯(clodinafop-propargyl)、噻草酮(cycloxydim)、氰氟草酸(cyhalofop)、氰氟草酯(cyhalofop-butyl)、禾草灵(diclofop)、禾草灵甲酯(diclofop-methyl)、恶唑禾草灵酸(fenoxaprop)、恶唑禾草灵(fenoxaprop-ethyl)、精恶唑禾草灵酸(fenoxaprop-P)、精恶唑禾草灵(fenoxaprop-P-ethyl)、吡氟禾草灵酸(fluazifop)、吡氟禾草灵(fluazifop-butyl)、精吡氟禾草灵酸(fluazifop-P)、精吡氟禾草灵(fluazifop-P-butyl)、吡氟氯禾灵酸(haloxyfop)、吡氟氯禾灵(haloxyfop-methyl)、精吡氟氯禾灵酸(haloxyfop-P)、精吡氟氯禾灵(haloxyfop-P-methyl)、恶唑酰草胺(metamifop)、唑啉草酯(pinoxaden)、环苯草酮(profoxydim)、喔草酯(propaquizafop)、喹禾灵酸(quizalofop)、喹禾灵(quizalofop-ethyl)、喹禾糠酯(quizalofop-tefuryl)、精喹禾灵酸(quizalofop-P)、精喹禾灵(quizalofop-P-ethyl)、精喹禾糠酯(quizalofop-P-tefuryl)、烯禾啶(sethoxydim)、吡喃草酮(tepraloxydim)、肟草酮(tralkoxydim);以及非ACC除草剂如呋草黄(benfuresate)、苏达灭(butylate)、草灭特(cycloate)、茅草枯(dalapon)、哌草丹(dimepiperate)、扑草灭(EPTC)、禾草畏(esprocarb)、乙呋草黄(ethofumesate)、四氟丙酸(flupropanate)、禾大壮(molinate)、坪草丹(orbencarb)、克草猛(pebulate)、苄草丹(prosulfocarb)、TCA、杀草丹(thiobencarb)、丁草威(tiocarbazil)、野麦畏(triallate)和灭草猛(vernolate);
b2)选自如下的ALS抑制剂:磺酰脲类,如磺氨磺隆(amidosulfuron)、四唑磺隆(azimsulfuron)、苄嘧磺隆(bensulfuron)、苄嘧磺隆(bensulfuron-methyl)、氯嘧磺隆酸(chlorimuron)、氯嘧磺隆(chlorimuron-ethyl)、氯磺隆(chlorsulfuron)、醚磺隆(cinosulfuron)、环丙磺隆(cyclosulfamuron)、胺苯磺隆酸酸(ethametsulfuron)、胺苯磺隆(ethametsulfuron-methyl)、乙氧嘧磺隆(ethoxysulfuron)、啶嘧磺隆(flazasulfuron)、氟吡磺隆(flucetosulfuron)、氟啶嘧磺隆酸(flupyrsulfuron)、氟啶嘧磺隆(flupyrsulfuron-methyl-sodium)、甲酰氨磺隆(foramsulfuron)、吡氯磺隆(halosulfuron)、吡氯磺隆(halosulfuron-methyl)、咪唑磺隆(imazosulfuron)、碘磺隆(iodosulfuron)、碘甲磺隆钠(iodosulfuron-methyl-sodium)、iofensulfuron、iofensulfuron-sodium、甲基二磺隆(mesosulfuron)、metazosulfuron、甲磺隆酸(metsulfuron)、甲磺隆(metsulfuron-methyl)、烟嘧磺隆(nicosulfuron)、嘧苯胺磺隆(orthosulfamuron)、环丙氧磺隆(oxasulfuron)、氟嘧磺隆酸(primisulfuron)、氟嘧磺隆(primisulfuron-methyl)、propyrisulfuron、氟丙磺隆(prosulfuron)、吡嘧磺隆酸(pyrazosulfuron)、吡嘧磺隆(pyrazosulfuron-ethyl)、玉嘧磺隆(rimsulfuron)、嘧磺隆酸(sulfometuron)、嘧磺隆(sulfometuron-methyl)、磺酰磺隆(sulfosulfuron)、噻磺隆酸(thifensulfuron)、噻磺隆(thifensulfuron-methyl)、醚苯磺隆(triasulfuron)、苯磺隆酸(tribenuron)、苯磺隆(tribenuron-methyl)、三氟啶磺隆(trifloxysulfuron)、氟胺磺隆(triflusulfuron)、氟胺磺隆(triflusulfuron-methyl)、单嘧磺隆(monosulfuron)、单嘧磺酯(monosulfuron-ester)和三氟甲磺隆(tritosulfuron),咪唑啉酮类如咪草酯(imazamethabenz)、咪草酯(imazamethabenz-methyl)、咪草啶酸(imazamox)、甲基咪草烟(imazapic)、灭草烟(imazapyr)、灭草喹(imazaquin)和咪草烟(imazethapyr),三唑并嘧啶类除草剂和磺酰苯胺类如唑嘧磺胺酸(cloransulam)、唑嘧磺胺盐(cloransulam-methyl)、唑嘧磺胺(diclosulam)、唑嘧磺草胺(flumetsulam)、双氟磺草胺(florasulam)、唑草磺胺(metosulam)、五氟磺草胺(penoxsulam)、pyrimisulfan和啶磺草胺(pyroxsulam),嘧啶基苯甲酸酯类如双嘧苯甲酸(bispyribac)、双嘧苯甲酸钠(bispyribac-sodium)、嘧啶肟草醚(pyribenzoxim)、环酯草醚(pyriftalid)、肟啶草(pyriminobac)、肟啶草(pyriminobacmethyl)、嘧硫苯甲酸(pyrithiobac)、嘧硫苯甲酸钠(pyrithiobac-sodium),磺酰氨基羰基三唑啉酮类除草剂如氟酮磺隆(flucarbazone)、氟酮磺隆钠(flucarbazonesodium)、丙苯磺隆(propoxycarbazone)、丙苯磺隆钠盐(propoxycarbazone-sodium)、thiencarbazone和thiencarbazone-methyl,以及氟酮磺草胺(triafamone);
b3)选自如下的光合成抑制剂:胺唑草酮(amicarbazone),三嗪类除草剂,包括氯代三嗪类、三嗪酮类、三嗪二酮类、甲硫基三嗪类和哒嗪酮类,如莠灭净(ametryn)、莠去津(atrazine)、杀草敏(chloridazone)、草净津(cyanazine)、敌草净(desmetryn)、戊草津(dimethametryn)、六嗪同(hexazinone)、赛克津(metribuzin)、扑灭通(prometon)、扑草净(prometryn)、扑灭津(propazine)、西玛津(simazine)、西草净(simetryn)、甲氧去草净(terbumeton)、特丁津(terbuthylazin)、去草净(terbutryn)和草达津(trietazin);芳基脲类如氯溴隆(chlorobromuron)、苯嘧磺草胺(saflufenacil)、枯草隆(chloroxuron)、丁隆(dimefuron)、敌草隆(diuron)、伏草隆(fluometuron)、异丙隆(isoproturon)、异恶隆(isouron)、利谷隆(linuron)、苯嗪草(metamitron)、噻唑隆(methabenzthiazuron)、色满隆(metobenzuron)、甲氧隆(metoxuron)、绿谷隆(monolinuron)、草不隆(neburon)、环草隆(siduron)、丁唑隆(tebuthiuron)和赛二唑素(thidiazuron),苯基氨基甲酸酯类如异苯敌草(desmedipham)、卡草灵(karbutilat)、苯敌草(phenmedipham)、乙苯敌草(phenmedipham-ethyl),腈类除草剂如杀草全(bromofenoxim)、溴苯腈(bromoxynil)及其盐和酯、碘苯腈(ioxynil)及其盐和酯、cyclopyranil,尿嘧啶类如除草定(bromacil)、环草定(lenacil)和特草定(terbacil),以及苯达松(bentazone)、苯达松钠盐(bentazone-sodium),哒草特(pyridate)、pyridafol、蔬草灭(pentanochlor)和敌稗(propanil)以及光合系统I抑制剂如敌草快(diquat)、敌草快二溴盐(diquat-dibromide)、百草枯(paraquat)、百草枯二氯盐(paraquat-dichloride)和百草枯二甲硫酸盐(paraquat-dimetilsulfate);
b4)选自如下的原卟啉原氧化酶抑制剂:三氟羧草醚(acifluorfen)、三氟羧草醚钠盐(acifluorfen-sodium)、唑啶草酮(azafenidin)、bencarbazone、双苯嘧草酮(benzfendizone)、治草醚(bifenox)、氟丙嘧草酯(butafenacil)、唑草酮酸(carfentrazone)、唑草酮(carfentrazone-ethyl)、氯硝醚(chlomethoxyfen)、chlorphthalim、吲哚酮草酯(cinidon-ethyl)、异丙吡草酯(fluazolate)、氟哒嗪草酯(flufenpyr)、氟哒嗪草酯(flufenpyr-ethyl)、酰亚胺苯氧乙酸(flumiclorac)、酰亚胺苯氧乙酸戊酯(flumiclorac-pentyl)、氟嗪酮(flumioxazin)、乙羧氟草醚(fluoroglycofen)、乙羧氟草醚乙酯(fluoroglycofen-ethyl)、嗪草酸(fluthiacet)、嗪草酸甲酯(fluthiacet-methyl)、氟磺胺草醚(fomesafen)、氟硝磺酰胺(halosafen)、乳氟禾草灵(lactofen)、丙炔恶草酮(oxadiargyl)、恶草灵(oxadiazon)、乙氧氟草醚(oxyfluorfen)、戊唑草(pentoxazone)、氟唑草胺(profluazol)、双唑草腈(pyraclonil)、氟唑草酸(pyraflufen)、氟唑草酯(pyraflufen-ethyl)、苯嘧磺草胺(saflufenacil)、磺胺草唑(sulfentrazone)、噻二唑胺(thidiazimin)、tiafenacil和trifludimoxazin;
b5)选自如下的色素合成抑制剂除草剂:PDS抑制剂:氟丁酰草胺(beflubutamid)、精氟丁酰草胺(beflubutamid-M)、吡氟草胺(diflufenican)、氟草酮(fluridone)、氟咯草酮(flurochloridone)、呋草酮(flurtamone)、达草灭(norflurazon)、氟吡酰草胺(picolinafen),HPPD抑制剂:双环磺草酮(benzobicyclon)、吡草酮(benzofenap)、氟吡草酮(bicyclopyrone)、异恶草松(clomazone)、fenquintrione、bixlozone(CAS 81777-95-9)、异恶唑草酮(isoxaflutole)、硝磺草酮(mesotrione)、oxotrione(CAS 1486617-21-3)、pyrasulfotole、吡唑特(pyrazolynate)、苄草唑(pyrazoxyfen)、磺草酮(sulcotrione)、tefuryltrione、tembotrione、tolpyralate、lancotrione、苯唑草酮(topramezone)、喹草酮、甲基喹草酮、吡唑喹草酯、二氯喹啉草酮、环吡氟草酮、双唑草酮、三唑磺草酮和苯唑氟草酮,其他还有:苯草醚(aclonifen)、杀草强(amitrole)和伏草隆(flumeturon);
