CN117642069A - 非编码氨基酸的新型衍生物及其作为除草剂的用途 - Google Patents
非编码氨基酸的新型衍生物及其作为除草剂的用途 Download PDFInfo
- Publication number
- CN117642069A CN117642069A CN202280049483.7A CN202280049483A CN117642069A CN 117642069 A CN117642069 A CN 117642069A CN 202280049483 A CN202280049483 A CN 202280049483A CN 117642069 A CN117642069 A CN 117642069A
- Authority
- CN
- China
- Prior art keywords
- methyl
- compound
- composition
- substituted
- applying
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 239000004009 herbicide Substances 0.000 title claims description 61
- 150000001413 amino acids Chemical class 0.000 title claims description 23
- 239000000203 mixture Substances 0.000 claims abstract description 113
- 150000001875 compounds Chemical class 0.000 claims abstract description 106
- 238000000034 method Methods 0.000 claims abstract description 77
- 230000002363 herbicidal effect Effects 0.000 claims abstract description 62
- -1 isooxadiazon Chemical compound 0.000 claims description 104
- 241000196324 Embryophyta Species 0.000 claims description 67
- 229910052740 iodine Inorganic materials 0.000 claims description 53
- 229910052757 nitrogen Inorganic materials 0.000 claims description 51
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 claims description 45
- 150000003839 salts Chemical class 0.000 claims description 41
- 125000003118 aryl group Chemical group 0.000 claims description 38
- 229910052731 fluorine Inorganic materials 0.000 claims description 38
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 37
- 230000008635 plant growth Effects 0.000 claims description 37
- 125000005842 heteroatom Chemical group 0.000 claims description 35
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 32
- 239000005499 Clomazone Substances 0.000 claims description 30
- KIEDNEWSYUYDSN-UHFFFAOYSA-N clomazone Chemical compound O=C1C(C)(C)CON1CC1=CC=CC=C1Cl KIEDNEWSYUYDSN-UHFFFAOYSA-N 0.000 claims description 30
- 125000000217 alkyl group Chemical group 0.000 claims description 28
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 claims description 28
- 229920006395 saturated elastomer Polymers 0.000 claims description 23
- 125000004122 cyclic group Chemical group 0.000 claims description 22
- 229910052760 oxygen Inorganic materials 0.000 claims description 22
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 21
- 239000011814 protection agent Substances 0.000 claims description 21
- 125000004432 carbon atom Chemical group C* 0.000 claims description 20
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 20
- 239000005648 plant growth regulator Substances 0.000 claims description 20
- 239000011734 sodium Substances 0.000 claims description 20
- 125000001072 heteroaryl group Chemical group 0.000 claims description 19
- 229910052717 sulfur Inorganic materials 0.000 claims description 17
- 150000003512 tertiary amines Chemical class 0.000 claims description 17
- 239000005500 Clopyralid Substances 0.000 claims description 16
- PNKUSGQVOMIXLU-UHFFFAOYSA-N Formamidine Chemical group NC=N PNKUSGQVOMIXLU-UHFFFAOYSA-N 0.000 claims description 16
- 239000005588 Oxadiazon Substances 0.000 claims description 16
- CHNUNORXWHYHNE-UHFFFAOYSA-N Oxadiazon Chemical compound C1=C(Cl)C(OC(C)C)=CC(N2C(OC(=N2)C(C)(C)C)=O)=C1Cl CHNUNORXWHYHNE-UHFFFAOYSA-N 0.000 claims description 16
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 16
- HUBANNPOLNYSAD-UHFFFAOYSA-N clopyralid Chemical compound OC(=O)C1=NC(Cl)=CC=C1Cl HUBANNPOLNYSAD-UHFFFAOYSA-N 0.000 claims description 16
- 125000005843 halogen group Chemical group 0.000 claims description 16
- 125000003454 indenyl group Chemical group C1(C=CC2=CC=CC=C12)* 0.000 claims description 16
- WMLPCIHUFDKWJU-UHFFFAOYSA-N Cinosulfuron Chemical compound COCCOC1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(OC)=NC(OC)=N1 WMLPCIHUFDKWJU-UHFFFAOYSA-N 0.000 claims description 15
- XVOKUMIPKHGGTN-UHFFFAOYSA-N Imazethapyr Chemical compound OC(=O)C1=CC(CC)=CN=C1C1=NC(C)(C(C)C)C(=O)N1 XVOKUMIPKHGGTN-UHFFFAOYSA-N 0.000 claims description 15
- ACIAHEMYLLBZOI-ZZXKWVIFSA-N Unsaturated alcohol Chemical group CC\C(CO)=C/C ACIAHEMYLLBZOI-ZZXKWVIFSA-N 0.000 claims description 15
- 230000015572 biosynthetic process Effects 0.000 claims description 15
- 150000003857 carboxamides Chemical class 0.000 claims description 15
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 15
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 claims description 15
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 15
- 238000003786 synthesis reaction Methods 0.000 claims description 15
- 239000003112 inhibitor Substances 0.000 claims description 13
- OORLZFUTLGXMEF-UHFFFAOYSA-N sulfentrazone Chemical compound O=C1N(C(F)F)C(C)=NN1C1=CC(NS(C)(=O)=O)=C(Cl)C=C1Cl OORLZFUTLGXMEF-UHFFFAOYSA-N 0.000 claims description 13
- NUPJIGQFXCQJBK-UHFFFAOYSA-N 2-(4-isopropyl-4-methyl-5-oxo-4,5-dihydro-1H-imidazol-2-yl)-5-(methoxymethyl)nicotinic acid Chemical compound OC(=O)C1=CC(COC)=CN=C1C1=NC(C)(C(C)C)C(=O)N1 NUPJIGQFXCQJBK-UHFFFAOYSA-N 0.000 claims description 12
- 239000005566 Imazamox Substances 0.000 claims description 12
- AMFGTOFWMRQMEM-UHFFFAOYSA-N triazophos Chemical compound N1=C(OP(=S)(OCC)OCC)N=CN1C1=CC=CC=C1 AMFGTOFWMRQMEM-UHFFFAOYSA-N 0.000 claims description 12
- UWHURBUBIHUHSU-UHFFFAOYSA-N 2-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)carbamoylsulfamoyl]benzoic acid Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(O)=O)=N1 UWHURBUBIHUHSU-UHFFFAOYSA-N 0.000 claims description 11
- 239000005562 Glyphosate Substances 0.000 claims description 11
- VAIZTNZGPYBOGF-UHFFFAOYSA-N butyl 2-(4-{[5-(trifluoromethyl)pyridin-2-yl]oxy}phenoxy)propanoate Chemical group C1=CC(OC(C)C(=O)OCCCC)=CC=C1OC1=CC=C(C(F)(F)F)C=N1 VAIZTNZGPYBOGF-UHFFFAOYSA-N 0.000 claims description 11
- XDDAORKBJWWYJS-UHFFFAOYSA-N glyphosate Chemical compound OC(=O)CNCP(O)(O)=O XDDAORKBJWWYJS-UHFFFAOYSA-N 0.000 claims description 11
- 229940097068 glyphosate Drugs 0.000 claims description 11
- 239000005531 Flufenacet Substances 0.000 claims description 10
- 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 claims description 10
- 239000005591 Pendimethalin Substances 0.000 claims description 10
- YLPGTOIOYRQOHV-UHFFFAOYSA-N Pretilachlor Chemical compound CCCOCCN(C(=O)CCl)C1=C(CC)C=CC=C1CC YLPGTOIOYRQOHV-UHFFFAOYSA-N 0.000 claims description 10
- IANUJLZYFUDJIH-UHFFFAOYSA-N flufenacet Chemical compound C=1C=C(F)C=CC=1N(C(C)C)C(=O)COC1=NN=C(C(F)(F)F)S1 IANUJLZYFUDJIH-UHFFFAOYSA-N 0.000 claims description 10
- CHIFOSRWCNZCFN-UHFFFAOYSA-N pendimethalin Chemical compound CCC(CC)NC1=C([N+]([O-])=O)C=C(C)C(C)=C1[N+]([O-])=O CHIFOSRWCNZCFN-UHFFFAOYSA-N 0.000 claims description 10
- USSIUIGPBLPCDF-KEBDBYFISA-N pyriminobac-methyl Chemical group CO\N=C(/C)C1=CC=CC(OC=2N=C(OC)C=C(OC)N=2)=C1C(=O)OC USSIUIGPBLPCDF-KEBDBYFISA-N 0.000 claims description 10
- 239000005631 2,4-Dichlorophenoxyacetic acid Substances 0.000 claims description 9
- IAJOBQBIJHVGMQ-UHFFFAOYSA-N 2-amino-4-[hydroxy(methyl)phosphoryl]butanoic acid Chemical compound CP(O)(=O)CCC(N)C(O)=O IAJOBQBIJHVGMQ-UHFFFAOYSA-N 0.000 claims description 9
- 239000005476 Bentazone Substances 0.000 claims description 9
- 239000005592 Penoxsulam Substances 0.000 claims description 9
- SYJGKVOENHZYMQ-UHFFFAOYSA-N Penoxsulam Chemical compound N1=C2C(OC)=CN=C(OC)N2N=C1NS(=O)(=O)C1=C(OCC(F)F)C=CC=C1C(F)(F)F SYJGKVOENHZYMQ-UHFFFAOYSA-N 0.000 claims description 9
- GPGLBXMQFQQXDV-UHFFFAOYSA-N Primisulfuron Chemical compound OC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(OC(F)F)=CC(OC(F)F)=N1 GPGLBXMQFQQXDV-UHFFFAOYSA-N 0.000 claims description 9
- HFCYZXMHUIHAQI-UHFFFAOYSA-N Thidiazuron Chemical compound C=1C=CC=CC=1NC(=O)NC1=CN=NS1 HFCYZXMHUIHAQI-UHFFFAOYSA-N 0.000 claims description 9
- MXWJVTOOROXGIU-UHFFFAOYSA-N atrazine Chemical group CCNC1=NC(Cl)=NC(NC(C)C)=N1 MXWJVTOOROXGIU-UHFFFAOYSA-N 0.000 claims description 9
- ZOMSMJKLGFBRBS-UHFFFAOYSA-N bentazone Chemical compound C1=CC=C2NS(=O)(=O)N(C(C)C)C(=O)C2=C1 ZOMSMJKLGFBRBS-UHFFFAOYSA-N 0.000 claims description 9
- CNBGNNVCVSKAQZ-UHFFFAOYSA-N benzidamine Natural products C12=CC=CC=C2C(OCCCN(C)C)=NN1CC1=CC=CC=C1 CNBGNNVCVSKAQZ-UHFFFAOYSA-N 0.000 claims description 9
- WVQBLGZPHOPPFO-LBPRGKRZSA-N (S)-metolachlor Chemical compound CCC1=CC=CC(C)=C1N([C@@H](C)COC)C(=O)CCl WVQBLGZPHOPPFO-LBPRGKRZSA-N 0.000 claims description 8
- YHKBGVDUSSWOAB-UHFFFAOYSA-N 2-chloro-3-{2-chloro-5-[4-(difluoromethyl)-3-methyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]-4-fluorophenyl}propanoic acid Chemical compound O=C1N(C(F)F)C(C)=NN1C1=CC(CC(Cl)C(O)=O)=C(Cl)C=C1F YHKBGVDUSSWOAB-UHFFFAOYSA-N 0.000 claims description 8
- 239000005944 Chlorpyrifos Substances 0.000 claims description 8
- 239000005496 Chlorsulfuron Substances 0.000 claims description 8
- 239000005504 Dicamba Substances 0.000 claims description 8
- 239000005507 Diflufenican Substances 0.000 claims description 8
- 239000005586 Nicosulfuron Substances 0.000 claims description 8
- 239000005616 Rimsulfuron Substances 0.000 claims description 8
- SBPBAQFWLVIOKP-UHFFFAOYSA-N chlorpyrifos Chemical compound CCOP(=S)(OCC)OC1=NC(Cl)=C(Cl)C=C1Cl SBPBAQFWLVIOKP-UHFFFAOYSA-N 0.000 claims description 8
- 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 claims description 8
- MZZBPDKVEFVLFF-UHFFFAOYSA-N cyanazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)(C)C#N)=N1 MZZBPDKVEFVLFF-UHFFFAOYSA-N 0.000 claims description 8
- IWEDIXLBFLAXBO-UHFFFAOYSA-N dicamba Chemical group COC1=C(Cl)C=CC(Cl)=C1C(O)=O IWEDIXLBFLAXBO-UHFFFAOYSA-N 0.000 claims description 8
- WYEHFWKAOXOVJD-UHFFFAOYSA-N diflufenican Chemical compound FC1=CC(F)=CC=C1NC(=O)C1=CC=CN=C1OC1=CC=CC(C(F)(F)F)=C1 WYEHFWKAOXOVJD-UHFFFAOYSA-N 0.000 claims description 8
- BGZZWXTVIYUUEY-UHFFFAOYSA-N fomesafen Chemical compound C1=C([N+]([O-])=O)C(C(=O)NS(=O)(=O)C)=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 BGZZWXTVIYUUEY-UHFFFAOYSA-N 0.000 claims description 8
- RTCOGUMHFFWOJV-UHFFFAOYSA-N nicosulfuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CN=2)C(=O)N(C)C)=N1 RTCOGUMHFFWOJV-UHFFFAOYSA-N 0.000 claims description 8
- MEFOUWRMVYJCQC-UHFFFAOYSA-N rimsulfuron Chemical compound CCS(=O)(=O)C1=CC=CN=C1S(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 MEFOUWRMVYJCQC-UHFFFAOYSA-N 0.000 claims description 8
- 239000002794 2,4-DB Substances 0.000 claims description 7
- YIVXMZJTEQBPQO-UHFFFAOYSA-N 2,4-DB Chemical compound OC(=O)CCCOC1=CC=C(Cl)C=C1Cl YIVXMZJTEQBPQO-UHFFFAOYSA-N 0.000 claims description 7
- MZHCENGPTKEIGP-UHFFFAOYSA-N 2-(2,4-dichlorophenoxy)propanoic acid Chemical compound OC(=O)C(C)OC1=CC=C(Cl)C=C1Cl MZHCENGPTKEIGP-UHFFFAOYSA-N 0.000 claims description 7
- 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 claims description 7
- LLWADFLAOKUBDR-UHFFFAOYSA-N 2-methyl-4-chlorophenoxybutyric acid Chemical compound CC1=CC(Cl)=CC=C1OCCCC(O)=O LLWADFLAOKUBDR-UHFFFAOYSA-N 0.000 claims description 7
- ZPSJGADGUYYRKE-UHFFFAOYSA-N 2H-pyran-2-one Chemical compound O=C1C=CC=CO1 ZPSJGADGUYYRKE-UHFFFAOYSA-N 0.000 claims description 7
- UPMXNNIRAGDFEH-UHFFFAOYSA-N 3,5-dibromo-4-hydroxybenzonitrile Chemical compound OC1=C(Br)C=C(C#N)C=C1Br UPMXNNIRAGDFEH-UHFFFAOYSA-N 0.000 claims description 7
- MBFHUWCOCCICOK-UHFFFAOYSA-N 4-iodo-2-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)carbamoylsulfamoyl]benzoic acid Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=C(I)C=2)C(O)=O)=N1 MBFHUWCOCCICOK-UHFFFAOYSA-N 0.000 claims description 7
- VTNQPKFIQCLBDU-UHFFFAOYSA-N Acetochlor Chemical compound CCOCN(C(=O)CCl)C1=C(C)C=CC=C1CC VTNQPKFIQCLBDU-UHFFFAOYSA-N 0.000 claims description 7
- 239000005489 Bromoxynil Substances 0.000 claims description 7
- 239000005497 Clethodim Substances 0.000 claims description 7
- GUVLYNGULCJVDO-UHFFFAOYSA-N EPTC Chemical compound CCCN(CCC)C(=O)SCC GUVLYNGULCJVDO-UHFFFAOYSA-N 0.000 claims description 7
- UWVKRNOCDUPIDM-UHFFFAOYSA-N Ethoxysulfuron Chemical compound CCOC1=CC=CC=C1OS(=O)(=O)NC(=O)NC1=NC(OC)=CC(OC)=N1 UWVKRNOCDUPIDM-UHFFFAOYSA-N 0.000 claims description 7
- 239000005514 Flazasulfuron Substances 0.000 claims description 7
- HWATZEJQIXKWQS-UHFFFAOYSA-N Flazasulfuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CN=2)C(F)(F)F)=N1 HWATZEJQIXKWQS-UHFFFAOYSA-N 0.000 claims description 7
- 239000005561 Glufosinate Substances 0.000 claims description 7
- 239000005568 Iodosulfuron Substances 0.000 claims description 7
- 239000005571 Isoxaflutole Substances 0.000 claims description 7
- 239000005574 MCPA Substances 0.000 claims description 7
- 239000005575 MCPB Substances 0.000 claims description 7
- 101150039283 MCPB gene Proteins 0.000 claims description 7
- 239000005578 Mesotrione Substances 0.000 claims description 7
- 239000005580 Metazachlor Substances 0.000 claims description 7
- CSPPKDPQLUUTND-NBVRZTHBSA-N Sethoxydim Chemical compound CCO\N=C(/CCC)C1=C(O)CC(CC(C)SCC)CC1=O CSPPKDPQLUUTND-NBVRZTHBSA-N 0.000 claims description 7
- 239000005621 Terbuthylazine Substances 0.000 claims description 7
- 239000005623 Thifensulfuron-methyl Substances 0.000 claims description 7
- WHKUVVPPKQRRBV-UHFFFAOYSA-N Trasan Chemical compound CC1=CC(Cl)=CC=C1OCC(O)=O WHKUVVPPKQRRBV-UHFFFAOYSA-N 0.000 claims description 7
- 208000014347 autosomal dominant hyaline body myopathy Diseases 0.000 claims description 7
- FUHMZYWBSHTEDZ-UHFFFAOYSA-M bispyribac-sodium Chemical compound [Na+].COC1=CC(OC)=NC(OC=2C(=C(OC=3N=C(OC)C=C(OC)N=3)C=CC=2)C([O-])=O)=N1 FUHMZYWBSHTEDZ-UHFFFAOYSA-M 0.000 claims description 7
- JBDHZKLJNAIJNC-LLVKDONJSA-N clodinafop-propargyl Chemical group C1=CC(O[C@H](C)C(=O)OCC#C)=CC=C1OC1=NC=C(Cl)C=C1F JBDHZKLJNAIJNC-LLVKDONJSA-N 0.000 claims description 7
- SDIXRDNYIMOKSG-UHFFFAOYSA-L disodium methyl arsenate Chemical compound [Na+].[Na+].C[As]([O-])([O-])=O SDIXRDNYIMOKSG-UHFFFAOYSA-L 0.000 claims description 7
- PQKBPHSEKWERTG-LLVKDONJSA-N ethyl (2r)-2-[4-[(6-chloro-1,3-benzoxazol-2-yl)oxy]phenoxy]propanoate Chemical group C1=CC(O[C@H](C)C(=O)OCC)=CC=C1OC1=NC2=CC=C(Cl)C=C2O1 PQKBPHSEKWERTG-LLVKDONJSA-N 0.000 claims description 7
