TW202400564A - 作為除草劑之嘧啶氧基苯衍生物 - Google Patents
作為除草劑之嘧啶氧基苯衍生物 Download PDFInfo
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- TW202400564A TW202400564A TW112134013A TW112134013A TW202400564A TW 202400564 A TW202400564 A TW 202400564A TW 112134013 A TW112134013 A TW 112134013A TW 112134013 A TW112134013 A TW 112134013A TW 202400564 A TW202400564 A TW 202400564A
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- alkyl
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- methyl
- haloalkyl
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- 239000004009 herbicide Substances 0.000 title claims description 50
- CEBDRQUBQYQBEV-UHFFFAOYSA-N 2-phenoxypyrimidine Chemical class N=1C=CC=NC=1OC1=CC=CC=C1 CEBDRQUBQYQBEV-UHFFFAOYSA-N 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims abstract description 459
- 239000000203 mixture Substances 0.000 claims abstract description 101
- 238000000034 method Methods 0.000 claims abstract description 40
- 150000003839 salts Chemical class 0.000 claims abstract description 36
- -1 C 2 –C 4 alkoxy Chemical group 0.000 claims description 288
- SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 173
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 120
- 241000196324 Embryophyta Species 0.000 claims description 101
- 229910052736 halogen Inorganic materials 0.000 claims description 69
- 150000002367 halogens Chemical class 0.000 claims description 67
- 239000003112 inhibitor Substances 0.000 claims description 61
- 230000002363 herbicidal effect Effects 0.000 claims description 46
- 125000000171 (C1-C6) haloalkyl group Chemical group 0.000 claims description 43
- 125000000217 alkyl group Chemical group 0.000 claims description 35
- 239000004480 active ingredient Substances 0.000 claims description 32
- 229910052739 hydrogen Inorganic materials 0.000 claims description 32
- 125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 28
- 229910052799 carbon Inorganic materials 0.000 claims description 27
- 239000003085 diluting agent Substances 0.000 claims description 27
- 125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 26
- 239000007788 liquid Substances 0.000 claims description 25
- 125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 23
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 23
- 239000007787 solid Substances 0.000 claims description 23
- 239000004094 surface-active agent Substances 0.000 claims description 22
- 239000003795 chemical substances by application Substances 0.000 claims description 20
- 239000002253 acid Substances 0.000 claims description 19
- 125000001188 haloalkyl group Chemical group 0.000 claims description 18
- 229930192334 Auxin Natural products 0.000 claims description 15
- 125000005119 alkyl cycloalkyl group Chemical group 0.000 claims description 15
- 239000002363 auxin Substances 0.000 claims description 15
- SEOVTRFCIGRIMH-UHFFFAOYSA-N indole-3-acetic acid Chemical compound C1=CC=C2C(CC(=O)O)=CNC2=C1 SEOVTRFCIGRIMH-UHFFFAOYSA-N 0.000 claims description 15
- 125000005112 cycloalkylalkoxy group Chemical group 0.000 claims description 14
- 239000005562 Glyphosate Substances 0.000 claims description 12
- 230000012010 growth Effects 0.000 claims description 12
- 125000004767 (C1-C4) haloalkoxy group Chemical group 0.000 claims description 11
- 125000006656 (C2-C4) alkenyl group Chemical group 0.000 claims description 11
- 125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 11
- 229910052801 chlorine Inorganic materials 0.000 claims description 11
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 11
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 11
- 125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 11
- 229910052760 oxygen Inorganic materials 0.000 claims description 11
- 150000004669 very long chain fatty acids Chemical class 0.000 claims description 11
- 125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 10
- 239000005631 2,4-Dichlorophenoxyacetic acid Substances 0.000 claims description 10
- XDDAORKBJWWYJS-UHFFFAOYSA-N glyphosate Chemical compound OC(=O)CNCP(O)(O)=O XDDAORKBJWWYJS-UHFFFAOYSA-N 0.000 claims description 10
- 229940097068 glyphosate Drugs 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- 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
- 108010068327 4-hydroxyphenylpyruvate dioxygenase Proteins 0.000 claims description 9
- 102100028626 4-hydroxyphenylpyruvate dioxygenase Human genes 0.000 claims description 9
- 102000000452 Acetyl-CoA carboxylase Human genes 0.000 claims description 8
- 108010016219 Acetyl-CoA carboxylase Proteins 0.000 claims description 8
- 239000005578 Mesotrione Substances 0.000 claims description 8
- 108010060806 Photosystem II Protein Complex Proteins 0.000 claims description 8
- 229910052731 fluorine Inorganic materials 0.000 claims description 8
- 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 8