b6)选自如下的EPSP合成酶抑制剂:草甘膦(glyphosate)、草甘膦异丙胺盐(glyphosate-isopropylammonium)、草甘膦钾盐(glyhosate potassium salt)和草硫膦(glyphosate-trimesium);
b7)选自如下的谷氨酰胺合成酶抑制剂:双丙氨酰膦(bilanaphos(bialaphos))、双丙氨酰膦(bilanaphos-sodium)、草铵膦(glufosinate)、精草铵膦(glufosinate-P)和草铵膦铵盐(glufosinate-ammonium);
b8)选自如下的DHP合成酶抑制剂:磺草灵(asulam);
b9)选自如下的有丝分裂抑制剂:K1组化合物:二硝基苯胺类如氟草胺(benfluralin)、地乐胺(butralin)、敌乐胺(dinitramine)、丁氟消草(ethalfluralin)、氟消草(fluchloralin)、氨磺乐灵(oryzalin)、二甲戊灵(pendimethalin)、氨基丙氟灵(prodiamine)和氟乐灵(trifluralin),氨基磷酸酯类如胺草磷(amiprophos)、甲基胺草磷(amiprophos-methyl)和草胺磷(butamiphos),苯甲酸类除草剂如敌草索酸(chlorthal)、敌草索(chlorthal-dimethyl),吡啶类如氟硫草定(dithiopyr)和噻氟啶草(thiazopyr),苯甲酰胺类如拿草特(propyzamide)和丙戊草胺(tebutam),K2组化合物:长杀草(carbetamide)、氯苯胺灵(chlorpropham)、氟燕灵(flamprop)、氟燕灵(flampropisopropyl)、甲氟燕灵(flamprop-methyl)、强氟燕灵(flamprop-M-isopropyl)、麦草伏(flamprop-M-methyl)和苯胺灵(propham);
b10)选自如下的VLCFA抑制剂:氯乙酰胺类如乙草胺(acetochlor)、甲草胺(alachlor)、amidochlor、丁草胺(butachlor)、克草胺(dimethachlor)、噻吩草胺(dimethenamid)、精噻吩草胺(dimethenamid-P)、吡草胺(metazachlor)、异丙甲草胺(metolachlor)、S-异丙甲草胺(metolachlor-S)、烯草胺(pethoxamid)、丙草胺(pretilachlor)、扑草胺(propachlor)、异丙草胺(propisochlor)和噻醚草胺(thenylchlor),羟基乙酰苯胺类(oxyacetanilide)如氟噻草胺(flufenacet)和苯噻草胺(mefenacet),乙酰苯胺类如草乃敌(diphenamid)、萘丙胺(naproanilide)、草萘胺(napropamide)和精草萘胺(napropamide-M),四唑啉酮类如四唑酰草胺(fentrazamide)以及其他除草剂如莎稗磷(anilofos)、唑草胺(cafenstrole)、fenoxasulfone、ipfencarbazone、哌草磷(piperophos)和罗克杀草砜(pyroxasulfone);
b11)选自如下的纤维素生物合成抑制剂:草克乐(chlorthiamid)、敌草腈(dichlobenil)、胺草唑(flupoxam)、茚嗪氟草胺(indaziflam)、异恶草胺(isoxaben)、苯氧丙胺津(triaziflam);
b12)选自如下的氧化膦酸化解偶联剂除草剂:地乐酚(dinoseb)、地乐消酚(dinoterb)以及二硝甲酚(DNOC)及其盐;
b13)选自如下的激素合成类除草剂:2,4-D及其盐和酯,如氯酰草膦(clacyfos),2,4-D B及其盐和酯,环丙嘧啶酸(aminocyclopyrachlor)及其盐和酯,氨草啶(aminopyralid)及其盐如氨草啶二甲铵盐(aminopyralid-dimethylammonium)、氨草啶异丙醇铵盐(aminopyralid-tris(2-hydroxy-propyl)ammonium)及其酯、草除灵(benazolin)、草除灵(benazolin-ethyl)、草灭平(chloramben)及其盐和酯、稗草胺(clomeprop)、二氯皮考啉酸(clopyralid)及其盐和酯、麦草畏(dicamba)及其盐和酯、2,4-滴丙酸(dichlorprop)及其盐和酯、高2,4-滴丙酸(dichlorprop-P)及其盐和酯、flopyrauxifen、氟草烟(fluroxypyr)、氟草烟丁氧丙酯(fluroxypyr-butometyl)、氟氯胺啶(fluroxypyr-meptyl)、氟氯吡啶酸(halauxifen)及其盐和酯(CAS 943832-60-8)、MCPA及其盐和酯、2甲4氯乙硫酯(MCPA-thioethyl)、MCPB及其盐和酯、2甲4氯丙酸(mecoprop)及其盐和酯、高2甲4氯丙酸(mecoprop-P)及其盐和酯、毒莠定(picloram)及其盐和酯、二氯喹啉酸(quinclorac)、喹草酸(quinmerac)、TBA(2,3,6)及其盐和酯、绿草定(triclopyr)及其盐和酯、氯氟吡啶酸(florpyrauxifen)和氯氟吡啶酯(florpyrauxifen-benzyl)(CAS1390661-72-9);
b14)选自如下的激素传导抑制剂:二氟吡隆(diflufenzopyr)、二氟吡隆钠(diflufenzopyr-sodium)、抑草生(naptalam)和抑草生(naptalam-sodium);
b15)选自如下的其他除草剂:溴丁酰草胺(bromobutide)、氯甲丹(chlorflurenol)、氯甲丹(chlorflurenol-methyl)、环庚草醚(cinmethylin)、苄草隆(cumyluron)、cyclopyrimorate(CAS 499223-49-3)及其盐和酯、茅草枯(dalapon)、棉隆(dazomet)、苯敌快(difenzoquat)、苯敌快(difenzoquat-metilsulfate)、噻节因(dimethipin)、甲胂钠(DSMA)、香草隆(dymron)、敌草腈(endothal)及其盐、乙苯酰草(etobenzanid)、抑草丁(flurenol)、抑草丁(flurenol-butyl)、调嘧醇(flurprimidol)、膦铵素(fosamine)、膦铵素(fosamine-ammonium)、茚草酮(indanofan)、抑芽丹(maleichydrazide)、氟草磺(mefluidide)、威百亩(metam)、叠氮甲烷(methyl azide)、溴甲烷(methyl bromide)、苯丙隆(methyl-dymron)、碘甲烷(methyl iodide)、甲胂一钠(MSMA)、油酸(oleic acid)、氯嗪草(oxaziclomefone)、壬酸(pelargonic acid)、稗草畏(pyributicarb)、灭藻醌(quinoclamine)和灭草环(tridiphane)、methiozolin(CAS403640-27-7)和tetflupyrolimet。
进一步的说组合物中优选除草剂B为:
b1)选自如下的类脂生物合成抑制剂:烯草酮(clethodim)、炔草酯(clodinafop-propargyl)、噻草酮(cycloxydim)、氰氟草酯(cyhalofop-butyl)、禾草灵(diclofop-methyl)、精恶唑禾草灵(fenoxaprop-P-ethyl)、精吡氟禾草灵(fluazifop-P-butyl)、精吡氟氯禾灵(haloxyfop-P-methyl)、恶唑酰草胺(metamifop)、唑啉草酯(pinoxaden)、环苯草酮(profoxydim)、喔草酯(propaquizafop)、精喹禾灵(quizalofop-P-ethyl)、精喹禾糠酯(quizalofop-P-tefuryl)、烯禾啶(sethoxydim)、吡喃草酮(tepraloxydim)、肟草酮(tralkoxydim)、呋草黄(benfuresate)、哌草丹(dimepiperate)、扑草灭(EPTC)、禾草畏(esprocarb)、乙呋草黄(ethofumesate)、禾大壮(molinate)、坪草丹(orbencarb)、苄草丹(prosulfocarb)、杀草丹(thiobencarb)和野麦畏(triallate);
b2)选自如下的ALS抑制剂:磺氨磺隆(amidosulfuron)、四唑磺隆(azimsulfuron)、苄嘧磺隆(bensulfuron-methyl)、双嘧苯甲酸钠(bispyribac-sodium)、氯嘧磺隆(chlorimuron-ethyl)、氯磺隆(chlorsulfuron)、唑嘧磺胺盐(cloransulammethyl)、环丙磺隆(cyclosulfamuron)、唑嘧磺胺(diclosulam)、胺苯磺隆(ethametsulfuron-methyl)、乙氧嘧磺隆(ethoxysulfuron)、啶嘧磺隆(flazasulfuron)、双氟磺草胺(florasulam)、氟酮磺隆钠(flucarbazone-sodium)、氟吡磺隆(flucetosulfuron)、唑嘧磺草胺(flumetsulam)、氟定磺隆(flupyrsulfuron-methylsodium)、甲酰氨磺隆(foramsulfuron)、吡氯磺隆(halosulfuron-methyl)、咪草酯(imazamethabenz-methyl)、咪草啶酸(imazamox)、甲基咪草烟(imazapic)、灭草烟(imazapyr)、灭草喹(imazaquin)、咪草烟(imazethapyr)、咪唑磺隆(imazosulfuron)、碘磺隆(iodosulfuron)、碘甲磺隆钠(iodosulfuron-methyl-sodium)、iofensulfuron、iofensulfuron-sodium、甲基二磺隆(mesosulfuron)、metazosulfuron、唑草磺胺(metosulam)、甲磺隆(metsulfuron-methyl)、烟嘧磺隆(nicosulfuron)、嘧苯胺磺隆(orthosulfamuron)、环丙氧磺隆(oxasulfuron)、五氟磺草胺(penoxsulam)、氟嘧磺隆(primisulfuron-methyl)、丙苯磺隆(propoxycarbazon-sodium)、propyrisulfuron、氟丙磺隆(prosulfuron)、吡嘧磺隆(pyrazosulfuron-ethyl)、嘧啶肟草醚(pyribenzoxim)、pyrimisulfan、环酯草醚(pyriftalid)、肟啶草(pyriminobac-methyl)、嘧硫苯甲酸钠(pyrithiobac-sodium)、啶磺草胺(pyroxsulam)、玉嘧磺隆(rimsulfuron)、嘧磺隆(sulfometuron-methyl)、磺酰磺隆(sulfosulfuron)、thiencarbazone-methyl、噻磺隆(thifensulfuron-methyl)、醚苯磺隆(triasulfuron)、苯磺隆(tribenuron-methyl)、三氟啶磺隆(trifloxysulfuron)、氟胺磺隆(triflusulfuron-methyl)、单嘧磺隆(monosulfuron)、单嘧磺酯(monosulfuron-ester)、三氟甲磺隆(tritosulfuron)和氟酮磺草胺(triafamone);