- PUIYMUZLKQOUOZ-UHFFFAOYSA-N isoproturon Chemical compound CC(C)C1=CC=C(NC(=O)N(C)C)C=C1 PUIYMUZLKQOUOZ-UHFFFAOYSA-N 0.000 claims description 7
- OYIKARCXOQLFHF-UHFFFAOYSA-N isoxaflutole Chemical compound CS(=O)(=O)C1=CC(C(F)(F)F)=CC=C1C(=O)C1=C(C2CC2)ON=C1 OYIKARCXOQLFHF-UHFFFAOYSA-N 0.000 claims description 7
- 229940088649 isoxaflutole Drugs 0.000 claims description 7
- XIGAUIHYSDTJHW-UHFFFAOYSA-N mefenacet Chemical compound N=1C2=CC=CC=C2SC=1OCC(=O)N(C)C1=CC=CC=C1 XIGAUIHYSDTJHW-UHFFFAOYSA-N 0.000 claims description 7
- KPUREKXXPHOJQT-UHFFFAOYSA-N mesotrione Chemical compound [O-][N+](=O)C1=CC(S(=O)(=O)C)=CC=C1C(=O)C1C(=O)CCCC1=O KPUREKXXPHOJQT-UHFFFAOYSA-N 0.000 claims description 7
- STEPQTYSZVCJPV-UHFFFAOYSA-N metazachlor Chemical compound CC1=CC=CC(C)=C1N(C(=O)CCl)CN1N=CC=C1 STEPQTYSZVCJPV-UHFFFAOYSA-N 0.000 claims description 7
- JITOKQVGRJSHHA-UHFFFAOYSA-M monosodium methyl arsenate Chemical compound [Na+].C[As](O)([O-])=O JITOKQVGRJSHHA-UHFFFAOYSA-M 0.000 claims description 7
- AIMMSOZBPYFASU-UHFFFAOYSA-N n-(4,6-dimethoxypyrimidin-2-yl)-n'-[3-(2,2,2-trifluoroethoxy)pyridin-1-ium-2-yl]sulfonylcarbamimidate Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CN=2)OCC(F)(F)F)=N1 AIMMSOZBPYFASU-UHFFFAOYSA-N 0.000 claims description 7
- FZXISNSWEXTPMF-UHFFFAOYSA-N terbutylazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)(C)C)=N1 FZXISNSWEXTPMF-UHFFFAOYSA-N 0.000 claims description 7
- AHTPATJNIAFOLR-UHFFFAOYSA-N thifensulfuron-methyl Chemical group S1C=CC(S(=O)(=O)NC(=O)NC=2N=C(OC)N=C(C)N=2)=C1C(=O)OC AHTPATJNIAFOLR-UHFFFAOYSA-N 0.000 claims description 7
- 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 claims description 7
- RORFIYBSDKQWBH-UHFFFAOYSA-N 2-chloro-2-phenoxypropanoic acid Chemical compound OC(=O)C(Cl)(C)OC1=CC=CC=C1 RORFIYBSDKQWBH-UHFFFAOYSA-N 0.000 claims description 6
- SJOPUJCPGGXQKF-UHFFFAOYSA-N 3-methyl-2h-oxazine Chemical compound CC1=CC=CON1 SJOPUJCPGGXQKF-UHFFFAOYSA-N 0.000 claims description 6
- 239000003666 Amidosulfuron Substances 0.000 claims description 6
- CTTHWASMBLQOFR-UHFFFAOYSA-N Amidosulfuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)N(C)S(C)(=O)=O)=N1 CTTHWASMBLQOFR-UHFFFAOYSA-N 0.000 claims description 6
- 235000005781 Avena Nutrition 0.000 claims description 6
- DHHFDKNIEVKVKS-FMOSSLLZSA-N Betanin Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1OC(C(=C1)O)=CC(C[C@H]2C([O-])=O)=C1[N+]2=C\C=C\1C=C(C(O)=O)N[C@H](C(O)=O)C/1 DHHFDKNIEVKVKS-FMOSSLLZSA-N 0.000 claims description 6
- DHHFDKNIEVKVKS-MVUYWVKGSA-N Betanin Natural products O=C(O)[C@@H]1NC(C(=O)O)=C/C(=C\C=[N+]/2\[C@@H](C(=O)[O-])Cc3c\2cc(O)c(O[C@H]2[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O2)c3)/C1 DHHFDKNIEVKVKS-MVUYWVKGSA-N 0.000 claims description 6
- 239000005758 Cyprodinil Substances 0.000 claims description 6
- 239000005781 Fludioxonil Substances 0.000 claims description 6
- 239000005564 Halosulfuron methyl Substances 0.000 claims description 6
- FMGZEUWROYGLAY-UHFFFAOYSA-N Halosulfuron-methyl Chemical group ClC1=NN(C)C(S(=O)(=O)NC(=O)NC=2N=C(OC)C=C(OC)N=2)=C1C(=O)OC FMGZEUWROYGLAY-UHFFFAOYSA-N 0.000 claims description 6
- 239000002253 acid Substances 0.000 claims description 6
- 150000003862 amino acid derivatives Chemical class 0.000 claims description 6
- 239000001654 beetroot red Substances 0.000 claims description 6
- 235000012677 beetroot red Nutrition 0.000 claims description 6
- PPWBRCCBKOWDNB-UHFFFAOYSA-N bensulfuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)CC=2C(=CC=CC=2)C(O)=O)=N1 PPWBRCCBKOWDNB-UHFFFAOYSA-N 0.000 claims description 6
- 235000002185 betanin Nutrition 0.000 claims description 6
- HAORKNGNJCEJBX-UHFFFAOYSA-N cyprodinil Chemical compound N=1C(C)=CC(C2CC2)=NC=1NC1=CC=CC=C1 HAORKNGNJCEJBX-UHFFFAOYSA-N 0.000 claims description 6
- GINFBXXYGUODAT-UHFFFAOYSA-N flucarbazone Chemical compound O=C1N(C)C(OC)=NN1C(=O)NS(=O)(=O)C1=CC=CC=C1OC(F)(F)F GINFBXXYGUODAT-UHFFFAOYSA-N 0.000 claims description 6
- MUJOIMFVNIBMKC-UHFFFAOYSA-N fludioxonil Chemical compound C=12OC(F)(F)OC2=CC=CC=1C1=CNC=C1C#N MUJOIMFVNIBMKC-UHFFFAOYSA-N 0.000 claims description 6
- 239000000417 fungicide Substances 0.000 claims description 6
- 239000002917 insecticide Substances 0.000 claims description 6
- ODCWYMIRDDJXKW-UHFFFAOYSA-N simazine Chemical compound CCNC1=NC(Cl)=NC(NCC)=N1 ODCWYMIRDDJXKW-UHFFFAOYSA-N 0.000 claims description 6
- 229910052708 sodium Inorganic materials 0.000 claims description 6
- IROINLKCQGIITA-UHFFFAOYSA-N terbutryn Chemical compound CCNC1=NC(NC(C)(C)C)=NC(SC)=N1 IROINLKCQGIITA-UHFFFAOYSA-N 0.000 claims description 6
- 239000004308 thiabendazole Substances 0.000 claims description 6
- WJCNZQLZVWNLKY-UHFFFAOYSA-N thiabendazole Chemical compound S1C=NC(C=2NC3=CC=CC=C3N=2)=C1 WJCNZQLZVWNLKY-UHFFFAOYSA-N 0.000 claims description 6
- 235000010296 thiabendazole Nutrition 0.000 claims description 6
- 229960004546 thiabendazole Drugs 0.000 claims description 6
- ZSDSQXJSNMTJDA-UHFFFAOYSA-N trifluralin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O ZSDSQXJSNMTJDA-UHFFFAOYSA-N 0.000 claims description 6
- 239000008434 yi-zhi Substances 0.000 claims description 6
- IRJQWZWMQCVOLA-ZBKNUEDVSA-N 2-[(z)-n-[(3,5-difluorophenyl)carbamoylamino]-c-methylcarbonimidoyl]pyridine-3-carboxylic acid Chemical compound N=1C=CC=C(C(O)=O)C=1C(/C)=N\NC(=O)NC1=CC(F)=CC(F)=C1 IRJQWZWMQCVOLA-ZBKNUEDVSA-N 0.000 claims description 5
- CABMTIJINOIHOD-UHFFFAOYSA-N 2-[4-methyl-5-oxo-4-(propan-2-yl)-4,5-dihydro-1H-imidazol-2-yl]quinoline-3-carboxylic acid Chemical compound N1C(=O)C(C(C)C)(C)N=C1C1=NC2=CC=CC=C2C=C1C(O)=O CABMTIJINOIHOD-UHFFFAOYSA-N 0.000 claims description 5
- IRCMYGHHKLLGHV-UHFFFAOYSA-N 2-ethoxy-3,3-dimethyl-2,3-dihydro-1-benzofuran-5-yl methanesulfonate Chemical compound C1=C(OS(C)(=O)=O)C=C2C(C)(C)C(OCC)OC2=C1 IRCMYGHHKLLGHV-UHFFFAOYSA-N 0.000 claims description 5
- 239000005512 Ethofumesate Substances 0.000 claims description 5
- 239000005981 Imazaquin Substances 0.000 claims description 5
- NQRFDNJEBWAUBL-UHFFFAOYSA-N N-[cyano(2-thienyl)methyl]-4-ethyl-2-(ethylamino)-1,3-thiazole-5-carboxamide Chemical compound S1C(NCC)=NC(CC)=C1C(=O)NC(C#N)C1=CC=CS1 NQRFDNJEBWAUBL-UHFFFAOYSA-N 0.000 claims description 5
- 239000005604 Prosulfuron Substances 0.000 claims description 5
- LTUNNEGNEKBSEH-UHFFFAOYSA-N Prosulfuron Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)CCC(F)(F)F)=N1 LTUNNEGNEKBSEH-UHFFFAOYSA-N 0.000 claims description 5
- 241000209140 Triticum Species 0.000 claims description 5
- 235000021307 Triticum Nutrition 0.000 claims description 5
- XCSGPAVHZFQHGE-UHFFFAOYSA-N alachlor Chemical compound CCC1=CC=CC(CC)=C1N(COC)C(=O)CCl XCSGPAVHZFQHGE-UHFFFAOYSA-N 0.000 claims description 5
- RIOXQFHNBCKOKP-UHFFFAOYSA-N benomyl Chemical compound C1=CC=C2N(C(=O)NCCCC)C(NC(=O)OC)=NC2=C1 RIOXQFHNBCKOKP-UHFFFAOYSA-N 0.000 claims description 5
- MITFXPHMIHQXPI-UHFFFAOYSA-N benzoxaprofen Natural products N=1C2=CC(C(C(O)=O)C)=CC=C2OC=1C1=CC=C(Cl)C=C1 MITFXPHMIHQXPI-UHFFFAOYSA-N 0.000 claims description 5
- CONWAEURSVPLRM-UHFFFAOYSA-N lactofen Chemical compound C1=C([N+]([O-])=O)C(C(=O)OC(C)C(=O)OCC)=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 CONWAEURSVPLRM-UHFFFAOYSA-N 0.000 claims description 5
- ZTYVMAQSHCZXLF-UHFFFAOYSA-N methyl 2-[[4,6-bis(difluoromethoxy)pyrimidin-2-yl]carbamoylsulfamoyl]benzoate Chemical group COC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(OC(F)F)=CC(OC(F)F)=N1 ZTYVMAQSHCZXLF-UHFFFAOYSA-N 0.000 claims description 5
- XOPFESVZMSQIKC-UHFFFAOYSA-N triasulfuron Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)OCCCl)=N1 XOPFESVZMSQIKC-UHFFFAOYSA-N 0.000 claims description 5
- CAAMSDWKXXPUJR-UHFFFAOYSA-N 3,5-dihydro-4H-imidazol-4-one Chemical compound O=C1CNC=N1 CAAMSDWKXXPUJR-UHFFFAOYSA-N 0.000 claims description 4
- 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 claims description 4
- OFSLKOLYLQSJPB-UHFFFAOYSA-N Cyclosulfamuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)NC=2C(=CC=CC=2)C(=O)C2CC2)=N1 OFSLKOLYLQSJPB-UHFFFAOYSA-N 0.000 claims description 4
- 239000005502 Cyhalofop-butyl Substances 0.000 claims description 4
- TYIYMOAHACZAMQ-CQSZACIVSA-N Cyhalofop-butyl Chemical group C1=CC(O[C@H](C)C(=O)OCCCC)=CC=C1OC1=CC=C(C#N)C=C1F TYIYMOAHACZAMQ-CQSZACIVSA-N 0.000 claims description 4
- YUBJPYNSGLJZPQ-UHFFFAOYSA-N Dithiopyr Chemical compound CSC(=O)C1=C(C(F)F)N=C(C(F)(F)F)C(C(=O)SC)=C1CC(C)C YUBJPYNSGLJZPQ-UHFFFAOYSA-N 0.000 claims description 4
- 239000005510 Diuron Substances 0.000 claims description 4
- VXMNDQDDWDDKOQ-UHFFFAOYSA-N Pyrazosulfuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2N(N=CC=2C(O)=O)C)=N1 VXMNDQDDWDDKOQ-UHFFFAOYSA-N 0.000 claims description 4
- 229940100389 Sulfonylurea Drugs 0.000 claims description 4
- 239000005857 Trifloxystrobin Substances 0.000 claims description 4
- NUFNQYOELLVIPL-UHFFFAOYSA-N acifluorfen Chemical compound C1=C([N+]([O-])=O)C(C(=O)O)=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 NUFNQYOELLVIPL-UHFFFAOYSA-N 0.000 claims description 4
- NOOCSNJCXJYGPE-UHFFFAOYSA-N flunixin Chemical compound C1=CC=C(C(F)(F)F)C(C)=C1NC1=NC=CC=C1C(O)=O NOOCSNJCXJYGPE-UHFFFAOYSA-N 0.000 claims description 4
- 229960000588 flunixin Drugs 0.000 claims description 4
- JZMJDSHXVKJFKW-UHFFFAOYSA-M methyl sulfate(1-) Chemical compound COS([O-])(=O)=O JZMJDSHXVKJFKW-UHFFFAOYSA-M 0.000 claims description 4
- AAEVYOVXGOFMJO-UHFFFAOYSA-N prometryn Chemical compound CSC1=NC(NC(C)C)=NC(NC(C)C)=N1 AAEVYOVXGOFMJO-UHFFFAOYSA-N 0.000 claims description 4
- LFULEKSKNZEWOE-UHFFFAOYSA-N propanil Chemical compound CCC(=O)NC1=CC=C(Cl)C(Cl)=C1 LFULEKSKNZEWOE-UHFFFAOYSA-N 0.000 claims description 4
- 229940124530 sulfonamide Drugs 0.000 claims description 4
- 150000003456 sulfonamides Chemical class 0.000 claims description 4
- YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical class OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 claims description 4
- LOQQVLXUKHKNIA-UHFFFAOYSA-N thifensulfuron Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C2=C(SC=C2)C(O)=O)=N1 LOQQVLXUKHKNIA-UHFFFAOYSA-N 0.000 claims description 4
- ONCZDRURRATYFI-TVJDWZFNSA-N trifloxystrobin Chemical compound CO\N=C(\C(=O)OC)C1=CC=CC=C1CO\N=C(/C)C1=CC=CC(C(F)(F)F)=C1 ONCZDRURRATYFI-TVJDWZFNSA-N 0.000 claims description 4
- XEJNEDVTJPXRSM-UHFFFAOYSA-N 1-(2,4-dichlorophenyl)-5-methyl-4,5-dihydro-1H-pyrazole-3,5-dicarboxylic acid Chemical compound OC(=O)C1(C)CC(C(O)=O)=NN1C1=CC=C(Cl)C=C1Cl XEJNEDVTJPXRSM-UHFFFAOYSA-N 0.000 claims description 3
- YPSCQJTUAKNUNF-UHFFFAOYSA-N 2-chloro-n-[(4-chlorophenyl)carbamoyl]benzamide Chemical compound C1=CC(Cl)=CC=C1NC(=O)NC(=O)C1=CC=CC=C1Cl YPSCQJTUAKNUNF-UHFFFAOYSA-N 0.000 claims description 3
- 239000005472 Bensulfuron methyl Substances 0.000 claims description 3
- YRMLFORXOOIJDR-UHFFFAOYSA-N Dichlormid Chemical compound ClC(Cl)C(=O)N(CC=C)CC=C YRMLFORXOOIJDR-UHFFFAOYSA-N 0.000 claims description 3
- 239000005760 Difenoconazole Substances 0.000 claims description 3
- 239000005630 Diquat Substances 0.000 claims description 3
- 239000005529 Florasulam Substances 0.000 claims description 3
- QZXATCCPQKOEIH-UHFFFAOYSA-N Florasulam Chemical compound N=1N2C(OC)=NC=C(F)C2=NC=1S(=O)(=O)NC1=C(F)C=CC=C1F QZXATCCPQKOEIH-UHFFFAOYSA-N 0.000 claims description 3
- 239000005780 Fluazinam Substances 0.000 claims description 3
- DHAHEVIQIYRFRG-UHFFFAOYSA-N Fluoroglycofen Chemical compound C1=C([N+]([O-])=O)C(C(=O)OCC(=O)O)=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 DHAHEVIQIYRFRG-UHFFFAOYSA-N 0.000 claims description 3
- 239000005867 Iprodione Substances 0.000 claims description 3
- 239000005570 Isoxaben Substances 0.000 claims description 3
- 239000005579 Metamitron Substances 0.000 claims description 3
- 239000005584 Metsulfuron-methyl Substances 0.000 claims description 3
- 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 3
- 239000005590 Oxyfluorfen Substances 0.000 claims description 3
- OQMBBFQZGJFLBU-UHFFFAOYSA-N Oxyfluorfen Chemical compound C1=C([N+]([O-])=O)C(OCC)=CC(OC=2C(=CC(=CC=2)C(F)(F)F)Cl)=C1 OQMBBFQZGJFLBU-UHFFFAOYSA-N 0.000 claims description 3
- 239000005602 Propyzamide Substances 0.000 claims description 3
- 239000005603 Prosulfocarb Substances 0.000 claims description 3
- BGNQYGRXEXDAIQ-UHFFFAOYSA-N Pyrazosulfuron-ethyl Chemical group C1=NN(C)C(S(=O)(=O)NC(=O)NC=2N=C(OC)C=C(OC)N=2)=C1C(=O)OCC BGNQYGRXEXDAIQ-UHFFFAOYSA-N 0.000 claims description 3
- 239000005614 Quizalofop-P-ethyl Substances 0.000 claims description 3
- FYZBOYWSHKHDMT-UHFFFAOYSA-N benfuracarb Chemical compound CCOC(=O)CCN(C(C)C)SN(C)C(=O)OC1=CC=CC2=C1OC(C)(C)C2 FYZBOYWSHKHDMT-UHFFFAOYSA-N 0.000 claims 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 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
- NSWAMPCUPHPTTC-UHFFFAOYSA-N chlorimuron-ethyl Chemical group CCOC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(Cl)=CC(OC)=N1 NSWAMPCUPHPTTC-UHFFFAOYSA-N 0.000 claims description 3
- AFZSMODLJJCVPP-UHFFFAOYSA-N dibenzothiazol-2-yl disulfide Chemical compound C1=CC=C2SC(SSC=3SC4=CC=CC=C4N=3)=NC2=C1 AFZSMODLJJCVPP-UHFFFAOYSA-N 0.000 claims description 3
- BQYJATMQXGBDHF-UHFFFAOYSA-N difenoconazole Chemical compound O1C(C)COC1(C=1C(=CC(OC=2C=CC(Cl)=CC=2)=CC=1)Cl)CN1N=CN=C1 BQYJATMQXGBDHF-UHFFFAOYSA-N 0.000 claims description 3
- SYJFEGQWDCRVNX-UHFFFAOYSA-N diquat Chemical compound C1=CC=[N+]2CC[N+]3=CC=CC=C3C2=C1 SYJFEGQWDCRVNX-UHFFFAOYSA-N 0.000 claims description 3
- OSUHJPCHFDQAIT-UHFFFAOYSA-N ethyl 2-{4-[(6-chloroquinoxalin-2-yl)oxy]phenoxy}propanoate Chemical group C1=CC(OC(C)C(=O)OCC)=CC=C1OC1=CN=C(C=C(Cl)C=C2)C2=N1 OSUHJPCHFDQAIT-UHFFFAOYSA-N 0.000 claims description 3
- VAIZTNZGPYBOGF-CYBMUJFWSA-N fluazifop-P-butyl Chemical group C1=CC(O[C@H](C)C(=O)OCCCC)=CC=C1OC1=CC=C(C(F)(F)F)C=N1 VAIZTNZGPYBOGF-CYBMUJFWSA-N 0.000 claims description 3
- UZCGKGPEKUCDTF-UHFFFAOYSA-N fluazinam Chemical compound [O-][N+](=O)C1=CC(C(F)(F)F)=C(Cl)C([N+]([O-])=O)=C1NC1=NC=C(C(F)(F)F)C=C1Cl UZCGKGPEKUCDTF-UHFFFAOYSA-N 0.000 claims description 3
- ONUFESLQCSAYKA-UHFFFAOYSA-N iprodione Chemical compound O=C1N(C(=O)NC(C)C)CC(=O)N1C1=CC(Cl)=CC(Cl)=C1 ONUFESLQCSAYKA-UHFFFAOYSA-N 0.000 claims description 3