- FBUKVWPVBMHYJY-UHFFFAOYSA-N nonanoic acid Chemical compound CCCCCCCCC(O)=O FBUKVWPVBMHYJY-UHFFFAOYSA-N 0.000 claims description 8
- 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
- 239000005489 Bromoxynil Substances 0.000 claims description 7
- VYNOULHXXDFBLU-UHFFFAOYSA-N Cumyluron Chemical compound C=1C=CC=CC=1C(C)(C)NC(=O)NCC1=CC=CC=C1Cl VYNOULHXXDFBLU-UHFFFAOYSA-N 0.000 claims description 7
- 239000005504 Dicamba Substances 0.000 claims description 7
- OTSAMNSACVKIOJ-UHFFFAOYSA-N azane;carbamoyl(ethoxy)phosphinic acid Chemical compound [NH4+].CCOP([O-])(=O)C(N)=O OTSAMNSACVKIOJ-UHFFFAOYSA-N 0.000 claims description 7
- 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 7
- IWEDIXLBFLAXBO-UHFFFAOYSA-N dicamba Chemical compound COC1=C(Cl)C=CC(Cl)=C1C(O)=O IWEDIXLBFLAXBO-UHFFFAOYSA-N 0.000 claims description 7
- 108010001545 phytoene dehydrogenase Proteins 0.000 claims description 7
- 239000005529 Florasulam Substances 0.000 claims description 6
- 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 6
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 6
- MXWJVTOOROXGIU-UHFFFAOYSA-N atrazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)C)=N1 MXWJVTOOROXGIU-UHFFFAOYSA-N 0.000 claims description 6
- WVQBLGZPHOPPFO-UHFFFAOYSA-N 2-chloro-N-(2-ethyl-6-methylphenyl)-N-(1-methoxypropan-2-yl)acetamide Chemical compound CCC1=CC=CC(C)=C1N(C(C)COC)C(=O)CCl WVQBLGZPHOPPFO-UHFFFAOYSA-N 0.000 claims description 5
- CASLETQIYIQFTQ-UHFFFAOYSA-N 3-[[5-(difluoromethoxy)-1-methyl-3-(trifluoromethyl)pyrazol-4-yl]methylsulfonyl]-5,5-dimethyl-4h-1,2-oxazole Chemical compound CN1N=C(C(F)(F)F)C(CS(=O)(=O)C=2CC(C)(C)ON=2)=C1OC(F)F CASLETQIYIQFTQ-UHFFFAOYSA-N 0.000 claims description 5
- VTNQPKFIQCLBDU-UHFFFAOYSA-N Acetochlor Chemical compound CCOCN(C(=O)CCl)C1=C(C)C=CC=C1CC VTNQPKFIQCLBDU-UHFFFAOYSA-N 0.000 claims description 5
- 239000005492 Carfentrazone-ethyl Substances 0.000 claims description 5
- LBGPXIPGGRQBJW-UHFFFAOYSA-N Difenzoquat Chemical compound C[N+]=1N(C)C(C=2C=CC=CC=2)=CC=1C1=CC=CC=C1 LBGPXIPGGRQBJW-UHFFFAOYSA-N 0.000 claims description 5
- ICWUMLXQKFTJMH-UHFFFAOYSA-N Etobenzanid Chemical compound C1=CC(OCOCC)=CC=C1C(=O)NC1=CC=CC(Cl)=C1Cl ICWUMLXQKFTJMH-UHFFFAOYSA-N 0.000 claims description 5
- 239000005531 Flufenacet Substances 0.000 claims description 5
- 239000005534 Flupyrsulfuron-methyl Substances 0.000 claims description 5
- 239000005561 Glufosinate Substances 0.000 claims description 5
- 239000005571 Isoxaflutole Substances 0.000 claims description 5
- 239000005574 MCPA Substances 0.000 claims description 5
- 239000005584 Metsulfuron-methyl Substances 0.000 claims description 5
- 108090000854 Oxidoreductases Proteins 0.000 claims description 5
- 102000004316 Oxidoreductases Human genes 0.000 claims description 5
- 239000005616 Rimsulfuron Substances 0.000 claims description 5
- 239000005620 Tembotrione Substances 0.000 claims description 5
- 239000005623 Thifensulfuron-methyl Substances 0.000 claims description 5
- WHKUVVPPKQRRBV-UHFFFAOYSA-N Trasan Chemical compound CC1=CC(Cl)=CC=C1OCC(O)=O WHKUVVPPKQRRBV-UHFFFAOYSA-N 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
- 125000004183 alkoxy alkyl group Chemical group 0.000 claims description 5
- VGPYEHKOIGNJKV-UHFFFAOYSA-N asulam Chemical compound COC(=O)NS(=O)(=O)C1=CC=C(N)C=C1 VGPYEHKOIGNJKV-UHFFFAOYSA-N 0.000 claims description 5
- WZDDLAZXUYIVMU-UHFFFAOYSA-N bromobutide Chemical compound CC(C)(C)C(Br)C(=O)NC(C)(C)C1=CC=CC=C1 WZDDLAZXUYIVMU-UHFFFAOYSA-N 0.000 claims description 5
- BIKACRYIQSLICJ-UHFFFAOYSA-N cloransulam-methyl Chemical group N=1N2C(OCC)=NC(F)=CC2=NC=1S(=O)(=O)NC1=C(Cl)C=CC=C1C(=O)OC BIKACRYIQSLICJ-UHFFFAOYSA-N 0.000 claims description 5
- MLKCGVHIFJBRCD-UHFFFAOYSA-N ethyl 2-chloro-3-{2-chloro-5-[4-(difluoromethyl)-3-methyl-5-oxo-4,5-dihydro-1H-1,2,4-triazol-1-yl]-4-fluorophenyl}propanoate Chemical group C1=C(Cl)C(CC(Cl)C(=O)OCC)=CC(N2C(N(C(F)F)C(C)=N2)=O)=C1F MLKCGVHIFJBRCD-UHFFFAOYSA-N 0.000 claims description 5
- QMTNOLKHSWIQBE-FGTMMUONSA-N exo-(+)-cinmethylin Chemical compound O([C@H]1[C@]2(C)CC[C@@](O2)(C1)C(C)C)CC1=CC=CC=C1C QMTNOLKHSWIQBE-FGTMMUONSA-N 0.000 claims description 5
- 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 5
- FOUWCSDKDDHKQP-UHFFFAOYSA-N flumioxazin Chemical compound FC1=CC=2OCC(=O)N(CC#C)C=2C=C1N(C1=O)C(=O)C2=C1CCCC2 FOUWCSDKDDHKQP-UHFFFAOYSA-N 0.000 claims description 5
- 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 5
- 229940088649 isoxaflutole Drugs 0.000 claims description 5
- 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 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- DWSPRBSLSXQIEJ-UHFFFAOYSA-N pyrasulfotole Chemical compound CC1=NN(C)C(O)=C1C(=O)C1=CC=C(C(F)(F)F)C=C1S(C)(=O)=O DWSPRBSLSXQIEJ-UHFFFAOYSA-N 0.000 claims description 5
- VTRWMTJQBQJKQH-UHFFFAOYSA-N pyributicarb Chemical compound COC1=CC=CC(N(C)C(=S)OC=2C=C(C=CC=2)C(C)(C)C)=N1 VTRWMTJQBQJKQH-UHFFFAOYSA-N 0.000 claims description 5