b3)选自如下的光合成抑制剂:莠灭净(ametryn)、胺唑草酮(amicarbazone)、莠去津(atrazine)、苯达松(bentazone)、苯达松钠盐(bentazone-sodium)、溴苯腈(bromoxynil)及其盐和酯、杀草敏(chloridazone)、苯嘧磺草胺(saflufenacil)、草净津(cyanazine)、异苯敌草(desmedipham)、敌草快(diquat-dibromide)、敌草隆(diuron)、伏草隆(fluometuron)、六嗪同(hexazinone)、碘苯腈(ioxynil)及其盐和酯、cyclopyranil、异丙隆(isoproturon)、环草定(lenacil)、利谷隆(linuron)、苯嗪草(metamitron)、噻唑隆(methabenzthiazuron)、赛克津(metribuzin)、百草枯阳离子(paraquat)、百草枯(paraquat-dichloride)、苯敌草(phenmedipham)、敌稗(propanil)、哒草特(pyridate)、西玛津(simazine)、去草净(terbutryn)、特丁津(terbuthylazine)、赛二唑素(thidiazuron)
b4)选自如下的原卟啉原氧化酶抑制剂:三氟羧草醚(acifluorfen-sodium)、bencarbazone、双苯嘧草酮(benzfendizone)、氟丙嘧草酯(butafenacil)、唑草酮(carfentrazone-ethyl)、吲哚酮草酯(cinidon-ethyl)、氟哒嗪草酯(flufenpyr-ethyl)、酰亚胺苯氧乙酸戊酯(flumiclorac-pentyl)、氟嗪酮(flumioxazin)、乙羧氟草醚(fluoroglycofen-ethyl)、氟黄胺草醚(fomesafen)、乳氟禾草灵(lactofen)、丙炔恶草酮(oxadiargyl)、恶草灵(oxadiazon)、乙氧氟草醚(oxyfluorfen)、戊唑草(pentoxazone)、氟唑草酸(pyraflufen)、氟唑草酯(pyraflufen-ethyl)、苯嘧磺草胺(saflufenacil)、磺胺草唑(sulfentrazone)、tiafenacil、trifludimoxazin;
b5)选自如下的色素抑制剂除草剂:苯草醚(aclonifen)、杀草强(amitrole)、氟丁酰草胺(beflubutamid)、精氟丁酰草胺(beflubutamid-M)、双环磺草酮(benzobicyclon)、氟吡草酮(bicyclopyrone)、异恶草松(clomazone)、吡氟草胺(diflufenican)、fenquinotrione、伏草隆(flumeturon)、氟咯草酮(flurochloridone)、呋草酮(flurtamone)、异恶唑草酮(isoxaflutole)、硝磺草酮(mesotrione)、bixlozone、oxotrione(CAS1486617-21-3)、达草灭(norflurazon)、氟吡酰草胺(picolinafen)、pyrasulfotole、吡唑特(pyrazolynate)、磺草酮(sulcotrione)、苯唑草酮(topramezone)、tefuryltrione、tembotrione、tolpyralate、lancotrione、喹草酮、甲基喹草酮、吡唑喹草酯、二氯喹啉草酮、环吡氟草酮、双唑草酮、三唑磺草酮和苯唑氟草酮;
b6)选自如下的EPSP合成酶抑制剂:草甘膦(glyphosate)、草甘膦异丙胺盐(glyphosate-isopropylammonium)和草甘膦钾盐(glyhosate potassium salt);
b7)选自如下的谷氨酰胺合成酶抑制剂:草铵膦(glufosinate)、精草铵膦(glufosinate-P)和草铵膦铵盐(glufosinate-ammonium);
b8)选自如下的DHP合成酶抑制剂:磺草灵(asulam);
b9)选自如下的有丝分裂抑制剂:氟草胺(benfluralin)、氟硫草定(dithiopyr)、丁氟消草(ethalfluralin)、氟燕灵(flamprop)、氟燕灵(flamprop-isopropyl)、甲氟燕灵(flamprop-methyl)、强氟燕灵(flamprop-M-isopropyl)、麦草伏(flamprop-M-methyl)、氨磺乐灵(oryzalin)、二甲戊灵(pendimethalin)、噻氟啶草(thiazopyr)和氟乐灵(trifluralin);
b10)选自如下的VLCFA抑制剂:乙草胺(acetochlor)、甲草胺(alachlor)、amidochlor、莎稗磷(anilofos)、丁草胺(butachlor)、唑草胺(cafenstrole)、噻吩草胺(dimethenamid)、精噻吩草胺(dimethenamid-P)、四唑酰草胺(fentrazamide)、氟噻草胺(flufenacet)、苯噻草胺(mefenacet)、吡草胺(metazachlor)、异丙甲草胺(metolachlor)、S-异丙甲草胺(S-metolachlor)、萘丙胺(naproanilide)、草萘胺(napropamide)、精草萘胺(napropamide-M)、丙草胺(pretilachlor)、fenoxasulfone、ipfencarbazone、罗克杀草砜(pyroxasulfone)和噻醚草胺(thenylchlor)
b11)选自如下的纤维素生物合成抑制剂:敌草腈(dichlobenil)、胺草唑(flupoxam)、茚嗪氟草胺(indaziflam)、异恶草胺(isoxaben)、苯氧丙胺津(triaziflam);
b12)选自如下的氧化膦酸化解偶联剂除草剂:地乐酚(dinoseb)、地乐消酚(dinoterb)以及二硝甲酚(DNOC)及其盐;
b13)选自如下的激素合成类除草剂:2,4-D及其盐和酯,环丙嘧啶酸(aminocyclopyrachlor)及其盐和酯,氨草啶(aminopyralid)及其盐如氨草啶二甲铵盐(aminopyralid-dimethylammonium)、氨草啶异丙醇铵盐(aminopyralid-tris(2-hydroxypropyl)ammonium)和其酯,二氯皮考啉酸(clopyralid)及其盐和酯,麦草畏(dicamba)及其盐和酯,高2,4-滴丙酸(dichlorprop-P)及其盐和酯,flopyrauxifen,氟氯胺啶(fluroxypyr-meptyl),氟氯吡啶酸(halauxifen)及其盐和酯(CAS943832-60-8),MCPA及其盐和酯,MCPB及其盐和酯,高2甲4氯丙酸(mecoprop-P)及其盐和酯,毒莠定(picloram)及其盐和酯,二氯喹啉酸(quinclorac),喹草酸(quinmerac),绿草定(triclopyr)及其盐和酯,氯氟吡啶酸(florpyrauxifen),氯氟吡啶酯(florpyrauxifen-benzyl)(CAS 1390661-72-9);
b14)选自如下的激素传导抑制剂:二氟吡隆(diflufenzopyr)和二氟吡隆钠(diflufenzopyr-sodium);
b15)选自如下的其他除草剂:溴丁酰草胺(bromobutide)、环庚草醚(cinmethylin)、苄草隆(cumyluron)、cyclopyrimorate(CAS 499223-49-3)及其盐和酯、茅草枯(dalapon)、苯敌快(difenzoquat)、苯敌快(difenzoquat-metilsulfate)、甲胂钠(DSMA)、香草隆(dymron)(=daimuron)、茚草酮(indanofan)、威百亩(metam)、溴甲烷(methylbromide)、甲胂一钠(MSMA)、氯嗪草(oxaziclomefone)、稗草畏(pyributicarb)、灭草环(tridiphane)、methiozolin和tetflupyrolimet。
更一步的说组合物中优选除草剂B为:
b1)选自如下的类脂生物合成抑制剂:炔草酯(clodinafop-propargyl)、噻草酮(cycloxydim)、氰氟草酯(cyhalofop-butyl)、精恶唑禾草灵(fenoxaprop-P-ethyl)、精吡氟禾草灵(fluazifop-P-butyl)、精吡氟氯禾灵(haloxyfop-P-methyl)、唑啉草酯(pinoxaden)、环苯草酮(profoxydim)、精喹禾灵(quizalofop-P-ethyl)、烯禾啶(sethoxydim)、吡喃草酮(tepraloxydim)、肟草酮(tralkoxydim)、禾草畏(esprocarb)、苄草丹(prosulfocarb)、杀草丹(thiobencarb)和野麦畏(triallate);
b2)选自如下的ALS抑制剂:苄嘧磺隆(bensulfuron-methyl)、双嘧苯甲酸钠(bispyribac-sodium)、环丙磺隆(cyclosulfamuron)、唑嘧磺胺(diclosulam)、唑嘧磺草胺(flumetsulam)、氟定磺隆(flupyrsulfuron-methyl-sodium)、甲酰氨磺隆(foramsulfuron)、咪草啶酸(imazamox)、甲基咪草烟(imazapic)、灭草烟(imazapyr)、灭草喹(imazaquin)、咪草烟(imazethapyr)、啶咪磺隆(imazosulfuron)、碘磺隆(iodosulfuron)、碘甲磺隆钠(iodosulfuron-methyl-sodium)、iofensulfuron、iofensulfuron-sodium、甲基二磺隆(mesosulfuron)、metazosulfuron、烟嘧磺隆(nicosulfuron)、五氟磺草胺(penoxsulam)、丙苯磺隆(propoxycarbazon-sodium)、propyrisulfuron、吡嘧磺隆(pyrazosulfuron-ethyl)、啶磺草胺(pyroxsulam)、玉嘧磺隆(rimsulfuron)、磺酰磺隆(sulfosulfuron)、thiencarbazon-methyl、三氟甲磺隆(tritosulfuron)、单嘧磺隆(monosulfuron)、单嘧磺酯(monosulfuron-ester)和氟酮磺草胺(triafamone);
b3)选自如下的光合成抑制剂:莠灭净(ametryn)、莠去津(atrazine)、敌草隆(diuron)、伏草隆(fluometuron)、六嗪同(hexazinone)、异丙隆(isoproturon)、利谷隆(linuron)、赛克津(metribuzin)、百草枯阳离子(paraquat)、百草枯(paraquatdichloride)、敌稗(propanil)、去草净(terbutryn)、特丁津(terbuthylazine)和cyclopyranil;