- UFHLMYOGRXOCSL-UHFFFAOYSA-N isoprothiolane Chemical compound CC(C)OC(=O)C(C(=O)OC(C)C)=C1SCCS1 UFHLMYOGRXOCSL-UHFFFAOYSA-N 0.000 claims description 3
- PMHURSZHKKJGBM-UHFFFAOYSA-N isoxaben Chemical compound O1N=C(C(C)(CC)CC)C=C1NC(=O)C1=C(OC)C=CC=C1OC PMHURSZHKKJGBM-UHFFFAOYSA-N 0.000 claims description 3
- VHCNQEUWZYOAEV-UHFFFAOYSA-N metamitron Chemical compound O=C1N(N)C(C)=NN=C1C1=CC=CC=C1 VHCNQEUWZYOAEV-UHFFFAOYSA-N 0.000 claims description 3
- RSMUVYRMZCOLBH-UHFFFAOYSA-N metsulfuron methyl Chemical group COC(=O)C1=CC=CC=C1S(=O)(=O)NC(=O)NC1=NC(C)=NC(OC)=N1 RSMUVYRMZCOLBH-UHFFFAOYSA-N 0.000 claims description 3
- DEDOPGXGGQYYMW-UHFFFAOYSA-N molinate Chemical compound CCSC(=O)N1CCCCCC1 DEDOPGXGGQYYMW-UHFFFAOYSA-N 0.000 claims 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 claims description 3
- NQLVQOSNDJXLKG-UHFFFAOYSA-N prosulfocarb Chemical compound CCCN(CCC)C(=O)SCC1=CC=CC=C1 NQLVQOSNDJXLKG-UHFFFAOYSA-N 0.000 claims description 3
- OSUHJPCHFDQAIT-GFCCVEGCSA-N quizalofop-P-ethyl Chemical group C1=CC(O[C@H](C)C(=O)OCC)=CC=C1OC1=CN=C(C=C(Cl)C=C2)C2=N1 OSUHJPCHFDQAIT-GFCCVEGCSA-N 0.000 claims description 3
- QAZLUNIWYYOJPC-UHFFFAOYSA-M sulfenamide Chemical compound [Cl-].COC1=C(C)C=[N+]2C3=NC4=CC=C(OC)C=C4N3SCC2=C1C QAZLUNIWYYOJPC-UHFFFAOYSA-M 0.000 claims description 3
- 229960005294 triamcinolone Drugs 0.000 claims description 3
- IXWKBUKANTXHJH-UHFFFAOYSA-N 1-[5-chloro-2-methyl-4-(5-methyl-5,6-dihydro-1,4,2-dioxazin-3-yl)pyrazol-3-yl]sulfonyl-3-(4,6-dimethoxypyrimidin-2-yl)urea Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2N(N=C(Cl)C=2C=2OC(C)CON=2)C)=N1 IXWKBUKANTXHJH-UHFFFAOYSA-N 0.000 claims description 2
- 239000005784 Fluoxastrobin Substances 0.000 claims description 2
- CAWXEEYDBZRFPE-UHFFFAOYSA-N Hexazinone Chemical compound O=C1N(C)C(N(C)C)=NC(=O)N1C1CCCCC1 CAWXEEYDBZRFPE-UHFFFAOYSA-N 0.000 claims description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 claims description 2
- RQVYBGPQFYCBGX-UHFFFAOYSA-N ametryn Chemical compound CCNC1=NC(NC(C)C)=NC(SC)=N1 RQVYBGPQFYCBGX-UHFFFAOYSA-N 0.000 claims description 2
- ORFPWVRKFLOQHK-UHFFFAOYSA-N amicarbazone Chemical compound CC(C)C1=NN(C(=O)NC(C)(C)C)C(=O)N1N ORFPWVRKFLOQHK-UHFFFAOYSA-N 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- UFEODZBUAFNAEU-NLRVBDNBSA-N fluoxastrobin Chemical compound C=1C=CC=C(OC=2C(=C(OC=3C(=CC=CC=3)Cl)N=CN=2)F)C=1C(=N/OC)\C1=NOCCO1 UFEODZBUAFNAEU-NLRVBDNBSA-N 0.000 claims description 2
- IAJOBQBIJHVGMQ-BYPYZUCNSA-N glufosinate-P Chemical compound CP(O)(=O)CC[C@H](N)C(O)=O IAJOBQBIJHVGMQ-BYPYZUCNSA-N 0.000 claims description 2
- HYYBABOKPJLUIN-UHFFFAOYSA-N mefenamic acid Chemical compound CC1=CC=CC(NC=2C(=CC=CC=2)C(O)=O)=C1C HYYBABOKPJLUIN-UHFFFAOYSA-N 0.000 claims description 2
- 229960003464 mefenamic acid Drugs 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- 150000003141 primary amines Chemical class 0.000 claims description 2
- DEIKMOQTJBGGAX-DJKKODMXSA-N pyriminobac Chemical compound CO\N=C(/C)C1=CC=CC(OC=2N=C(OC)C=C(OC)N=2)=C1C(O)=O DEIKMOQTJBGGAX-DJKKODMXSA-N 0.000 claims description 2
- 150000003335 secondary amines Chemical class 0.000 claims description 2
- 241000209761 Avena Species 0.000 claims 3
- SILSDTWXNBZOGF-KUZBFYBWSA-N chembl111058 Chemical compound CCSC(C)CC1CC(O)=C(\C(CC)=N\OC\C=C\Cl)C(=O)C1 SILSDTWXNBZOGF-KUZBFYBWSA-N 0.000 claims 3
- ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 claims 2
- WURBVZBTWMNKQT-UHFFFAOYSA-N 1-(4-chlorophenoxy)-3,3-dimethyl-1-(1,2,4-triazol-1-yl)butan-2-one Chemical compound C1=NC=NN1C(C(=O)C(C)(C)C)OC1=CC=C(Cl)C=C1 WURBVZBTWMNKQT-UHFFFAOYSA-N 0.000 claims 1
- 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 claims 1
- 239000005736 Benthiavalicarb Substances 0.000 claims 1
- 239000005885 Buprofezin Substances 0.000 claims 1
- 239000005644 Dazomet Substances 0.000 claims 1
- LXKOADMMGWXPJQ-UHFFFAOYSA-N Halosulfuron Chemical compound COC1=CC(OC)=NC(NC(=O)NS(=O)(=O)C=2N(N=C(Cl)C=2C(O)=O)C)=N1 LXKOADMMGWXPJQ-UHFFFAOYSA-N 0.000 claims 1
- 239000005589 Oxasulfuron Substances 0.000 claims 1
- RRKHIAYNPVQKEF-UHFFFAOYSA-N Pyriftalid Chemical compound COC1=CC(OC)=NC(SC=2C=3C(=O)OC(C)C=3C=CC=2)=N1 RRKHIAYNPVQKEF-UHFFFAOYSA-N 0.000 claims 1
- 125000003275 alpha amino acid group Chemical group 0.000 claims 1
- VVSLYIKSEBPRSN-PELKAZGASA-N benthiavalicarb Chemical compound C1=C(F)C=C2SC([C@@H](C)NC(=O)[C@@H](NC(O)=O)C(C)C)=NC2=C1 VVSLYIKSEBPRSN-PELKAZGASA-N 0.000 claims 1
- PRLVTUNWOQKEAI-VKAVYKQESA-N buprofezin Chemical compound O=C1N(C(C)C)\C(=N\C(C)(C)C)SCN1C1=CC=CC=C1 PRLVTUNWOQKEAI-VKAVYKQESA-N 0.000 claims 1
- QAYICIQNSGETAS-UHFFFAOYSA-N dazomet Chemical compound CN1CSC(=S)N(C)C1 QAYICIQNSGETAS-UHFFFAOYSA-N 0.000 claims 1
- 125000003784 fluoroethyl group Chemical group [H]C([H])(F)C([H])([H])* 0.000 claims 1
- 235000010299 hexamethylene tetramine Nutrition 0.000 claims 1
- VKYKSIONXSXAKP-UHFFFAOYSA-N hexamethylenetetramine Chemical compound C1N(C2)CN3CN1CN2C3 VKYKSIONXSXAKP-UHFFFAOYSA-N 0.000 claims 1
- 229960004011 methenamine Drugs 0.000 claims 1
- IOXAXYHXMLCCJJ-UHFFFAOYSA-N oxetan-3-yl 2-[(4,6-dimethylpyrimidin-2-yl)carbamoylsulfamoyl]benzoate Chemical compound CC1=CC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(=O)OC2COC2)=N1 IOXAXYHXMLCCJJ-UHFFFAOYSA-N 0.000 claims 1
- 150000002923 oximes Chemical class 0.000 claims 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 claims 1
- 239000004299 sodium benzoate Substances 0.000 claims 1
- 235000010234 sodium benzoate Nutrition 0.000 claims 1
- 239000010902 straw Substances 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 abstract description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 21
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 21
- 229910052799 carbon Inorganic materials 0.000 description 20
- 238000012360 testing method Methods 0.000 description 20
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 18
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Natural products CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 14
- 239000000463 material Substances 0.000 description 14
- 239000002689 soil Substances 0.000 description 14
- 238000009472 formulation Methods 0.000 description 13
- 239000007787 solid Substances 0.000 description 13
- 125000001424 substituent group Chemical group 0.000 description 13
- 238000006243 chemical reaction Methods 0.000 description 11
- 239000007788 liquid Substances 0.000 description 11
- 230000012010 growth Effects 0.000 description 10
- 230000009036 growth inhibition Effects 0.000 description 10
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 125000004429 atom Chemical group 0.000 description 9
- 230000000694 effects Effects 0.000 description 9
- 239000002609 medium Substances 0.000 description 9
- YNQLUTRBYVCPMQ-UHFFFAOYSA-N Ethylbenzene Chemical compound CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 8
- 241000208822 Lactuca Species 0.000 description 8
- 235000003228 Lactuca sativa Nutrition 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 7
- 239000002202 Polyethylene glycol Substances 0.000 description 7
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 239000004480 active ingredient Substances 0.000 description 7
- 239000012267 brine Substances 0.000 description 7
- 235000019439 ethyl acetate Nutrition 0.000 description 7
- 239000003921 oil Substances 0.000 description 7
- 235000019198 oils Nutrition 0.000 description 7
- 239000012044 organic layer Substances 0.000 description 7
- 229920001223 polyethylene glycol Polymers 0.000 description 7
- HPALAKNZSZLMCH-UHFFFAOYSA-M sodium;chloride;hydrate Chemical compound O.[Na+].[Cl-] HPALAKNZSZLMCH-UHFFFAOYSA-M 0.000 description 7
- 239000004094 surface-active agent Substances 0.000 description 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
- 239000000969 carrier Substances 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 6
- 229910052739 hydrogen Inorganic materials 0.000 description 6
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 6
- 239000010410 layer Substances 0.000 description 6
- 244000075850 Avena orientalis Species 0.000 description 5
- 239000002671 adjuvant Substances 0.000 description 5
- 239000012141 concentrate Substances 0.000 description 5
- 238000011161 development Methods 0.000 description 5
- 239000003085 diluting agent Substances 0.000 description 5
- 125000006575 electron-withdrawing group Chemical group 0.000 description 5
- 239000000839 emulsion Substances 0.000 description 5
- 230000008121 plant development Effects 0.000 description 5
- 229920001451 polypropylene glycol Polymers 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- ZDDDIYOBAOJYAZ-UHFFFAOYSA-N 1-(2,3-dihydro-1h-inden-1-yl)ethanone Chemical compound C1=CC=C2C(C(=O)C)CCC2=C1 ZDDDIYOBAOJYAZ-UHFFFAOYSA-N 0.000 description 4
- INZNCCYOZSCIAA-UHFFFAOYSA-N 1-(2,3-dihydro-1h-inden-1-yl)propan-1-one Chemical compound C1=CC=C2C(C(=O)CC)CCC2=C1 INZNCCYOZSCIAA-UHFFFAOYSA-N 0.000 description 4
- PIMNFNXBTGPCIL-UHFFFAOYSA-N 1-(2-bromophenyl)ethanone Chemical compound CC(=O)C1=CC=CC=C1Br PIMNFNXBTGPCIL-UHFFFAOYSA-N 0.000 description 4
- ITWQJJVSGURLET-UHFFFAOYSA-N 1-(3h-inden-1-yl)ethanone Chemical compound C1=CC=C2C(C(=O)C)=CCC2=C1 ITWQJJVSGURLET-UHFFFAOYSA-N 0.000 description 4
- NRGGMCIBEHEAIL-UHFFFAOYSA-N 2-ethylpyridine Chemical compound CCC1=CC=CC=N1 NRGGMCIBEHEAIL-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- XBFOCTDLAPFCPL-UHFFFAOYSA-N CCC(C1=CCC2=C1C=CC=C2)=O Chemical compound CCC(C1=CCC2=C1C=CC=C2)=O XBFOCTDLAPFCPL-UHFFFAOYSA-N 0.000 description 4
- 229910019142 PO4 Inorganic materials 0.000 description 4
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 4
- 239000004927 clay Substances 0.000 description 4
- SILSDTWXNBZOGF-JWGBMQLESA-N clethodim Chemical compound CCSC(C)CC1CC(O)=C(C(CC)=NOC\C=C\Cl)C(=O)C1 SILSDTWXNBZOGF-JWGBMQLESA-N 0.000 description 4
- 230000018109 developmental process Effects 0.000 description 4
- 238000002474 experimental method Methods 0.000 description 4
- 235000013312 flour Nutrition 0.000 description 4
- 230000035784 germination Effects 0.000 description 4
- 239000000575 pesticide Substances 0.000 description 4
- 235000021317 phosphate Nutrition 0.000 description 4
- 102000004196 processed proteins & peptides Human genes 0.000 description 4
- 108090000765 processed proteins & peptides Proteins 0.000 description 4
- 239000000047 product Substances 0.000 description 4
- 239000007921 spray Substances 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 description 3
- ODIGIKRIUKFKHP-UHFFFAOYSA-N (n-propan-2-yloxycarbonylanilino) acetate Chemical compound CC(C)OC(=O)N(OC(C)=O)C1=CC=CC=C1 ODIGIKRIUKFKHP-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- 229910021591 Copper(I) chloride Inorganic materials 0.000 description 3
- 229920000742 Cotton Polymers 0.000 description 3
- 244000068988 Glycine max Species 0.000 description 3
- 235000010469 Glycine max Nutrition 0.000 description 3
- 244000299507 Gossypium hirsutum Species 0.000 description 3
- 239000005909 Kieselgur Substances 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 150000001721 carbon Chemical group 0.000 description 3
- 239000003153 chemical reaction reagent Substances 0.000 description 3
- RIUXZHMCCFLRBI-UHFFFAOYSA-N chlorimuron Chemical compound COC1=CC(Cl)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)C(O)=O)=N1 RIUXZHMCCFLRBI-UHFFFAOYSA-N 0.000 description 3
- OXBLHERUFWYNTN-UHFFFAOYSA-M copper(I) chloride Chemical compound [Cu]Cl OXBLHERUFWYNTN-UHFFFAOYSA-M 0.000 description 3
- 239000004495 emulsifiable concentrate Substances 0.000 description 3
- 230000009969 flowable effect Effects 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 239000004615 ingredient Substances 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 108090000623 proteins and genes Proteins 0.000 description 3
- 102000004169 proteins and genes Human genes 0.000 description 3
- 238000000746 purification Methods 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 230000007226 seed germination Effects 0.000 description 3
- 238000006467 substitution reaction Methods 0.000 description 3
- IOGXOCVLYRDXLW-UHFFFAOYSA-N tert-butyl nitrite Chemical compound CC(C)(C)ON=O IOGXOCVLYRDXLW-UHFFFAOYSA-N 0.000 description 3
- 239000012414 tert-butyl nitrite Substances 0.000 description 3
- 238000001644 13C nuclear magnetic resonance spectroscopy Methods 0.000 description 2
- 238000004293 19F NMR spectroscopy Methods 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
- 102000052866 Amino Acyl-tRNA Synthetases Human genes 0.000 description 2
- 108700028939 Amino Acyl-tRNA Synthetases Proteins 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 2
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- SBJKKFFYIZUCET-JLAZNSOCSA-N Dehydro-L-ascorbic acid Chemical compound OC[C@H](O)[C@H]1OC(=O)C(=O)C1=O SBJKKFFYIZUCET-JLAZNSOCSA-N 0.000 description 2
- KRHAHEQEKNJCSD-UHFFFAOYSA-N Dihydroasparagusic acid Natural products OC(=O)C(CS)CS KRHAHEQEKNJCSD-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- BZLVMXJERCGZMT-UHFFFAOYSA-N Methyl tert-butyl ether Chemical compound COC(C)(C)C BZLVMXJERCGZMT-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 2
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 2
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 2
- 240000008042 Zea mays Species 0.000 description 2
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 2
- 235000002017 Zea mays subsp mays Nutrition 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 125000000304 alkynyl group Chemical group 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 230000000975 bioactive effect Effects 0.000 description 2
- 238000004166 bioassay Methods 0.000 description 2
- 239000011203 carbon fibre reinforced carbon Substances 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 230000001413 cellular effect Effects 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 238000004440 column chromatography Methods 0.000 description 2
- 235000005822 corn Nutrition 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- JYGAZEJXUVDYHI-UHFFFAOYSA-N dihydroartemisininic acid Natural products C1CC(C)=CC2C(C(C)C(O)=O)CCC(C)C21 JYGAZEJXUVDYHI-UHFFFAOYSA-N 0.000 description 2