- 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 5
- GNHDVXLWBQYPJE-UHFFFAOYSA-N saflufenacil Chemical compound C1=C(Cl)C(C(=O)NS(=O)(=O)N(C)C(C)C)=CC(N2C(N(C)C(=CC2=O)C(F)(F)F)=O)=C1F GNHDVXLWBQYPJE-UHFFFAOYSA-N 0.000 claims description 5
- IUQAXCIUEPFPSF-UHFFFAOYSA-N tembotrione Chemical compound ClC1=C(COCC(F)(F)F)C(S(=O)(=O)C)=CC=C1C(=O)C1C(=O)CCCC1=O IUQAXCIUEPFPSF-UHFFFAOYSA-N 0.000 claims description 5
- 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 5
- RFZZKBWDDKMWNM-GTBMBKLPSA-N (5s,7r,8s,9r)-8,9-dihydroxy-7-(hydroxymethyl)-6-oxa-1,3-diazaspiro[4.4]nonane-2,4-dione Chemical compound O[C@@H]1[C@H](O)[C@@H](CO)O[C@]11C(=O)NC(=O)N1 RFZZKBWDDKMWNM-GTBMBKLPSA-N 0.000 claims description 4
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- GXAMYUGOODKVRM-UHFFFAOYSA-N Flurecol Chemical compound C1=CC=C2C(C(=O)O)(O)C3=CC=CC=C3C2=C1 GXAMYUGOODKVRM-UHFFFAOYSA-N 0.000 claims description 4
- 239000005563 Halauxifen-methyl Substances 0.000 claims description 4
- RFZZKBWDDKMWNM-UHFFFAOYSA-N Hydantocidin Natural products OC1C(O)C(CO)OC11C(=O)NC(=O)N1 RFZZKBWDDKMWNM-UHFFFAOYSA-N 0.000 claims description 4
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- FMINYZXVCTYSNY-UHFFFAOYSA-N Methyldymron Chemical compound C=1C=CC=CC=1N(C)C(=O)NC(C)(C)C1=CC=CC=C1 FMINYZXVCTYSNY-UHFFFAOYSA-N 0.000 claims description 4
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- 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 4
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- 125000006254 cycloalkyl carbonyl group Chemical group 0.000 claims description 4
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- JLYFCTQDENRSOL-VIFPVBQESA-N dimethenamid-P Chemical compound COC[C@H](C)N(C(=O)CCl)C=1C(C)=CSC=1C JLYFCTQDENRSOL-VIFPVBQESA-N 0.000 claims description 4
- KDHKOPYYWOHESS-UHFFFAOYSA-N halauxifen-methyl Chemical group NC1=C(Cl)C(C(=O)OC)=NC(C=2C(=C(OC)C(Cl)=CC=2)F)=C1 KDHKOPYYWOHESS-UHFFFAOYSA-N 0.000 claims description 4
- 125000000262 haloalkenyl group Chemical group 0.000 claims description 4
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- GLBLPMUBLHYFCW-UHFFFAOYSA-N n-(5,7-dimethoxy-[1,2,4]triazolo[1,5-a]pyrimidin-2-yl)-2-methoxy-4-(trifluoromethyl)pyridine-3-sulfonamide Chemical compound N1=C2N=C(OC)C=C(OC)N2N=C1NS(=O)(=O)C1=C(OC)N=CC=C1C(F)(F)F GLBLPMUBLHYFCW-UHFFFAOYSA-N 0.000 claims description 4
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- 229910019142 PO4 Inorganic materials 0.000 claims description 3
- 125000004448 alkyl carbonyl group Chemical group 0.000 claims description 3
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- 238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- NKFLEFWUYAUDJV-UHFFFAOYSA-N pyridine-3-sulfonamide Chemical compound NS(=O)(=O)C1=CC=CN=C1 NKFLEFWUYAUDJV-UHFFFAOYSA-N 0.000 description 1
- 125000000714 pyrimidinyl group Chemical group 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 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 description 1
- BBKDWPHJZANJGB-IKJXHCRLSA-N quizalofop-P-tefuryl Chemical group O=C([C@H](OC=1C=CC(OC=2N=C3C=CC(Cl)=CC3=NC=2)=CC=1)C)OCC1CCCO1 BBKDWPHJZANJGB-IKJXHCRLSA-N 0.000 description 1
- 229920005604 random copolymer Polymers 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- 230000002940 repellent Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 125000006413 ring segment Chemical group 0.000 description 1
- 235000005713 safflower oil Nutrition 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- FSYKKLYZXJSNPZ-UHFFFAOYSA-N sarcosine Chemical class C[NH2+]CC([O-])=O FSYKKLYZXJSNPZ-UHFFFAOYSA-N 0.000 description 1
- 235000003441 saturated fatty acids Nutrition 0.000 description 1
- 150000004671 saturated fatty acids Chemical class 0.000 description 1
- DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
- 150000003335 secondary amines Chemical class 0.000 description 1
- 230000001568 sexual effect Effects 0.000 description 1
- 239000000429 sodium aluminium silicate Substances 0.000 description 1
- 235000012217 sodium aluminium silicate Nutrition 0.000 description 1
- ODZPKZBBUMBTMG-UHFFFAOYSA-N sodium amide Chemical compound [NH2-].[Na+] ODZPKZBBUMBTMG-UHFFFAOYSA-N 0.000 description 1
- 235000009518 sodium iodide Nutrition 0.000 description 1
- 229920005552 sodium lignosulfonate Polymers 0.000 description 1
- 229960001922 sodium perborate Drugs 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- PDEFQWNXOUGDJR-UHFFFAOYSA-M sodium;2,2-dichloropropanoate Chemical compound [Na+].CC(Cl)(Cl)C([O-])=O PDEFQWNXOUGDJR-UHFFFAOYSA-M 0.000 description 1
- STAPBGVGYWCRTF-UHFFFAOYSA-M sodium;2-(4-chloro-2-methylphenoxy)acetate Chemical compound [Na+].CC1=CC(Cl)=CC=C1OCC([O-])=O STAPBGVGYWCRTF-UHFFFAOYSA-M 0.000 description 1
- AXKBOWBNOCUNJL-UHFFFAOYSA-M sodium;2-nitrophenolate Chemical compound [Na+].[O-]C1=CC=CC=C1[N+]([O-])=O AXKBOWBNOCUNJL-UHFFFAOYSA-M 0.000 description 1