b4)选自如下的原卟啉原氧化酶抑制剂:氟嗪酮(flumioxazin)、乙氧氟草醚(oxyfluorfen)、氟唑草酸(pyraflufen)、氟唑草酯(pyraflufen-ethyl)、苯嘧磺草胺(saflufenacil)、磺胺草唑(sulfentrazone)和trifludimoxazin;
b5)选自如下的色素抑制剂除草剂:双环磺草酮(benzobicyclon)、杀草强(amitrole)、氟吡草酮(bicyclopyrone)、异恶草松(clomazone)、吡氟草胺(diflufenican)、fenquinotrione、bixlozone、伏草隆(flumeturon)、氟咯草酮(flurochloridone)、异恶唑草酮(isoxaflutole)、硝磺草酮(mesotrione)、oxotrione(CAS1486617-21-3)、氟吡酰草胺(picolinafen)、磺草酮(sulcotrione)、tefuryltrione、tembotrione、tolpyralate、lancotrione、苯唑草酮(topramezone)、喹草酮、甲基喹草酮、吡唑喹草酯、二氯喹啉草酮、环吡氟草酮、双唑草酮、三唑磺草酮和苯唑氟草酮;
b6)选自如下的EPSP合成酶抑制剂:草甘膦(glyphosate)、草甘膦异丙胺盐(glyphosate-isopropylammonium)和草甘膦钾盐(glyhosate potassium salt);
b7)选自如下的谷氨酰胺合成酶抑制剂:草铵膦(glufosinate)、精草铵膦(glufosinate-P)和草铵膦铵盐(glufosinate-ammonium);
b9)选自如下的有丝分裂抑制剂:二甲戊灵(pendimethalin)和氟乐灵(trifluralin);
b10)选自如下的VLCFA抑制剂:乙草胺(acetochlor)、莎稗磷(anilofos)、唑草胺(cafenstrole)、精噻吩草胺(dimethenamid-P)、四唑酰草胺(fentrazamide)、氟噻草胺(flufenacet)、苯噻草胺(mefenacet)、吡草胺(metazachlor)、异丙甲草胺(metolachlor)、S-异丙甲草胺(S-metolachlor)、fenoxasulfone、ipfencarbazone和罗克杀草砜(pyroxasulfone);
b11)选自如下的纤维素生物合成抑制剂:茚嗪氟草胺(indaziflam)、异恶草胺(isoxaben)和苯氧丙胺津(triaziflam);
b13)选自如下的激素合成类除草剂:2,4-D及其盐和酯,如氯酰草膦(clacyfos),以及环丙嘧啶酸(aminocyclopyrachlor)及其盐和酯,氨草啶(aminopyralid)及其盐和其酯,二氯皮考啉酸(clopyralid)及其盐和酯,麦草畏(dicamba)及其盐和酯,flopyrauxifen,氟氯胺啶(fluroxypyr-meptyl),氟氯吡啶酸(halauxifen),氟氯吡啶酯(halauxifen-methyl),二氯喹啉酸(quinclorac),喹草酸(quinmerac),氯氟吡啶酸(florpyrauxifen),氯氟吡啶酯(florpyrauxifen-benzyl)(CAS 1390661-72-9);
b14)选自如下的激素传导抑制剂:二氟吡隆(diflufenzopyr)和二氟吡隆钠(diflufenzopyr-sodium);
b15)选自如下的其他除草剂:环庚草醚(cinmethylin)、香草隆(dymon)(=daimuron)、茚草酮(indanofan)、氯嗪草(oxaziclomefone)、methiozolin和tetflupyrolimet。
特别优选除草剂B为如上所定义的除草剂B;尤其是下面在表B中所列的除草剂
表B
活性成分C为至少一种安全剂C。
安全剂是防止或降低对有用植物的损害但不对本发明组合物的除草活性组分对不想要的植物的除草作用具有显著影响的化合物。它们可以在播种之前施用(例如在种子处理时、在嫩枝或秧苗上)或以有用植物的出苗前施用或出苗后施用方式施用。安全剂和式(I)的苯基异噁唑啉类和除草剂B可以同时或依次施用。
合适的安全剂可选自(喹啉-8-氧基)乙酸类、1-苯基-5-卤代烷基-1H-1,2,4-三唑-3-甲酸、1-苯基-4,5-二氢-5-烷基-1H-吡唑-3,5-二甲酸、4,5-二氢-5,5-二芳基-3-异唑甲酸、二氯乙酰胺类、α-肟基苯基乙腈、苯乙酮肟类、4,6-二卤代-2-苯基嘧啶类、N-[[4-(氨基羰基)苯基]磺酰基]-2-苯甲酰胺类、1,8-萘二甲酸酐、2-卤代-4-卤代烷基-5-噻唑羧酸、硫代磷酸酯类和N-烷基-O-苯基氨基甲酸酯类及其可农用盐和其可农用衍生物如酰胺、酯和硫酯,条件是它们具有酸基。
优选安全剂C可选自解草酮(benoxacor)、解草酸(cloquintocet)、抑害腈(cyometrinil)、cyprosulfamide、烯丙酰草胺(dichlormid)、dicyclonon、dietholate、解草唑(fenchlorazole)、解草啶(fenclorim)、解草安(flurazole)、肟草安(fluxofenim)、解草呋(furilazole)、双苯唑酸(isoxadifen)、吡咯二酸(mefenpyr)、mephenate、萘二甲酸酐(naphthalic anhydride)、解草腈(oxabetrinil)、metcamifen、4-二氯乙酰基-1-氧杂-4-氮杂螺[4.5]癸烷(MON4660,CAS71526-07-3)、2,2,5-三甲基-3-二氯乙酰基-1,3-唑烷(R-29148,CAS 52836-31-4)和N-(2-甲氧基苯甲酰基)-4-[(甲基氨基羰基)氨基]苯磺酰胺(CAS 129531-12-0)。
更为优选的安全剂C可选自解草酮(benoxacor)、解草酸(cloquintocet)、cyprosulfamide、烯丙酰草胺(dichlormid)、解草唑(fenchlorazole)、解草啶(fenclorim)、解草安(flurazole)、肟草安(fluxofenim)、解草呋(furilazole)、双苯唑酸(isoxadifen)、吡咯二酸(mefenpyr)、萘二甲酸酐(naphthalic anhydride)、解草腈(oxabetrinil)、metcamifen、4-二氯乙酰基-1-氧杂-4-氮杂螺[4.5]癸烷(MON4660,CAS71526-07-3)、2,2,5-三甲基-3-二氯乙酰基-1,3-唑烷(R-29148,CAS 52836-31-4)和N-(2-甲氧基苯甲酰基)-4-[(甲基氨基羰基)氨基]苯磺酰胺(CAS 129531-12-0)。
最为优选的安全剂C可选自解草酮(benoxacor)、解草酸(cloquintocet)、cyprosulfamide、烯丙酰草胺(dichlormid)、解草唑(fenchlorazole)、解草啶(fenclorim)、解草呋(furilazole)、双苯唑酸(isoxadifen)、吡咯二酸(mefenpyr)、萘二甲酸酐(naphthalicanhydride)、metcamifen、4-二氯乙酰基-1-氧杂-4-氮杂螺[4.5]癸烷(MON4660,CAS71526-07-3)、2,2,5-三甲基-3-二氯乙酰基-1,3-唑烷(R-29148,CAS 52836-31-4)和N-(2-甲氧基苯甲酰基)-4-[(甲基氨基羰基)氨基]苯磺酰胺(CAS 129531-12-0)。
作为构成本发明组合物的成分安全剂C优选下表C中化合物。
表C
上述活性成分A、B、C为具有可离子化官能基团时,则它们还可以以其可农用盐形式使用。合适的通常是其阳离子和阴离子分别对活性化合物的活性没有不利影响的那些阳离子的盐和那些酸的酸加成盐。
优选的阳离子是碱金属的离子,优选锂、钠和钾离子,碱土金属的离子,优选钙和镁离子,以及过渡金属的离子,优选锰、铜、锌和铁离子,此外还有铵和其中1-4个氢原子被C1-C4烷基、羟基-C1-C4烷基、C1-C4烷氧基-C1-C4烷基、羟基-C1-C4烷氧基-C1-C4烷基、苯基或苄基替代的取代铵,优选铵、甲基铵、异丙基铵、二甲基铵、二异丙基铵、三甲基铵、庚基铵、十二烷基铵、十四烷基铵、四甲基铵、四乙基铵、四丁基铵、2-羟基乙基铵(醇胺盐)、2-(2-羟基乙-1-氧基)乙-1-基铵(二甘醇胺盐)、二(2-羟基乙-1-基)铵(二醇胺盐)、三(2-羟基乙基)铵(三醇胺盐)、三(2-羟基丙基)铵、苄基三甲基铵、苄基三乙基铵、N,N,N-三甲基乙醇铵(胆碱盐),此外还有离子,锍离子,优选三(C1-C4烷基)锍,如三甲基锍,以及氧化锍离子,优选三(C1-C4烷基)氧化锍,最后还有多元胺如N,N-二(3-氨基丙基)甲基胺和二亚乙基三胺的盐。
有用酸加成盐的阴离子主要是氯离子、溴离子、氟离子、碘离子、硫酸氢根、甲基硫酸根、硫酸根、磷酸二氢根、磷酸氢根、硝酸根、碳酸氢根、碳酸根、六氟硅酸根、六氟磷酸根、苯甲酸根以及还有C1-C4链烷酸的阴离子,优选甲酸根、乙酸根、丙酸根和丁酸根。
或,上述A、B、C组分还可以以酸的形式、以如上所述可农用盐的形式或者以可农用衍生物的形式,例如作为酰胺,如单-和二-C1-C6烷基酰胺或芳基酰胺,作为酯,例如作为烯丙基酯、炔丙基酯、C1-C10烷基酯、烷氧基烷基酯、四氢呋喃基甲基((四氢呋喃-2-基)甲基)酯以及还有作为硫酯,例如作为C1-C10烷硫基酯使用。优选的单-和二-C1-C6烷基酰胺是甲基和二甲基酰胺。优选的芳基酰胺例如为酰替苯胺和2-氯酰替苯胺。优选的烷基酯例如为甲基、乙基、丙基、异丙基、丁基、异丁基、戊基、甲基己基(1-甲基己基)、甲基庚基(1-甲基庚基)、庚基、辛基或异辛基(2-乙基己基)酯。
优选的C1-C4烷氧基-C1-C4烷基酯是直链或支化C1-C4烷氧基乙基酯,例如2-甲氧基乙基、2-乙氧基乙基、2-丁氧基乙基(丁氧乙基)、2-丁氧基丙基或3-丁氧基丙基酯。直链或支化C1-C10烷硫基酯的实例是乙硫基酯。
b1)-b15)组的除草剂B和安全剂C均是已知的除草剂和安全剂,例如参见TheCompendium of Pesticide Common Names(http://www.alanwood.net/pesticides/);Farm Chemicals Handbook 2000,第86卷,Meister Publishing Company,2000;B.Hock,C.Fedtke,R.R.Schmidt,Herbizide[除草剂],Georg Thieme Verlag,Stuttgart,1995;W.H.Ahrens,Herbicide Handbook,第7版,Weed Science Society of America,1994以及K.K.Hatzios,Herbicide Handbook,第7版增补,Weed Science Society of America,1998。2,2,5-三甲基-3-二氯乙酰基-1,3-唑烷[CAS号52836-31-4]也称为R-29148。4-二氯乙酰基-1-氧杂-4-氮杂螺[4.5]癸烷[CAS号71526-07-3]也称为AD-67和MON 4660。
活性化合物的相应作用机理的归属基于现有知识。若几种作用机理适用于一种活性化合物,则该物质仅归属于一种作用机理。
具有羧基的活性化合物B和C在本发明组合物中可以如上所述以酸的形式、可农用盐形式或可农用衍生物的形式使用。