- 235000021186 dishes Nutrition 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000000428 dust Substances 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- GDBMSRIBYRPJFM-UHFFFAOYSA-N ethyl 2-(2-amino-1,3-thiazol-4-yl)-2,2-difluoroacetate Chemical compound CCOC(=O)C(F)(F)C1=CSC(N)=N1 GDBMSRIBYRPJFM-UHFFFAOYSA-N 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 239000000284 extract Substances 0.000 description 2
- 239000003337 fertilizer Substances 0.000 description 2
- 239000008187 granular material Substances 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 230000002262 irrigation Effects 0.000 description 2
- 238000003973 irrigation Methods 0.000 description 2
- QPJVMBTYPHYUOC-UHFFFAOYSA-N methyl benzoate Chemical compound COC(=O)C1=CC=CC=C1 QPJVMBTYPHYUOC-UHFFFAOYSA-N 0.000 description 2
- 239000004530 micro-emulsion Substances 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 125000002950 monocyclic group Chemical group 0.000 description 2
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- 150000002894 organic compounds Chemical class 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 125000001820 oxy group Chemical group [*:1]O[*:2] 0.000 description 2
- 125000004430 oxygen atom Chemical group O* 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 2
- 239000010452 phosphate Substances 0.000 description 2
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 2
- 230000035790 physiological processes and functions Effects 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000021 stimulant Substances 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 230000035882 stress Effects 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- 238000001665 trituration Methods 0.000 description 2
- 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 1
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 description 1
- ADDQHLREJDZPMT-AWEZNQCLSA-N (S)-metamifop Chemical compound O=C([C@@H](OC=1C=CC(OC=2OC3=CC(Cl)=CC=C3N=2)=CC=1)C)N(C)C1=CC=CC=C1F ADDQHLREJDZPMT-AWEZNQCLSA-N 0.000 description 1
- PXMNMQRDXWABCY-UHFFFAOYSA-N 1-(4-chlorophenyl)-4,4-dimethyl-3-(1H-1,2,4-triazol-1-ylmethyl)pentan-3-ol Chemical compound C1=NC=NN1CC(O)(C(C)(C)C)CCC1=CC=C(Cl)C=C1 PXMNMQRDXWABCY-UHFFFAOYSA-N 0.000 description 1
- 125000004972 1-butynyl group Chemical group [H]C([H])([H])C([H])([H])C#C* 0.000 description 1
- ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 1
- 125000000530 1-propynyl group Chemical group [H]C([H])([H])C#C* 0.000 description 1
- YBYIRNPNPLQARY-UHFFFAOYSA-N 1H-indene Chemical group C1=CC=C2CC=CC2=C1 YBYIRNPNPLQARY-UHFFFAOYSA-N 0.000 description 1
- 125000003660 2,3-dimethylpentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- HCSBTDBGTNZOAB-UHFFFAOYSA-N 2,3-dinitrobenzoic acid Chemical compound OC(=O)C1=CC=CC([N+]([O-])=O)=C1[N+]([O-])=O HCSBTDBGTNZOAB-UHFFFAOYSA-N 0.000 description 1
- JMZXUBICVRRNPV-UHFFFAOYSA-N 2-(2,5-dichlorothiophen-3-yl)acetic acid Chemical compound OC(=O)CC=1C=C(Cl)SC=1Cl JMZXUBICVRRNPV-UHFFFAOYSA-N 0.000 description 1
- SBASXUCJHJRPEV-UHFFFAOYSA-N 2-(2-methoxyethoxy)ethanol Chemical compound COCCOCCO SBASXUCJHJRPEV-UHFFFAOYSA-N 0.000 description 1
- PAWQVTBBRAZDMG-UHFFFAOYSA-N 2-(3-bromo-2-fluorophenyl)acetic acid Chemical compound OC(=O)CC1=CC=CC(Br)=C1F PAWQVTBBRAZDMG-UHFFFAOYSA-N 0.000 description 1
- ZSAROPYHJCBWKE-UHFFFAOYSA-N 2-(thiadiazol-4-yl)acetic acid Chemical compound OC(=O)CC1=CSN=N1 ZSAROPYHJCBWKE-UHFFFAOYSA-N 0.000 description 1
- SZMPQRMBDVOLBZ-UHFFFAOYSA-N 2-amino-3-(2,5-dichloro-1,3-thiazol-4-yl)propanoic acid Chemical compound NC(CC(N=C(S1)Cl)=C1Cl)C(O)=O SZMPQRMBDVOLBZ-UHFFFAOYSA-N 0.000 description 1
- VORSHCWTZIFIRK-UHFFFAOYSA-N 2-amino-3-(2,5-dichlorothiophen-3-yl)propanoic acid Chemical compound OC(=O)C(N)CC=1C=C(Cl)SC=1Cl VORSHCWTZIFIRK-UHFFFAOYSA-N 0.000 description 1
- ZXRSFYYBYBBZQH-UHFFFAOYSA-N 2-amino-3-(2-bromopyridin-4-yl)propanoic acid Chemical compound OC(=O)C(N)CC1=CC=NC(Br)=C1 ZXRSFYYBYBBZQH-UHFFFAOYSA-N 0.000 description 1
- PPKLROFQLFUYPS-UHFFFAOYSA-N 2-amino-3-(2-chlorothiophen-3-yl)propanoic acid Chemical compound OC(=O)C(N)CC=1C=CSC=1Cl PPKLROFQLFUYPS-UHFFFAOYSA-N 0.000 description 1
- RFVNOJDQRGSOEL-UHFFFAOYSA-N 2-hydroxyethyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCO RFVNOJDQRGSOEL-UHFFFAOYSA-N 0.000 description 1
- 125000006022 2-methyl-2-propenyl group Chemical group 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- 125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
- 125000004975 3-butenyl group Chemical group C(CC=C)* 0.000 description 1
- 125000000474 3-butynyl group Chemical group [H]C#CC([H])([H])C([H])([H])* 0.000 description 1
- 125000003469 3-methylhexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- HEGXJUJXMQAWMZ-UHFFFAOYSA-N 4-(2-aminoethyl)-1,3-thiazol-2-amine;dihydrochloride Chemical compound Cl.Cl.NCCC1=CSC(N)=N1 HEGXJUJXMQAWMZ-UHFFFAOYSA-N 0.000 description 1
- SJZRECIVHVDYJC-UHFFFAOYSA-N 4-hydroxybutyric acid Chemical compound OCCCC(O)=O SJZRECIVHVDYJC-UHFFFAOYSA-N 0.000 description 1
- OBKXEAXTFZPCHS-UHFFFAOYSA-N 4-phenylbutyric acid Chemical compound OC(=O)CCCC1=CC=CC=C1 OBKXEAXTFZPCHS-UHFFFAOYSA-N 0.000 description 1
- 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 description 1
- 125000006043 5-hexenyl group Chemical group 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 108010000700 Acetolactate synthase Proteins 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- 241000219318 Amaranthus Species 0.000 description 1
- 229930192334 Auxin Natural products 0.000 description 1
- 241000894006 Bacteria Species 0.000 description 1
- 244000056139 Brassica cretica Species 0.000 description 1
- 235000003351 Brassica cretica Nutrition 0.000 description 1
- 235000003343 Brassica rupestris Nutrition 0.000 description 1
- CPELXLSAUQHCOX-UHFFFAOYSA-M Bromide Chemical compound [Br-] CPELXLSAUQHCOX-UHFFFAOYSA-M 0.000 description 1
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
- DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- 240000006162 Chenopodium quinoa Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- 244000045195 Cicer arietinum Species 0.000 description 1
- 235000010523 Cicer arietinum Nutrition 0.000 description 1
- KRKNYBCHXYNGOX-UHFFFAOYSA-K Citrate Chemical compound [O-]C(=O)CC(O)(CC([O-])=O)C([O-])=O KRKNYBCHXYNGOX-UHFFFAOYSA-K 0.000 description 1
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 1
- 239000005888 Clothianidin Substances 0.000 description 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 229920005682 EO-PO block copolymer Polymers 0.000 description 1
- BDAGIHXWWSANSR-UHFFFAOYSA-M Formate Chemical compound [O-]C=O BDAGIHXWWSANSR-UHFFFAOYSA-M 0.000 description 1
- 241000233866 Fungi Species 0.000 description 1
- AEMRFAOFKBGASW-UHFFFAOYSA-M Glycolate Chemical compound OCC([O-])=O AEMRFAOFKBGASW-UHFFFAOYSA-M 0.000 description 1
- 241000238631 Hexapoda Species 0.000 description 1
- 206010020649 Hyperkeratosis Diseases 0.000 description 1
- 239000005797 Iprovalicarb Substances 0.000 description 1
- 240000007049 Juglans regia Species 0.000 description 1
- 235000009496 Juglans regia Nutrition 0.000 description 1
- NWUWYYSKZYIQAE-ZBFHGGJFSA-N L-(R)-iprovalicarb Chemical compound CC(C)OC(=O)N[C@@H](C(C)C)C(=O)N[C@H](C)C1=CC=C(C)C=C1 NWUWYYSKZYIQAE-ZBFHGGJFSA-N 0.000 description 1
- ONIBWKKTOPOVIA-BYPYZUCNSA-N L-Proline Chemical compound OC(=O)[C@@H]1CCCN1 ONIBWKKTOPOVIA-BYPYZUCNSA-N 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-L L-tartrate(2-) Chemical compound [O-]C(=O)[C@H](O)[C@@H](O)C([O-])=O FEWJPZIEWOKRBE-JCYAYHJZSA-L 0.000 description 1
- JVTAAEKCZFNVCJ-UHFFFAOYSA-M Lactate Chemical compound CC(O)C([O-])=O JVTAAEKCZFNVCJ-UHFFFAOYSA-M 0.000 description 1
- 235000014647 Lens culinaris subsp culinaris Nutrition 0.000 description 1
- 244000043158 Lens esculenta Species 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-L Malonate Chemical compound [O-]C(=O)CC([O-])=O OFOBLEOULBTSOW-UHFFFAOYSA-L 0.000 description 1
- RRVIAQKBTUQODI-UHFFFAOYSA-N Methabenzthiazuron Chemical compound C1=CC=C2SC(N(C)C(=O)NC)=NC2=C1 RRVIAQKBTUQODI-UHFFFAOYSA-N 0.000 description 1
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 1
- AMQJEAYHLZJPGS-UHFFFAOYSA-N N-Pentanol Chemical compound CCCCCO AMQJEAYHLZJPGS-UHFFFAOYSA-N 0.000 description 1
- 238000005481 NMR spectroscopy Methods 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 240000007594 Oryza sativa Species 0.000 description 1
- 235000007164 Oryza sativa Nutrition 0.000 description 1
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-L Phosphate ion(2-) Chemical compound OP([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-L 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- ONIBWKKTOPOVIA-UHFFFAOYSA-N Proline Natural products OC(=O)C1CCCN1 ONIBWKKTOPOVIA-UHFFFAOYSA-N 0.000 description 1
- 244000272459 Silybum marianum Species 0.000 description 1
- 235000010841 Silybum marianum Nutrition 0.000 description 1
- ULUAUXLGCMPNKK-UHFFFAOYSA-N Sulfobutanedioic acid Chemical class OC(=O)CC(C(O)=O)S(O)(=O)=O ULUAUXLGCMPNKK-UHFFFAOYSA-N 0.000 description 1
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 1
- 239000005839 Tebuconazole Substances 0.000 description 1
- 235000011941 Tilia x europaea Nutrition 0.000 description 1
- 239000005626 Tribenuron Substances 0.000 description 1
- 244000250129 Trigonella foenum graecum Species 0.000 description 1
- 235000001484 Trigonella foenum graecum Nutrition 0.000 description 1
- 241000700605 Viruses Species 0.000 description 1
- ZZXDRXVIRVJQBT-UHFFFAOYSA-M Xylenesulfonate Chemical compound CC1=CC=CC(S([O-])(=O)=O)=C1C ZZXDRXVIRVJQBT-UHFFFAOYSA-M 0.000 description 1
- 241000607479 Yersinia pestis Species 0.000 description 1
- 230000036579 abiotic stress Effects 0.000 description 1
- 230000000895 acaricidal effect Effects 0.000 description 1
- 239000000642 acaricide Substances 0.000 description 1
- 125000000738 acetamido group Chemical group [H]C([H])([H])C(=O)N([H])[*] 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N acetic acid Substances CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 1
- IPBVNPXQWQGGJP-UHFFFAOYSA-N acetic acid phenyl ester Natural products CC(=O)OC1=CC=CC=C1 IPBVNPXQWQGGJP-UHFFFAOYSA-N 0.000 description 1
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 1
- YTIVTFGABIZHHX-UHFFFAOYSA-L acetylenedicarboxylate(2-) Chemical compound [O-]C(=O)C#CC([O-])=O YTIVTFGABIZHHX-UHFFFAOYSA-L 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 230000006978 adaptation Effects 0.000 description 1
- 125000003158 alcohol group Chemical group 0.000 description 1
- 125000003545 alkoxy group Chemical group 0.000 description 1
- 125000005262 alkoxyamine group Chemical group 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- HSFWRNGVRCDJHI-UHFFFAOYSA-N alpha-acetylene Natural products C#C HSFWRNGVRCDJHI-UHFFFAOYSA-N 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 229940093740 amino acid and derivative Drugs 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 229940072049 amyl acetate Drugs 0.000 description 1
- PGMYKACGEOXYJE-UHFFFAOYSA-N anhydrous amyl acetate Natural products CCCCCOC(C)=O PGMYKACGEOXYJE-UHFFFAOYSA-N 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 239000007798 antifreeze agent Substances 0.000 description 1
- 125000006615 aromatic heterocyclic group Chemical group 0.000 description 1
- 229960000892 attapulgite Drugs 0.000 description 1
- 239000005667 attractant Substances 0.000 description 1
- 239000002363 auxin Substances 0.000 description 1
- 125000003828 azulenyl group Chemical group 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- USRKFGIXLGKMKU-ABAIWWIYSA-N benthiavalicarb-isopropyl Chemical compound C1=C(F)C=C2SC([C@@H](C)NC(=O)[C@H](C(C)C)NC(=O)OC(C)C)=NC2=C1 USRKFGIXLGKMKU-ABAIWWIYSA-N 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 1
- 125000003236 benzoyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C(*)=O 0.000 description 1
- 125000002619 bicyclic group Chemical group 0.000 description 1
- 239000003139 biocide Substances 0.000 description 1
- 239000003124 biologic agent Substances 0.000 description 1
- 230000033228 biological regulation Effects 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 230000004790 biotic stress Effects 0.000 description 1
- QKSKPIVNLNLAAV-UHFFFAOYSA-N bis(2-chloroethyl) sulfide Chemical compound ClCCSCCCl QKSKPIVNLNLAAV-UHFFFAOYSA-N 0.000 description 1
- 150000005693 branched-chain amino acids Chemical class 0.000 description 1
- 239000000872 buffer Substances 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000004063 butyryl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- OOCMUZJPDXYRFD-UHFFFAOYSA-L calcium;2-dodecylbenzenesulfonate Chemical compound [Ca+2].CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O.CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O OOCMUZJPDXYRFD-UHFFFAOYSA-L 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 230000036755 cellular response Effects 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000002738 chelating agent Substances 0.000 description 1
- 239000013043 chemical agent Substances 0.000 description 1
- 230000003559 chemosterilizing effect Effects 0.000 description 1
- KVSASDOGYIBWTA-UHFFFAOYSA-N chloro benzoate Chemical compound ClOC(=O)C1=CC=CC=C1 KVSASDOGYIBWTA-UHFFFAOYSA-N 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
- 238000005260 corrosion Methods 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- GHVNFZFCNZKVNT-UHFFFAOYSA-N decanoic acid Chemical compound CCCCCCCCCC(O)=O GHVNFZFCNZKVNT-UHFFFAOYSA-N 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000007123 defense Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 235000014113 dietary fatty acids Nutrition 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-M dihydrogenphosphate Chemical compound OP(O)([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-M 0.000 description 1