- GABUSZPTCJGKGB-UHFFFAOYSA-M sodium;4-(4-chloro-2-methylphenoxy)butanoate Chemical compound [Na+].CC1=CC(Cl)=CC=C1OCCCC([O-])=O GABUSZPTCJGKGB-UHFFFAOYSA-M 0.000 description 1
- QGKPUZOFTJQTHL-UHFFFAOYSA-M sodium;4-cyano-2,6-diiodophenolate Chemical compound [Na+].[O-]C1=C(I)C=C(C#N)C=C1I QGKPUZOFTJQTHL-UHFFFAOYSA-M 0.000 description 1
- JRQGDDUXDKCWRF-UHFFFAOYSA-M sodium;n-(2-methoxycarbonylphenyl)sulfonyl-4-methyl-5-oxo-3-propoxy-1,2,4-triazole-1-carboximidate Chemical compound [Na+].O=C1N(C)C(OCCC)=NN1C(=O)[N-]S(=O)(=O)C1=CC=CC=C1C(=O)OC JRQGDDUXDKCWRF-UHFFFAOYSA-M 0.000 description 1
- YKLJGMBLPUQQOI-UHFFFAOYSA-M sodium;oxidooxy(oxo)borane Chemical compound [Na+].[O-]OB=O YKLJGMBLPUQQOI-UHFFFAOYSA-M 0.000 description 1
- 239000004550 soluble concentrate Substances 0.000 description 1
- JNYAEWCLZODPBN-CTQIIAAMSA-N sorbitan Polymers OCC(O)C1OCC(O)[C@@H]1O JNYAEWCLZODPBN-CTQIIAAMSA-N 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 238000001694 spray drying Methods 0.000 description 1
- 239000000021 stimulant Substances 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 239000004575 stone Substances 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000003445 sucroses Chemical class 0.000 description 1
- 150000008163 sugars Chemical class 0.000 description 1
- 125000000446 sulfanediyl group Chemical group *S* 0.000 description 1
- TYLSDQJYPYQCRK-UHFFFAOYSA-N sulfo 4-amino-4-oxobutanoate Chemical compound NC(=O)CCC(=O)OS(O)(=O)=O TYLSDQJYPYQCRK-UHFFFAOYSA-N 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 239000003447 supported reagent Substances 0.000 description 1
- 239000000375 suspending agent Substances 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- 239000000271 synthetic detergent Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 229940104261 taurate Drugs 0.000 description 1
- RJKCKKDSSSRYCB-UHFFFAOYSA-N tebutam Chemical compound CC(C)(C)C(=O)N(C(C)C)CC1=CC=CC=C1 RJKCKKDSSSRYCB-UHFFFAOYSA-N 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- DPKBAXPHAYBPRL-UHFFFAOYSA-M tetrabutylazanium;iodide Chemical compound [I-].CCCC[N+](CCCC)(CCCC)CCCC DPKBAXPHAYBPRL-UHFFFAOYSA-M 0.000 description 1
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
- OBSZRRSYVTXPNB-UHFFFAOYSA-N tetraphosphorus Chemical compound P12P3P1P32 OBSZRRSYVTXPNB-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 150000007970 thio esters Chemical class 0.000 description 1
- 230000009974 thixotropic effect Effects 0.000 description 1
- 210000002377 thylakoid Anatomy 0.000 description 1
- 210000001519 tissue Anatomy 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- 235000010215 titanium dioxide Nutrition 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 231100000167 toxic agent Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- 231100000419 toxicity Toxicity 0.000 description 1
- 230000001988 toxicity Effects 0.000 description 1
- 239000003053 toxin Substances 0.000 description 1
- 231100000765 toxin Toxicity 0.000 description 1
- 108700012359 toxins Proteins 0.000 description 1
- 238000000844 transformation Methods 0.000 description 1
- 230000014616 translation Effects 0.000 description 1
- 229960002622 triacetin Drugs 0.000 description 1
- 150000003626 triacylglycerols Chemical class 0.000 description 1
- ZDRNMODJXFOYMN-UHFFFAOYSA-N tridecyl acetate Chemical compound CCCCCCCCCCCCCOC(C)=O ZDRNMODJXFOYMN-UHFFFAOYSA-N 0.000 description 1
- DQWPFSLDHJDLRL-UHFFFAOYSA-N triethyl phosphate Chemical compound CCOP(=O)(OCC)OCC DQWPFSLDHJDLRL-UHFFFAOYSA-N 0.000 description 1
- ZMANZCXQSJIPKH-UHFFFAOYSA-O triethylammonium ion Chemical compound CC[NH+](CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-O 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 125000000725 trifluoropropyl group Chemical group [H]C([H])(*)C([H])([H])C(F)(F)F 0.000 description 1
- OUYCCCASQSFEME-UHFFFAOYSA-N tyrosine Natural products OC(=O)C(N)CC1=CC=C(O)C=C1 OUYCCCASQSFEME-UHFFFAOYSA-N 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 229940035893 uracil Drugs 0.000 description 1
- 235000016788 valerian Nutrition 0.000 description 1
- 229940005605 valeric acid Drugs 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000010792 warming Methods 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000004563 wettable powder 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
- 239000011787 zinc oxide Substances 0.000 description 1
- 235000014692 zinc oxide Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more 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, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/34—One oxygen 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
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
-
- 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