在麦草畏的情况下,合适的盐包括其中抗衡离子为可农用阳离子的那些。例如,麦草畏的合适盐是麦草畏钠(dicamba-sodium)、麦草畏钾(dicamba-potassium)、麦草畏甲基铵(dicamba-methylammonium)、麦草畏二甲基铵(dicamba-dimethylammonium)、麦草畏异丙基铵(dicamba-isopropylammonium)、麦草畏二甘醇胺(dicamba-diglycolamine)、麦草畏乙醇胺(dicamba-olamine)、麦草畏二乙醇胺(dicamba-diolamine)、麦草畏三乙醇胺(dicamba-trolamine)、麦草畏-N,N-二(3-氨基丙基)甲基胺和麦草畏-二亚乙基三胺。合适酯的实例是麦草畏甲酯(dicamba-methyl)和麦草畏丁氧基乙酯(dicamba-butoyl)。
2,4-D的合适盐是2,4-D铵、2,4-D二甲基铵、2,4-D二乙基铵、2,4-D二乙醇铵(2,4-D二醇胺)、2,4-D三乙醇铵、2,4-D异丙基铵、2,4-D三异丙醇铵、2,4-D庚基铵、2,4-D十二烷基铵、2,4-D十四烷基铵、2,4-D三乙基铵、2,4-D三(2-羟基丙基)铵、2,4-D三异丙基铵、2,4-D三乙醇胺、2,4-D锂、2,4-D钠。2,4-D的合适酯的实例是2,4-D丁氧基乙酯(2,4–Dbutotyl)、2,4-D-2-丁氧基丙酯、2,4-D-3-丁氧基丙酯、2,4-D丁酯(2,4-D-butyl)、2,4-D乙酯(2,4-D-e thy l)、2,4-D乙基己基酯(2,4-D-ethylhexyl)、2,4-D异丁酯(2,4-Disobutyl)、2,4-D异辛酯(2,4-D-isooctyl)、2,4-D异丙酯(2,4-D-isopropyl)、2,4-D甲基庚基酯(2,4-D-meptyl)、2,4-D甲酯(2,4-D-methyl)、2,4-D辛酯(2,4-D-octyl)、2,4-D戊酯(2,4-D-pentyl)、2,4-D丙酯(2,4-D-propyl)、2,4-D四氢呋喃酯(2,4-D-tefuryl)和氯酰草膦(clacyfos)。
2,4-DB的合适盐例如为2,4-DB钠、2,4-DB钾和2,4-DB二甲基铵。2,4-DB的合适酯例如为2,4-DB丁酯(2,4-DB-butyl)和2,4-DB异辛酯(2,4-DB-isoctyl)。
2,4-滴丙酸的合适盐例如为2,4-滴丙酸钠(dichlorprop-sodium)、2,4-滴丙酸钾(dichlorprop-potassium)和2,4-滴丙酸二甲基铵(dichlorprop-dimethylammonium)。2,4-滴丙酸的合适酯的实例是2,4-滴丙酸丁氧基乙酯(dichlorprop-butotyl)和2,4-滴丙酸异辛酯(dichlorprop-isoctyl)。
MCPA的合适盐和酯包括MCPA丁氧基乙酯(MCPA-butotyl)、MCPA丁酯(MCPAbutyl)、MCPA二甲基铵、MCPA二乙醇胺(MCPA-diolamine)、MCPA乙酯(MCPA-ethyl)、MCPA硫代乙酯(MCPA-thioethyl)、MCPA-2-乙基己基酯(MCPA-2-ethylhexyl)、MCPA异丁酯(MCPAisobutyl)、MCPA异辛酯(MCPA-isoctyl)、MCPA异丙酯(MCPA-isopropyl)、MCPA异丙基铵、MCPA甲酯(MCPA-methyl)、MCPA乙醇胺(MCPA-olamine)、MCPA钾(MCPA-potassium)、MCPA钠(MCPA-sodium)和MCPA三乙醇胺(MCPA三乙醇胺)。
MCPB的合适盐是MCPB钠。MCPB的合适酯是MCPB乙酯(MCPB-ethyl)。
二氯皮考啉酸的合适盐是二氯皮考啉酸钾(clopyralid-potassium)、二氯皮考啉酸乙醇铵和二氯皮考啉酸三异丙醇铵(clopyralid-tri-(2-hydroxypropyl)ammonium)。二氯皮考啉酸的合适酯的实例是二氯皮考啉酸甲酯。
氟草烟的合适酯的实例是是氟氯胺啶和氟草烟2-丁氧基-1-甲基乙基酯(fluroxypyr-2-butoxy-1-methylethyl),其中优选氟氯胺啶。
毒莠定的合适盐是毒莠定二甲基铵(picloram-dimethylammonium)、毒莠定钾(picloram-potassium)、毒莠定三异丙醇铵(picloram-triisopropanolammonium)、毒莠定三异丙基铵(picloram-triisopropylammonium)和毒莠定三乙醇胺(picloram-trolamine)。毒莠定的合适酯是毒莠定异辛酯(picloram-isoctyl)。
绿草定的合适盐是绿草定三乙基铵(triclopyr-triethylammonium)。绿草定的合适酯例如是绿草定乙酯(triclopyr-ethyl)和绿草定丁氧基乙酯(triclopyr-butotyl)。
草灭平的合适盐和酯包括草灭平铵(chloramben-ammonium)、草灭平二乙醇胺(chloramben-diolamine)、草灭平甲酯(chloramben-methyl)、草灭平甲基铵(chlorambenmethylammonium)和草灭平钠(chloramben-sodium)。2,3,6-TBA的合适盐和酯包括2,3,6-TBA二甲基铵、2,3,6-TBA锂、2,3,6-TBA钾和2,3,6-TBA钠。
氨草啶的合适盐和酯包括氨草啶钾(aminopyralid-potassium)、氨草啶二甲铵盐(aminopyralid-dimethylammonium)和氨草啶异丙醇铵盐(aminopyralid-tris(2-hydroxypropyl)ammonium)。
草甘膦的合适盐例如为草甘膦铵盐、草甘膦二铵盐(glyphosate-diammonium)、草甘膦二甲铵(glyphoste-dimethylammonium)、草甘膦异丙胺盐、草甘膦钾、草甘膦钠(glyphosate-sodium)、草硫膦以及乙醇胺和二乙醇胺盐,优选草甘膦二铵盐、草甘膦异丙胺盐和草甘膦钾。
草铵膦的合适盐例如为草铵膦铵盐。
草铵膦(glufosinate-P)的合适盐例如为草铵膦铵盐(glufosinate-P-ammonium)。
溴苯腈的合适盐和酯例如为溴苯腈丁酸酯(bromoxynil-butyrate)、溴苯腈庚酸酯(bromoxynil-heptanoate)、溴苯腈辛酸酯(bromoxynil-octa noate)、溴苯腈钾(bromoxynil-potassium)和溴苯腈钠(bromoxynil-sodium)。
碘苯腈的合适盐和酯例如为碘苯腈辛酸酯(ioxonil-octanoate)、碘苯腈钾(ioxonil-potassium)和碘苯腈钠(ioxonil-sodium)。
2甲4氯丙酸的合适盐和酯包括2甲4氯丙酸丁氧基乙酯(mecoprop-butotyl)、2甲4氯丙酸二甲铵(mecoprop-dimethylammonium)、2甲4氯丙酸二乙醇胺(mecoprop-diolamine)、mecoprop-ethadyl、2甲4氯丙酸2-乙基己基酯(mecoprop-2-ethylhexyl)、2甲4氯丙酸异辛酯(mecoprop-isoctyl)、2甲4氯丙酸甲酯(mecoprop-methyl)、2甲4氯丙酸钾(mecoprop-potassium)、2甲4氯丙酸钠(mecoprop-sodium)和2甲4氯丙酸三乙醇胺(mecoprop-trolamine)。
高2甲4氯丙酸的合适盐例如为高2甲4氯丙酸丁氧基酯(mecoprop-P-butotyl)、高2甲4氯丙酸二甲基铵(mecoprop-P-dimethylammonium)、高2甲4氯丙酸2-乙基己基酯(mecoprop-P-2-ethylhexyl)、高2甲4氯丙酸异丁酯(mecoprop-P-isobutyl)、高2甲4氯丙酸钾和高2甲4氯丙酸钠。
二氟吡隆的合适盐例如为二氟吡隆钠。
抑草生的合适盐例如为抑草生钠(naptalam-sodium)。
环丙嘧啶酸的合适盐和酯例如为环丙嘧啶酸二甲基铵、环丙嘧啶酸甲酯、环丙嘧啶酸三异丙醇铵、环丙嘧啶酸钠和环丙嘧啶酸钾。
二氯喹啉酸的合适盐例如为二氯喹啉酸二甲基铵。
喹草酸的合适盐例如为喹草酸二甲基铵。
咪草啶酸的合适盐例如为咪草啶酸铵。
甲基咪草烟的合适盐例如为甲基咪草烟铵和甲基咪草烟异丙基铵。
灭草烟的合适盐例如为灭草烟铵和灭草烟异丙基铵。
灭草喹的合适盐例如为灭草喹铵。
咪草烟的合适盐例如为咪草烟铵和咪草烟异丙基铵。
苯唑草酮的合适盐例如为苯唑草酮钠。
本发明组合物可为活性成分A和至少一种的活性成分B;或,至少一种的活性成分A、至少一种的活性成分B和至少一种安全剂C;
其中,活性成分B选自两者或两种以上时,除草剂选自作用机理不相同的除草剂。
下述为本发明组合物的部分,详见下表7:包含化合物1-6的组合物见表7,组合物编号为7-1~7-3761。
表7
表8:包含化合物1-10的组合物,其中除草剂B和安全剂C与表1中所列B、C一致,相应的组合物编号为8-1~8-3761。
表9:包含化合物2-2的组合物,其中除草剂B和安全剂C与表1中所列B、C一致,相应的组合物编号为9-1~9-3761。
表10:包含化合物2-6的组合物,其中除草剂B和安全剂C与表1中所列B、C一致,相应的组合物编号为10-1~10-3761。
表11:包含化合物3-2的组合物,其中除草剂B和安全剂C与表1中所列B、C一致,相应的组合物编号为11-1~11-3761。
表12:包含化合物3-6的组合物,其中除草剂B和安全剂C与表1中所列B、C一致,相应的组合物编号为12-1~12-3761。
本发明通式I化合物可借助文献描述的方法由氨基化合物II得到,如SyntheticCommunications,2016,46(8),673-677;WO2003029225、WO2014026893、WO2012080239、WO 2010145992或CN 104011044等。通式I化合物的旋光异构体是由其相应的旋光活性的氨基化合物II合成得到。
反应在适宜的溶剂中进行,适宜的溶剂可选自苯、甲苯、二甲苯、丙酮、四氢呋喃、乙腈、N,N-二甲基甲酰胺、N-甲基吡咯烷酮、二氯甲烷、氯仿、二氯乙烷或乙酸乙酯等。反应可以在碱性条件下进行。所述的碱可以选自碱金属氢化物,如氢化钠、氢化锂或氨基钠等;碱金属氢氧化物,如氢氧化钠或氢氧化钾;碱金属碳酸盐,如碳酸钠或碳酸钾;有机碱类,如吡啶、4-二甲氨基吡啶、三乙胺、N-甲基吡咯或二异丙基乙基胺等。反应温度可在-10℃至反应中所选用的适宜的溶剂沸点温度之间,通常为0~100℃。反应时间为30分钟至40小时,通常5~30小时。
氨基化合物II可由硝基化合物III按照常规方法利用铁、锌、钯碳、氯化亚锡等还原试剂得到,具体可参照EP2044006;US20070155738;European Journal of MedicinalChemistry,2013,65,32-40;Synlett,2010,(20),3019-3022;Heterocycles,2008,75(1):57-64等。硝基化合物III可由醛VII按照现有文献描述经三步合成,文献如J.Agric.FoodChem.2005,53,8639-8643或WO2006090234。具有旋光活性的氨基化合物II,可以通过采用手性柱对消旋的氨基化合物II进行拆分获得。拆分填料优选Amylose tris(3,5-dimethylphenylcarbamate)以及quinidines等。