- XPPKVPWEQAFLFU-UHFFFAOYSA-J diphosphate(4-) Chemical compound [O-]P([O-])(=O)OP([O-])([O-])=O XPPKVPWEQAFLFU-UHFFFAOYSA-J 0.000 description 1
- 235000011180 diphosphates Nutrition 0.000 description 1
- 239000004491 dispersible concentrate Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 239000006185 dispersion Substances 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- MOTZDAYCYVMXPC-UHFFFAOYSA-N dodecyl hydrogen sulfate Chemical compound CCCCCCCCCCCCOS(O)(=O)=O MOTZDAYCYVMXPC-UHFFFAOYSA-N 0.000 description 1
- 229940043264 dodecyl sulfate Drugs 0.000 description 1
- DDXLVDQZPFLQMZ-UHFFFAOYSA-M dodecyl(trimethyl)azanium;chloride Chemical class [Cl-].CCCCCCCCCCCC[N+](C)(C)C DDXLVDQZPFLQMZ-UHFFFAOYSA-M 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 210000002257 embryonic structure Anatomy 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 238000005538 encapsulation Methods 0.000 description 1
- 239000003623 enhancer Substances 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 125000002534 ethynyl group Chemical group [H]C#C* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 239000000194 fatty acid Substances 0.000 description 1
- 229930195729 fatty acid Natural products 0.000 description 1
- 150000004665 fatty acids Chemical class 0.000 description 1
- 239000000796 flavoring agent Substances 0.000 description 1
- UOUXAYAIONPXDH-UHFFFAOYSA-M flucarbazone-sodium Chemical compound [Na+].O=C1N(C)C(OC)=NN1C(=O)[N-]S(=O)(=O)C1=CC=CC=C1OC(F)(F)F UOUXAYAIONPXDH-UHFFFAOYSA-M 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- QEWYKACRFQMRMB-UHFFFAOYSA-M fluoroacetate Chemical compound [O-]C(=O)CF QEWYKACRFQMRMB-UHFFFAOYSA-M 0.000 description 1
- 230000004907 flux Effects 0.000 description 1
- 235000013355 food flavoring agent Nutrition 0.000 description 1
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
- VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical compound [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- 229940100242 glycol stearate Drugs 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 239000001963 growth medium Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical group 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- COYBRKAVBMYYSF-UHFFFAOYSA-N heptan-2-yl [(5-chloroquinolin-8-yl)oxy]acetate Chemical group C1=CN=C2C(OCC(=O)OC(C)CCCCC)=CC=C(Cl)C2=C1 COYBRKAVBMYYSF-UHFFFAOYSA-N 0.000 description 1
- MNWFXJYAOYHMED-UHFFFAOYSA-M heptanoate Chemical compound CCCCCCC([O-])=O MNWFXJYAOYHMED-UHFFFAOYSA-M 0.000 description 1
- MNWFXJYAOYHMED-UHFFFAOYSA-N heptanoic acid Chemical compound CCCCCCC(O)=O MNWFXJYAOYHMED-UHFFFAOYSA-N 0.000 description 1
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- KKLGDUSGQMHBPB-UHFFFAOYSA-N hex-2-ynedioic acid Chemical compound OC(=O)CCC#CC(O)=O KKLGDUSGQMHBPB-UHFFFAOYSA-N 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-M hydrogensulfate Chemical compound OS([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-M 0.000 description 1
- 125000004356 hydroxy functional group Chemical group O* 0.000 description 1
- 125000003392 indanyl group Chemical group C1(CCC2=CC=CC=C12)* 0.000 description 1
- SEOVTRFCIGRIMH-UHFFFAOYSA-N indole-3-acetic acid Chemical compound C1=CC=C2C(CC(=O)O)=CNC2=C1 SEOVTRFCIGRIMH-UHFFFAOYSA-N 0.000 description 1
- 230000006698 induction Effects 0.000 description 1
- 239000000077 insect repellent Substances 0.000 description 1
- 230000003834 intracellular effect Effects 0.000 description 1
- NRXQIUSYPAHGNM-UHFFFAOYSA-N ioxynil Chemical compound OC1=C(I)C=C(C#N)C=C1I NRXQIUSYPAHGNM-UHFFFAOYSA-N 0.000 description 1
- 230000002427 irreversible effect Effects 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- KQNPFQTWMSNSAP-UHFFFAOYSA-N isobutyric acid Chemical compound CC(C)C(O)=O KQNPFQTWMSNSAP-UHFFFAOYSA-N 0.000 description 1
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 239000004571 lime Substances 0.000 description 1
- 239000012669 liquid formulation Substances 0.000 description 1
- 239000007937 lozenge Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 230000036244 malformation Effects 0.000 description 1
- IWYDHOAUDWTVEP-UHFFFAOYSA-M mandelate Chemical compound [O-]C(=O)C(O)C1=CC=CC=C1 IWYDHOAUDWTVEP-UHFFFAOYSA-M 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000000442 meristematic effect Effects 0.000 description 1
- 230000002503 metabolic effect Effects 0.000 description 1
- 125000005341 metaphosphate group Chemical group 0.000 description 1
- IZYBEMGNIUSSAX-UHFFFAOYSA-N methyl benzenecarboperoxoate Chemical compound COOC(=O)C1=CC=CC=C1 IZYBEMGNIUSSAX-UHFFFAOYSA-N 0.000 description 1
- 229940095102 methyl benzoate Drugs 0.000 description 1
- 235000010460 mustard Nutrition 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- PSZYNBSKGUBXEH-UHFFFAOYSA-N naphthalene-1-sulfonic acid Chemical compound C1=CC=C2C(S(=O)(=O)O)=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-N 0.000 description 1
- KVBGVZZKJNLNJU-UHFFFAOYSA-N naphthalene-2-sulfonic acid Chemical compound C1=CC=CC2=CC(S(=O)(=O)O)=CC=C21 KVBGVZZKJNLNJU-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 238000003947 neutron activation analysis Methods 0.000 description 1
- 125000000018 nitroso group Chemical group N(=O)* 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- WWZKQHOCKIZLMA-UHFFFAOYSA-M octanoate Chemical compound CCCCCCCC([O-])=O WWZKQHOCKIZLMA-UHFFFAOYSA-M 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-M oleate Chemical compound CCCCCCCC\C=C/CCCCCCCC([O-])=O ZQPPMHVWECSIRJ-KTKRTIGZSA-M 0.000 description 1
- 229940049964 oleate Drugs 0.000 description 1
- 210000000056 organ Anatomy 0.000 description 1
- 239000002357 osmotic agent Substances 0.000 description 1
- 229910052625 palygorskite Inorganic materials 0.000 description 1
- 239000010690 paraffinic oil Substances 0.000 description 1
- 238000005192 partition Methods 0.000 description 1
- 239000008188 pellet Substances 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- DYUMLJSJISTVPV-UHFFFAOYSA-N phenyl propanoate Chemical compound CCC(=O)OC1=CC=CC=C1 DYUMLJSJISTVPV-UHFFFAOYSA-N 0.000 description 1
- 229940049953 phenylacetate Drugs 0.000 description 1
- WLJVXDMOQOGPHL-UHFFFAOYSA-N phenylacetic acid Chemical compound OC(=O)CC1=CC=CC=C1 WLJVXDMOQOGPHL-UHFFFAOYSA-N 0.000 description 1
- 229950009215 phenylbutanoic acid Drugs 0.000 description 1
- 239000003016 pheromone Substances 0.000 description 1
- XNGIFLGASWRNHJ-UHFFFAOYSA-L phthalate(2-) Chemical compound [O-]C(=O)C1=CC=CC=C1C([O-])=O XNGIFLGASWRNHJ-UHFFFAOYSA-L 0.000 description 1
- 231100000208 phytotoxic Toxicity 0.000 description 1
- 230000000885 phytotoxic effect Effects 0.000 description 1
- 230000008654 plant damage Effects 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000003140 primary amides Chemical group 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 230000035755 proliferation Effects 0.000 description 1
- KCXFHTAICRTXLI-UHFFFAOYSA-N propane-1-sulfonic acid Chemical compound CCCS(O)(=O)=O KCXFHTAICRTXLI-UHFFFAOYSA-N 0.000 description 1
- 125000001501 propionyl group Chemical group O=C([*])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000008262 pumice Substances 0.000 description 1
- 229910052903 pyrophyllite Inorganic materials 0.000 description 1
- 230000006340 racemization Effects 0.000 description 1
- 230000003938 response to stress Effects 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- YGSDEFSMJLZEOE-UHFFFAOYSA-M salicylate Chemical compound OC1=CC=CC=C1C([O-])=O YGSDEFSMJLZEOE-UHFFFAOYSA-M 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 229940116351 sebacate Drugs 0.000 description 1
- CXMXRPHRNRROMY-UHFFFAOYSA-L sebacate(2-) Chemical compound [O-]C(=O)CCCCCCCCC([O-])=O CXMXRPHRNRROMY-UHFFFAOYSA-L 0.000 description 1
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000003334 secondary amides Chemical group 0.000 description 1
- 239000003620 semiochemical Substances 0.000 description 1
- 230000009758 senescence Effects 0.000 description 1
- 230000019491 signal transduction Effects 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- APSBXTVYXVQYAB-UHFFFAOYSA-M sodium docusate Chemical compound [Na+].CCCCC(CC)COC(=O)CC(S([O-])(=O)=O)C(=O)OCC(CC)CCCC APSBXTVYXVQYAB-UHFFFAOYSA-M 0.000 description 1
- RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 1
- KZOJQMWTKJDSQJ-UHFFFAOYSA-M sodium;2,3-dibutylnaphthalene-1-sulfonate Chemical compound [Na+].C1=CC=C2C(S([O-])(=O)=O)=C(CCCC)C(CCCC)=CC2=C1 KZOJQMWTKJDSQJ-UHFFFAOYSA-M 0.000 description 1
- FJPYVLNWWICYDW-UHFFFAOYSA-M sodium;5,5-diphenylimidazolidin-1-ide-2,4-dione Chemical compound [Na+].O=C1[N-]C(=O)NC1(C=1C=CC=CC=1)C1=CC=CC=C1 FJPYVLNWWICYDW-UHFFFAOYSA-M 0.000 description 1
- 239000004550 soluble concentrate Substances 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 230000007480 spreading Effects 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000003206 sterilizing agent Substances 0.000 description 1
- TYFQFVWCELRYAO-UHFFFAOYSA-L suberate(2-) Chemical compound [O-]C(=O)CCCCCCC([O-])=O TYFQFVWCELRYAO-UHFFFAOYSA-L 0.000 description 1
- KDYFGRWQOYBRFD-UHFFFAOYSA-L succinate(2-) Chemical compound [O-]C(=O)CCC([O-])=O KDYFGRWQOYBRFD-UHFFFAOYSA-L 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 239000004546 suspension concentrate Substances 0.000 description 1
- 238000004114 suspension culture Methods 0.000 description 1
- 239000003826 tablet Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 229940095064 tartrate Drugs 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003511 tertiary amides Chemical group 0.000 description 1
- 125000001712 tetrahydronaphthyl group Chemical group C1(CCCC2=CC=CC=C12)* 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- GFNANZIMVAIWHM-OBYCQNJPSA-N triamcinolone Chemical compound O=C1C=C[C@]2(C)[C@@]3(F)[C@@H](O)C[C@](C)([C@@]([C@H](O)C4)(O)C(=O)CO)[C@@H]4[C@@H]3CCC2=C1 GFNANZIMVAIWHM-OBYCQNJPSA-N 0.000 description 1
- 150000003852 triazoles Chemical class 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
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002827 triflate group Chemical group FC(S(=O)(=O)O*)(F)F 0.000 description 1
- 125000001889 triflyl group Chemical group FC(F)(F)S(*)(=O)=O 0.000 description 1
- 235000001019 trigonella foenum-graecum Nutrition 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 244000045561 useful plants Species 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 235000020234 walnut Nutrition 0.000 description 1
- 239000004562 water dispersible granule Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 229940071104 xylenesulfonate Drugs 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/46—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom rings with more than six members
-
- 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
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01G—HORTICULTURE; CULTIVATION OF VEGETABLES, FLOWERS, RICE, FRUIT, VINES, HOPS OR SEAWEED; FORESTRY; WATERING
- A01G7/00—Botany in general
- A01G7/06—Treatment of growing trees or plants, e.g. for preventing decay of wood, for tingeing flowers or wood, for prolonging the life of plants
-
- 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
- A01N31/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic oxygen or sulfur compounds
- A01N31/08—Oxygen or sulfur directly attached to an aromatic ring system
- A01N31/14—Ethers
-
- 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
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/04—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom
- A01N43/06—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings
- A01N43/10—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with one hetero atom five-membered rings with sulfur as the ring hetero atom
-
- 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
- A01N43/02—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms
- A01N43/24—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms
- A01N43/26—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings
- A01N43/28—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one or more oxygen or sulfur atoms as the only ring hetero atoms with two or more hetero atoms five-membered rings with two hetero atoms in positions 1,3
-
- 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
- A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
- A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
-
- 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
- A01N43/72—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
- A01N43/74—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 1,3
- A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
-
- 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
- A01N59/00—Biocides, pest repellants or attractants, or plant growth regulators containing elements or inorganic compounds
- A01N59/26—Phosphorus; Compounds thereof
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
- A01P13/00—Herbicides; Algicides
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01P—BIOCIDAL, PEST REPELLANT, PEST ATTRACTANT OR PLANT GROWTH REGULATORY ACTIVITY OF CHEMICAL COMPOUNDS OR PREPARATIONS
- A01P21/00—Plant growth regulators
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
- C07D213/54—Radicals substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/61—Halogen atoms or nitro radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/74—Amino or imino radicals substituted by hydrocarbon or substituted hydrocarbon radicals
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/76—Nitrogen atoms to which a second hetero atom is attached
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D263/34—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D275/00—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings
- C07D275/02—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings not condensed with other rings
- C07D275/03—Heterocyclic compounds containing 1,2-thiazole or hydrogenated 1,2-thiazole rings not condensed with other rings with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