- A01N2300/00—Combinations or mixtures of active ingredients covered by classes A01N27/00 - A01N65/48 with other active or formulation relevant ingredients, e.g. specific carrier materials or surfactants, covered by classes A01N25/00 - A01N65/48
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Environmental Sciences (AREA)
- Wood Science & Technology (AREA)
- Plant Pathology (AREA)
- Zoology (AREA)
- Engineering & Computer Science (AREA)
- Pest Control & Pesticides (AREA)
- General Health & Medical Sciences (AREA)
- Dentistry (AREA)
- Health & Medical Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Fertilizers (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
Abstract
所揭示者為式
1之化合物(包括所有立體異構物)、其
N‑氧化物、及鹽,
其中A、Z、R
1、R
2、R
3、及m係如本揭露中所定義。亦揭露者係含式
1之化合物之組合物與用於防治非所欲植物之方法,該方法包含使該非所欲植物或其環境與有效量之本發明化合物或組合物接觸。
Description
本發明涉及特定嘧啶基氧基苯(pyrimidinyloxy benzene)衍生物、其
N‑氧化物、鹽、及組合物,以及將其用於防治非所欲植物之方法。
非所欲植物的防治對於達成高作物產率極為重要。尤其是對於有用作物如稻米、大豆、甜菜、玉米、馬鈴薯、小麥、大麥、番茄與栽植作物等其他作物而言,達成選擇性防治雜草生長是極為理想的。在這類有用作物中未受控制的雜草生長可致使生產力顯著降低,從而導致消費者的成本增加。在非作物區中的非所欲植物防治亦為重要。市面上有許多針對此等目的之產品,但仍持續有對於更有效、成本更低、毒性更低、對環境更安全或具有不同作用部位之新化合物的需求。
本發明係關於式1之化合物(包括所有幾何及立體異構物)、其
N‑氧化物、及鹽、含有這些化合物之農業組合物、及彼等作為除草劑之用途:
其中
A係
B係O或S;
R
1係H、C
1–C
6烷基、C
2–C
6烯基、C
2–C
6炔基、C
1–C
6鹵烷基、C
2–C
6鹵烯基、C
2–C
6鹵炔基、C
3–C
6環烷基、C
3–C
6鹵環烷基、C
3–C
6鹵環烷基烷基、C
4–C
8烷基環烷基、C
4–C
8環烷基烷基、C
1–C
6烷基胺基、C
1–C
6鹵烷基胺基、C
2–C
10二烷基胺基、C
2–C
10鹵二烷基胺基、C
3–C
6環胺基、C
1–C
6烷氧基、C
3–C
6烯基氧基、C
3–C
6炔基氧基、C
1–C
6鹵烷氧基、C
3–C
6鹵烯基氧基、C
3–C
6鹵炔基氧基、C
3–C
6環烷氧基、C
3–C
6鹵環烷氧基、C
4–C
8環烷基烷氧基、C
4–C
8鹵環烷基烷氧基、C
2–C
6烷氧基烷基、C
2–C
6鹵烷氧基烷基、C
2–C
6烷氧基鹵烷基、C
2–C
6烷氧基烷氧基、C
2–C
6氰基烷基、C
2–C
6氰基烷氧基、C
3–C
7氰基烷氧基烷基、C
1–C
6羥基烷基、C
1–C
6硝基烷基、C
1–C
6烷基硫基、C
1–C
6鹵烷基硫基、C
3–C
8環烷基硫基、C
1–C
6烯基硫基、C
1–C
6烷基亞磺醯基、C
1–C
6鹵烷基亞磺醯基、C
1–C
6烷基磺醯基、C
1–C
6鹵烷基磺醯基、C
3–C
8環烷基磺醯基、C
2–C
6烷基硫基烷基、C
2–C
6鹵烷基硫基烷基、苄基、-N(R
7)(OR
8)、-ON(R
9a)(R
9b)、或-N(R
7)N(R
9a)(R
9b);
Z係O或S;
R
2係鹵素、氰基、硝基、C
1–C
6烷氧基、C
1–C
6烷基、C
2–C
6烯基、C
2–C
6炔基、C
1–C
6鹵烷基、C
3–C
6環烷基、或-SO
nR
10;
各R
3獨立地係鹵素、氰基、硝基、CHO、C(=O)NH
2、C(=S)NH
2、SO
2NH
2、C
1–C
4烷基、C
2–C
4烯基、C
2–C
4炔基、C
1–C
4鹵烷基、C
2–C
4鹵烯基、C
2–C
4鹵炔基、C
3–C
6環烷基、C
3–C
6鹵環烷基、C
4–C
8烷基環烷基、C
4–C
8環烷基烷基、C
2–C
6烷基羰基、C
2–C
6鹵烷基羰基、C
2–C
6烷氧基羰基、C
3–C
7環烷基羰基、C
2–C
4烷氧基、C
3–C
4烯基氧基、C
3–C
4炔基氧基、C
1–C
4鹵烷氧基、C
3–C
6環烷氧基、C
3–C
6鹵環烷氧基、C
4–C
8環烷基烷氧基、C
2–C
6烷氧基烷基、C
2–C
6鹵烷氧基烷基、C
2–C
6烷氧基鹵烷基、C
2–C
6烷氧基烷氧基、C
2–C
4烷基羰基氧基、C
2–C
6氰基烷基、C
2–C
6氰基烷氧基、C
2–C
4烷基硫基烷基、-C(=O)N(R
11a)(R
11b)、-C(=NOR
12)H、-C(=N(R
13))H、或-SO
nR
14;
m係0、1、2、或3;
各n獨立地係0、1或2;
R
4係H、C
1–C
6烷基、或C
1–C
6鹵烷基;
R
5係H、C
1–C
6烷基、C
2–C
6烯基、C
2–C
6炔基、C
1–C
6鹵烷基、C
2–C
6鹵烯基、C
2–C
6鹵炔基、C
3–C
6環烷基、C
3–C
6鹵環烷基、C
4–C
8烷基環烷基、C
4–C
8環烷基烷基、C
2–C
6烷氧基烷基、C
2–C
6鹵烷氧基烷基、C
2–C
6烷氧基鹵烷基、C
2–C
6氰基烷基、C
3–C
7氰基烷氧基烷基、C
1–C
6羥基烷基、C
1–C
6硝基烷基、C
2–C
6烷基硫基烷基、C
2–C
6鹵烷基硫基烷基、或苄基;
各R
6a及R
6b獨立地係H、C
1–C
6烷基、或C
1–C
6鹵烷基;
R
7係H、C
1–C
6烷基、或C
1–C
6鹵烷基;
R
8係H、C
1–C
6烷基、C
1–C
6鹵烷基、C
2–C
6烷氧基烷基、C
2–C
6鹵烷氧基烷基、或C
2–C
6氰基烷基;
各R
9a及R
9b獨立地係H、C
1–C
6烷基、或C
1–C
6鹵烷基;
R
10獨立地係C
1–C
6烷基、C
1–C
6鹵烷基、C
1–C
6烷基胺基、或C
2–C
10二烷基胺基;
各R
11a獨立地係C
1–C
4烷基、或C
1–C
4鹵烷基;
各R
11b獨立地係H、C
1–C
4烷基、或C
1–C
4鹵烷基;
各R
12獨立地係H或C
1–C
4烷基;
各R
13獨立地係H、胺基、C
1–C
4烷基、或C
1–C
4烷基胺基;
各R
14獨立地係C
1–C
6烷基、C
1–C
6鹵烷基、C
1–C
6烷基胺基、或C
2–C
10二烷基胺基;且
R
15係H或C
1–C
6烷基;
其限制條件為
(i) 當A係A-1時,則R
1非係H、C
1–C
6烷基、或C
2–C
6烯基;
(ii) 當A係A-6時,則R
1非係C
1–C
6烷基磺醯基;
(iii) 當A係A-1、R
2係Cl、且R
3係3-Br時,則R
1非係C
2烷基硫基、C
2烷基亞磺醯基、或C
2烷基磺醯基;及
(iv) 式1之化合物非係2-[(5-氯-2-嘧啶基)氧基]苯甲酸甲酯(CAS登錄號854215-38-6)、2-[(5-溴-2-嘧啶基)氧基]苯甲酸甲酯(CAS登錄號1086397-52-5)、1-[2-[(5-溴-2-嘧啶基)氧基]苯基]-乙酮(CAS登錄號1147704-06-0)、及2-[(5-溴-2-嘧啶基)氧基]-苯乙腈(CAS登錄號138193-83-6)。
、 | 、 | 、 | 、 | 、 | 或 | |||||||
A-1 | A-2 | A-3 | A-4 | A-5 | A-6 | A-7 |
更特定而言,本發明關於式
1之化合物(包括所有立體異構物)、其
N-氧化物、或鹽。本發明亦關於一種除草組合物,其包含本發明之化合物(即以除草有效量)與至少一種選自由界面活性劑、固體稀釋劑、與液體稀釋劑所組成之群組的組分。本發明進一步關於一種用於防治非所欲植物之生長的方法,其包含使該植物或其環境與除草有效量的本發明化合物(例如以本文中所述之組合物)接觸。
本發明亦包括一種除草混合物,其包含(a)選自式
1、其
N-氧化物、及鹽之化合物,以及(b)至少一種選自如下所述之(b1)至(b16);及(b1)至(b16)之化合物之鹽的額外活性成分。
如本文中所使用,用語「包含(comprises/comprising)」、「包括(includes/including)」、「具有(has/having)」、「含有(contains/containing)」、「特徵在於(characterized by)」或其任何其他變型係意圖涵蓋非排他性的涵括,並受到任何明確指示的限制。例如,包含元件列表之組合物、混合物、製程或方法不一定僅限於那些元件,而是可以包括其他未明確列出的元件或為該組合物、混合物、製程或方法固有的元件。
連接詞「由……組成(consisting of)」排除任何未指明的元件、步驟或、成分。假使在請求項中,該連接詞會使請求項不包括列舉材料以外的材料,但原本與該等材料相關的雜質除外。當該詞「由......組成(consisting of)」出現在請求項主體的子句而非緊接著前言,其只限制在該子句中提到的元件;其他元件並不會從請求項的整體排除。
連接詞「主要由...組成(consisting essentially of)」係用以界定除了字面揭示的材料、步驟、特徵、組分、或元件以外還包括材料、步驟、特徵、組分、或元件的組合物或方法,前提是這些額外的材料、步驟、特徵、組分、或元件不會實質影響請求保護的發明之基本和新穎特徵。用語「主要由……組成(consisting essentially of)」居於「包含(comprising)」與「由……組成(consisting of)」之間的中間地帶。
當申請人使用開放式用語如「包含(comprising)」定義發明或其部分時,應易於理解(除非另有陳述)該描述應解讀為亦使用用語「主要由......組成(consisting essentially of)」或「由......組成(consisting of)」來描述該發明。
再者,除非有明確相反陳述,否則「或(or)」係指涵括性的或而非排他性的或。例如,以下任何一種情況均滿足條件A或B:A為真(或存在)且B為假(或不存在)、A為假(或不存在)且B為真(或存在)、以及A和B皆為真(或存在)。
同時,在本發明之元件或組分之前的不定冠詞「一(a, an)」在關於該元件或組分的出現數量(即出現次數)方面意為非限制性。因此「一(a, an)」應理解為包括一或至少一,且該元件或組分的單數詞形亦包括複數,除非該數目顯然是指單數。
如本文中所提及,用語「幼苗(seedling)」無論是單獨使用或與其他字詞組合,意指從種子胚芽發育出來的幼嫩植物。
如本文中所指及,用語「闊葉(broadleaf)」無論是單獨使用或在如「闊葉雜草(broadleaf weed)」之字詞中使用,意指雙子葉或雙子葉植物,即用以描述一群特徵在於胚具有兩個子葉之被子植物的用語。