除另有注明外,反应式中各基团定义同前。
本发明的化合物可以有效地控制各种阔叶杂草和禾本科杂草,如稗草、狗尾草、异型莎草、水莎草、马唐、荩草、苘麻、百日草、反枝苋、马齿苋、苍耳、龙葵、决明、野西瓜苗、野大豆、长芒苋、具瘤苋、鬼针草、地肤、圆叶牵牛、牛筋草、猩猩草、野荞麦、绿狗尾草、假高粱、小飞蓬、看麦娘、野燕麦、早熟禾、不实雀麦、小籽虉草、野萝卜、繁缕、矢车菊、猪殃殃、紫花野芝麻、小白菊、虞美人、卷茎蓼、婆婆纳或三色堇等杂草,在低剂量下就可以获得很好的效果,而且可以防除各种抗性杂草,如对三嗪类、草甘膦及乙酰乳酸合成酶抑制剂存在抗性的杂草。对小麦、玉米、水稻、大豆、甜菜等具有一定的安全性,在农业上可作为选择性除草剂用作作物,亦可作为灭生性除草剂用于非耕地\休闲地、林地、果园、田埂等。本发明化合物可以用于苗前、苗后防除杂草,亦可用作土壤处理。因此本发明还包括通式(I)化合物用于控制杂草的用途。
本发明通式(I)化合物也适用于植物的干燥和/或脱叶。
所述组合物中活性成分A和活性成分B质量份数比优选为1:60-20:1,活性成分A和活性成分C质量份数比优选为1:1-50:1。
此外,本发明还提供了一种除草组合物,可用作除草剂,制剂以所述除草剂组合物作为有效成分,有效成分的重量含量为1~99%。所述除草剂制剂可为水乳剂、可分散油悬浮剂、可分散油剂、微乳剂、乳油、可溶液剂、水剂、悬浮剂、悬浮乳剂、超低容量剂、粉剂、可湿性粉剂、颗粒剂、水分散粒剂、干悬浮剂、微胶囊悬浮剂、微胶囊颗粒剂、泡腾颗粒剂、泡腾片剂、水分散片剂。本发明的组合物中还可以加入乳化剂、分散剂、润湿剂等表面活性物质,增加组合物的稳定性、渗透性和润湿性。
适合于制备本发明组合物的分散剂可以为萘或烷基萘甲醛缩合物磺酸盐、脂肪醇环氧乙烷加成物磺酸盐、烷基酚聚氧乙烯基醚磺酸盐、聚羧酸盐、脂肪醇环氧乙烷加成物磷酸盐、烷基酚聚氧乙烯基、醚甲醛缩合物硫酸盐、聚氧乙烯聚氧丙烯基醚嵌段共聚物、烷基酚聚氧乙烯基磷酸盐、木质素磺酸盐、明胶、阿拉伯胶、羧甲基纤维素、聚氧乙烯醇、聚乙烯吡咯烷酮,聚丙烯酸钠、聚乙二醇,可以为其中的一种或几种。
适合于制备本发明组合物的润湿剂可以为脂肪醇硫酸盐、烷基醇聚氧乙烯基醚硫酸钠、烷基酚聚氧乙烯基、醚硫酸钠、烷基酚聚氧乙烯基醚甲醛缩合物硫酸盐、烷基硫酸钠、烷基萘磺酸盐、脂肪醇环氧乙烷加成物磺酸盐、烷基酚甲醛缩合物环氧乙烷加成物磺酸盐、烷酰胺基磺酸盐、脂肪醇聚氧乙烯基醚、烷基酚聚氧乙烯基醚、失水三梨醇脂肪酸酯、失水三梨醇脂肪酸酯聚氧乙烯剂醚、聚氧乙烯聚氧丙烯醚嵌段共聚物、烷基酚甲醛缩合物聚氧乙烯基醚,可以为其中的一种或几种。
适合于制备本发明组合物的固体载体可以为粘土、高岭土、石膏、膨润土、硅藻土、滑石粉、陶土、硅酸铝镁、活性白土、白炭黑、石灰石、轻质碳酸钙、玉米淀粉、可溶性淀粉、六甲撑二铵、苯并呋喃树脂、苯乙烯聚合物和共聚物等。
适合于制备本发明的除草剂组合物的粘合剂可以是天然的或合成的,例如黄原胶、明胶、阿拉伯树胶、聚乙烯吡咯烷酮、硅酸铝镁、聚乙烯醇、酚醛树脂、虫胶、羧甲基纤维素、甲基纤维素和海藻酸钠。消泡剂可以是泡敌、硅酮类、C8~10脂肪醇、C10~20饱和脂肪酸类及酰胺等。
适合于制备本发明组合物的崩解剂可以为氯化钙、氯化钙、硫酸钠、硫酸铵、聚丙烯酸乙酯、碳酸钠、聚乙烯吡咯烷酮、海藻酸钠、羧甲基淀粉钠的一种或几种。
组合物制剂制备的实例为:
i)水溶性浓缩物(SL,LS)将10-60重量%本发明组合物和5-15重量%润湿剂(例如醇烷氧基化物)溶于加至100重量%的水和/或水溶性溶剂(例如醇)中。活性物质在用水稀释时溶解。
ii)分散性浓缩物(DC)将5-25重量%本发明组合物和1-10重量%分散剂(例如聚乙烯吡咯烷酮)溶于加至100重量%的有机溶剂(例如环己酮)中。用水稀释得到分散体。
iii)可乳化浓缩物(EC)将15-70重量%本发明组合物和5-10重量%乳化剂(例如十二烷基苯磺酸钙和蓖麻油乙氧基化物)溶于加至100重量%的水不溶性有机溶剂(例如芳族烃)中。用水稀释得到乳液。
iv)乳液(EW,EO,ES)将5-40重量%本发明组合物和1-10重量%乳化剂(例如十二烷基苯磺酸钙和蓖麻油乙氧基化物)溶于20-40重量%水不溶性有机溶剂(例如芳族烃)中。借助乳化机将该混合物引入加至100重量%的水中并制成均相乳液。用水稀释得到乳液。
v)悬浮液(SC,OD,FS)在搅拌的球磨机中将20-60重量%本发明组合物在加入2-10重量%分散剂和润湿剂(例如木素磺酸钠和醇乙氧基化物)、0.1-2重量%增稠剂(例如黄原胶)和加至100重量%的水下粉碎,得到细碎活性物质悬浮液。用水稀释得到稳定的活性物质悬浮液。对于FS类型组合物加入至多40重量%粘合剂(例如聚乙烯醇)。
vi)水分散性颗粒和水溶性颗粒(WG,SG)在加入加至100重量%的分散剂和润湿剂(例如木素磺酸钠和醇乙氧基化物)下精细研磨50-80重量%本发明组合物并借助工业装置(例如挤出机、喷雾塔、流化床)将其制成水分散性或水溶性颗粒。用水稀释得到稳定的活性物质分散体或溶液。
vii)水分散性粉末和水溶性粉末(WP,SP,WS)将50-80重量%本发明组合物在加入1-5重量%分散剂(例如木素磺酸钠)、1-3重量%润湿剂(例如醇乙氧基化物)和加至100重量%的固体载体(例如硅胶)下在转子-定子磨机中研磨。用水稀释得到稳定的活性物质分散体或溶液。
viii)凝胶(GW,GF)在搅拌的球磨机中在加入3-10重量%分散剂(例如木素磺酸钠)、1-5重量%增稠剂(例如羧甲基纤维素)和加至100重量%的水下粉碎5-25重量%本发明组合物,得到活性物质的精细悬浮液。用水稀释得到稳定的活性物质悬浮液。
iv)微乳液(ME)将5-20重量%本发明组合物加入5-30重量%有机溶剂共混物(例如脂肪酸二甲基酰胺和环己酮)、10-25重量%表面活性剂共混物(例如醇乙氧基化物和芳基酚乙氧基化物)和加至100重量%的水中。将该混合物搅拌1小时,以自发产生热力学稳定的微乳液。
iv)微胶囊(CS)将包含5-50重量%本发明组合物、0-40重量%水不溶性有机溶剂(例如芳族烃)、2-15重量%丙烯酸系单体(例如甲基丙烯酸甲酯、甲基丙烯酸和二-或三丙烯酸酯)的油相分散到保护性胶体(例如聚乙烯醇)的水溶液中。由自由基引发剂引发的自由基聚合导致形成聚(甲基)丙烯酸酯微胶囊。或者将包含5-50重量%本发明化合物I、0-40重量%水不溶性有机溶剂(例如芳族烃)和异氰酸酯单体(例如二苯基甲烷-4,4’-二异氰酸酯)的油相分散到保护性胶体(例如聚乙烯醇)的水溶液中。加入多胺(例如六亚甲基二胺)导致形成聚脲微胶囊。单体量为1-10重量%。重量%涉及整个CS组合物。
ix)可撒粉粉末(DP,DS)将1-10重量%本发明组合物细碎研磨并与加至100重量%的固体载体(例如细碎高岭土)充分混合。
x)颗粒(GR,FG)将0.5-30重量%本发明组合物细碎研磨并结合加至100重量%的固体载体(例如硅酸盐)。通过挤出、喷雾干燥或流化床实现造粒。
xi)超低容量液体(UL)将1-50重量%本发明组合物溶于加至100重量%的有机溶剂(例如芳族烃)中。
以上剂型i)-xi)可以任选包含其他助剂,如0.1-1重量%杀菌剂,5-15重量%防冻剂,0.1-1重量%消泡剂和0.1-1重量%着色剂。
本发明组合物作为除草剂的使用方法,即分开、依次或同时施用组分A和组分B或者添加安全剂C,可以选择性或非选择性地对杂草进行茎叶喷雾处理,或作物种植前或播种后出苗前的烧荒及耐受作物及非耐受作物的苗后处理,均能取得良好的防除效果。
本发明除草剂组合物施用于存在或预期存在的不希望植被的场所,及可以选择性或非选择性地用于存在或预期存在的不希望植被的场所。具体是可以施用于不希望植被生存的土壤中、不希望植被的茎叶,或作物种植前或播种后出苗前的烧荒及耐受作物及非耐受作物的苗后处理。
所述的除草剂组合物施用于耕地、非耕地、果园、橡胶园、闲置耕地、橡胶园、桉树林、杉树林、森林、防火道、草坪、铁路、公路、机场及仓库场所。所述耐受和非耐受作物选自水稻、玉米、豆类作物、油菜、蔬菜、棉花、甜菜、小粒谷物(包括小麦、大麦、燕麦等)、大豆、花生、甘蔗、向日葵、马铃薯、栽培作物、木本植物。所述的果园包括苹果园、桃园、葡萄园、梨园、茶园、桑园、柑橘园。所述不希望的植被包括禾本科杂草、阔叶杂草、莎草科杂草、藻类、蕨类和木本灌木。
本发明提出的组合物具有以下优点:
1、本发明两种活性成分之间具有非常明显的增效作用,降低了各组分的用量;
2、本发明组合物利用不同作用机制的互补,兼具触杀和内吸的特性,增加了对田间干旱、低温等不良环境的适应性,加快了反应速度,除草更彻底;
3、本发明组合物扩大了施药适期,特别对较大叶龄阔叶杂草,持续抑制和防除作用增强;
4、本发明组合物对草甘膦抗性杂草如小飞蓬、狗牙根、牛筋草等具有很高的防除效果;
5、本发明组合物茎叶喷雾处理,可用于防除耕地、非耕地、果园、闲置耕地、橡胶园、桉树林、森林、防火道、草坪、铁路、公路、机场及仓库等场所的大多数杂草。也可以用于苗前或苗后防除玉米、小麦、大豆、水稻、棉花、马铃薯等防除杂草。
6、本发明在组合物中添加安全剂,其有效增加作物的耐受性,减轻对作物的药害,提高农药在作物上使用的便利度,如玉米、小麦、大豆、水稻等。
具体实施方式
以下具体实施例用来进一步说明本发明,但本发明绝非限于这些例子。(除另有注明外,所用原料均有市售)
合成实施例
实施例1化合物1-6的制备
1)2-氯-4-氟-5-硝基苯甲醛肟的制备
将42g(0.206mol)2-氯-4-氟-5-硝基苯甲醛溶于200mL乙醇中,降至0℃,搅拌下滴加17.4g(0.25mol)盐酸羟胺的水溶液,随后升至室温搅拌反应。2小时后,TLC监测反应完全。倒入水中,过滤得白色固体38.3g。熔点103℃。
2)3-(2-氯-4-氟-5-硝基苯基)-5-甲基-4,5-二氢异恶唑-5-羧酸乙酯的制备
将43.7g(0.2mol)2-氯-4-氟-5-硝基苯甲醛肟溶于150mLN,N-二甲基甲酰胺中,升温至30℃,在该温度下分批加入32g(0.24mol)NCS,形成浅黄色溶液,保持在35℃下反应1小时。降至室温,加入300mL二氯甲烷,随后用1N盐酸洗两次,饱和食盐水洗两次,无水硫酸镁干燥,抽滤,将二氯甲烷溶液降至0-5℃,滴加34.2g(0.3mol)甲代丙烯酸乙酯和31g(0.3mol)三乙胺的混合液,保持在该温度下反应1小时。依次用1N盐酸和饱和食盐水洗,有机相用无水硫酸镁干燥,脱溶后柱层析(乙酸乙酯:石油醚=1:3)得浅黄色固体57g。熔点73.5℃。1H-NMR(300MHz,内标TMS,溶剂CDCl3)δ(ppm):1.28(t,3H),1.71(s,3H),3.32(d,1H),3.92(d,1H),4.27(q,2H),7.42(d,1H),8.45(d,1H)。
3)3-(2-氯-4-氟-5-氨基苯基)-5-甲基-4,5-二氢异恶唑-5-羧酸乙酯的制备
将57g(0.18mol)3-(2-氯-4-氟-5-硝基苯基)-5-甲基-4,5-二氢异恶唑-5-羧酸乙酯溶于300mL乙酸乙酯中,加热下分批加入163g(0.72mol)二水合氯化亚锡,随后在回流下反应8小时。TLC监测反应完全。冷至室温,加入到冰水中,用氢氧化钠调节pH至8,乙酸乙酯萃取,饱和食盐水洗,无水硫酸镁干燥后减压蒸馏得31g油状物,未经提纯直接用于下一步反应。
4)化合物1-6的制备