- C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D277/56—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/28—Halogen atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
- C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
- C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
- C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D333/30—Hetero atoms other than halogen
- C07D333/36—Nitrogen atoms
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Environmental Sciences (AREA)
- Engineering & Computer Science (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Plant Pathology (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Biodiversity & Conservation Biology (AREA)
- Ecology (AREA)
- Forests & Forestry (AREA)
- Botany (AREA)
- Inorganic Chemistry (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
提供了具有除草活性的新型化合物、农用组合物、其制造方法及其在作物保护中的用途。
Description
技术领域
本发明涉及具有除草活性的新型化合物、其制造方法及其在作物保护中的用途。
背景技术
氨基酸及其衍生物参与了过多的细胞反应,因此它们影响许多生理过程,如植物生长和发育、细胞内pH控制、代谢能或氧化还原能力的产生以及对非生物胁迫和生物胁迫两者的抗性。在应激期间诱导所有氨基酸的池。例如,脯氨酸显著增加若干植物中的胁迫反应,并且被认为是相容的渗透剂。另外,在各种应激条件下,支链氨基酸也被显著诱导。
最近讨论了氨基酸在植物中信号传导中的作用。在这个背景下,氨基酸含量、通量和通过植物传输的调节对于植物适应碳和氮状态、发育和防御是关键的。
氨基酸池调节下面的机制需要进一步的阐明。局部氨基酸浓度取决于蛋白质以及氨基酸的合成和降解速率以及传输过程。这些过程反而改变了总池大小,当发生大量降解时,如在萌发和衰老期间,这是尤其相关的。
持续需要有效控制不期望的植被生长的新化合物。在最常见的情况下,寻求这样的化合物以选择性地控制有用作物(举几个例子,如棉花、水稻、玉米、小麦和大豆)中的野草生长。在这样的作物中野草的肆意生长会造成重大损失,降低农民的利润,并且增加消费者的成本。在其他情况下,期望控制所有植物生长的除草剂。其中期望完全控制所有植被的区域的实例是铁路轨道、储罐和工业储存区域周围的区域。鉴定更有效、成本更低和环境安全的具有除草活性的新化合物仍然是长期和未满足的需求。
发明内容
本发明的主要目的是提供新型安全和有效的除草剂。
本发明提供了一种农用组合物,其包含具有以下结构的化合物:
或其盐,其中:
A是包含1至4个杂原子的环戊二烯、苯和茚骨架;其中每个杂原子独立地选自N、S、Se和O;并且其中环的一个或多个碳原子任选地化学附接到由以下组成的基团中的至少一个:-SO2CF3、-O-SO2CF3、-NR3 +、-SO2R、-C≡N、-CX3、CX2R、-COX、-CHO、-COR、-CO2R、-CONH2、-CONHR、-CONR2、-N=O、-N≡N+、-N=NR、-CR=NR、-N=CR2、-F、-Cl、-Br和-I,并且其中X选自F、Cl、Br和I;
n是0至5;
T是未取代的或被一个或两个以下基团取代的亚甲基:卤基、氧、-SO2CF3、-O-SO2CF3、-NR3 +、-SO2R、-C≡N、-CX3、CX2R-COX、-CHO、-COR、-CO2R、-CONH2、-CONHR、-CONR2、-F、-N=O、-N≡N+、-N=NR、-CR=NR、-N=CR2,并且其中X选自-F、-Cl、-Br和-I;并且
Z是-COOH、COO-、OH、-O-R、具有饱和或不饱和的醇残基的COOR,所述醇残基具有直链、支链、环状、芳族或杂芳族链;-O-(CH2CH2O)nR(n≥1);-O-(CHMeCH2O)nR(n≥1);磺酰基、氨基甲酰基、伯胺、仲胺、叔胺、甲酰胺、-NR-O-R、-O-NR2、肼、-NH-COR和甲脒部分或其盐;
其中R选自H、取代的或未取代的烷基和取代的或未取代的芳基;并且,其中所述组合物包含至少一种农业上可接受的载体。
本发明进一步提供了一种控制不期望的植物生长的方法,其包括向不期望的植物生长的场所施用除草有效量的具有以下结构的化合物:
或其盐,其中:
A是包含1至4个杂原子的环戊二烯、苯和茚骨架;其中每个杂原子独立地选自N、S、Se和O;并且其中环的一个或多个碳原子任选地化学附接到由以下组成的基团中的至少一个:-SO2CF3、-O-SO2CF3、-NR3 +、-SO2R、-C≡N、-CX3、CX2R、-COX、-CHO、-COR、-CO2R、-CONH2、-CONHR、-CONR2、-N=O、-N≡N+、-N=NR、-CR=NR、-N=CR2、-F、-Cl、-Br和-I;并且其中X选自F、Cl、Br和I;
n是0至5;
T是未取代的或被一个或两个以下基团取代的亚甲基:卤基、氧、-SO2CF3、-O-SO2CF3、-NR3 +、-SO2R、-C≡N、-CX3、CX2R、-COX、-CHO、-COR、-CO2R、-CONH2、-CONHR、-CONR2、-F、-N=O、-N≡N+、-N=NR、-CR=NR、-N=CR2,并且其中X选自F、Cl、Br和I;并且
Z是-COOH、COO-、OH、-O-R、具有饱和或不饱和的醇残基的COOR,所述醇残基具有直链、支链、环状、芳族或杂芳族链;-O-(CH2CH2O)nR(n≥1);-O-(CHMeCH2O)nR(n≥1);磺酰基、氨基甲酰基、伯胺、仲胺、叔胺、甲酰胺、-NR-O-R、-O-NR2、肼、-NH-COR和甲脒部分或其盐;
其中R选自H、取代的或未取代的烷基和取代的或未取代的芳基。
本发明进一步提供了一种控制不期望的植物生长的方法,其包括向不期望的植物生长的场所施用:
a.具有以下结构的第一除草剂:
或其盐,其中:
A是包含1至4个杂原子的环戊二烯、苯和茚骨架;其中每个杂原子独立地选自N、S、Se和O;并且其中环的一个或多个碳原子任选地化学附接到由以下组成的基团中的至少一个:-SO2CF3、-O-SO2CF3、-NR3 +、-SO2R、-C≡N、-CX3、CX2R-COX、-CHO、-COR、-CO2R、-CONH2、-CONHR、-CONR2、-F、-N=O、-N≡N+、-N=NR、-CR=NR、-N=CR2、-Cl、-Br和-I;并且其中X选自F、Cl、Br和I;
n是0至5;
T是未取代的或被一个或两个以下基团取代的亚甲基:卤基、氧、-SO2CF3、-O-SO2CF3、-NR3 +、-SO2R、-C≡N、-CX3、CX2R、-COX、-CHO、-COR、-CO2R、-CONH2、-CONHR、-CONR2、-F、-N=O、-N≡N+、-N=NR、-CR=NR、-N=CR2,并且其中X选自F、Cl、Br和I;并且
Z是-COOH、COO-、OH、-O-R、具有饱和或不饱和的醇残基的COOR,所述醇残基具有直链、支链、环状、芳族或杂芳族链;-O-(CH2CH2O)nR(n≥1);-O-(CHMeCH2O)nR(n≥1);磺酰基、氨基甲酰基、伯胺、仲胺、叔胺、甲酰胺、-NR-O-R、-O-NR2、肼、-NH-COR和甲脒部分或其盐;
其中R选自H、取代的或未取代的烷基和取代的或未取代的芳基,
b.第二除草剂,
由此有效地控制不期望的植物生长。
本发明进一步提供了一种用于控制不期望的植物生长的组合物,其包含以下物质的混合物:
a.具有以下结构的化合物:
或其盐,其中:
A是包含1至4个杂原子的环戊二烯、苯和茚骨架;其中每个杂原子独立地选自N、S、Se和O;并且其中环的一个或多个碳原子任选地化学附接到由以下组成的基团中的至少一个:-SO2CF3、-O-SO2CF3、-NR3 +、-SO2R、-C≡N、-CX3、CX2R、-COX、-CHO、-COR、-CO2R、-CONH2、-CONHR、-CONR2、-F、-N=O、-N≡N+、-N=NR、-CR=NR、-N=CR2、-Cl、-Br和-I;并且其中X选自F、Cl、Br和I;
n是0至5;
T是未取代的或被一个或两个以下基团取代的亚甲基:卤基、氧、-SO2CF3、-O-SO2CF3、-NR3 +、-SO2R、-C≡N、-CX3、CX2R-COX、-CHO、-COR、-CO2R、-CONH2、-CONHR、-CONR2、-F、-N=O、-N≡N+、-N=NR、-CR=NR、-N=CR2,并且其中X选自F、Cl、Br和I;并且
Z是-COOH、COO-、OH、-O-R、具有饱和或不饱和的醇残基的COOR,所述醇残基具有直链、支链、环状、芳族或杂芳族链;-O-(CH2CH2O)nR(n≥1);-O-(CHMeCH2O)nR(n≥1);磺酰基、氨基甲酰基、伯胺、仲胺、叔胺、甲酰胺、-NR-O-R、-O-NR2、肼、-NH-COR和甲脒部分或其盐;
其中R选自H、取代的或未取代的烷基和取代的或未取代的芳基;
b.至少一种选自以下物质的除草剂:莠去津、特丁津、(S)-异丙甲草胺、异丙甲草胺、特丁净、西玛津、噻吩草胺、(S)-噻吩草胺、氟噻草胺、乙草胺、甲草胺、异噁唑草酮、异噁氯草酮、硝磺草酮、磺草酮、磺草唑胺、唑嘧磺草胺、二甲戊乐灵、溴草腈、灭草松、唑草酮、异噁草酮、烟嘧磺隆、砜嘧磺隆、氯吡嘧磺隆、草克净、氟烯草戊酯、氟丙磺隆、氟嘧磺隆、麦草畏、嗪草酸甲酯、达草止、2,4-D、二氯吡啶酸、氟吡草腙、氟草定、MCPA、MCPB、氯苯氧丙酸(MCPP)、吡喃隆、噻吩磺隆、苯草醚、EPTC、草甘膦、草铵膦、草硫膦、氰草津、喔草酯、苯嗪草酮、甜菜灵、甜菜宁、甜菜安、乙呋草黄、醚苯磺隆、氯草敏、环草定、燕麦畏、吡氟禾草灵、稀禾啶、喹禾灵、二氯吡啶酸、烯草酮、环氧嘧磺隆、氟锁草醚、氯噻草灵乙酯、甲磺草胺、氯嘧磺隆乙酯、氯酯磺草胺、氟黄胺草醚、甲氧咪草烟、灭草喹、咪草烟、依灭草、乳氟禾草灵、精噁唑禾草灵、噻苯隆、脱叶磷、氟乐灵、二甲草胺、敌草胺、氯甲喹啉酸、吡唑草胺、双酰草胺、噁唑隆、炔苯酰草胺、胺苯磺隆、牧草胺、伏草隆、扑草净、达草灭、嘧醚苯甲酸钠、MSMA、DSMA、敌草隆、氟咯草酮、氟硫草定、噻草啶、氟硝草醚、乙丁烯氟灵、炔草酯、酰嘧磺隆、禾草灵甲酯、吡氟酰草胺、乙氧嘧磺隆、四唑酰草胺、啶嘧磺隆、双氟磺草胺、异丙吡草酯、氟唑磺隆、氟啶磺隆钠、呋草酮、碘磺隆、异丙隆、绿麦隆、氯磺隆、甲磺隆、乙磺隆、苯磺隆、2,4-DB、2,4-DP、治草醚、麦草伏-M、咪草酯甲酯、碘苯腈、肟草酮、乙羧氟草醚、甲基苯噻隆、异噁草胺、苄草丹、苯敌快甲基硫酸盐、丙草胺、醚磺隆、解草啶、苄嘧磺隆、唑吡嘧磺隆、吡嘧磺隆、四唑嘧磺隆、戊草丹、苯噻草胺、禾草特、敌稗、吡唑特、氰氟草酯、双草醚钠、嘧草醚、唑草胺、丙炔噁草酮、噁草酮、溴丁酰草胺、MY-100、杀草隆、NB 061、MK243、HW-52、AC 014、莠天净、环嗪酮、磺草灵、唑啶草酮、丁噻隆、胺苯磺隆或其组合;以及
c.至少一种农业上可接受的载体。
本发明进一步提供了一种用于控制不期望的植物生长的组合物,其包含以下物质的混合物:
a.具有以下结构的化合物:
或其盐,其中:
A是包含1至4个杂原子的环戊二烯、苯和茚骨架;其中每个杂原子独立地选自N、S、Se和O;并且其中环的一个或多个碳原子任选地化学附接到由以下组成的基团中的至少一个:-SO2CF3、-O-SO2CF3、-NR3 +、-SO2R、-C≡N、-CX3、CX2R-COX、-CHO、-COR、-CO2R、-CONH2、-CONHR、-CONR2、-F、-N=O、-N≡N+、-N=NR、-CR=NR、-N=CR2、-Cl、-Br和-I;并且其中X选自F、Cl、Br和I;
n是0至5;
T是未取代的或被一个或两个以下基团取代的亚甲基:卤原子、氧、-SO2CF3、-O-SO2CF3、-NR3+、-SO2R、-C≡N、-CX3、-COX、-CHO、-COR、-CO2R、-CONH2、-CONHR、-CONR2、-F、-N=O、-N≡N+、-N=NR、-CR=NR、-N=CR2,并且其中X选自F、Cl、Br和I;并且
Z是-COOH、COO-、OH、-O-R、具有饱和或不饱和的醇残基的COOR,所述醇残基具有直链、支链、环状、芳族或杂芳族链;-O-(CH2CH2O)nR(n≥1);-O-(CHMeCH2O)nR(n≥1);磺酰基、氨基甲酰基、伯胺、仲胺、叔胺、甲酰胺、-NR-O-R、-O-NR2、肼、-NH-COR和甲脒部分或其盐;
其中R选自H、取代的或未取代的烷基和取代的或未取代的芳基;
b.至少一种植物生长调节剂;和
c.至少一种农业上可接受的载体。
具体实施方式
现在将在下文中参考实例更全面地描述本发明,其中显示本发明的实施方案。然而,本发明可以许多不同的形式体现,并且不应被解释为限于本文阐述的实施方案;相反,提供这些实施方案是为了使本公开透彻和完整,并将本发明的范围完全传达给本领域技术人员。
在一个实施方案中,本发明提供了一种农用组合物,其包含具有以下结构的化合物或其盐:
或其盐,其中:
A是包含1至4个杂原子的环戊二烯、苯和茚骨架;其中每个杂原子独立地选自N、S、Se和O;并且其中环的一个或多个碳原子任选地化学附接到由以下组成的基团中的至少一个:-SO2CF3、-O-SO2CF3、-NR3 +、-SO2R、-C≡N、-CX3、CX2R、-COX、-CHO、-COR、-CO2R、-CONH2、-CONHR、-CONR2、-N=O、-N≡N+、-N=NR、-CR=NR、-N=CR2、-F、-Cl、-Br和-I;并且其中X选自F、Cl、Br和I;
n是0至5;
T是未取代的或被一个或两个以下基团取代的亚甲基:卤基、氧、-SO2CF3、-O-SO2CF3、-NR3 +、-SO2R、-C≡N、-CX3、CX2R-COX、-CHO、-COR、-CO2R、-CONH2、-CONHR、-CONR2、-F、-N=O、-N≡N+、-N=NR、-CR=NR、-N=CR2,并且其中X选自-F、-Cl、-Br和-I;并且
Z是-COOH、COO-、OH、-O-R、具有饱和或不饱和的醇残基的COOR,所述醇残基具有直链、支链、环状、芳族或杂芳族链;-O-(CH2CH2O)nR(n≥1);-O-(CHMeCH2O)nR(n≥1);磺酰基、氨基甲酰基、伯胺、仲胺、叔胺、甲酰胺、-NR-O-R、-O-NR2、肼、-NH-COR和甲脒部分或其盐;
其中R选自H、取代的或未取代的烷基和取代的或未取代的芳基;并且,其中所述组合物包含至少一种农业上可接受的载体。
根据本发明组合物的一些实施方案,A是被一个或多个吸电子基团(EWG)取代的杂环芳族环。如本文所用,术语“吸电子基团”(EWG)是指而不限于通常通过共振或诱导作用从相邻原子或芳环吸取电子密度的原子或基团。在本发明的上下文中,本发明的EWG的非限制性列表包括:三氟甲磺酰基和三氟甲磺酸酯基;取代的铵基,诸如而不限于-NR3+(R是烷基或H);硝基和亚硝基,-NO2、-N=O;磺酸和磺酰基(-O)-SO3H、-SO2R;氰基、三卤代甲基-CX3(X是F、Cl、Br、I);卤代甲酰基-COX(X是F、Cl、Br、I);甲酰基和酰基-CHO、-COR;(取代的)氨基羰基-CONH2、-CONHR、-CONR2;卤素基团-F、-Cl、-Br、-I;偶氮基-N≡N+或-N=NR;亚氨基-CR=NR或-N=CR2。
根据上述组合物的一些实施方案,Z可以是而不限于羧基或其盐-COOH或COO-、羟基-OH、醚-O-R、具有饱和或不饱和醇基团的酯COOR,所述醇基团具有直链、支链、环状链或芳族/杂芳基链、乙二醇和聚乙二醇-O-(CH2CH2O)nR(n≥1,R是H或烷基)、丙二醇和聚丙二醇-O-(CHMeCH2O)nR(n≥1,R是H或烷基)、磷酸酯(取代的和未取代的)、硫酸酯/磺酰基、氨基甲酰基(其由被直链、支链、环状脂族链、环状芳族/杂芳族链、乙二醇和聚乙二醇(如上)、丙二醇、聚丙二醇(如上)取代的伯、仲和叔酰胺组成)、伯胺、仲胺、叔胺、甲酰胺、-NR-O-R和-O-NR2型的烷氧基胺基团、肼、乙酰胺基团-NH-COR和甲脒部分或其盐。
根据上述组合物的一些实施方案,Z可以是而不限于:
根据一些实施方案,上述组合物包含具有以下结构的化合物:
或其盐,其中每个R1和R2独立地选自H、Cl、Br、I、-CF3和-CN,其中它们中的至少一个不是H;R3是H、-COH、-CN、O或F;并且R4选自H、饱和或不饱和的脂族直链、支链、环状或芳族链;乙二醇;聚乙二醇;丙二醇;聚丙二醇;乙基吡啶;乙苯;1-(溴苯基)乙-1-酮;1-(1H-茚-3-基)乙-1-酮;1-(2,3-二氢-1H-茚-1-基)乙-1-酮;1-(2,3-二氢-1H-茚-1-基)丙-1-酮;和1-(1H-茚-3-基)丙-1-酮。
根据一些实施方案,上述组合物包含具有以下结构的化合物:
其中R1和R2选自H、Cl、Br、I、-CF3和-CN,其中它们中的至少一个不是H;R3是H、-COH、-CN、O或F;并且R4选自H、饱和或不饱和的脂族直链、支链、环状或芳族链;乙二醇;聚乙二醇;丙二醇;聚丙二醇;乙基吡啶;乙苯;1-(溴苯基)乙-1-酮;1-(1H-茚-3-基)乙-1-酮;1-(2,3-二氢-1H-茚-1-基)乙-1-酮;1-(2,3-二氢-1H-茚-1-基)丙-1-酮;和1-(1H-茚-3-基)丙-1-酮。
根据一些实施方案,上述组合物包含具有以下结构的化合物:
其中R1和R2选自H、Cl、Br、I、-CF3和-CN,其中它们中的至少一个不是H;R3是H、-COH、-CN、O或F;R4选自H、饱和或不饱和的脂族直链、支链、环状或芳族链;乙二醇;聚乙二醇;丙二醇;聚丙二醇;乙基吡啶;乙苯;1-(溴苯基)乙-1-酮;1-(1H-茚-3-基)乙-1-酮;1-(2,3-二氢-1H-茚-1-基)乙-1-酮;1-(2,3-二氢-1H-茚-1-基)丙-1-酮;和1-(1H-茚-3-基)丙-1-酮。
根据一些实施方案,上述组合物包含具有以下结构的化合物:
其中R1选自Cl、Br、I、-CF3,R2和R3是H或F;并且R4选自H、饱和或不饱和的脂族直链、支链、环状或芳族链;乙二醇;聚乙二醇;丙二醇;聚丙二醇;乙基吡啶;乙苯;1-(溴苯基)乙-1-酮;1-(1H-茚-3-基)乙-1-酮;1-(2,3-二氢-1H-茚-1-基)乙-1-酮;1-(2,3-二氢-1H-茚-1-基)丙-1-酮;和1-(1H-茚-3-基)丙-1-酮。
根据一些实施方案,上述组合物包含选自以下项的化合物:(2-溴-1,3-噻唑-4-基)(二氟)乙酸;二氟[2-(三氟甲基)-1,3-噻唑-4-基]乙酸;(2-氰基-1,3-噻唑-4-基)(二氟)乙酸;(2-氯-1,3-噻唑-4-基)(二氟)乙酸;(2-氯-1,3-噻唑-4-基)(二氟)乙酸2-[2-(2-乙氧基乙氧基)乙氧基]乙酯;(2-氯-1,3-噻唑-4-基)(二氟)乙酸2-(2-溴苯基)-2-氧代乙酯;(2-氯-1,3-噻唑-4-基)(二氟)乙酸2-(2,7-甲基-2,3-二氢-1H-茚-1-基)-2-氧代乙酯;(2-氯-1,3-噁唑-4-基)(二氟)乙酸;(2-氯-1,3-噁唑-4-基)(二氟)乙酸乙酯;二氟(1,2,3-噻二唑-4-基)乙酸;(1,2,3-噻二唑-4-基)乙酸;(3-氯-1,2-噻唑-4-基)(二氟)乙酸。
根据上述组合物的一些实施方案,化合物或农业上可接受的盐的非限制性列表包括:
根据上述组合物的一些实施方案,所述农用组合物进一步包含至少一种作物保护剂。在一个实施方案中,所述至少一种作物保护剂选自杀真菌剂、杀昆虫剂、除草剂和植物生长调节剂。在一个实施方案中,所述作物保护剂是除草剂。在另一个实施方案中,所述作物保护剂是植物生长调节剂。在一个实施方案中,所述至少一种作物保护剂选自莠去津、特丁津、(S)-异丙甲草胺、异丙甲草胺、特丁净、西玛津、噻吩草胺、(S)-噻吩草胺、氟噻草胺、乙草胺、甲草胺、异噁唑草酮、异噁氯草酮、硝磺草酮、磺草酮、磺草唑胺、唑嘧磺草胺、二甲戊乐灵、溴草腈、灭草松、唑草酮、异噁草酮、烟嘧磺隆、砜嘧磺隆、氯吡嘧磺隆、草克净、氟烯草戊酯、氟丙磺隆、氟嘧磺隆、麦草畏、嗪草酸甲酯、达草止、2,4-D、二氯吡啶酸、氟吡草腙、氟草定、MCPA、MCPB、氯苯氧丙酸(MCPP)、吡喃隆、噻吩磺隆、苯草醚、EPTC、草甘膦、草铵膦、草硫膦、氰草津、喔草酯、苯嗪草酮、甜菜灵、甜菜宁、甜菜安、乙呋草黄、醚苯磺隆、氯草敏、环草定、燕麦畏、吡氟禾草灵、稀禾啶、喹禾灵、二氯吡啶酸、烯草酮、环氧嘧磺隆、氟锁草醚、氯噻草灵乙酯、甲磺草胺、氯嘧磺隆乙酯、氯酯磺草胺、氟黄胺草醚、甲氧咪草烟、灭草喹、咪草烟、依灭草、乳氟禾草灵、精噁唑禾草灵、噻苯隆、脱叶磷、氟乐灵、二甲草胺、敌草胺、氯甲喹啉酸、吡唑草胺、双酰草胺、噁唑隆、炔苯酰草胺、胺苯磺隆、牧草胺、伏草隆、扑草净、达草灭、嘧醚苯甲酸钠、MSMA、DSMA、敌草隆、氟咯草酮、氟硫草定、噻草啶、氟硝草醚、乙丁烯氟灵、炔草酯、酰嘧磺隆、禾草灵甲酯、吡氟酰草胺、乙氧嘧磺隆、四唑酰草胺、啶嘧磺隆、双氟磺草胺、异丙吡草酯、氟唑磺隆、氟啶磺隆钠、呋草酮、碘磺隆、异丙隆、绿麦隆、氯磺隆、甲磺隆、乙磺隆、苯磺隆、2,4-DB、2,4-DP、治草醚、麦草伏-M、咪草酯甲酯、碘苯腈、肟草酮、乙羧氟草醚、甲基苯噻隆、异噁草胺、苄草丹、苯敌快甲基硫酸盐、丙草胺、醚磺隆、解草啶、苄嘧磺隆、唑吡嘧磺隆、吡嘧磺隆、四唑嘧磺隆、戊草丹、苯噻草胺、禾草特、敌稗、吡唑特、氰氟草酯、双草醚钠、嘧草醚、唑草胺、丙炔噁草酮、噁草酮、溴丁酰草胺、MY-100、杀草隆、NB 061、MK243、HW-52、AC 014、莠天净、环嗪酮、磺草灵、唑啶草酮、丁噻隆、胺苯磺隆或其组合。
根据一些实施方案,本发明提供了一种控制不期望的植物生长的方法,其包括向所述不期望的植物生长的场所施用根据上述组合物的一个或多个实施方案的农用组合物。
根据一些实施方案,本发明提供了一种控制不期望的植物生长的方法,其包括向不期望的植物生长的场所施用除草有效量的具有以下结构的化合物:
或其盐,其中:
A是包含1至4个杂原子的环戊二烯、苯和茚骨架;其中每个杂原子独立地选自N、S、Se和O;并且其中环的一个或多个碳原子任选地化学附接到由以下组成的基团中的至少一个:-SO2CF3、-O-SO2CF3、-NR3 +、-SO2R、-C≡N、-CX3、CX2R、-COX、-CHO、-COR、-CO2R、-CONH2、-CONHR、-CONR2、-N=O、-N≡N+、-N=NR、-CR=NR、-N=CR2、-F、-Cl、-Br和-I;并且其中X选自F、Cl、Br和I;
n是0至5;
T是未取代的或被一个或两个以下基团取代的亚甲基:卤基、氧、-SO2CF3、-O-SO2CF3、-NR3 +、-SO2R、-C≡N、-CX3、CX2R、-COX、-CHO、-COR、-CO2R、-CONH2、-CONHR、-CONR2、-F、-N=O、-N≡N+、-N=NR、-CR=NR、-N=CR2,并且其中X选自F、Cl、Br和I;并且
Z是-COOH、COO-、OH、-O-R、具有饱和或不饱和的醇残基的COOR,所述醇残基具有直链、支链、环状、芳族或杂芳族链;-O-(CH2CH2O)nR(n≥1);-O-(CHMeCH2O)nR(n≥1);磺酰基、氨基甲酰基、伯胺、仲胺、叔胺、甲酰胺、-NR-O-R、-O-NR2、肼、-NH-COR和甲脒部分或其盐;
其中R选自H、取代的或未取代的烷基和取代的或未取代的芳基。
根据一些实施方案,Z可以选自而不限于包括以下项的组:
根据上述方法的一些实施方案,化合物或农业上可接受的盐的不受限制的列表包括:
根据上述组合物的一些实施方案,化合物或农业上可接受的盐的非限制性列表包括:
/>
/>
根据上述方法的一些实施方案,所述方法进一步包括向不期望的植物生长的场所施用至少一种作物保护剂。在一个实施方案中,所述作物保护剂选自除草剂、杀真菌剂、杀昆虫剂和植物生长调节剂。根据上述方法的一些实施方案,所述作物保护剂是除草剂。在一个实施方案中,所述作物保护剂是氨基酸合成抑制剂除草剂。在一个实施方案中,本发明的氨基酸合成抑制剂除草剂的非限制性列表包括:磺酰脲除草剂、咪唑啉酮除草剂、磺酰胺除草剂、氨基酸衍生物、甲氧咪草烟、甲咪唑烟酸、咪草烟、灭草喹、依灭草和咪草酸、氯嘧磺隆、氟嘧磺隆酸、噻吩磺隆酸、醚苯磺隆、烟嘧磺隆、甲磺隆酸、苯磺隆酸、砜嘧磺隆、氟胺磺隆酸、草甘膦或其任意组合。
根据上述方法的一些实施方案,所述作物保护剂是植物生长调节剂。在一个实施方案中,本发明的植物生长调节剂的非限制性列表包括:麦草畏、2,4-D、二氯吡啶酸和氟草定。
根据一些实施方案,本发明提供了一种控制不期望的植物生长的方法,其包括向不期望的植物生长的场所施用以下物质以有效地控制不期望的植物生长:
a.具有以下结构的第一除草剂:
或其盐,其中:
A是包含1至4个杂原子的环戊二烯、苯和茚骨架;其中每个杂原子独立地选自N、S、Se和O;并且其中环的一个或多个碳原子任选地化学附接到由以下组成的基团中的至少一个:-SO2CF3、-O-SO2CF3、-NR3 +、-SO2R、-C≡N、-CX3、CX2R-COX、-CHO、-COR、-CO2R、-CONH2、-CONHR、-CONR2、-F、-N=O、-N≡N+、-N=NR、-CR=NR、-N=CR2、-Cl、-Br和-I;并且其中X选自F、Cl、Br和I;
n是0至5;
T是未取代的或被一个或两个以下基团取代的亚甲基:卤基、氧、-SO2CF3、-O-SO2CF3、-NR3 +、-SO2R、-C≡N、-CX3、CX2R、-COX、-CHO、-COR、-CO2R、-CONH2、-CONHR、-CONR2、-F、-N=O、-N≡N+、-N=NR、-CR=NR、-N=CR2,并且其中X选自F、Cl、Br和I;并且
Z是-COOH、COO-、OH、-O-R、具有饱和或不饱和的醇残基的COOR,所述醇残基具有直链、支链、环状、芳族或杂芳族链;-O-(CH2CH2O)nR(n≥1);-O-(CHMeCH2O)nR(n≥1);磺酰基、氨基甲酰基、伯胺、仲胺、叔胺、甲酰胺、-NR-O-R、-O-NR2、肼、-NH-COR和甲脒部分或其盐;
其中R选自H、取代的或未取代的烷基和取代的或未取代的芳基;
b.第二除草剂,以有效地控制不期望的植物生长。
由此有效地控制不期望的植物生长。
根据上述方法的一些实施方案,Z可以是而不限于:
/>
根据上述方法的一些实施方案,第二除草剂是氨基酸合成抑制剂除草剂。
根据上述方法的一些实施方案,第二除草剂选自磺酰脲除草剂、咪唑啉酮除草剂、磺酰胺除草剂和氨基酸衍生物。
根据上述方法的一些实施方案,本发明的第二除草剂的非限制性列表包括:甲氧咪草烟、甲咪唑烟酸、咪草烟、灭草喹、依灭草、咪草酸、氯嘧磺隆、氟嘧磺隆酸、噻吩磺隆酸、醚苯磺隆、烟嘧磺隆、甲磺隆酸、苯磺隆酸、砜嘧磺隆、氟胺磺隆酸、草甘膦、莠去津、特丁津、(S)-异丙甲草胺、异丙甲草胺、特丁净、西玛津、噻吩草胺、(S)-噻吩草胺、氟噻草胺、乙草胺、甲草胺、异噁唑草酮、异噁氯草酮、硝磺草酮、磺草酮、磺草唑胺、唑嘧磺草胺、二甲戊乐灵、溴草腈、灭草松、唑草酮、异噁草酮、烟嘧磺隆、砜嘧磺隆、氯吡嘧磺隆、草克净、氟烯草戊酯、氟丙磺隆、氟嘧磺隆、麦草畏、嗪草酸甲酯、达草止、2,4-D、二氯吡啶酸、氟吡草腙、氟草定、MCPA、MCPB、氯苯氧丙酸(MCPP)、吡喃隆、噻吩磺隆、苯草醚、EPTC、草甘膦、草铵膦、草硫膦、氰草津、喔草酯、苯嗪草酮、甜菜灵、甜菜宁、甜菜安、乙呋草黄、醚苯磺隆、氯草敏、环草定、燕麦畏、吡氟禾草灵、稀禾啶、喹禾灵、二氯吡啶酸、烯草酮、环氧嘧磺隆、氟锁草醚、氯噻草灵乙酯、甲磺草胺、氯嘧磺隆乙酯、氯酯磺草胺、氟黄胺草醚、甲氧咪草烟、灭草喹、咪草烟、依灭草、乳氟禾草灵、精噁唑禾草灵、噻苯隆、脱叶磷、氟乐灵、二甲草胺、敌草胺、氯甲喹啉酸、吡唑草胺、双酰草胺、噁唑隆、炔苯酰草胺、胺苯磺隆、牧草胺、伏草隆、扑草净、达草灭、嘧醚苯甲酸钠、MSMA、DSMA、敌草隆、氟咯草酮、氟硫草定、噻草啶、氟硝草醚、乙丁烯氟灵、炔草酯、酰嘧磺隆、禾草灵甲酯、吡氟酰草胺、乙氧嘧磺隆、四唑酰草胺、啶嘧磺隆、双氟磺草胺、异丙吡草酯、氟唑磺隆、氟啶磺隆钠、呋草酮、碘磺隆、异丙隆、绿麦隆、氯磺隆、甲磺隆、乙磺隆、苯磺隆、2,4-DB、2,4-DP、治草醚、麦草伏-M、咪草酯甲酯、碘苯腈、肟草酮、乙羧氟草醚、甲基苯噻隆、异噁草胺、苄草丹、苯敌快甲基硫酸盐、丙草胺、醚磺隆、解草啶、苄嘧磺隆、唑吡嘧磺隆、吡嘧磺隆、四唑嘧磺隆、戊草丹、苯噻草胺、禾草特、敌稗、吡唑特、氰氟草酯、双草醚钠、嘧草醚、唑草胺、丙炔噁草酮、噁草酮、溴丁酰草胺、MY-100、杀草隆、NB 061、MK243、HW-52、AC 014、莠天净、环嗪酮、磺草灵、唑啶草酮、丁噻隆、胺苯磺隆。
根据上述方法的一些实施方案,所述方法进一步包括施用第三除草剂或植物生长调节剂。
根据一些实施方案,本发明提供了一种用于控制不期望的植物生长的组合物,其包含以下物质的混合物:
a.具有以下结构的化合物或其盐:
或其盐,其中:
A是包含1至4个杂原子的环戊二烯、苯和茚骨架;其中每个杂原子独立地选自N、S、Se和O;并且其中环的一个或多个碳原子任选地化学附接到由以下组成的基团中的至少一个:-SO2CF3、-O-SO2CF3、-NR3 +、-SO2R、-C≡N、-CX3、CX2R-COX、-CHO、-COR、-CO2R、-CONH2、-CONHR、-CONR2、-F、-N=O、-N≡N+、-N=NR、-CR=NR、-N=CR2、-Cl、-Br和-I;并且其中X选自F、Cl、Br和I;
n是0至5;
T是未取代的或被一个或两个以下基团取代的亚甲基:卤基、氧、-SO2CF3、-O-SO2CF3、-NR3 +、-SO2R、-C≡N、-CX3、CX2R、-COX、-CHO、-COR、-CO2R、-CONH2、-CONHR、-CONR2、-F、-N=O、-N≡N+、-N=NR、-CR=NR、-N=CR2,并且其中X选自F、Cl、Br和I;并且
Z是-COOH、COO-、OH、-O-R、具有饱和或不饱和的醇残基的COOR,所述醇残基具有直链、支链、环状、芳族或杂芳族链;-O-(CH2CH2O)nR(n≥1);-O-(CHMeCH2O)nR(n≥1);磺酰基、氨基甲酰基、伯胺、仲胺、叔胺、甲酰胺、-NR-O-R、-O-NR2、肼、-NH-COR和甲脒部分或其盐;
其中R选自H、取代的或未取代的烷基和取代的或未取代的芳基;
b.至少一种选自以下物质的除草剂:莠去津、特丁津、(S)-异丙甲草胺、异丙甲草胺、特丁净、西玛津、噻吩草胺、(S)-噻吩草胺、氟噻草胺、乙草胺、甲草胺、异噁唑草酮、异噁氯草酮、硝磺草酮、磺草酮、磺草唑胺、唑嘧磺草胺、二甲戊乐灵、溴草腈、灭草松、唑草酮、异噁草酮、烟嘧磺隆、砜嘧磺隆、氯吡嘧磺隆、草克净、氟烯草戊酯、氟丙磺隆、氟嘧磺隆、麦草畏、嗪草酸甲酯、达草止、2,4-D、二氯吡啶酸、氟吡草腙、氟草定、MCPA、MCPB、氯苯氧丙酸(MCPP)、吡喃隆、噻吩磺隆、苯草醚、EPTC、草甘膦、草铵膦、草硫膦、氰草津、喔草酯、苯嗪草酮、甜菜灵、甜菜宁、甜菜安、乙呋草黄、醚苯磺隆、氯草敏、环草定、燕麦畏、吡氟禾草灵、稀禾啶、喹禾灵、二氯吡啶酸、烯草酮、环氧嘧磺隆、氟锁草醚、氯噻草灵乙酯、甲磺草胺、氯嘧磺隆乙酯、氯酯磺草胺、氟黄胺草醚、甲氧咪草烟、灭草喹、咪草烟、依灭草、乳氟禾草灵、精噁唑禾草灵、噻苯隆、脱叶磷、氟乐灵、二甲草胺、敌草胺、氯甲喹啉酸、吡唑草胺、双酰草胺、噁唑隆、炔苯酰草胺、胺苯磺隆、牧草胺、伏草隆、扑草净、达草灭、嘧醚苯甲酸钠、MSMA、DSMA、敌草隆、氟咯草酮、氟硫草定、噻草啶、氟硝草醚、乙丁烯氟灵、炔草酯、酰嘧磺隆、禾草灵甲酯、吡氟酰草胺、乙氧嘧磺隆、四唑酰草胺、啶嘧磺隆、双氟磺草胺、异丙吡草酯、氟唑磺隆、氟啶磺隆钠、呋草酮、碘磺隆、异丙隆、绿麦隆、氯磺隆、甲磺隆、乙磺隆、苯磺隆、2,4-DB、2,4-DP、治草醚、麦草伏-M、咪草酯甲酯、碘苯腈、肟草酮、乙羧氟草醚、甲基苯噻隆、异噁草胺、苄草丹、苯敌快甲基硫酸盐、丙草胺、醚磺隆、解草啶、苄嘧磺隆、唑吡嘧磺隆、吡嘧磺隆、四唑嘧磺隆、戊草丹、苯噻草胺、禾草特、敌稗、吡唑特、氰氟草酯、双草醚钠、嘧草醚、唑草胺、丙炔噁草酮、噁草酮、溴丁酰草胺、MY-100、杀草隆、NB 061、MK243、HW-52、AC 014、莠天净、环嗪酮、磺草灵、唑啶草酮、丁噻隆、胺苯磺隆或其组合;以及