在以上敘述中,用語「烷基(alkyl)」無論是單獨使用或在複合詞如「烷基硫基(alkylthio)」或「鹵烷基(haloalkyl)」中使用,皆包括直鏈或支鏈烷基,諸如甲基、乙基、正丙基、異丙基、或不同的丁基、戊基、或己基異構物。「烯基(alkenyl)」包括直鏈或支鏈烯,如乙烯基、1‑丙烯基、2‑丙烯基、以及不同的丁烯基、戊烯基、及己烯基異構物。「烯基(alkenyl)」亦包括多烯,如1,2‑丙二烯基、及2,4‑己二烯基。「炔基(alkynyl)」包括直鏈或支鏈炔如乙炔基、1‑丙炔基、2‑丙炔基、與不同的丁炔基、戊炔基、與己炔基異構物。「炔基(alkynyl)」亦可包括含多個三鍵的部分如2,5‑己二炔基。
「烷氧基(alkoxy)」包括例如甲氧基、乙氧基、正丙氧基、異丙氧基、以及不同的丁氧基、戊氧基、和己氧基異構物。「烷氧基烷基(alkoxyalkyl)」表示在烷基上有烷氧基取代。「烷氧基烷基(alkoxyalkyl)」之實例包括CH
3OCH
2、CH
3OCH
2CH
2、CH
3CH
2OCH
2、CH
3CH
2CH
2CH
2OCH
2、及CH
3CH
2OCH
2CH
2。「烷氧基烷氧基(alkoxyalkoxy)」表示在烷氧基上有烷氧基取代。「烷氧基烷氧基(alkoxyalkoxy)」包括CH
3OCH
2O、(CH
3)
2CHOCH
2O、CH
3OCH
2CH
2O、及CH
3CH
2OCH
2CH
2CH
2O。「烯基氧基(alkenyloxy)」包括直‑鏈或支鏈烯基氧基部分。「烯基氧基(alkenyloxy)」之實例包括H
2C=CHCH
2O、(CH
3)
2C=CHCH
2O、(CH
3)CH=CHCH
2O、(CH
3)CH=C(CH
3)CH
2O、及CH
2=CHCH
2CH
2O。「炔基氧基(alkynyloxy)」包括直鏈或支鏈炔基氧基部分。「炔基氧基(alkynyloxy)」之實例包括HC≡CCH
2O、CH
3C≡CCH
2O、及CH
3C≡CCH
2CH
2O。「烷基硫基(alkylthio)」包括支鏈或直鏈烷基硫基部分,像是甲基硫基、乙基硫基、以及不同的丙基硫基、丁基硫基、戊基硫基、及己基硫基異構物。「烷基亞磺醯基(alkylsulfinyl)」包含烷基亞磺醯基之兩種鏡像異構物。「烷基亞磺醯基(alkylsulfinyl)」之實例包括CH
3S(O)-、CH
3CH
2S(O)-、CH
3CH
2CH
2S(O)-、(CH
3)
2CHS(O)-、及不同之丁基亞磺醯基、戊基亞磺醯基、及己基亞磺醯基異構物。「烷基磺醯基(alkylsulfonyl)」之實例包括CH
3S(O)
2-、CH
3CH
2S(O)
2-、CH
3CH
2CH
2S(O)
2-、(CH
3)
2CHS(O)
2-、及不同之丁基磺醯基、戊基磺醯基、及己基磺醯基異構物。「烷基硫基烷基(alkylthioalkyl)」表示在烷基上有烷基硫基取代。「烷基硫基烷基(alkylthioalkyl)」之實例包括CH
3SCH
2、CH
3SCH
2CH
2、CH
3CH
2SCH
2、CH
3CH
2CH
2CH
2SCH
2、及CH
3CH
2SCH
2CH
2。「氰基烷基(Cyanoalkyl)」表示經一個氰基取代的烷基。「氰基烷氧基(cyanoalkoxy)」表示經一個氰基取代的烷氧基。「氰基烷氧基烷基(cyanoalkoxyalkyl)」表示經一個氰基取代的烷氧基烷基。「氰基烷基(cyanoalkyl)」之實例包括NCCH
2、NCCH
2CH
2、及CH
3CH(CN)CH
2。用語「羥基烷基(hydroxyalkyl)」表示經一個羥基取代的烷基。「羥基烷基(hydroxyoalkyl)」之實例包括HOCH
2-、HOCH
2CH
2-、及CH
3CH(OH)CH
2-。用語「硝基烷基(nitroalkyl)」表示經一個硝基取代的烷基。「硝基烷基(nitroalkyl)」之實例包括O
2NCH
2-、O
2NCH
2CH
2-、及CH
3CH(NO
2)CH
2-。「烷基胺基(alkylamino)」、「二烷基胺基(dialkylamino)」、「烯基硫基(alkenylthio)」、「烯基亞磺醯基(alkenylsulfinyl)」、「烯基磺醯基(alkenylsulfonyl)」、「炔基硫基(alkynylthio)」、「炔基亞磺醯基(alkynylsulfinyl)」、「炔基磺醯基(alkynylsulfonyl)」、及類似者的定義皆類似上述實例。
「環烷基(cycloalkyl)」包括例如環丙基、環丁基、環戊基、及環己基。用語「烷基環烷基(alkylcycloalkyl)」表示在環烷基部分上有烷基取代,並且包括例如乙基環丙基、異丙基環丁基、3-甲基環戊基、及4‑甲基環己基。用語「環烷基烷基(cycloalkylalkyl)」表示在烷基部分上有環烷基取代。「環烷基烷基(cycloalkylalkyl)」的實例包括環丙基甲基、環戊基乙基、及其他鍵結至直鏈或支鏈烷基的環烷基部分。用語「環烷基烷氧基(cycloalkylalkoxy)」表示在烷氧基部分上有環烷基取代。用語「環烷基羰基(cycloalkylcarbonyl)」表示環烷基取代透過羰基部分鍵結。「環烷基羰基(cycloalkylcarbonyl)」之實例包括
c-Pr(C=O)-、環戊基(C=O)-。用語「環烷基磺醯基(cycloalkylsulfonyl)」表示環烷基取代透過磺醯基部分鍵結。「環烷基磺醯基(cycloalkylsulfonyl)」之實例包括
c-Pr(S=O
2)-、環戊基(S=O
2)-。用語「環烷基硫基(cycloalkylthio)」表示環烷基取代透過硫原子鍵結。「環烷基硫基(cycloalkylthio)」之實例包括
c-Pr(S)-、環戊基(S)-。「環烷基烷氧基(cycloalkylalkoxy)」之實例包括環丙基甲氧基、環戊基乙氧基。用語「環烷氧基(cycloalkoxy)」表示環烷基透過氧原子連接,如環戊氧基、及環己氧基。用語「環胺基(cycloamino)」表示環狀胺透過氮鍵結。「環胺基(cycloamino)」之實例包括-N[CH
2CH
2CH
2](即吖呾)及-N[CH
2CH
2CH
2CH
2](即吡咯啶)。
用語「鹵素(halogen)」無論是單獨使用或在複合詞如「鹵烷基(haloalkyl)」中使用,或者當使用於如「經鹵素取代之烷基(alkyl substituted with halogen)」的描述中時,包括氟、氯、溴、或碘。再者,當使用於複合詞如「鹵烷基(haloalkyl)」中,或者當使用於如「經鹵素取代之烷基(alkyl substituted with halogen)」的描述中時,該烷基可經相同或不同的鹵素原子部分或全部取代。「鹵烷基(haloalkyl)」或「經鹵素取代之烷基(alkyl substituted with halogen)」之實例包括F
3C、ClCH
2、CF
3CH
2、及CF
3CCl
2。用語「鹵環烷基(halocycloalkyl)」、「鹵烷氧基(haloalkoxy)」、「鹵烷基硫基(haloalkylthio)」、「鹵烷基亞磺醯基(haloalkylsulfinyl)」、「鹵烷基磺醯基(haloalkylsulfonyl)」、「鹵烯基(haloalkenyl)」、「鹵炔基(haloalkynyl)」、「鹵烷氧基烷氧基(haloalkoxyalkoxy)」、「烷氧基鹵烷基(alkoxyhaloalkyl)」、及類似者之定義皆類似於用語「鹵烷基(haloalkyl)」。鹵環烷基之實例包括
c-Pr(2-Cl)、
c-Bu(2,2-二-Br)、及
c-Hex(3,5-二-Cl)。「鹵烷氧基(haloalkoxy)」之實例包括CF
3O-、CCl
3CH
2O-、HCF
2CH
2CH
2O-、及CF
3CH
2O-。「鹵烷基硫基(haloalkylthio)」之實例包括CCl
3S-、CF
3S-、CCl
3CH
2S-、及ClCH
2CH
2CH
2S-。「鹵烷基亞磺醯基(haloalkylsulfinyl)」之實例包括CF
3S(O)-、CCl
3S(O)-、CF
3CH
2S(O)-、及CF
3CF
2S(O)-。「鹵烷基磺醯基(haloalkylsulfonyl)」之實例包括CF
3S(O)
2-、CCl
3S(O)
2-、CF
3CH
2S(O)
2-、及CF
3CF
2S(O)
2-。「鹵烯基(haloalkenyl)」之實例包括(Cl)
2C=CHCH
2-及CF
3CH
2CH=CHCH
2-。「鹵炔基(haloalkynyl)」之實例包括HC≡CCHCl-、CF
3C≡C-、CCl
3C≡C-、及FCH
2C≡CCH
2-。「鹵烷氧基烷氧基(haloalkoxyalkoxy)」之實例包括CF
3OCH
2O-、ClCH
2CH
2OCH
2CH
2O-、Cl
3CCH
2OCH
2O-、以及支鏈烷基衍生物。「烷氧基鹵烷基(alkoxyhaloalkyl)」之實例包括CH
3OCF
2CH
2-、CH
3CH
2OCH
2CCl
2-、CF
3CH
2CH
2OCH
2-、以及支鏈烷基衍生物。
用語「鹵烯基氧基(haloalkenyloxy)」係指鹵烯基透過氧鍵結。「鹵烯基氧基(haloalkenyloxy)」之實例包括(Cl)
2C=CHCH
2O-及CF
3CH
2CH=CHCH
2O-。用語「鹵烷基胺基(haloalkylamino)」係指鹵烷基透過氮原子(即,作為二級胺)鍵結。「鹵烷基胺基(haloalkylamino)」之實例包括CF
3NH-、CCl
3CH
2NH-、HCF
2CH
2CH
2NH-、及CF
3CH
2NH-。用語「鹵烷基羰基(haloalkylcarbonyl)」係指鹵烷基透過羰基部分鍵結。「鹵烷基羰基(haloalkylcarbonyl)」之實例包括CH
2ClC(=O)-、CH
3CHClCH
2C(=O)-、及(CH
3)
2CCl(=O)-。用語「鹵烷基硫基烷基(haloalkylthioalkyl)」係指鹵烷基硫基透過烷基部分鍵結。「鹵烷基硫基烷基(haloalkylthioalkyl)」之實例包括CCl
3SCH
2-、CF
3SCH
2-、CCl
3CH
2SCH
2-、及ClCH
2CH
2CH
2SCH
2-。「鹵炔基氧基(haloalkynyloxy)」係指鹵炔基透過氧原子鍵結。「鹵炔基氧基(haloalkynyloxy)」之實例包括HC≡CCHClO-、CF
3C≡CO-、CCl
3C≡CO-、及FCH
2C≡CCH
2O-鹵炔基氧基。「鹵烷氧基烷基(haloalkoxyalkyl)」係指鹵烷氧基透過烷基部分鍵結。「鹵烷氧基烷基(haloalkoxyalkyl)」之實例包括CF
3OCH
2-、ClCH
2CH
2OCH
2CH
2-、Cl
3CCH
2OCH
2-、以及支鏈烷基衍生物。用語「鹵環烷氧基(halocycloalkoxy)」係指鹵環烷基透過氧原子鍵結。「鹵環烷氧基(halocycloalkoxy)」之實例包括
c‑Pr(2-Cl) CH
2O-及
c-Bu(1-Cl) CH
2CH
2O-。用語「鹵二烷基胺基(halodialkylamino)」係指兩個鹵烷基透過氮鍵結。「鹵二烷基胺基(halodialkylamino)」之實例包括(CH
2Cl)
2N-、(CH
2CH