室温下将49g(0.2994mol)碳酰二咪唑、10g(0.0998mol)三乙胺、300mL乙酸乙酯依次加入到1000mL三口烧瓶中,搅拌下分批加入30g(0.0998mol)3-(2-氯-4-氟-5-氨基苯基)-5-甲基-4,5-二氢异恶唑-5-羧酸乙酯,随后将反应升温至55℃,并在该温度下分批加入12.5g(0.12mol)N,N’-二甲基硫脲。随后将反应升至回流反应25小时,TLC监测反应完成。冷至室温并将反应液倒入装有30mL浓盐酸的冰水混合物中,搅拌30分钟。静置分离有机相,水相分别加入100mL乙酸乙酯萃取两次,合并有机相并用无水硫酸镁干燥,减压蒸馏,柱层析(乙酸乙酯:石油醚=1:5)得39g白色固体。熔点151-152℃。
1H-NMR(300MHz,内标TMS,溶剂CDCl3)δ(ppm):7.72(d,J=7.7Hz,1H),7.35(d,J=9.0Hz,1H),4.25(qd,J=7.1,1.8Hz,2H),3.99(d,J=17.4Hz,1H),3.75(s,6H),3.38(d,J=17.4Hz,1H),1.69(s,3H),1.31(t,J=7.1Hz,3H)。
实施例2化合物2-2和3-2的制备
1)(R)-3-(5-氨基-2-氯-4-氟苯基)-5-甲基-4,5-二氢-5-异恶唑羧酸乙酯的制备
将25g Amylose tris(3,5-dimethylphenylcarbamate)硅胶装入色谱柱中,将含有1g 3-(5-氨基-2-氯-4-氟苯基)-5-甲基-4,5-二氢-5-异恶唑羧酸乙酯的5ml二氯甲烷溶液吸附到色谱柱中,利用Biotage快速制备色谱分离,收集相应成分,分别得到光学异构(R)-3-(5-氨基-2-氯-4-氟苯基)-5-甲基-4,5-二氢-5-异恶唑羧酸乙酯0.47g(光学纯度99.8%),(S)-3-(5-氨基-2-氯-4-氟苯基)-5-甲基-4,5-二氢-5-异恶唑羧酸乙酯0.46g(纯度99.4%)。
旋光度R异构体[α]26℃ 589.44nm=150.65°;S异构体[α]26℃ 589.44nm=-111.66°(申光WZZ-2S/2SS,钠灯波长:589.44nm,溶剂:乙腈)。
2)化合物2-2的制备制备
参照化合物1-6的合成,将3-(2-氯-4-氟-5-氨基苯基)-5-甲基-4,5-二氢异恶唑-5-羧酸乙酯换为(R)-3-(5-氨基-2-氯-4-氟苯基)-5-甲基-4,5-二氢-5-异恶唑羧酸乙酯,可得到化合物2-2。
3)化合物2-3的制备制备
参照化合物1-6的合成,将3-(2-氯-4-氟-5-氨基苯基)-5-甲基-4,5-二氢异恶唑-5-羧酸乙酯换为(S)-3-(5-氨基-2-氯-4-氟苯基)-5-甲基-4,5-二氢-5-异恶唑羧酸乙酯,可得到化合物3-2。
制剂实施例
配方中活性成分折百后计量加入,所有百分含量均为重量百分含量。
实施例3 35%乳油
将亚磷酸溶解在环已酮中,再加入化合物1-6和乙氧基化甘油三酸酯,得到透明的溶液。
实施例4 10%可湿性粉剂
将化合物2-2、十二烷基萘磺酸钠、木质素磺酸钠及高岭土(均为固体)混合在一起,在粉碎机中粉碎,直到颗粒达到标准。
实施例5 10%水悬浮液
将化合物3-2与应加水量的80%及十二烷基萘磺酸钠在球磨机中(1mm珠)中一起粉碎。半纤维素和环氧丙烷溶解在其余20%的水中,然后搅拌加入上述组分。
实施例6 45%水分散粒剂
将上述成分加入釜中,搅拌混合均匀,加入适量水混合,用挤压式造粒机进行造粒。
生物活性测定
实施例7室内除草活性测定
本发明化合物的除草活性测试方法如下:
将定量的禾本科杂草(稗草、金色狗尾草)和阔叶杂草(百日草、苘麻)种子分别播于直径为7cm的装有营养土的纸杯中,播后覆土1cm,镇压、淋水后在温室按常规方法培养。禾本科杂草长至2~3叶期、阔叶杂草2~4叶期茎叶喷雾处理;苗前土壤喷雾处理于播种后24小时进行。按试验设计剂量,在履带式作物喷雾机(英国Engineer Research Ltd.设计生产)上进行喷雾处理(喷雾压力1.95kg/cm2,喷液量500L/hm2,履带速度1.48km/h)。试验设3次重复。试材处理后置于操作大厅,待药液自然阴干后,放于温室内按常规方法管理,观察并记录杂草对药剂的反应情况,处理后定期目测供试药剂对杂草的防除效果。
防除效果分级标准:0为无效,100%为将杂草完全杀死或严重抑制。化合物1-6、1-10、2-2、2-6、3-2、3-6等在600g a.i./hm2对百日草、苘麻、金狗尾草和稗草防效为100%。
表13部分化合物除草活性结果
实施例8室内组合物除草活性测定
除草活性测定方法同上。采用Colby法对提出的组合物的联合作用进行评价(S.R.Colby(1967)“计算除草剂组合的协同增效和拮抗响应”,Weeds 15,第22页)。
式中:
X—除草剂组分A用量为P时的杂草防效;
Y—除草剂组分B用量为Q时的杂草防效;
E0—除草剂组分A用量为P时的理论防效+除草剂组分B用量为Q时的理论防效;
E—除草剂组分A与除草剂组分B按上述比例混用后的实测防效。
当E>E0时,为增效作用;当E<E0时,为拮抗作用;当E=E0值时,为加成作用。
生测结果表明组合物7-32、7-40、7-114、7-115、7-116、7-118、7-120、7-121、7-122、7-123、7-135、7-142、7-155、7-202对禾本科杂草、阔叶杂草以及抗草甘膦小飞蓬和牛筋草的实测值均大于理论值,二者之差甚至超过10%,具有明显的增效作用。
Claims (14)
1.一种三嗪酮类化合物,其特征在于:化合物结构如通式(I)所示:
式中:
R1、R2分别选自C1-C6烷基或C1-C6卤代烷基;
R3、R4分别选自氢、卤素、C1-C6烷基、C1-C6烷氧基、C1-C6卤代烷氧基、C1-C6烷硫基或C1-C6烷基磺酰基;
R5、R6分别相同或不同选自氢、氰基、C1-C6烷基、CO2R9、CH2OR10、未取代或被1-4个独立选自以下基团取代的苯基:卤素、CN、NO2、C1-C8烷基、C1-C8卤代烷基、C1-C8烷氧基、C1-C8卤代烷氧基、C1-C8烷氧基羰基、C1-C8烷硫基或C1-C8烷基磺酰基;
R7、R8分别相同或不同选自氢、氰基、C1-C6烷基、C1-C6卤代烷基、C1-C6烷基CO2R9、CO2R9、CH2OR10、CH2NR11R12、CONR11R12、未取代或被1-4个独立选自以下基团取代的苯基,以下基团卤素、CN、NO2、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基、C1-C4卤代烷氧基、C1-C4烷氧基羰基、C1-C4烷硫基、C1-C4烷基磺酰基;
R9选自氢、C1-C6烷基、C1-C6卤代烷基、C3-C6烯基、C3-C6炔基、C1-C6烷氧基C1-C6烷基、C1-C6烷羰基氧基C2-C4烷基,未取代或者被1-4个独立选自以下基团取代的苄基、呋喃亚甲基、噻唑亚甲基、四氢呋喃亚甲基或吡啶亚甲基,以下基团为卤素、CN、NO2、C1-C8烷基、C1-C8卤代烷基、C1-C8烷氧基、C1-C8卤代烷氧基、C1-C8烷氧基羰基、C1-C8烷硫基、C1-C8烷基磺酰基;
R10选自氢、C1-C6烷基、C1-C6卤代烷基、C1-C6烷氧基羰基、C1-C6烷基羰基、C1-C6卤代烷基羰基、C3-C6环烷基羰基、C3-C6卤代环烷基羰基、C1-C6烷基磺酰基、C1-C6卤代烷基磺酰基、C1-C6烷基氨基磺酰基、二(C1-C6)烷基氨基磺酰基、C1-C6烷基氨基羰基、二(C1-C6)烷基氨基羰基、二(C1-C6)烷基氨基硫代羰基、C1-C6烷硫基C2-C6烷基羰基,未取代或者被1-4个独立选自以下基团取代的苯基、苯基C1-C2烷基、苯基C2-C4烯基、苯基羰基、苯基C1-C2烷基羰基、苯氧基C1-C2烷基羰基、苯基C2-C4烯基羰基、杂芳基、杂芳基C1-C2烷基、杂芳基羰基,以下基团为卤素、CN、NO2、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基、C1-C4卤代烷氧基、C1-C4烷氧基羰基、C1-C4烷硫基、C1-C4烷基磺酰基或被1-4个卤素、CN、NO2、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基或C1-C4卤代烷氧基独立取代的苯氧基;
R11、R12分别选自氢、C1-C6烷基、C1-C6卤代烷基、C1-C6烷氧基羰基C1-C6烷基、SO2NH(C1-C6烷基)或SO2N(C1-C6烷基)(C1-C6烷基);
X选自O、S、NCH3、NN(CH3)2、NCN或NOCH3;
R5、R6选自不同取代基时所连接的碳原子为不对称碳原子,其构型为R或S;
R7、R8选自不同取代基时所连接的碳原子为不对称碳原子,其构型为R或S;或,式(I)所示化合物、式(I)所示化合物的旋光异构体的可农用盐或衍生物。
2.按照权利要求1所述的化合物,其特征在于:通式(I)中
R1、R2分别选自C1-C4烷基或C1-C4卤代烷基;
R3、R4分别选自氢、卤素、C1-C6烷基或C1-C6烷氧基;
R5选自氢或C1-C6烷基;
R6选自氢、C1-C6烷基、CO2R9或CH2OR10;
R7选自氢、氰基、C1-C6烷基、C1-C6卤代烷基、C1-C6烷基CO2R9、CO2R9、CH2OR10、CH2NR11R12或CONR11R12;
R8选自氢、C1-C6烷基、C1-C6卤代烷基、苯基或被1-4个独立选自以下基团取代的苯基:卤素、CN、NO2、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基、C1-C4卤代烷氧基、C1-C4烷氧基羰基、C1-C4烷硫基或C1-C4烷基磺酰基;
R9选自氢、C1-C6烷基、C3-C4烯基、C1-C6卤代烷基、C3-C4炔基、C1-C4烷氧基C1-C4烷基、C1-C4烷羰基氧基C2-C3烷基,未取代或者被1-4个独立选自以下基团取代的苄基、呋喃亚甲基或四氢呋喃亚甲基:卤素、CN、NO2、C1-C6烷基或C1-C6卤代烷基;
R10选自氢、C1-C6烷基、C1-C6卤代烷基、C1-C6烷氧基羰基、C1-C6烷基羰基、C1-C6卤代烷基羰基、C3-C6环烷基羰基、C3-C6卤代环烷基羰基、C1-C6烷基磺酰基、C1-C6卤代烷基磺酰基、C1-C6烷基氨基磺酰基、二(C1-C6)烷基氨基磺酰基、C1-C6烷基氨基羰基、二(C1-C6)烷基氨基羰基、二(C1-C6)烷基氨基硫代羰基、C1-C6烷硫基C2-C6烷基羰基,未取代或者被1-4个独立选自以下基团取代的苯基C1-C2烷基、苯基羰基、苯基C1-C2烷基羰基、苯基C2-C4烯基羰基、苯氧基C1-C2烷基羰基、噻吩羰基、吡唑羰基、喹啉羰基:卤素、CN、NO2、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基、C1-C4卤代烷氧基、C1-C4烷氧基羰基、C1-C4烷硫基、C1-C4烷基磺酰基或被1-4个卤素、CN、NO2、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基或C1-C4卤代烷氧基独立取代的苯氧基;
R11、R12分别选自氢、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基羰基C1-C4烷基、SO2NH(C1-C4烷基)或SO2N(C1-C4烷基)(C1-C4烷基);
X选自O、S、NCH3、NN(CH3)2、NCN或NOCH3;
R5、R6选自不同取代基时所连接的碳原子为不对称碳原子,其构型为R或S;
R7、R8选自不同取代基时所连接的碳原子为不对称碳原子,其构型为R或S;或,式(I)所示化合物、式(I)所示化合物的旋光异构体的可农用盐或衍生物。
3.按照权利要求2所述的化合物,其特征在于:通式(I)中