c.至少一种农业上可接受的载体。
根据一些实施方案,本发明提供了一种用于控制不期望的植物生长的组合物,其包含以下物质的混合物:
a.具有以下结构的化合物:
或其盐,其中:
A是包含1至4个杂原子的环戊二烯、苯和茚骨架;其中每个杂原子独立地选自N、S、Se和O;并且其中环的一个或多个碳原子任选地化学附接到由以下组成的基团中的至少一个:-SO2CF3、-O-SO2CF3、-NR3 +、-SO2R、-C≡N、-CX3、CX2R-COX、-CHO、-COR、-CO2R、-CONH2、-CONHR、-CONR2、-F、-N=O、-N≡N+、-N=NR、-CR=NR、-N=CR2、-Cl、-Br和-I;并且其中X选自F、Cl、Br和I;
n是0至5;
T是未取代的或被一个或两个以下基团取代的亚甲基:卤基、氧、-SO2CF3、-O-SO2CF3、-NR3 +、-SO2R、-C≡N、-CX3、CX2R、-COX、-CHO、-COR、-CO2R、-CONH2、-CONHR、-CONR2、-F、-N=O、-N≡N+、-N=NR、-CR=NR、-N=CR2,并且其中X选自F、Cl、Br和I;并且
Z是-COOH、COO-、OH、-O-R、具有饱和或不饱和的醇残基的COOR,所述醇残基具有直链、支链、环状、芳族或杂芳族链;-O-(CH2CH2O)nR(n≥1);-O-(CHMeCH2O)nR(n≥1);磺酰基、氨基甲酰基、伯胺、仲胺、叔胺、甲酰胺、-NR-O-R、-O-NR2、肼、-NH-COR和甲脒部分或其盐;
其中R选自H、取代的或未取代的烷基和取代的或未取代的芳基;
b.至少一种植物生长调节剂;和
c.至少一种农业上可接受的载体。
根据一些实施方案,控制植物或其植物部分中的氨基酸含量的方法,其包括施用有效量的根据本发明的上述实施方案的农用组合物。
根据一些实施方案,本发明提供了一种控制植物或其植物部分中的氨基酸含量的方法,其包括施用有效量的根据本发明的上述实施方案的农用组合物。
根据一些实施方案,本发明提供了一种控制植物生长的方法,其包括向植物或其植物部分施用有效量的根据本发明的上述实施方案的农用组合物。
根据一些实施方案,本发明提供了一种控制至少部分地对选自HPAC 9组(EPSP合成抑制剂)、2(乙酰乳酸合酶(ALS)抑制剂)和4(植物生长调节剂或合成生长素)的除草剂有抗性的植物生长的方法,其包括向植物或其植物部分施用有效量的根据本发明的上述实施方案的农用组合物。
根据一些实施方案,本发明提供了一种农用组合物,其包含表2、3、4和5中列出的一种或多种化合物以及至少一种农业上可接受的载体。
根据一些实施方案,本发明提供了控制不期望的植物生长的方法,其包括施用表2、3、4和5中列出的一种或多种化合物。
根据一些实施方案,本发明提供了控制不期望的植物生长的方法,其包括施用包含表2、3、4和5中列出的一种或多种化合物和至少一种农业上可接受的载体的农用组合物。
实施例
在以下实施例中,如果缩写没有在上面定义,则其具有其普遍接受的含义。此外,所有温度都是以摄氏度计(除非另外指示)。使用以下方法来制备如下所指示的化合物。
实施例1:N-[2-(2,5-二氯-1,3-噻唑-4-基)乙基]乙酰胺(ID FP5650)的合成
步骤A:将4-(2-氨基乙基)噻唑-2-胺二盐酸盐(5g,23.3mmol)悬浮于DCM中并冷却至0℃,随后以逐滴方式添加TEA(7g,70mmol)和乙酸酐(2.4g,24mmol)。反应完成之后,将混合物蒸发至干并且用甲苯再蒸发3次,得到粗制N-(2-(2-氨基噻唑-4-基)乙基)乙酰胺(4.5g,粗品),其不经纯化而用于下一步骤。
步骤B:将N-(2-(2-氨基噻唑-4-基)乙基)乙酰胺(4.5g,24.2mmol)溶解在CH3CN(50mL)中,冷却至0℃,并且一次性添加NCS(3.33g,25mmol)。反应完成(通过HNMR得出结论)之后,将有机溶剂蒸发至干,并且将粗混合物在EtOAc(50mL)和H2O(50mL)之间分配。将有机层用H2O和盐水洗涤,经Na2SO4干燥并且在减压下蒸发,得到呈黄色油的乙基N-(2-(2-氨基-5-氯噻唑-4-基)乙基)乙酰胺(3.7g,17.0mmol,70%收率)。
步骤C:向预冷却至0℃的N-(2-(2-氨基-5-氯噻唑-4-基)乙基)乙酰胺(3.7g,17.0mmol)在CH3CN(50mL)中的溶液中一次性添加无水CuCl2(2.3g,17mmol)。10分钟之后,以逐滴方式添加亚硝酸叔丁酯(1.8g,17.5mmol)(反应在添加约10%的试剂之后起始;所述起始可以通过剧烈的气体放出开始来确定)。反应完成(通过HNMR得出结论)之后,将反应混合物的体积小心地在减压下减半;将所得粗混合物溶解于EtOAc(100mL)中,并且用5%HCl水溶液和盐水充分洗涤。将有机层经Na2SO4干燥并且在减压下蒸发,得到粗产物,将其通过FCC纯化,得到N-(2-(2,5-二氯噻唑-4-基)乙基)乙酰胺(1.22g,5.1mmol,30%收率)。
1H NMR(500MHz,DMSO-d6)δ7.94(s,1H),3.29(q,J=6.4Hz,2H),2.76(t,J=6.8Hz,2H),1.76(s,3H)。
LCMS239[M+H]+。MW 239.12;熔点87℃,纯度90%。
实施例2:2-(2,5-二氯-1,3-噻唑-4-基)-2,2-二氟乙酸(ID FP5667)的合成
步骤A:将2-(2-氨基噻唑-4-基)-2,2-二氟乙酸乙酯(350g,1.58mol)溶解于CH3CN(3L)中,冷却至0℃,并且一次性添加NCS(215g,1.6mol)。反应完成(通过HNMR得出结论)之后,将有机溶剂蒸发至干,并且将粗混合物在EtOAc(3L)和H2O(1L)之间分配。将有机层用H2O和盐水洗涤,经Na2SO4干燥并且在减压下蒸发,得到呈黄色固体的2-(2-氨基-5-氯噻唑-4-基)-2,2-二氟乙酸乙酯(283g,1.1mol,70%收率)。
步骤B:向预冷却至0℃的2-(2-氨基-5-氯噻唑-4-基)-2,2-二氟乙酸乙酯(283g,1.1mol)在CH3CN(3L)中的溶液中一次性添加无水CuCl2(155g,1.15mol)。10分钟之后,以逐滴方式添加亚硝酸叔丁酯(121g,1.16mol)(反应在添加约10%的试剂之后起始;所述起始可以通过剧烈的气体放出开始来确定)。反应完成(通过HNMR得出结论)之后,将反应混合物的体积小心地在减压下减半;将所得粗混合物溶解于EtOAc(3L)中,并且用5%HCl水溶液和盐水充分洗涤。将有机层经Na2SO4干燥,并且在减压下蒸发,得到呈深棕色油的粗制2-(2,5-二氯噻唑-4-基)-2,2-二氟乙酸乙酯(210g,粗品),其不经纯化而用于下一步骤。
步骤C:将来自先前步骤的粗制2-(2,5-二氯噻唑-4-基)-2,2-二氟乙酸乙酯(210g,粗品)溶解在EtOH(2L)中,并且一次性添加20%K2CO3水溶液(0.5L)。反应完成(通常3小时)之后,将溶剂蒸发至干,并且将粗混合物溶解在H2O(0.5L)中;将澄清溶液用CHCl3(3*200mL)和MTBE(100mL)洗涤。将水层用NaHSO4酸化至pH=4,并且用乙醚(3*150mL)萃取。将合并的有机层用盐水洗涤,经Na2SO4干燥并且在减压下蒸发,得到油状产物。在柱色谱法和用戊烷研磨之后,获得呈黄色固体的纯2-(2,5-二氯噻唑-4-基)-2,2-二氟乙酸(113g,0.46mol,经3个步骤的收率为27%)。
1H NMR(500MHz,cdcl3)δ10.38(s,1H)。
13C NMR(126MHz,cdcl3)δ165.29(t,J=33.4Hz),149.86(s),140.45(t,J=29.7Hz),129.24(s),109.64(t,J=253.2Hz)。
19F NMR(470MHz,cdcl3)δ-102.57(s)。
LCMS248[M+H]+。纯度>95%。
实施例3:2-氯-1,3-噻唑-4-基)-2,2-二氟乙酸(ID FP5666)的合成
步骤A:向预冷却至0℃的2-(2-氨基噻唑-4-基)-2,2-二氟乙酸乙酯(250g,1.12mol)在CH3CN(3L)中的溶液中一次性添加无水CuCl2(155g,1.15mol)(小心!观察到放热效应!加热至10℃)。10分钟之后,以逐滴方式添加亚硝酸叔丁酯(121g,1.16mol)(反应在添加约10%的试剂之后起始;所述起始可以通过剧烈的气体放出开始来确定)。反应完成(通过HNMR得出结论)之后,将反应混合物的体积小心地在减压下减半;将所得粗混合物溶解于EtOAc(3L)中,并且用5%HCl水溶液和盐水充分洗涤。将有机层经Na2SO4干燥,并且在减压下蒸发,得到粗制2-(2-氯噻唑-4-基)-2,2-二氟乙酸乙酯(205g,粗品),其不经纯化而用于下一步骤。
步骤B:将来自先前步骤的粗制2-(2-氯噻唑-4-基)-2,2-二氟乙酸乙酯(205g,粗品)溶解在EtOH(1.5L)中,并且一次性添加20%K2CO3水溶液(0.5L)。反应完成(通常3小时)之后,将溶剂蒸发至干,并且将粗混合物溶解在H2O(500mL)中;将澄清溶液用CHCl3(3*200mL)和MTBE(100mL)洗涤。将水层用NaHSO4酸化至pH=4,并且用乙醚(3*150mL)萃取。将合并的有机层用盐水洗涤,经Na2SO4干燥并且在减压下蒸发,得到油状产物。在柱色谱法和用戊烷研磨之后,获得呈黄色固体的纯2-(2-氯噻唑-4-基)-2,2-二氟乙酸(108g,0.5mol,经2个步骤的收率为45%)。
1H NMR(400MHz,CDCl3)δ11.61(s,1H),7.70(s,1H)。
13C NMR(101MHz,CDCl3)δ165.10(t,J=33.6Hz),154.53(s),145.63(t,J=30.9Hz),122.62(t,J=4.7Hz),109.40(t,J=251.0Hz)。
19F NMR(376MHz,CDCl3)δ-103.92(s)。
LCMS214[M+H]+。MP 92℃;纯度>95%。
实施例4:杂环氨基酸衍生物对萌发和早期植物发育的影响。
材料:罗马生菜的种子(Super-Jericho,未灭菌的)从Ben Shahar Moshe Ltd.获得,纯度为99%。下表2中所列的测试化合物是从头合成的或购自不同的供应商。
使用生菜种子进行滤纸生物测定:方案遵循Bertin等人2009和Movellan等人2014,并且具有如下所述的特定修改。
将种子置于佩特里培养皿中的Whatman 1号滤纸(Whatman,Middlesex,U.K.)上(每板10粒种子),其中将2.0ml浓度范围为0(对照)至1mmol/l的测试材料的水溶液置于倾斜45°的托盘中。将托盘在黑暗中保持48小时,然后转移至生长室,6/18暗/亮循环持续4天。每个实验至少重复两次。
在测试开始后6天目测评估植物的胚根和嫩芽的发育,以确定测试材料的最小有效浓度(MEC)。在本发明的上下文中,MEC定义为引起与对照组中的植物发育的偏差(没有萌发或胚根或嫩芽畸形)的测试材料的最低浓度水平。MEC以任意单位表示为活性评分,如表1所呈现的:
MEC | 活性评分 |
高于0.1mM | 弱 |
0.1mM | 中等 |
0.01mM | 强 |
0.001mM和更低 | 非常强 |
所选化合物对种子萌发和早期植物发育的除草活性总结在表2中:
/>
/>
/>
/>
/>
/>
/>
/>
实施例6:所选非编码氨基酸的衍生物(DNAA)的芽后除草活性。
对2-3期叶的罗马生菜(生菜(Lactuca sativa L.))植物进行测试。植物在尺寸为2×2×5cm的装有土壤的微型盆中生长,每个微型盆一株植物。将测试化合物溶解在Silwet助剂的0.1%水溶液中,使最终浓度范围为0(对照)至0.0001%。将测试化合物用喷枪施用到土壤(每盆1ml)或叶(每盆0.1ml)上。对20株植物测试各浓度。处理之后两周,目视评价相应测试材料(地上部分和根)的除草效果。然后,将植物的地上部分整齐地切割并称重(湿重)以评估由测试化合物引起的生长抑制。生长抑制(GI)计算如下:
GI=1-Mt*100%/Mc
其中Mt和Mc分别是经处理的植物和对照植物的湿重中位数。在本发明的上下文中,除草效果通过引起超过85%的生长抑制(GI)或不可逆的植物损害的化合物浓度来评估(表3)。所选DHAA的除草活性总结在表4(土壤施用)和表5(叶施用)中。
表3.成功标准(除草活性的评分)
表4:所选DNAA的除草活性(土壤施用)
/>
/>
表5.所选DNAA的除草活性(叶施用)。
/>
实施例7:所选DNAA对野草发育的除草活性。
将野草种子在0.3-升盆中锯开,所述盆含有来自有机田地的中等重量的粘壤土土壤(55%粘土、23%淤泥、20%沙、2%有机物,pH 7.1)。以完全随机的设计进行实验。每种处理重复3次(3个盆)。每种化合物通常在作物(玉米、小麦、大豆、棉花、燕麦、鹰嘴豆)和野草(苋属、藜属、扁豆、芥子属、水飞蓟)上进行测试。
除草剂以0(对照)至5毫克/盆的剂量施用。在锯开当天进行处理(芽前处理)。然后在除草剂施用后24小时将盆转移至网室,并且用喷灌灌溉至土壤的田间容量。可替代地,对2-3期真叶的生长植物施用除草剂(芽后处理)。
在整个实验期间,植物在网室中生长。以0至5的量表评价施用(DAA)后6、12、19、26和32天的植物发育,其中0代表死亡植物,而5代表与对照类似或没有不同的健康植物。在本发明的上下文中,除草效果表示为评分,其计算为植物活力、高度和叶色的评估的平均值。
表6.DHAA对盆栽野草的平均除草效果
实施例8:杂环氨基酸衍生物对萌发的影响
材料:罗马生菜的种子(Super-Jericho,未灭菌的)从Ben Shahar Moshe Ltd.获得,纯度为99%。下表2中所列的测试化合物是从头合成的或购自不同的供应商。
使用生菜种子进行滤纸生物测定:方案遵循Bertin等人2009和Movellan等人2014,并且具有如下所述的特定修改。
将种子置于佩特里培养皿中的Whatman 1号滤纸(Whatman,Middlesex,U.K.)上(每板10粒种子),其中将2.0ml浓度范围为0(对照)至1mmol/l的测试材料的水溶液置于倾斜45°的托盘中。将托盘在黑暗中保持48小时,然后转移至生长室,6/18暗/亮循环持续4天。每个实验至少重复两次。
在测试开始后6天目测评估植物的胚根和嫩芽的发育,以确定测试材料的完全有效浓度(FEC)。在本发明的上下文中,FED定义为大部分防止种子萌发的测试材料的最低浓度水平。
所选化合物对种子萌发的抑制效果总结在表7中。
表7.所选化合物的完全有效浓度(FEC)
/>
/>
实施例9:所选非编码氨基酸的衍生物(DNAA)与结构相关的非编码氨基酸的除草活性的比较
对2-3期叶的罗马生菜(生菜)植物进行测试。植物在尺寸为2×2×5cm的装有土壤的微型盆中生长,每个微型盆一株植物。将测试化合物溶解在Silwet助剂的0.1%水溶液中。测试材料以0(对照)、0.01、0.05和0.5毫克/盆的比率施用。将测试化合物用喷枪施用到土壤或叶上(每盆0.1ml)。对20株植物测试各浓度。处理之后两周,目视评价相应测试材料(地上部分和根)的除草效果。然后,将植物的地上部分整齐地切割并称重(湿重)以评估由测试化合物引起的生长抑制。生长抑制(GI)计算如下:
GI=1-Mt*100%/Mc
其中Mt和Mc分别是经处理的植物和对照植物的湿重中位数。选择用于比较抑制效果的化合物列于表8中。非编码氨基酸(NAA)及其结构类似物DNAA的除草效果的比较总结在表9中。
表8.所选NAA和结构相关DNAA的列表
ID | 化学名称 |
517 | 2-氨基-3-(2,5-二氯噻吩-3-基)丙酸 |
5640 | (2,5-二氯噻吩-3-基)(二氟)乙酸 |
527 | 2-氨基-3-(2,5-二氯-1,3-噻唑-4-基)丙酸 |
5667 | (2,5-二氯-1,3-噻唑-4-基)(二氟)乙酸 |
586 | 2-(2,5-二氯噻吩-3-基)乙酸 |
516 | 2-氨基-3-(2-氯噻吩-3-基)丙酸 |
5623 | 2-(2-氯噻吩-3-基)-2,2-二氟乙酸 |
632 | 2-氨基-3-(2-溴吡啶-4-基)丙酸 |
6617 | 2-(6-溴吡啶-2-基)-2,2-二氟乙酸 |
表9:所选NAA和结构相关的DNAA的除草效果的比较,生长施用(%,土壤施用)
表10:所选NAA和结构相关的DNAA的除草效果的比较,生长施用(%,叶施用)
讨论
确定了氨酰基-tRNA合成酶可以用所选非编码氨基酸酰化tRNA,因此促进这些分子包含在新生肽中。过去还提出,所选非编码氨基酸的除草活性是基于其酰化tRNA的能力,tRNA被包括在肽中,并且因此改变细胞蛋白的3D结构。
本发明的NCAAD缺乏羧基或氨基。鉴于此,氨酰基-tRNA合成酶无法用缺乏羧基的NCAAD酰化tRNA,并且缺乏氨基的NCAAD无法与新生肽连接。因此,本发明的NCAAD中没有一种可以结合到肽中,并且对细胞蛋白的3D结构发挥预期的作用。
如从上述实验数据显而易见,本发明的NCAAD具有强除草活性。这与最初的假设相反,最初的假设是这些化合物仅可以作为除草非编码AA(NCAA)的惰性结构类似物。此外,出人意料地,本发明的NCAAD表现出的除草活性是相应NCAA的10至100倍。
在叶施用和土壤施用两者中显示出除草活性的许多NCAAD表明叶、嫩芽和根的有效吸收。这与相应的NCAA相反,相应的NCAA仅在土壤施用中展现出除草活性。
除非另外定义,否则本文使用的所有技术术语和/或科学术语均具有与本发明所属领域的普通技术人员通常所理解相同的含义。虽然在本发明的实施方式的实践或测试中可以使用与本文所述的那些方法和材料类似或等效的方法和材料,但下面描述示例性方法和/或材料。在冲突的情况下,则以包括定义的专利说明书为准。另外,材料、方法和实施例仅是说明性的,而不旨在必然是限制性的。
如本文所用,术语“包含(comprises)”、“包含(comprising)”、“包括(includes)”、“包括(including)”、“具有”及其缀合物意指“包括但不限于”。
术语“由……组成”意指“包括且限于”。
如本文所用,除非上下文另外清楚地指出,否则单数形式“一个/种(a)”、“一个/种(an)”和“所述”包括复数个/种指代物。例如,术语“化合物”或“至少一种化合物”可以包括多种化合物,包括其混合物。
应该理解,当元件被称为在另一元件“上”、“附接到”另一元件、“连接到”另一元件、与另一元件“耦合”、“接触”另一元件等时,该元件可以直接在另一元件上、附接到另一元件、连接到另一元件、与另一元件耦合和/或接触另一元件,或者也可以存在中间元件。相反,当元件被称为例如“直接在另一元件上”、“直接附接到”另一元件、“直接连接到”另一元件、“直接与另一元件耦合”或“直接接触”另一元件时,不存在中间元件。本领域技术人员还应该理解,提及与另一特征“相邻”设置的结构或特征可以具有与相邻特征重叠或位于相邻特征之下的部分。
应当理解,尽管术语第一、第二等可以在本文用于描述各种元件、部件、区域、层和/或部分,但是这些元件、部件、区域、层和/或部分不应当受这些术语的限制。相反,这些术语仅用于将一个元件、部件、区域、层和/或部分与另一个元件、部件、区域、层和/或部分区分开。
如本领域技术人员所理解的,本文公开的各种式的化合物可以含有手性中心,例如不对称碳原子。因此,本公开涉及以下两者的合成:(i)活性化合物的外消旋混合物,和(ii)活性化合物的对映异构体形式。外消旋物拆分成对映异构体形式和光学活性对映异构体形式的外消旋化可以根据本领域已知的程序进行。双键的几何异构体等也可以存在于本文公开的化合物中,并且除非另外指定,否则所有这样的稳定异构体均包括在本公开内。本公开的化合物中还包括互变异构体(例如,三唑和/或咪唑的互变异构体)和旋转异构体。除非另外指示,否则由本文的式定义的其中包括三个或更多个碳的所有链可以是饱和的或不饱和的。
应当理解,本发明的方法中所用的化合物上的取代基和取代模式可以由本领域普通技术人员选择以提供在化学上稳定的化合物,并且所述化合物可以通过本领域已知的技术由容易获得的起始材料容易地合成。如果取代基本身被多于一个基团取代,则应当理解,这些多个基团可以在同一碳上或在不同的碳上,只要得到稳定的结构即可。
“任选取代的”基团是指其中所含的与氢原子相连的一个或多个键被与非氢或非碳原子相连的键所替代的官能团,条件是保持正常的化合价并且取代产生稳定的化合物。取代的基团还包括其中与一个或多个碳或一个或多个氢原子相连的一个或多个键被与杂原子相连的一个或多个键(包括双键或三键)替代的基团。当公开或要求保护多个取代基部分时,取代的化合物可以独立地被一个或多个所公开的或要求保护的取代基部分中单个或多个取代。独立地取代意指(两个或更多个)取代基可以相同或不同。在选择本发明的化合物时,本领域普通技术人员将认识到,各种取代基的选择符合熟知的化学结构连接性的原则。
如本文所用,“H”是指氢原子。“C”是指碳原子。“N”是指氮原子。“O”是指氧原子。“卤代”是指F、Cl、Br或I。如本文所用,术语“羟基”是指-OH部分。“Br”是指溴原子。“Cl”是指氯原子。“I”是指碘原子。“F”是指氟原子。“酰基”旨在指基团-C(O)-R,其中R是合适的取代基,例如乙酰基、丙酰基、丁酰基、苯甲酰基或烷基苯甲酰基。如本文所用,“烷基”是指含有1或2个至10或20个或更多个碳原子的直链或支链烃(例如,C2、C3、C4、C5、C6、C7、C8、C9、C10、C11、C12、C13、C14、C15等)。在一些实施方案中,烷基可以是低级烷基。“低级烷基”是指具有1至3个、或1至5个、或1至8个碳原子的直链或支链烷基。烷基的代表性实例包括但不限于甲基、乙基、正丙基、异丙基、正丁基、仲丁基、异丁基、叔丁基、正戊基、异戊基、新戊基、正己基、3-甲基己基、2,2-二甲基戊基、2,3-二甲基戊基、正庚基、正辛基、正壬基、正癸基等。如本文所用,碳数范围(例如,C1-C12烷基)的鉴定旨在包括在这样的范围内的组成碳数部分中的每一种,使得包括在该规定范围内的各中间碳数和任何其他规定或中间碳数值,使得在指定碳数范围内的碳数子范围可以独立地指定。例如,C1-C12烷基旨在包括甲基、乙基、丙基、丁基、戊基、己基、庚基、辛基、壬基、癸基、十一烷基和十二烷基,包括直链以及支链基团,如上所指出,并且碳数范围C1-C12烷基也可以更限制性地指定为子范围,如C1-C4烷基、C2-C8烷基、C2-C4烷基、C3-C5烷基或更宽碳数范围内的任何其他子范围。另外,考虑具体地排除一个或多个碳数的碳数范围,考虑排除指定范围的碳数极限中的任一个或两个的子范围。如本领域普通技术人员通常理解的,“饱和”是指其中原子(例如,碳)的所有可用价键都附接到其他原子的状态。类似地,“不饱和”是指其中并非所有可用价键都附接到其他原子的状态;在这样的化合物中,额外的键通常采取双键或三键的形式(通常与碳)。例如,当沿链不存在双键或三键或没有双键或三键直接连接到链时,碳链是“饱和的”(例如,羰基),而当沿链存在至少一个双键或三键或至少一个双键或三键直接连接到链时,碳链是“不饱和的”(例如,羰基)。此外,本领域普通技术人员应当理解,取决于链饱和的取代基的存在或不存在取决于取代基所键合的一个或多个原子(例如,碳)的化合价要求。如本文所用,“烯基”是指含有1或2个至10或20个或更多个碳并且含有至少一个碳-碳双键的直链或支链烃,其在结构上例如通过两个氢的替代而形成。“烯基”的代表性实例包括但不限于乙烯基、2-丙烯基、2-甲基-2-丙烯基、3-丁烯基、4-戊烯基、5-己烯基、2-庚烯基、2-甲基-1-庚烯基、3-癸烯基等。如本文所用,“炔基”是指含有1或2个至10或20个或更多个碳原子并且含有至少一个碳-碳三键的直链或支链烃基。炔基的代表性实例包括但不限于乙炔基、1-丙炔基、2-丙炔基、3-丁炔基、2-戊炔基、1-丁炔基等。如本文所用,术语“环烷基”是指含有3至8个或更多个碳的饱和环状烃基。
如本领域所理解的,术语“任选取代的”指示指定基团是未取代的或被一个或多个合适的取代基取代。“取代的”“取代基”是代替有机分子的母链或环上的氢原子的原子或基团。如本文所用,“杂环”是指单环、双环或三环环系。单环杂环环系由含有1、2、3或4个独立地选自O、N和S的杂原子的任何5元至9元环举例说明。如本文所用,“芳基”是指具有一个或多个芳族环的环系。芳基的代表性实例包括薁基、茚满基、茚基、萘基、苯基、四氢萘基等。“杂芳基”意指其中一个或多个碳原子已被杂原子(例如,N、O或S)替代的环状芳族烃。如果杂芳基含有多于一个杂原子,则杂原子可以相同或不同。如本文所用,“烷氧基”是指通过如本文所定义的氧基附加到母体分子部分的如本文所定义的烷基。“胺”或“氨基”旨在意指基团-NH2。“伯胺”具有三个氢原子之一被烷基或芳族基团替代。“仲胺”具有两个有机取代基与一个氢一起与氮键合。“叔胺”具有三个有机取代基与氮键合。如本文所用,“酰胺”是指具有与氮原子(N)连接的羰基(C=O)的官能团,或含有该基团的有机化合物,通常表示为:
其中,R和R'可以独立地是任何一个或多个共价连接的原子。如本文所用,术语“氧代”是指=O部分。如本文所用,术语“氧基”是指-O-部分。“硝基”是指有机化合物官能团-NO2。“羰基”是具有双键键合到氧原子的碳原子的官能团(-C=O)。如本文所用,“羧基”是指-COOH官能团,也写作-CO2H或-(C=O)-OH。
应当理解,本文提供的化合物、组合物和方法在一些实施方案中可以进一步通过排除特定取代基、基团、部分、结构、成分、步骤或条件的附带条件或限制来指定,如关于本文阐述的各种更广泛的说明和示例可适用。
本发明的“农业上可接受的载体”包括而不限于对化学式的应用有益的助剂、混合剂、增强剂等。合适的载体不应对有价值的作物产生植物毒性,特别是在施用用于在作物存在下选择性野草控制的组合物时所采用的浓度下,并且不应与本文的化学式的化合物或其他组合物成分发生化学反应。这样的混合物可以设计成直接施用于野草或其场所,或者可以是通常在施用前用另外的载体和助剂稀释的浓缩物或制剂。它们可以包含惰性或活性组分,并且可以是固体,例如粉尘剂、颗粒剂、水分散性颗粒剂或可湿性粉剂,或液体,例如可乳化的浓缩物、溶液、乳液或悬浮液。可用于制备本发明的农用组合物的合适的农业载体是本领域技术人员熟知的。例如,可以采用的液体载体包括水、甲苯、二甲苯、石脑油、作物油、丙酮、甲乙酮、环己酮、三氯乙烯、全氯乙烯、乙酸乙酯、乙酸戊酯、乙酸丁酯、丙二醇单甲醚和二乙二醇单甲醚、甲醇、乙醇、异丙醇、戊醇、乙二醇、丙二醇、甘油等。水通常是经选择用以稀释浓缩物的载体。合适的固体载体包括滑石、叶蜡石粘土、硅石、凹凸棒石粘土、硅藻土(kieselguhr)、白垩、硅藻土(diatomaceous earth)、石灰、碳酸钙、膨润土、漂白土、棉籽壳、小麦粉、大豆粉、浮石、木粉、胡桃壳粉、木质素等。
通常期望将一种或多种表面活性剂掺入本发明的组合物中。这样的表面活性剂有利地用于固体组合物和液体组合物两者中,尤其是设计成在施用前用载体稀释的那些。表面活性剂可以是阴离子、阳离子或非离子性质的,并且可以用作乳化剂、润湿剂、悬浮剂或用于其他目的。典型的表面活性剂包括烷基硫酸盐的盐,如月桂基硫酸二乙醇铵;烷基芳基磺酸盐,如十二烷基苯磺酸钙;烷基酚-氧化烯加成产物,如壬基酚-C18乙氧基化物;醇-氧化烯加成产物,如十三烷醇-C16乙氧基化物;皂,如硬脂酸钠;烷基萘磺酸盐,如二丁基萘磺酸钠;磺基琥珀酸盐的二烷基酯,如二(2-乙基己基)磺基琥珀酸钠;山梨糖醇酯,如油酸山梨糖醇酯;季胺,如月桂基三甲基氯化铵;脂肪酸的聚乙二醇酯,如聚乙二醇硬脂酸酯;环氧乙烷和环氧丙烷的嵌段共聚物;和磷酸单烷基酯和磷酸二烷基酯的盐。
通常用于农用组合物中的其他助剂包括消泡剂、相容剂、螯合剂、中和剂和缓冲剂、腐蚀抑制剂、染料、增香剂、渗透助剂、铺展剂、粘着剂、分散剂、增稠剂、防冻剂、抗微生物剂等。组合物还可以含有其他相容的组分,例如其他除草剂、植物生长调节剂、杀真菌剂、杀虫剂等,并且可以与液体肥料或固体颗粒肥料载体(如硝酸铵、尿素)等一起配制。
“农业上可接受的盐”旨在意指保持指定化合物的游离酸和碱的生物有效性并且在生物学或其他方面不是不期望的盐。农业上可接受的盐的实例包括硫酸盐、焦硫酸盐、硫酸氢盐、亚硫酸盐、亚硫酸氢盐、磷酸盐、磷酸一氢盐、磷酸二氢盐、偏磷酸盐、焦磷酸盐、氯化物、溴化物、碘化物、乙酸盐、丙酸盐、癸酸盐、辛酸盐、丙烯酸盐、甲酸盐、异丁酸盐、己酸盐、庚酸盐、丙酸盐、草酸盐、丙二酸盐、琥珀酸盐、辛二酸盐、癸二酸盐、富马酸盐、马来酸盐、丁炔-1,4-二酸盐、己炔-1,6-二酸盐、苯甲酸盐、氯苯甲酸盐、甲基苯甲酸盐、二硝基苯甲酸盐、羟基苯甲酸盐、甲氧基苯甲酸盐、邻苯二甲酸盐、磺酸盐、二甲苯磺酸盐、苯基乙酸盐、苯基丙酸盐、苯基丁酸盐、柠檬酸盐、乳酸盐、γ-羟基丁酸盐、乙醇酸盐、酒石酸盐、甲磺酸盐、丙磺酸盐、萘-1-磺酸盐、萘-2-磺酸盐和扁桃酸盐。
在整个本申请中,本发明的各种实施方案可以以范围的形式呈现。应当理解,范围形式的描述仅仅是为了方便和简洁,而不应当被解释为对本发明范围的硬性限制。因此,范围的描述应被认为具体地公开了所有可能的子范围以及该范围内的单个数值。例如,对如1至6的范围的描述应当认为具有特定公开的子范围,如1至3、1至4、1至5、2至4、2至6、3至6等,以及所述范围内的单个数字,例如1、2、3、4、5和6。这与范围的宽度无关。
无论何时在本文中指出数值范围,其意指包括在指出的范围内的任何引用的数字(分数或整数)。短语第一指示数字和第二指示数字之间的“范围/范围”和“从”第一指示数字“到”第二指示数字“的范围/范围”在本文中可互换使用,并且意指包括第一和第二指示数字以及其间的所有分数和整数。
为了清楚起见,在单独的实施方案的上下文中描述的本发明的某些特征也可以在单个实施方案中组合提供。相反地,为了简洁起见,在单个实施方案的上下文中描述的本发明的各种特征也可以单独地或以任何合适的子组合或如在本发明的任何其他描述的实施方案中合适地提供。在各种实施方案的上下文中描述的某些特征不被认为是那些实施方案的必要特征,除非在没有那些要素的情况下实施方案不可操作。
如本文所用的术语“方法”是指完成给定任务的方式、手段、技术和程序,包括但不限于化学、农业、生物和生物化学领域的从业者已知的或容易从已知的方式、手段、技术和程序发展而来的那些方式、手段、技术和程序。
如本文所用的术语“植物生长调节剂”是指但不限于天然或合成的化合物,其修饰或控制植物内的一种或多种特定生理过程。
如本文所用的术语“植物”是指但不限于整株植物、植物的祖先和后代以及植物部分,包括种子、嫩芽、茎、根(包括块茎)和植物细胞、组织和器官。植物可以是任何形式,包括悬浮培养物、胚胎、分生组织区、愈伤组织、叶、配子体、孢子体、花粉和小孢子。
如本文所用的术语“作物保护剂”是指但不限于为杀有害生物剂(或多于一种杀有害生物剂的混合物)或植物生长调节剂的试剂。
如本文所用的术语“杀有害生物剂”是指但不限于阻止、使丧失能力、杀死或以其他方式阻止有害生物的化学或生物试剂。
本发明的化合物通常将用作组合物中的除草活性成分。如本文所用的术语“组合物”是指但不限于制剂,其具有至少一种选自表面活性剂、固体稀释剂和液体稀释剂的另外组分,其用作载体。选择制剂或组合物成分以与活性成分的物理特性、应用方式和环境因素(如油类型、水分和温度)一致。有用的组合物可以包括液体制剂和固体制剂两者。液体制剂可以包括溶液(包括可乳化的浓缩物)、悬浮液、乳液(包括微乳液、水包油型乳液、可流动的浓缩物和/或悬乳液)等,其任选地可以增稠成凝胶。水性液体组合物的一般类型是可溶性浓缩物、悬浮浓缩物、胶囊悬浮液、浓缩的乳液、微乳液、水包油型乳液、可流动的浓缩物和悬乳液。非水性液体组合物的一般类型是可乳化的浓缩物、可微乳化的浓缩物、可分散的浓缩物和油分散体。
固体制剂的一般类型是粉尘剂、粉剂、颗粒剂、球剂、粒料、锭剂、片剂、填充膜(包括种子包衣)等,它们可以是水可分散的(“可湿性的”)或水溶性的。由成膜溶液或可流动的悬浮液形成的膜和包衣特别可用于种子处理。活性成分可以被(微)包封并进一步形成为悬浮液或固体制剂;可替代地,活性成分的整个制剂可以被包封(或“外包衣”)。包封可以控制或延迟活性成分的释放。可喷雾制剂通常在喷雾之前在合适的介质中被扩充。配制这样的液体和固体制剂以容易地在喷雾介质中稀释,所述喷雾介质通常是水,但偶尔是另一种合适的介质,如芳族或链烷烃或植物油。喷雾体积可以在约一至几千升/公顷的范围内,但更通常在约十至几百升/公顷的范围内。可喷雾制剂可以与水或另一种合适的介质桶混,用于通过空中或地面施用进行叶处理,或用于施用于植物的生长介质。液体和干燥制剂可以直接计量加入滴灌系统中或在种植期间计量加入犁沟中。
制剂通常将含有有效量的活性成分、稀释剂和表面活性剂,它们的含量在以下约数范围内,加起来总共100%重量。
本发明的化合物具有(芽前和芽后两者)除草活性。如本文所用的术语“控制不期望的植物生长”是指杀死或伤害植被或减少其生长。