2Cl)
2N-、及(CH
2CH
2Cl)(CH
2Br)N-。
「烷基羰基(alkylcarbonyl)」意指鍵結至C(=O)部分的直‑鏈或支鏈烷基部分。「烷基羰基(alkylcarbonyl)」之實例包括CH
3C(=O)-、CH
3CH
2CH
2C(=O)-、及(CH
3)
2CHC(=O)-。「烷氧基羰基(alkoxycarbonyl)」之實例包括CH
3OC(=O)-、CH
3CH
2OC(=O)-、CH
3CH
2CH
2OC(=O)-、(CH
3)
2CHOC(=O)-、及不同之丁氧基‑或戊氧基羰基異構物。「烷基羰基氧基(alkylcarbonyloxy)」之實例包括CH
3C(=O)O-、CH
3CH
2CH
2C(=O)O-、及(CH
3)
2CHC(=O)O-。
取代基中的碳原子總數係由「C
i–C
j」前綴表示,其中i和j是從1到10的數字。例如,C
1-C
4烷基磺醯基表示甲基磺醯基至丁基磺醯基;C
2烷氧基烷基表示CH
3OCH
2-;C
3烷氧基烷基表示例如CH
3CH(OCH
3)-、CH
3OCH
2CH
2-、或CH
3CH
2OCH
2-;而C
4烷氧基烷基表示總共含有4個碳原子之經烷氧基取代之烷基之各種異構物,實例包括CH
3CH
2CH
2OCH
2-及CH
3CH
2OCH
2CH
2-。
當化合物係經帶有下標之取代基取代以表示該取代基之數目可超過1個時,該等取代基(當它們超過1個時)係獨立地選自所界定取代基之群組,例如(R
3)
m,其中m係0、1、2、或3。再者,當下標表示範圍時,例如(R)
i–j,則取代基之數目可選自介於i與j之間(包括i與j)的整數。當基團含有可為氫之取代基(例如R
1或R
4)時,則當將此取代基採取為氫時,可得知此等同於該基團係未經取代。當可變基團係顯示為可選地連接至一位置時,例如(R
3)
m其中n可為0,則氫可能在該位置上,即使該可變基團的定義中並未述及。當基團上的一或多個位置係「未經取代(not substituted或unsubstituted)」時,則氫原子連接於該一或多個位置以佔據任何自由價。
除非另有說明,否則作為式
1之組分的「環(ring)」或「環系(ring system)」係碳環或雜環。用語「環系(ring system)」表示二或更多個稠環。用語「環員(ring member)」係指形成環或環系骨架的原子或其他部分(例如,C(=O)、C(=S)、S(O)、或S(O)
2)。
發明內容中之式
1之化合物可替代性地由下列表示:
1-A-1 | 1-A-2 |
1-A-3 | 1-A-4 |
1-A-5 | 1-A-6 |
及 | 1-A-7 |
用語「碳環(carbocyclic ring)」、「碳環(carbocycle)」或「碳環系(carbocyclic ring system)」表示其中形成環骨架的原子僅選自碳之環或環系。除非另有說明,碳環可以為飽和、部分不飽和、或完全不飽和環。當完全不飽和碳環滿足休克耳定則時,則該環亦稱作「芳環(aromatic ring)」。「飽和碳環(saturated carbocyclic)」係指具有由彼此以單鍵連接之碳原子所組成的骨架之環;除非有特別說明,餘下的碳價由氫原子佔據。
用語「雜環(heterocyclic ring)」、「雜環(heterocycle)」或「雜環系(heterocyclic ring system)」表示其中至少一個形成環骨架的原子不是碳(例如為氮、氧或硫)之環或環系。一般來說,雜環包含不超過4個氮、不超過2個氧、以及不超過2個硫。除非另有說明,雜環可以為飽和、部分不飽和、或完全不飽和環。當完全不飽和雜環滿足休克耳定則時,則該環亦稱作「雜芳環(heteroaromatic ring)」或「芳雜環(aromatic heterocyclic ring)」。除非另有說明,雜環及雜環系可透過任何可用的碳或氮,藉由取代在該碳或氮上之氫連接。
「芳族(aromatic)」意指各環原子基本上在相同平面上且具有垂直於該環平面之p軌域,且(4n + 2)個π電子(其中n係正整數)係與該環聯結以遵守休克爾定則。用語「芳環系(aromatic ring system)」表示該環系中的至少一個環係芳族之碳環系或雜環系。用語「芳碳環系(aromatic carbocyclic ring system)」表示該環系中的至少一個環係芳族之碳環系。用語「芳雜環系(aromatic heterocyclic ring system)」表示該環系中的至少一個環係芳族之雜環系。用語「非芳環系(nonaromatic ring system)」表示可為完全飽和、部分不飽合或完全不飽和之碳環或雜環系,惟該環系中沒有環是芳族。用語「非芳碳環系(nonaromatic carbocyclic ring system)」中該環系中沒有環是芳族。用語「非芳雜環系」表示該環系中沒有環是芳族之雜環系。
有關雜環之用語「可選地經取代(optionally substituted)」係指未經取代或具有至少一個非氫取代基之基團,該非氫取代基不會使未經取代的類似物所擁有之生物活性消失。如本文中所使用,下列定義應適用除非另有說明。用語「可選地經取代(optionally substituted)」係與詞語「經取代或未經取代(substituted or unsubstituted)」或用語「(未)經取代((un)substituted)」互換使用。除非另有說明,可選地經取代的基團在該基團的各可取代位置可具有一個取代基,而且各取代均彼此獨立。
在所屬領域中已知有各式各樣的合成方法能製備芳族及非芳族雜環和芳族及非芳族雜環系;相關方法的廣泛回顧請參見
Comprehensive Heterocyclic Chemistry, A. R. Katritzky及C. W. Rees總編輯,Pergamon Press, Oxford, 1984之第八卷集,以及
Comprehensive Heterocyclic Chemistry II, A. R. Katritzky, C. W. Rees及E. F. V. Scriven總編輯,Pergamon Press, Oxford, 1996之第十二卷集。
本發明之化合物可存在為一或多種立體異構物。各種立體異構物包括鏡像異構物、非鏡像異構物、阻轉異構物、和幾何異構物。鏡像異構物為組成相同但其原子在空間中之排列不同的異構物,並且包括鏡像異構物、非鏡像異構物、順反異構物(亦稱為幾何異構物)、及阻轉異構物。阻轉異構物係因繞著單鍵之旋轉受限而來,其中旋轉障壁高到足以能夠分離異構物物種。所屬領域中具有通常知識者將明瞭,一種立體異構物當相對於其他立體異構物經濃化(enriched)或當與其他立體異構物分離時,可具有更高活性及/或可能展現出有益的效果。此外,所屬技術領域具有通常知識者知道如何分離、濃化、及/或選擇性製備所述立體異構物。本發明的化合物可呈現為立體異構物之混合物、個別之立體異構物、或為光學活性形式。關於立體異構性之所有態樣的全面討論,參見Ernest L. Eliel及Samuel H. Wilen,
Stereochemistry of Organic Compounds, John Wiley & Sons, 1994。
本發明之化合物因為式
1中醯胺鍵(例如,C(=A)–R
1其中R
1係烷基胺基)的限制旋轉,而可存在為一或多個構形異構物。本發明包含構形異構物之混合物。此外,本發明包括一個構形異構物相對於其他者係經濃化之化合物。
式
1之化合物一般以超過一種形式存在,且式
1因而包括彼等所代表之化合物的所有結晶形式和非晶形式。非晶形式包括固體實施例(諸如蠟與膠)以及液體實施例(諸如溶液與熔體)。結晶形式包括基本上代表單晶類型的實施例及代表多形體(即不同結晶類型)混合物的實施例。用語「多形體(polymorph)」係指可以結晶成不同晶形之化合物的特定晶形,這些晶形在晶格內具有不同的分子排列及/或構形。雖然多形體可以有同樣的化學組成,它們也可以在組成上因為共結晶水或其他分子的存在或不存在而有所不同,該共結晶水或其他分子可弱結合或強結合在晶格內。多形體可以在化學、物理、和生物特性諸如晶體形狀、密度、硬度、顏色、化學穩定性、熔點、吸濕性、懸浮率、溶解速率、和生物利用性有所不同。所屬領域中具有通常知識者將瞭解到,式
1之化合物之多形體相較於相同式
1之化合物之另一種多形體或多形體混合物,可顯示出有利效果(例如適於製備有用的製劑、改善生物表現)。式
1之化合物的特定多形體之製備和分離可以藉由所屬領域中具有通常知識者所習知的方法完成,包括例如使用選定的溶劑和溫度來結晶。關於多形性之綜合論述,請參見R. Hilfiker, Ed.,
Polymorphism in the Pharmaceutical Industry, Wiley-VCH, Weinheim, 2006。
所屬技術領域中具有通常知識者將明瞭,並非所有含氮雜環皆可形成
N‑氧化物,因為氮原子需要可利用的孤電子對以氧化成氧化物;所屬技術領域中具有通常知識者會辨識該些可形成
N‑氧化物的含氮雜環。所屬技術領域中具有通常知識者亦將明瞭三級胺可形成
N‑氧化物。製備雜環及三級胺之
N‑氧化物的合成方法為所屬技術領域中具有通常知識者眾所皆知,包括以如過氧乙酸和間氯過氧苯甲酸(MCPBA)的過氧酸、過氧化氫、如三級丁基過氧化氫的烷基氫過氧化物、過硼酸鈉及如二甲基二環氧乙烷的二環氧乙烷來氧化雜環及三級胺。該等用於製備
N‑氧化物之方法已在文獻中廣泛描述及回顧,參見例如:T. L. Gilchrist在
Comprehensive Organic Synthesis, vol. 7, pp 748–750, S. V. Ley, Ed., Pergamon Press;M. Tisler與B. Stanovnik在
Comprehensive Heterocyclic Chemistry,vol. 3, pp 18–20, A. J. Boulton and A. McKillop, Eds., Pergamon PressM. R. Grimmett與B. R. T. Keene在
Advances in Heterocyclic Chemistry, vol. 43, pp 149–161, A. R. Katritzky, Ed., Academic Press;M. Tisler與B. Stanovnik在
Advances in Heterocyclic Chemistry, vol. 9, pp 285–291, A. R. Katritzky and A. J. Boulton, Eds., Academic Press;以及G. W. H. Cheeseman與E. S. G. Werstiuk在
Advances in Heterocyclic Chemistry, vol. 22, pp 390–392, A. R. Katritzky and A. J. Boulton, Eds., Academic Press。
所屬領域中具有通常知識者會瞭解到,因為化合物之鹽與它們對應之非鹽形式在環境和生理條件下會處於平衡狀態,所以鹽會分享非鹽形式的生物效用。因此式
1之化合物之廣泛各式鹽類可用於防治非所欲植物(即為農業上合適者)。式
1之化合物之鹽包括含無機酸或有機酸的酸加成鹽,諸如氫溴酸、鹽酸、硝酸、磷酸、硫酸、乙酸、丁酸、反丁烯二酸、乳酸、順丁烯二酸、丙二酸、草酸、丙酸、水楊酸、酒石酸、4‑甲苯磺酸或戊酸。當式