R1、R2分别选自甲基、乙基、正丙基、正丁基、异丙基或叔丁基;
R3、R4分别选自氢、氟、氯或甲基;
R5选自氢;
R6选自氢;
R7选自氢、氰基、甲基、乙基、正丙基、正丁基、异丙基、异丁基、叔丁基、C1-C3烷基CO2R9、CO2R9、CH2OR10、CH2NR11R12或CONR11R12;
R8选自氢、C1-C4烷基、C1-C4卤代烷基、苯基或被1-4个独立选自以下基团取代的苯基:卤素、CN、NO2、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基或C1-C4卤代烷氧基;
R9选自氢、C1-C4烷基、C1-C4卤代烷基、烯丙基、炔丙基、C1-C3烷氧基C1-C3烷基、C1-C4烷羰基氧基C2-C3烷基,未取代或者被1-4个独立选自以下基团取代的苄基、呋喃亚甲基或四氢呋喃亚甲基:卤素、CN、NO2或C1-C4烷基;
R10选自氢、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基羰基、C1-C4烷基羰基、C1-C4卤代烷基羰基、C3-C6环烷基羰基、C1-C4烷基磺酰基、C1-C4卤代烷基磺酰基、二(C1-C3)烷基氨基磺酰基、C1-C3烷基氨基羰基、二(C1-C3)烷基氨基羰基、二(C1-C3)烷基氨基硫代羰基、C1-C2烷硫基C2-C4烷基羰基,未取代或者被1-4个独立选自以下基团的苯基羰基、苯基C1-C2烷基羰基或苯氧基C1-C2烷基羰基:卤素、CN、NO2、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基或C1-C4卤代烷氧基;
R11、R12分别选自氢、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基羰基C1-C2烷基、SO2NH(C1-C4烷基)或SO2N(C1-C2烷基)(C1-C4烷基);
X选自O、S、NCH3、NN(CH3)2、NCN或NOCH3;
R7、R8选自不同取代基时所连接的碳原子为不对称碳原子,其构型为R或S;或,式(I)所示化合物、式(I)所示化合物的旋光异构体的可农用盐或衍生物。
4.按照权利要求3所述的化合物,其特征在于:通式(I)中
R1、R2分别选自甲基或乙基;
R3、R4分别选自氢、氟、氯或甲基;
R5选自氢;
R6选自氢;
R7选自氢、氰基、甲基、乙基、正丙基、正丁基、异丙基、异丁基、叔丁基、CH2CO2R9、CH2CH2CO2R9、CO2R9、CH2OR10或CONR11R12;
R8选自氢、甲基、乙基、三氟甲基、二氟甲基、苯基或被1-4个独立选自以下基团取代的苯基:卤素、CN、NO2、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基或C1-C4卤代烷氧基;
R9选自氢、甲基、乙基、正丙基、正丁基、异丙基、异丁基、叔丁基、三氟乙基、烯丙基、炔丙基、甲氧基乙基、乙氧基乙基、甲基羰基氧基乙基或四氢呋喃亚甲基;
R10选自氢、C1-C4烷氧基羰基、C1-C4烷基羰基、C1-C4卤代烷基羰基、C3-C6环烷基羰基、C1-C4烷基磺酰基、C1-C4卤代烷基磺酰基、二(C1-C2)烷基氨基磺酰基、C1-C2烷基氨基羰基、二(C1-C3)烷基氨基羰基、二(C1-C2)烷基氨基硫代羰基、C1-C2烷硫基C2-C4烷基羰基,未取代或者被1-4个独立选自以下基团的苯基羰基、苯基C1-C2烷基羰基或苯氧基C1-C2烷基羰基:卤素、CN、NO2、C1-C4烷基、C1-C4卤代烷基、C1-C4烷氧基或C1-C4卤代烷氧基;
R11选自氢、C1-C4烷基或C1-C4卤代烷基;
R12选自氢、C1-C4烷基、C1-C4烷氧基羰基C1-C4烷基、SO2NH(C1-C4烷基)或SO2N(C1-C2烷基)(C1-C4烷基);
X选自O、S、NCH3、NN(CH3)2、NCN或NOCH3;
R7、R8选自不同取代基时所连接的碳原子为不对称碳原子,其构型为R或S;或,式(I)所示化合物、式(I)所示化合物的旋光异构体的可农用盐或衍生物。
5.按照权利要求4所述的化合物,其特征在于:通式(I)中
R1、R2分别选自甲基或乙基;
R3、R4分别选自氢、氟、氯或甲基;
R5选自氢;
R6选自氢;
R7选自氢、氰基、甲基、乙基、正丙基、正丁基、异丙基、异丁基、叔丁基、CH2CO2R9、CH2CH2CO2R9、CO2R9、CH2OR10或CONR11R12;
R8选自氢、甲基、乙基、三氟甲基、二氟甲基、正丙基、正丁基、异丙基、叔丁基、苯基或被1-4个独立选自以下基团取代的苯基:卤素、CN、NO2或C1-C4烷基;
R9选自氢、甲基、乙基、正丙基、正丁基、异丙基、异丁基、叔丁基、三氟乙基、烯丙基、炔丙基、甲氧基乙基、乙氧基乙基、甲基羰基氧基乙基或四氢呋喃亚甲基;
R10选自氢、C1-C4烷基羰基、C1-C4卤代烷基羰基、环丙甲酰基、C1-C4烷基磺酰基或C1-C4卤代烷基磺酰基;
R11选自氢、C1-C4烷基或C1-C4卤代烷基;
R12选自氢、C1-C4烷基、C1-C4烷氧基羰基C1-C4烷基、SO2NH(C1-C4烷基)或SO2N(C1-C2烷基)(C1-C4烷基);
X选自O或S;
R7、R8选自不同取代基时所连接的碳原子为不对称碳原子,其构型为R或S;或,式(I)所示化合物、式(I)所示化合物的旋光异构体的可农用盐或衍生物。
6.按照权利要求5所述的化合物,其特征在于:通式(I)中
R1、R2分别选自甲基;
R3、R4分别选自氢、氟或氯;
R5选自氢;
R6选自氢;
R7选自氢、氰基、甲基、乙基、正丙基、正丁基、异丙基、异丁基、叔丁基、CH2CO2CH3、CH2CO2C2H5、CH2CH2CO2CH3、CH2CH2CO2C2H5、CO2R9或CH2OR10;
R8选自氢、甲基、乙基或三氟甲基;
R9选自氢、甲基、乙基、正丙基、正丁基、异丙基、异丁基、叔丁基、三氟乙基、烯丙基、炔丙基、甲氧基乙基、乙氧基乙基、甲基羰基氧基乙基或四氢呋喃亚甲基;
R10选自氢、C1-C4烷基羰基、C1-C4卤代烷基羰基、环丙甲酰基、C1-C4烷基磺酰基或C1-C4卤代烷基磺酰基。
X选自O或S;
R7、R8选自不同时所连接的碳原子为不对称碳原子,其构型为R或者S;
或,式(I)所示化合物、式(I)所示化合物的旋光异构体的可农用盐或衍生物。
7.一种根据权利要求1所述的通式(I)化合物在用于防治杂草的应用。
8.一种除草制剂,其特征在于:制剂以权利要求1所述的通式(I)化合物作为有效活性成分,与农业上可接受的载体和至少一种助剂混合;有效成分占制剂重量的1~99%。
9.一种权利要求8所述除草制剂的应用,其特征在于:所述除草剂在防除农作物耕地、园林地或非耕地中的一年生及多年生杂草、抗性或耐性杂草的应用。
10.一种除草组合物,其特征在于:组合物为活性成分A与活性成分B和/或活性成分C;其中,
活性成分A为至少一种以权利要求1所述的通式(I)化合物、具有羧基的式(I)化合物的农用盐或其衍生物;活性成分B为至少一种除草剂化合物、其盐或其衍生物;活性成分C为至少一种安全剂化合物、其盐或其衍生物;活性成分A和活性成分B质量份数比为1:100-100:1;活性成分A和活性成分C质量份数比为1:100-100:1。
11.根据权利要求10所述的除草组合物,其特征在于:所述活性成分B选自b1)-b15)类除草剂化合物,以及b1)-b15)类除草剂化合物的农用盐或衍生物中的一种或几种的混合;
其中,
b1)类脂生物合成抑制剂;
b2)乙酰乳酸合成酶抑制剂(ALS抑制剂);
b3)光合成抑制剂;
b4)原卟啉原氧化酶抑制剂(PPO抑制剂);
b5)色素合成抑制剂;
b6)5-烯醇丙酮莽草酸-3-磷酸合成酶抑制剂(EPSP抑制剂);
b7)谷氨酰胺合成酶抑制剂(GST抑制剂);
b8)7,8-二氢蝶酸合成酶抑制剂(DHP抑制剂);
b9)有丝分裂抑制剂;
b10)极长链脂肪酸合成抑制剂(VLCFA抑制剂);
b11)纤维素生物合成抑制剂;
b12)氧化磷酸化解偶联剂除草剂;
b13)激素合成类除草剂;
b14)激素传导抑制剂;以及
b15)选自由如下组成的其他除草剂:溴丁酰草胺(bromobutide)、氯甲丹(chlorflurenol)、氯甲丹(chlorflurenol-methyl)、环庚草醚(cinmethylin)、苄草隆(cumyluron)、茅草枯(dalapon)、棉隆(dazomet)、野燕枯(difenzoquat)、野燕枯硫酸盐(difenzoquat-metilsulfate)、噻节因(dimethipin)、甲胂钠(DSMA)、香草隆(dymron)、敌草腈(endothal)及其盐、乙苯酰草(etobenzanid)、氟燕灵(flamprop)、氟燕灵(flampropisopropyl)、甲氟燕灵(flamprop-methyl)、强氟燕灵(flamprop-M-isopropyl)、麦草伏(flamprop-M-methyl)、抑草丁酸(flurenol)、抑草丁(flurenol-butyl)、调嘧醇(flurprimidol)、调节膦(fosamine)、调节膦铵盐(fosamine-ammonium)、茚草酮(indanofan)、茚嗪氟草胺(indaziflam)、抑芽丹(maleic hydrazide)、氟草磺(mefluidide)、威百亩(metam)、叠氮甲烷(methyl azide)、溴甲烷(methyl bromide)、苯丙隆(methyl-dymron)、碘甲烷(methyl iodide)、甲胂一钠(MSMA)、油酸(oleic acid)、氯嗪草(oxaziclomefone)、壬酸(pelargonicacid)、稗草畏(pyributicarb)、灭藻醌(quinoclamine)、苯氧丙胺津(triaziflam)、灭草环(tridiphane)、methiozolin和tetflupyrolimet。
所述活性成分C选自解草酮(benoxacor)、解草酸(cloquintocet)、抑害腈(cyometrinil)、cyprosulfamide、烯丙酰草胺(dichlormid)、dicyclonon、dietholate、解草唑(fenchlorazole)、解草啶(fenclorim)、解草安(flurazole)、肟草安(fluxofenim)、解草呋(furilazole)、双苯唑酸(isoxadifen)、吡咯二酸(mefenpyr)、mephenate、萘二甲酸酐(naphthalic anhydride)、解草腈(oxabetrinil)、metcamifen、4-二氯乙酰基-1-氧杂-4-氮杂螺[4.5]癸烷(MON4660,CAS 71526-07-3)、2,2,5-三甲基-3-二氯乙酰基-1,3-唑烷(R-29148,CAS 52836-31-4)和N-(2-甲氧基苯甲酰基)-4-[(甲基氨基羰基)氨基]苯磺酰胺(CAS 129531-12-0)。
12.一种权利要求10所述除草组合物的应用,其特征在于:所述除草剂组合物在防除农作物耕地、园林地或非耕地中的一年生及多年生杂草、抗性或耐性杂草的应用。
13.一种除草制剂,其特征在于:制剂以权利要求10所述除草组合物作为有效活性成分,与农业上可接受的载体和至少一种助剂混合;有效成分占制剂重量的1~99%。
14.一种权利要求13所述除草制剂的应用,其特征在于:所述除草剂组合物在防除农作物耕地、园林地或非耕地中的一年生及多年生杂草、抗性或耐性杂草的应用。
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