本发明的化合物和组合物可以通过多种方法有用地施用,所述方法涉及使除草有效量的本发明的化合物或包含所述化合物和表面活性剂、固体稀释剂或液体稀释剂中的至少一种的组合物接触不期望的植物的叶或其他部分,或接触不期望的植物生长的环境,如其中不期望的植物生长的土壤或水,或围绕不期望的植物的种子或其他繁殖体的土壤或水。
本发明的化合物的除草有效量由许多因素决定:所选的制剂、施用方法、存在的不期望的植物生长的量和类型、生长条件等。通常,本发明的化合物的除草有效量为约0.001至20kg/ha,其中优选范围为约0.004至1kg/ha。本领域技术人员可以容易地确定野草控制的期望水平所需的除草有效量。
本发明的化合物通常以配制的组合物的形式施用于包含与生长介质(例如,土壤)接触的期望的植被(例如,作物)和不期望的植物生长(即野草)的场所,所述期望的植被和不期望的植物生长两者都可以是种子、幼苗和/或更大的植物。在该场所中,包含本发明的化合物的组合物可以直接施用于植物或植物的其任何部分,特别是不期望的植物生长的部分,和/或施用于与植物接触的生长介质。
本发明的化合物还可以与一种或多种其他生物活性化合物或试剂混合,以形成多组分杀有害生物剂,提供更广谱的农业保护,所述生物活性化合物或试剂包括除草剂、除草剂安全剂、杀真菌剂、杀昆虫剂、杀线虫剂、杀菌剂、杀螨剂、植物生长调节剂(如昆虫蜕皮抑制剂和生根刺激剂)、化学不育剂、化学信息素、驱虫剂、引诱剂、信息素、摄食刺激剂、植物营养素、其他生物活性化合物或细菌、病毒或真菌。本发明的化合物与其他除草剂的混合物可以拓宽对另外的野草种类的活性范围,并抑制任何抗性生物型的增殖。
在整个本申请中,引用了各种出版物、公开的专利申请和公开的专利。这些出版物的公开内容通过引用以其整体并入本申请,以更充分地描述本发明所属领域的状态。
为了清楚起见,在单独的实施方案的上下文中描述的本发明的某些特征也可以在单个实施方案中组合提供。相反地,为了简洁起见,在单个实施方案的上下文中描述的本发明的各种特征也可以单独地或以任何合适的子组合或如在本发明的任何其他描述的实施方案中合适地提供。在各种实施方案的上下文中描述的某些特征不被认为是那些实施方案的必要特征,除非在没有那些要素的情况下实施方案不可操作。
Claims (61)
1.一种农用组合物,其包含具有以下结构的化合物或其盐:
或其盐,其中:
A是包含1至4个杂原子的环戊二烯、苯和茚骨架;其中每个杂原子独立地选自N、S、Se和O;并且其中环的一个或多个碳原子任选地化学附接到由以下组成的基团中的至少一个:-SO2CF3、-O-SO2CF3、-NR3 +、-SO2R、-C≡N、-CX3、CX2R、-COX、-CHO、-COR、-CO2R、-CONH2、-CONHR、-CONR2、-N=O、-N≡N+、-N=NR、-CR=NR、-N=CR2、-F、-Cl、-Br和-I,并且其中X选自F、Cl、Br和I;
n是0至5;
T是未取代的或被一个或两个以下基团取代的亚甲基:卤基、氧、-SO2CF3、-O-SO2CF3、-NR3 +、-SO2R、-C≡N、-CX3、CX2R-COX、-CHO、-COR、-CO2R、-CONH2、-CONHR、-CONR2、-F、-N=O、-N≡N+、-N=NR、-CR=NR、-N=CR2,并且其中X选自-F、-Cl、-Br和-I;并且
Z是-COOH、COO-、OH、-O-R、具有饱和或不饱和的醇残基的COOR,所述醇残基具有直链、支链、环状、芳族或杂芳族链;
-O-(CH2CH2O)nR(n≥1);-O-(CHMeCH2O)nR(n≥1);磺酰基、氨基甲酰基、伯胺、仲胺、叔胺、甲酰胺、-NR-O-R、-O-NR2、肼、-NH-COR和甲脒部分或其盐;
其中R选自H、取代的或未取代的烷基和取代的或未取代的芳基;并且
其中所述组合物包含至少一种农业上可接受的载体。
2.根据权利要求1所述的组合物,其中Z选自
3.根据权利要求1或2所述的组合物,其包含具有以下结构的化合物:
4.根据权利要求1或2所述的组合物,其包含具有以下结构的化合物:
5.根据权利要求1或2所述的组合物,其包含具有以下结构的化合物:
6.根据权利要求1或2所述的组合物,其包含具有以下结构的化合物:
7.根据权利要求1或2所述的组合物,其包含具有以下结构的化合物:
8.根据权利要求1或2所述的组合物,其包含具有以下结构的化合物:
9.根据权利要求1或2所述的组合物,其包含具有以下结构的化合物:
10.根据权利要求1或2所述的组合物,其包含具有以下结构的化合物:
11.根据权利要求1或2所述的组合物,其包含具有以下结构的化合物:
12.根据权利要求1或2所述的组合物,其包含具有以下结构的化合物:
13.根据权利要求1或2所述的组合物,其包含具有以下结构的化合物:
14.根据权利要求1或2所述的组合物,其包含具有以下结构的化合物:
15.根据权利要求1或2所述的组合物,其包含具有以下结构的化合物:
16.根据权利要求1或2所述的组合物,其包含具有以下结构的化合物:
17.根据权利要求1或2所述的组合物,其包含具有以下结构的化合物:
18.根据权利要求1至17中任一项所述的组合物,其进一步包含至少一种作物保护剂。
19.根据权利要求18所述的组合物,其中所述至少一种作物保护剂选自杀真菌剂、杀昆虫剂、除草剂和植物生长调节剂。
20.根据权利要求19所述的农用组合物,其中所述作物保护剂是除草剂。
21.根据权利要求19所述的农用组合物,其中所述作物保护剂是植物生长调节剂。
22.根据权利要求19所述的农用组合物,其中所述至少一种作物保护剂选自莠去津、特丁津、(S)-异丙甲草胺、异丙甲草胺、特丁净、西玛津、噻吩草胺、(S)-噻吩草胺、氟噻草胺、乙草胺、甲草胺、异噁唑草酮、异噁氯草酮、硝磺草酮、磺草酮、磺草唑胺、唑嘧磺草胺、二甲戊乐灵、溴草腈、灭草松、唑草酮、异噁草酮、烟嘧磺隆、砜嘧磺隆、氯吡嘧磺隆、草克净、氟烯草戊酯、氟丙磺隆、氟嘧磺隆、麦草畏、嗪草酸甲酯、达草止、2,4-D、二氯吡啶酸、氟吡草腙、氟草定、MCPA、MCPB、氯苯氧丙酸(MCPP)、吡喃隆、噻吩磺隆、苯草醚、EPTC、草甘膦、草铵膦、草硫膦、氰草津、喔草酯、苯嗪草酮、甜菜灵、甜菜宁、甜菜安、乙呋草黄、醚苯磺隆、氯草敏、环草定、燕麦畏、吡氟禾草灵、稀禾啶、喹禾灵、二氯吡啶酸、烯草酮、环氧嘧磺隆、氟锁草醚、氯噻草灵乙酯、甲磺草胺、氯嘧磺隆乙酯、氯酯磺草胺、氟黄胺草醚、甲氧咪草烟、灭草喹、咪草烟、依灭草、乳氟禾草灵、精噁唑禾草灵、噻苯隆、脱叶磷、氟乐灵、二甲草胺、敌草胺、氯甲喹啉酸、吡唑草胺、双酰草胺、噁唑隆、炔苯酰草胺、胺苯磺隆、牧草胺、伏草隆、扑草净、达草灭、嘧醚苯甲酸钠、MSMA、DSMA、敌草隆、氟咯草酮、氟硫草定、噻草啶、氟硝草醚、乙丁烯氟灵、炔草酯、酰嘧磺隆、禾草灵甲酯、吡氟酰草胺、乙氧嘧磺隆、四唑酰草胺、啶嘧磺隆、双氟磺草胺、异丙吡草酯、氟唑磺隆、氟啶磺隆钠、呋草酮、碘磺隆、异丙隆、绿麦隆、氯磺隆、甲磺隆、乙磺隆、苯磺隆、2,4-DB、2,4-DP、治草醚、麦草伏-M、咪草酯甲酯、碘苯腈、肟草酮、乙羧氟草醚、甲基苯噻隆、异噁草胺、苄草丹、苯敌快甲基硫酸盐、丙草胺、醚磺隆、解草啶、苄嘧磺隆、唑吡嘧磺隆、吡嘧磺隆、四唑嘧磺隆、戊草丹、苯噻草胺、禾草特、敌稗、吡唑特、氰氟草酯、双草醚钠、嘧草醚、唑草胺、丙炔噁草酮、噁草酮、溴丁酰草胺、MY-100、杀草隆、NB 061、MK243、HW-52、AC 014、莠天净、环嗪酮、磺草灵、唑啶草酮、丁噻隆、胺苯磺隆或其组合。
23.一种控制不期望的植物生长的方法,其包括向所述不期望的植物生长的场所施用根据权利要求1至22中任一项所述的农用组合物。
24.一种控制不期望的植物生长的方法,其包括向所述不期望的植物生长的场所施用除草有效量的具有以下结构的化合物:
或其盐,其中:
A是包含1至4个杂原子的环戊二烯、苯和茚骨架;其中每个杂原子独立地选自N、S、Se和O;并且其中环的一个或多个碳原子任选地化学附接到由以下组成的基团中的至少一个:-SO2CF3、-O-SO2CF3、-NR3 +、-SO2R、-C≡N、-CX3、CX2R、-COX、-CHO、-COR、-CO2R、-CONH2、-CONHR、-CONR2、-N=O、-N≡N+、-N=NR、-CR=NR、-N=CR2、-F、-Cl、-Br和-I;并且其中X选自F、Cl、Br和I;
n是0至5;
T是未取代的或被一个或两个以下基团取代的亚甲基:卤基、氧、-SO2CF3、-O-SO2CF3、-NR3 +、-SO2R、-C≡N、-CX3、CX2R、-COX、-CHO、-COR、-CO2R、-CONH2、-CONHR、-CONR2、-F、-N=O、-N≡N+、-N=NR、-CR=NR、-N=CR2,并且其中X选自F、Cl、Br和I;并且
Z是-COOH、COO-、OH、-O-R、具有饱和或不饱和的醇残基的COOR,所述醇残基具有直链、支链、环状、芳族或杂芳族链;
-O-(CH2CH2O)nR(n≥1);-O-(CHMeCH2O)nR(n≥1);氨基甲酰基、伯胺、仲胺、叔胺、甲酰胺、-NR-O-R、-O-NR2、肼、-NH-COR和甲脒部分或其盐;
其中R选自H、取代的或未取代的烷基和取代的或未取代的芳基。
25.根据权利要求24所述的方法,其中Z选自
26.根据权利要求24或25所述的方法,其包括向所述不期望的植物生长的场所施用除草有效量的具有以下结构的化合物:
27.根据权利要求24或25所述的方法,其包括向所述不期望的植物生长的场所施用除草有效量的具有以下结构的化合物:
28.根据权利要求24或25所述的方法,其包括向所述不期望的植物生长的场所施用除草有效量的具有以下结构的化合物:
29.根据权利要求24或25所述的方法,其包括向所述不期望的植物生长的场所施用除草有效量的具有以下结构的化合物:
30.根据权利要求24或25所述的方法,其包括向所述不期望的植物生长的场所施用除草有效量的具有以下结构的化合物:
31.根据权利要求24或25所述的方法,其包括向所述不期望的植物生长的场所施用除草有效量的具有以下结构的化合物:
32.根据权利要求24或25所述的方法,其包括向所述不期望的植物生长的场所施用除草有效量的具有以下结构的化合物:
33.根据权利要求24或25所述的方法,其包括向所述不期望的植物生长的场所施用除草有效量的具有以下结构的化合物:
34.根据权利要求24或25所述的方法,其包括向所述不期望的植物生长的场所施用除草有效量的具有以下结构的化合物:
35.根据权利要求24或25所述的方法,其包括向所述不期望的植物生长的场所施用除草有效量的具有以下结构的化合物:
36.根据权利要求24或25所述的方法,其包括向所述不期望的植物生长的场所施用除草有效量的具有以下结构的化合物:
37.根据权利要求24或25所述的方法,其包括向所述不期望的植物生长的场所施用除草有效量的具有以下结构的化合物:
38.根据权利要求24或25所述的方法,其包括向所述不期望的植物生长的场所施用除草有效量的具有以下结构的化合物:
39.根据权利要求24或25所述的方法,其包括向所述不期望的植物生长的场所施用除草有效量的具有以下结构的化合物:
40.根据权利要求24或25所述的方法,其包括向所述不期望的植物生长的场所施用除草有效量的具有以下结构的化合物:
41.根据权利要求24至40中任一项所述的方法,其进一步包括向所述不期望的植物生长的场所施用至少一种作物保护剂。
42.根据权利要求41所述的方法,其中所述作物保护剂选自除草剂、杀真菌剂、杀昆虫剂和植物生长调节剂。
43.根据权利要求42所述的方法,其中所述作物保护剂是除草剂。
44.根据权利要求43所述的方法,其中所述作物保护剂是氨基酸合成抑制剂除草剂。
45.根据权利要求44所述的方法,其中所述氨基酸合成抑制剂除草剂选自磺酰脲除草剂、咪唑啉酮除草剂、磺酰胺除草剂和氨基酸衍生物或其组合。
46.根据权利要求44所述的方法,其中所述氨基酸合成抑制剂除草剂选自甲氧咪草烟、甲咪唑烟酸、咪草烟、灭草喹、依灭草和咪草酸或其组合。
47.根据权利要求44所述的方法,其中所述氨基酸合成抑制剂除草剂选自氯嘧磺隆、氟嘧磺隆酸、噻吩磺隆酸、醚苯磺隆、烟嘧磺隆、甲磺隆酸、苯磺隆酸、砜嘧磺隆和氟胺磺隆酸或其组合。
48.根据权利要求44所述的方法,其中所述氨基酸合成抑制剂除草剂是草甘膦。
49.根据权利要求42所述的方法,其中所述作物保护剂是植物生长调节剂。
50.根据权利要求49所述的方法,其中所述植物生长调节剂选自麦草畏、2,4-D、二氯吡啶酸和氟草定。
51.一种控制不期望的植物生长的方法,其包括向所述不期望的植物生长的场所施用:
a.具有以下结构的第一除草剂:
或其盐,其中:
A是包含1至4个杂原子的环戊二烯、苯和茚骨架;其中每个杂原子独立地选自N、S、Se和O;并且其中环的一个或多个碳原子任选地化学附接到由以下组成的基团中的至少一个:-SO2CF3、-O-SO2CF3、-NR3 +、-SO2R、-C≡N、-CX3、CX2R-COX、-CHO、-COR、-CO2R、-CONH2、-CONHR、-CONR2、-F、-N=O、-N≡N+、-N=NR、-CR=NR、-N=CR2、-Cl、-Br和-I;并且其中X选自F、Cl、Br和I;
n是0至5;
T是未取代的或被一个或两个以下基团取代的亚甲基:卤基、氧、-SO2CF3、-O-SO2CF3、-NR3 +、-SO2R、-C≡N、-CX3、CX2R、-COX、-CHO、-COR、-CO2R、-CONH2、-CONHR、-CONR2、-F、-N=O、-N≡N+、-N=NR、-CR=NR、-N=CR2,并且其中X选自F、Cl、Br和I;并且
Z是-COOH、COO-、OH、-O-R、具有饱和或不饱和的醇残基的COOR,所述醇残基具有直链、支链、环状、芳族或杂芳族链;
-O-(CH2CH2O)nR(n≥1);-O-(CHMeCH2O)nR(n≥1);磺酰基、氨基甲酰基、伯胺、仲胺、叔胺、甲酰胺、-NR-O-R、-O-NR2、肼、-NH-COR和甲脒部分或其盐;
其中R选自H、取代的或未取代的烷基和取代的或未取代的芳基;以及
b.第二除草剂,
由此有效地控制所述不期望的植物生长。
52.根据权利要求51所述的方法,其中Z选自
/>
53.根据权利要求51或52所述的方法,其中所述第二除草剂是氨基酸合成抑制剂除草剂。
54.根据权利要求53所述的方法,其中所述第二除草剂选自磺酰脲除草剂、咪唑啉酮除草剂、磺酰胺除草剂和氨基酸衍生物。
55.根据权利要求53所述的方法,其中所述第二除草剂选自甲氧咪草烟、甲咪唑烟酸、咪草烟、灭草喹、依灭草、咪草酸、氯嘧磺隆、氟嘧磺隆酸、噻吩磺隆酸、醚苯磺隆、烟嘧磺隆、甲磺隆酸、苯磺隆酸、砜嘧磺隆、氟胺磺隆酸和草甘膦。
56.根据权利要求51所述的方法,其中所述第二除草剂选自莠去津、特丁津、(S)-异丙甲草胺、异丙甲草胺、特丁净、西玛津、噻吩草胺、(S)-噻吩草胺、氟噻草胺、乙草胺、甲草胺、异噁唑草酮、异噁氯草酮、硝磺草酮、磺草酮、磺草唑胺、唑嘧磺草胺、二甲戊乐灵、溴草腈、灭草松、唑草酮、异噁草酮、烟嘧磺隆、砜嘧磺隆、氯吡嘧磺隆、草克净、氟烯草戊酯、氟丙磺隆、氟嘧磺隆、麦草畏、嗪草酸甲酯、达草止、2,4-D、二氯吡啶酸、氟吡草腙、氟草定、MCPA、MCPB、氯苯氧丙酸(MCPP)、吡喃隆、噻吩磺隆、苯草醚、EPTC、草甘膦、草铵膦、草硫膦、氰草津、喔草酯、苯嗪草酮、甜菜灵、甜菜宁、甜菜安、乙呋草黄、醚苯磺隆、氯草敏、环草定、燕麦畏、吡氟禾草灵、稀禾啶、喹禾灵、二氯吡啶酸、烯草酮、环氧嘧磺隆、氟锁草醚、氯噻草灵乙酯、甲磺草胺、氯嘧磺隆乙酯、氯酯磺草胺、氟黄胺草醚、甲氧咪草烟、灭草喹、咪草烟、依灭草、乳氟禾草灵、精噁唑禾草灵、噻苯隆、脱叶磷、氟乐灵、二甲草胺、敌草胺、氯甲喹啉酸、吡唑草胺、双酰草胺、噁唑隆、炔苯酰草胺、胺苯磺隆、牧草胺、伏草隆、扑草净、达草灭、嘧醚苯甲酸钠、MSMA、DSMA、敌草隆、氟咯草酮、氟硫草定、噻草啶、氟硝草醚、乙丁烯氟灵、炔草酯、酰嘧磺隆、禾草灵甲酯、吡氟酰草胺、乙氧嘧磺隆、四唑酰草胺、啶嘧磺隆、双氟磺草胺、异丙吡草酯、氟唑磺隆、氟啶磺隆钠、呋草酮、碘磺隆、异丙隆、绿麦隆、氯磺隆、甲磺隆、乙磺隆、苯磺隆、2,4-DB、2,4-DP、治草醚、麦草伏-M、咪草酯甲酯、碘苯腈、肟草酮、乙羧氟草醚、甲基苯噻隆、异噁草胺、苄草丹、苯敌快甲基硫酸盐、丙草胺、醚磺隆、解草啶、苄嘧磺隆、唑吡嘧磺隆、吡嘧磺隆、四唑嘧磺隆、戊草丹、苯噻草胺、禾草特、敌稗、吡唑特、氰氟草酯、双草醚钠、嘧草醚、唑草胺、丙炔噁草酮、噁草酮、溴丁酰草胺、MY-100、杀草隆、NB 061、MK243、HW-52、AC 014、莠天净、环嗪酮、磺草灵、唑啶草酮、丁噻隆和胺苯磺隆。
57.根据权利要求51至56中任一项所述的方法,其进一步包括施用第三除草剂或植物生长调节剂。
58.一种用于控制不期望的植物生长的组合物,其包含以下物质的混合物:
a.具有以下结构的化合物或其盐:
其中:
A是包含1至4个杂原子的环戊二烯、苯和茚骨架;其中每个杂原子独立地选自N、S、Se和O;并且其中环的一个或多个碳原子任选地化学附接到由以下组成的基团中的至少一个:-SO2CF3、-O-SO2CF3、-NR3 +、-SO2R、-C≡N、-CX3、CX2R、-COX、-CHO、-COR、-CO2R、-CONH2、-CONHR、-CONR2、-F、-N=O、-N≡N+、-N=NR、-CR=NR、-N=CR2、-Cl、-Br和-I;并且其中X选自F、Cl、Br和I;
n是0至5;
T是未取代的或被一个或两个以下基团取代的亚甲基:卤基、氧、-SO2CF3、-O-SO2CF3、-NR3 +、-SO2R、-C≡N、-CX3、CX2R-COX、-CHO、-COR、-CO2R、-CONH2、-CONHR、-CONR2、-F、-N=O、-N≡N+、-N=NR、-CR=NR、-N=CR2,并且其中X选自F、Cl、Br和I;并且
Z是-COOH、COO-、OH、-O-R、具有饱和或不饱和的醇残基的COOR,所述醇残基具有直链、支链、环状、芳族或杂芳族链;
-O-(CH2CH2O)nR(n≥1);-O-(CHMeCH2O)nR(n≥1);磺酰基、氨基甲酰基、伯胺、仲胺、叔胺、甲酰胺、-NR-O-R、-O-NR2、肼、-NH-COR和甲脒部分或其盐;
其中R选自H、取代的或未取代的烷基和取代的或未取代的芳基;
b.至少一种选自以下物质的除草剂:莠去津、特丁津、(S)-异丙甲草胺、异丙甲草胺、特丁净、西玛津、噻吩草胺、(S)-噻吩草胺、氟噻草胺、乙草胺、甲草胺、异噁唑草酮、异噁氯草酮、硝磺草酮、磺草酮、磺草唑胺、唑嘧磺草胺、二甲戊乐灵、溴草腈、灭草松、唑草酮、异噁草酮、烟嘧磺隆、砜嘧磺隆、氯吡嘧磺隆、草克净、氟烯草戊酯、氟丙磺隆、氟嘧磺隆、麦草畏、嗪草酸甲酯、达草止、2,4-D、二氯吡啶酸、氟吡草腙、氟草定、MCPA、MCPB、氯苯氧丙酸(MCPP)、吡喃隆、噻吩磺隆、苯草醚、EPTC、草甘膦、草铵膦、草硫膦、氰草津、喔草酯、苯嗪草酮、甜菜灵、甜菜宁、甜菜安、乙呋草黄、醚苯磺隆、氯草敏、环草定、燕麦畏、吡氟禾草灵、稀禾啶、喹禾灵、二氯吡啶酸、烯草酮、环氧嘧磺隆、氟锁草醚、氯噻草灵乙酯、甲磺草胺、氯嘧磺隆乙酯、氯酯磺草胺、氟黄胺草醚、甲氧咪草烟、灭草喹、咪草烟、依灭草、乳氟禾草灵、精噁唑禾草灵、噻苯隆、脱叶磷、氟乐灵、二甲草胺、敌草胺、氯甲喹啉酸、吡唑草胺、双酰草胺、噁唑隆、炔苯酰草胺、胺苯磺隆、牧草胺、伏草隆、扑草净、达草灭、嘧醚苯甲酸钠、MSMA、DSMA、敌草隆、氟咯草酮、氟硫草定、噻草啶、氟硝草醚、乙丁烯氟灵、炔草酯、酰嘧磺隆、禾草灵甲酯、吡氟酰草胺、乙氧嘧磺隆、四唑酰草胺、啶嘧磺隆、双氟磺草胺、异丙吡草酯、氟唑磺隆、氟啶磺隆钠、呋草酮、碘磺隆、异丙隆、绿麦隆、氯磺隆、甲磺隆、乙磺隆、苯磺隆、2,4-DB、2,4-DP、治草醚、麦草伏-M、咪草酯甲酯、碘苯腈、肟草酮、乙羧氟草醚、甲基苯噻隆、异噁草胺、苄草丹、苯敌快甲基硫酸盐、丙草胺、醚磺隆、解草啶、苄嘧磺隆、唑吡嘧磺隆、吡嘧磺隆、四唑嘧磺隆、戊草丹、苯噻草胺、禾草特、敌稗、吡唑特、氰氟草酯、双草醚钠、嘧草醚、唑草胺、丙炔噁草酮、噁草酮、溴丁酰草胺、MY-100、杀草隆、NB 061、MK243、HW-52、AC 014、莠天净、环嗪酮、磺草灵、唑啶草酮、丁噻隆、胺苯磺隆或其组合;以及
c.至少一种农业上可接受的载体。
59.一种用于控制不期望的植物生长的组合物,其包含以下物质的混合物:
a.具有以下结构的化合物:
或其盐,其中:
A是包含1至4个杂原子的环戊二烯、苯和茚骨架;其中每个杂原子独立地选自N、S、Se和O;并且其中环的一个或多个碳原子任选地化学附接到由以下组成的基团中的至少一个:-SO2CF3、-O-SO2CF3、-NR3 +、-SO2R、-C≡N、-CX3、CX2R-COX、-CHO、-COR、-CO2R、-CONH2、-CONHR、-CONR2、-F、-N=O、-N≡N+、-N=NR、-CR=NR、-N=CR2、-Cl、-Br和-I;并且其中X选自F、Cl、Br和I;
n是0至5;
T是未取代的或被一个或两个以下基团取代的亚甲基:卤原子、氧、-SO2CF3、-O-SO2CF3、-NR3 +、-SO2R、-C≡N、-CX3、-COX、-CHO、-COR、-CO2R、-CONH2、-CONHR、-CONR2、-F、-N=O、-N≡N+、-N=NR、-CR=NR、-N=CR2,并且其中X选自F、Cl、Br和I;并且
Z是-COOH、COO-、OH、-O-R、具有饱和或不饱和的醇残基的COOR,所述醇残基具有直链、支链、环状、芳族或杂芳族链;
-O-(CH2CH2O)nR(n≥1);-O-(CHMeCH2O)nR(n≥1);磺酰基、氨基甲酰基、伯胺、仲胺、叔胺、甲酰胺、-NR-O-R、-O-NR2、肼、-NH-COR和甲脒部分或其盐;
其中R选自H、取代的或未取代的烷基和取代的或未取代的芳基;并且其中Z被-O-R取代,R是取代的或未取代的芳基;
b.至少一种植物生长调节剂;和
c.至少一种农业上可接受的载体。
60.一种控制植物或其植物部分中的氨基酸含量的方法,其包括施用有效量的根据权利要求1至22中任一项所述的农用组合物。
61.一种控制植物生长的方法,其包括向所述植物或其植物部分施用有效量的根据权利要求1至22中任一项所述的农用组合物。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US202163203169P | 2021-07-12 | 2021-07-12 | |
US63/203169 | 2021-07-12 | ||
PCT/IL2022/050749 WO2023286057A1 (en) | 2021-07-12 | 2022-07-12 | Novel derivatives of non-coded amino acids and their use as herbicides |
Publications (1)
Publication Number | Publication Date |
---|---|
CN117642069A true CN117642069A (zh) | 2024-03-01 |
Family
ID=84920119
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN202280049483.7A Pending CN117642069A (zh) | 2021-07-12 | 2022-07-12 | 非编码氨基酸的新型衍生物及其作为除草剂的用途 |
Country Status (9)
Country | Link |
---|---|
EP (1) | EP4369933A1 (zh) |
KR (1) | KR20240015151A (zh) |
CN (1) | CN117642069A (zh) |
AR (1) | AR126433A1 (zh) |
AU (1) | AU2022309257A1 (zh) |
BR (1) | BR112023026391A2 (zh) |
CA (1) | CA3226024A1 (zh) |
IL (1) | IL310022A (zh) |
WO (1) | WO2023286057A1 (zh) |
Family Cites Families (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0590045A1 (en) * | 1991-06-12 | 1994-04-06 | E.I. Du Pont De Nemours And Company | Substituted pyridine herbicides |
AR023071A1 (es) * | 1998-12-23 | 2002-09-04 | Syngenta Participations Ag | Compuestos de piridincetona, compuestos intermediarios, composicion herbicida e inhibidora del crecimiento de plantas, metodo para controlar la vegetacion indeseada, metodo para inhibir el crecimiento de las plantas, y uso de la composicion para controlar el crecimiento indeseado de plantas. |
EP1211246B1 (en) * | 1999-09-09 | 2004-02-25 | Kumiai Chemical Industry Co., Ltd. | Pyrimidine derivatives and herbicides containing the same |
DE10118310A1 (de) * | 2001-04-12 | 2002-10-17 | Bayer Ag | Hetarylsubstituierte carbocyclische 1,3-Dione |
OA19202A (en) * | 2002-08-12 | 2006-10-13 | Trinity Bay Equipment Holdings, LLC | Protector assembly for flexible pipe coils and method of using same. |
TW200917961A (en) * | 2007-08-23 | 2009-05-01 | Sumitomo Chemical Co | Fluorine-containing organosulfur compound and pesticidal composition thereof |
-
2022
- 2022-07-12 CN CN202280049483.7A patent/CN117642069A/zh active Pending
- 2022-07-12 KR KR1020247002300A patent/KR20240015151A/ko active IP Right Grant
- 2022-07-12 AR ARP220101822A patent/AR126433A1/es unknown
- 2022-07-12 IL IL310022A patent/IL310022A/en unknown
- 2022-07-12 BR BR112023026391A patent/BR112023026391A2/pt unknown
- 2022-07-12 WO PCT/IL2022/050749 patent/WO2023286057A1/en active Application Filing
- 2022-07-12 EP EP22841612.9A patent/EP4369933A1/en active Pending
- 2022-07-12 AU AU2022309257A patent/AU2022309257A1/en active Pending
- 2022-07-12 CA CA3226024A patent/CA3226024A1/en active Pending
Also Published As
Publication number | Publication date |
---|---|
IL310022A (en) | 2024-03-01 |
AU2022309257A1 (en) | 2024-01-04 |
EP4369933A1 (en) | 2024-05-22 |
BR112023026391A2 (pt) | 2024-03-05 |
AR126433A1 (es) | 2023-10-11 |
WO2023286057A1 (en) | 2023-01-19 |
CA3226024A1 (en) | 2023-01-19 |
KR20240015151A (ko) | 2024-02-02 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
JP6695967B2 (ja) | ピラゾール化合物またはその塩、それらの製造方法、除草組成物およびその使用 | |
JP2020045357A (ja) | 選択的除草剤としての3−イソオキサゾリジノン化合物の使用 | |
KR101818803B1 (ko) | 페녹스술람 및 프레틸라클로르를 함유한 상승작용성 제초제 조성물 | |
KR101258301B1 (ko) | 제초 조성물 | |
UA126681C2 (uk) | Гербіцидно активний 3-фенілізоксазолін-5-карбоксамід амідів тетрагідро- та дифуранкарбонових кислот | |
EA032353B1 (ru) | Гербицидные соединения | |
EP0189458A1 (en) | Imidazole plant growth regulators | |
KR20040104643A (ko) | 피리딘계 화합물 또는 이의 염 및 이들을 함유하는 제초제 | |
JP2004051628A (ja) | ピリジン系化合物又はその塩、それらの製造方法及びそれらを含有する除草剤 | |
NO335622B1 (no) | Synergistiske, fungicidisk aktive substanskombinasjoner | |
KR20120123735A (ko) | 트리케톤계 화합물, 이들의 제조 방법 및 이들을 함유하는 제초제 | |
JP3662952B2 (ja) | 新規の殺ダニ活性テトラジン誘導体 | |
CN107207415A (zh) | 敌稗的结晶变型 | |
KR102276572B1 (ko) | 피라졸 화합물 또는 그의 염, 및 제조 방법, 제초제 조성물 및 그의 용도 | |
EA027024B1 (ru) | Полиморф n-(2-метоксибензоил)-4-[(метиламинокарбонил)амино]бензолсульфонамида | |
CN113939499A (zh) | 新型非编码杂环氨基酸(nchaa)及其作为除草剂的用途 | |
CN117320550A (zh) | 杂草控制方法 | |
RU2677980C2 (ru) | Способы селективной борьбы с сорняками | |
TWI677286B (zh) | 除草組合物及控制植株生長的方法 | |
CN117642069A (zh) | 非编码氨基酸的新型衍生物及其作为除草剂的用途 | |
JPS60116649A (ja) | フルオロフェノキシ化合物及びそれを含む除草剤 | |
KR101225441B1 (ko) | 트리케톤계 화합물, 이들의 제조 방법 및 이들을 함유하는제초제 | |
WO2024003899A1 (en) | Novel derivatives of non-coded amino acids and their use in crop protection | |
WO2023131951A1 (en) | Novel derivatives of non-coded amino acids and their use as herbicides | |
JP5814233B2 (ja) | 除草剤用薬害軽減剤、薬害が軽減された除草剤組成物及び作物の薬害軽減方法 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PB01 | Publication | ||
PB01 | Publication |