1之化合物含有酸性部分如羧酸或酚時,鹽亦包括該些以有機或無機鹼形成者,諸如吡啶、三乙胺、或氨、或鈉、鉀、鋰、鈣、鎂、或鋇之醯胺、氫化物、氫氧化物、或碳酸鹽。因此、本發明包含選自式
1、其
N‑氧化物、及農業上適用的鹽之化合物。
如發明內容中所述之本發明的實施例包括:
實施例1.一種式1之化合物(包括所有幾何及立體異構物)、其
N‑氧化物、及鹽、含有這些化合物之農業組合物、及彼等作為除草劑之用途。
實施例2.如實施例1之化合物,其中A係A-1、A-2、A-3、或A-5。
實施例3.如實施例2之化合物,其中A係A-1、A-2、或A-5。
實施例4.如實施例3之化合物,其中A係A-1或A-2。
實施例5.如實施例1之化合物,其中A係A-1或A-3。
實施例6.如實施例1之化合物,其中A係A-1。
實施例7.如實施例1之化合物,其中A係A-2。
實施例8.如實施例1之化合物,其中A係A-3。
實施例9.如實施例1之化合物,其中A係A-4。
實施例10.如實施例1之化合物,其中A係A-5。
實施例11.如實施例1之化合物,其中A係A-6。
實施例12.如實施例1之化合物,其中A係A-7。
實施例13.如實施例1、2、5、或8中任一者之化合物,其中B係O。
實施例14.如式
1或實施例1至14中任一者無論單獨或組合之化合物,其中R
1係C
1–C
6烷基、C
2–C
6烯基、C
2–C
6炔基、C
1–C
6鹵烷基、C
2–C
6鹵烯基、C
2–C
6鹵炔基、C
3–C
6環烷基、C
3–C
6鹵環烷基、C
3–C
6鹵環烷基烷基、C
4–C
8烷基環烷基、C
4–C
8環烷基烷基、C
1–C
6烷基胺基、C
1–C
6鹵烷基胺基、C
2–C
10二烷基胺基、C
2–C
10鹵二烷基胺基、C
1–C
6烷氧基、C
3–C
6烯基氧基、C
3–C
6炔基氧基、C
1–C
6鹵烷氧基、C
3–C
6鹵烯基氧基、C
3–C
6鹵炔基氧基、C
3–C
6環烷氧基、C
3–C
6鹵環烷氧基、C
4–C
8環烷基烷氧基、C
4–C
8鹵環烷基烷氧基、C
2–C
6烷氧基烷基、C
2–C
6鹵烷氧基烷基、C
2–C
6烷氧基鹵烷基、C
2–C
6烷氧基烷氧基、C
2–C
6氰基烷基、C
2–C
6氰基烷氧基、C
3–C
7氰基烷氧基烷基、C
1–C
6羥基烷基、C
1–C
6硝基烷基、C
1–C
6烷基硫基、C
1–C
6鹵烷基硫基、C
3–C
8環烷基硫基、C
1–C
6烯基硫基、C
1–C
6烷基亞磺醯基、C
1–C
6鹵烷基亞磺醯基、C
1–C
6烷基磺醯基、C
1–C
6鹵烷基磺醯基、C
3–C
8環烷基磺醯基、C
2–C
6烷基硫基烷基、C
2–C
6鹵烷基硫基烷基、苄基、-N(R
7)(OR
8)、-ON(R
9a)(R
9b)、或-N(R
7)N(R
9a)(R
9b)。
實施例15.如實施例14之化合物,其中R
1係C
1–C
6烷基、C
2–C
6烯基、C
2–C
6炔基、C
1–C
6鹵烷基、C
2–C
6鹵烯基、C
2–C
6鹵炔基、C
3–C
6環烷基、C
3–C
6鹵環烷基、C
3–C
6鹵環烷基烷基、C
4–C
8烷基環烷基、C
4–C
8環烷基烷基、C
1–C
6烷基胺基、C
1–C
6鹵烷基胺基、C
2–C
10二烷基胺基、C
2–C
10鹵二烷基胺基、C
1–C
6烷氧基、C
3–C
6烯基氧基、C
3–C
6炔基氧基、C
1–C
6鹵烷氧基、C
3–C
6鹵烯基氧基、C
3–C
6鹵炔基氧基、C
3–C
6環烷氧基、C
3–C
6鹵環烷氧基、C
4–C
8環烷基烷氧基、C
4–C
8鹵環烷基烷氧基、C
2–C
6烷氧基烷基、C
2–C
6鹵烷氧基烷基、C
2–C
6烷氧基鹵烷基、C
2–C
6烷氧基烷氧基、C
2–C
6氰基烷基、C
2–C
6氰基烷氧基、C
3–C
7氰基烷氧基烷基、C
1–C
6羥基烷基、C
1–C
6硝基烷基、C
1–C
6烷基硫基、C
1–C
6鹵烷基硫基、C
3–C
8環烷基硫基、C
1–C
6烯基硫基、C
1–C
6烷基亞磺醯基、C
1–C
6鹵烷基亞磺醯基、C
1–C
6烷基磺醯基、C
1–C
6鹵烷基磺醯基、C
3–C
8環烷基磺醯基、C
2–C
6烷基硫基烷基、或C
2–C
6鹵烷基硫基烷基。
實施例16.如實施例15之化合物,其中R
1係C
1–C
6烷基、C
2–C
6烯基、C
2–C
6炔基、C
1–C
6鹵烷基、C
1–C
6烷氧基、C
3–C
6烯基氧基、C
3–C
6炔基氧基、C
1–C
6鹵烷氧基、C
3–C
6鹵烯基氧基、C
3–C
6環烷氧基、C
4–C
8環烷基烷氧基、C
2–C
6氰基烷基、C
2–C
6氰基烷氧基、C
1–C
6烷基硫基、C
1–C
6鹵烷基硫基、或C
1–C
6烯基硫基。
實施例17.如實施例16之化合物,其中R
1係C
1–C
6烷基、C
2–C
6烯基、C
2–C
6炔基、C
1–C
6鹵烷基、C
1–C
6烷氧基、C
3–C
6烯基氧基、C
3–C
6炔基氧基、C
1–C
6鹵烷氧基、C
3–C
6鹵烯基氧基、C
2–C
6氰基烷基、C
2–C
6氰基烷氧基、C
1–C
6烷基硫基、C
1–C
6鹵烷基硫基、或C
1–C
6烯基硫基。
實施例18.如實施例17之化合物,其中R
1係C
1–C
6烷基、C
2–C
6烯基、C
2–C
6炔基、C
1–C
6鹵烷基、C
1–C
6烷氧基、C
3–C
6烯基氧基、C
3–C
6炔基氧基、C
1–C
6鹵烷氧基、C
3–C
6鹵烯基氧基、C
1–C
6烷基硫基、C
1–C
6鹵烷基硫基、或C
1–C
6烯基硫基。
實施例19.如實施例17之化合物,其中R
1係C
1–C
6烷基、C
2–C
6烯基、C
2–C
6炔基、C
1–C
6鹵烷基、C
1–C
6烷氧基、C
3–C
6烯基氧基、C
3–C
6炔基氧基、或C
3–C
6鹵烯基氧基。
實施例20.如實施例19之化合物,其中R
1係C
1–C
6烷基、C
2–C
6烯基、C
1–C
6鹵烷基、C
1–C
6烷氧基、或C
1–C
6鹵烷氧基。
實施例21.如實施例20之化合物,其中R
1係C
1–C
6烷基、C
1–C
6鹵烷基、C
1–C
6烷氧基、或C
1–C
6鹵烷氧基。
實施例22.如實施例21之化合物,其中R
1係C
1–C
6烷基。
實施例23.如實施例21之化合物,其中R
1係C
1–C
6鹵烷基。
實施例24.如實施例21之化合物,其中R
1係C
1–C
6烷氧基。
實施例25.如實施例21之化合物,其中R
1係C
2–C
6鹵烷氧基。
實施例26.如實施例21之化合物,其中R
1係C
4–C
6烷基、C
3–C
6鹵烷基、C
3–C
6烷氧基、或C
3–C
6鹵烷氧基。
實施例27.如實施例26之化合物,其中當A係A-3時,則R
1係C
3–C
6鹵烷基。
實施例28.如實施例26之化合物,其中當A係A-1時,則R
1係C
4–C
6鹵烷基。
實施例29.如實施例28之化合物,其中當A係A-1時,則R
1係C
4–C
5鹵烷基。
實施例30.如實施例29之化合物,其中當A係A-1時,則R
1係CH
2CH
2CH
2CF
3。
實施例31.如實施例29之化合物,其中當A係A-1時,則R
1係CH
2CH
2CF
2CF
3。
實施例32.如實施例19之化合物,其中當A係A-3時,則R
1係C
4–C
6鹵烯基氧基。
實施例33.如實施例26之化合物,其中當A係A-3時,則R
1係C
4–C
5鹵烷氧基。
實施例34.如實施例23之化合物,其中R
1係CH
2CH
2CH
2CH
2CH
2CF
3。
實施例35.如實施例23之化合物,其中R
1係CH
2CH
2CH
2CH
2CF
3。
實施例36.如實施例23之化合物,其中R
1係CH
2CH
2CH
2CF
3。
實施例37.如實施例23之化合物,其中R
1係CH
2CH
2CF
3。
實施例38.如實施例25之化合物,其中R
1係OCH
2CH
2CH
2CH
2CF
3。
實施例39.如實施例25之化合物,其中R
1係OCH
2CH
2CH
2CF
3。
實施例40.如實施例25之化合物,其中R
1係OCH
2CH
2CF
3。
實施例41.如實施例25之化合物,其中R
1係OCH
2CF
2CF
3。
實施例42.如實施例1至13中任一者之化合物,其中R
1非係H。
實施例43.如實施例1至14中任一者之化合物,其中R
1非係苄基(未經取代)。
實施例44.如實施例1至22中任一者之化合物,其中R
1非係CH
3、CH
2CH
3、或CH
2CH
2CH
3。
實施例45.如實施例1至20中任一者之化合物,其中R
1非係CH
2CH=CH
2、CH=CHCH
3、C(=CH
2)CH
3、或CH=C(CH
3)
2。
實施例46.如實施例1之化合物,其中R
1非係丙烯-2-基、丙烯-1-基、正丙基、乙基、1-甲基乙烯-2-基、或2-甲基丙烯-1-基(即R
1非係CH
2CH=CH
2、CH
2CH
2CH
3、CH=CHCH
3、CH
2CH
3、C(=CH
2)CH
3、或CH=C(CH
3)
2)。
實施例47.如實施例1至22或24中任一者之化合物,其中R
1非係OCH
3。
實施例48.如式
1或實施例1至47中任一者無論單獨或組合之化合物,其中Z係O。
實施例49.如式
1或實施例1至48中任一者無論單獨或組合之化合物,其中R
2係鹵素、C
1–C
4烷基、或C
1–C
4鹵烷基。
實施例50.如實施例49之化合物,其中R
2係鹵素或C
1–C
4烷基。
實施例51.如實施例50之化合物,其中R
2係鹵素或CH
3。
實施例52.如實施例51之化合物,其中R
2係鹵素。
實施例53.如實施例52之化合物,其中R
2係F、Cl、或Br。
實施例54.如實施例53之化合物,其中R
2係Cl。
實施例55.如式
1或實施例1至54中任一者無論單獨或組合之化合物,其中m係0、1、或2。
實施例56.如實施例55之化合物,其中m係0或1。
實施例57.如實施例56之化合物,其中m係1。
實施例58.如實施例57之化合物,其中m在3、4、或6位係1。
實施例59.如實施例58之化合物,其中m在3或4位係1。
實施例60.如實施例59之化合物,其中m係0(即3、4、5、及6位之各者係未經R
3取代)。
實施例61.如式
1或實施例1至60中任一者無論單獨或組合之化合物,其中各R
3獨立地係鹵素、氰基、CHO、C
1–C
4烷基、C
2–C
4烯基、C
2–C
4炔基、C
1–C
4鹵烷基、C
2–C
4鹵烯基、C
2–C
4鹵炔基、C
3–C
6環烷基、C
3–C
6鹵環烷基、C
4–C
8烷基環烷基、C
2–C
6烷基羰基、C
2–C
6鹵烷基羰基、C
2–C
6烷氧基羰基、C
1–C
4烷氧基、C
3–C
4烯基氧基、C
3–C
4炔基氧基、C
1–C
4鹵烷氧基、C
3–C
4鹵烯基氧基、C
3–C
4鹵炔基氧基、C
3–C
6環烷氧基、C
3–C
6鹵環烷氧基、C
2–C
6烷氧基烷基、C
2–C
6鹵烷氧基烷基、C
2–C
4烷基羰基氧基、C
2–C
6氰基烷基、-C(=O)N(R
11aR
11b)、-C(=NOR
12)H、或-SO
nR
14。
實施例62.如實施例61之化合物,其中各R
3獨立地係鹵素、氰基、CHO、C
1–C
4烷基、C
2–C
4烯基、C
2–C
4炔基、C
1–C
4鹵烷基、C
2–C
4鹵烯基、C
2–C
4鹵炔基、C
3–C
6環烷基、C
3–C
6鹵環烷基、C
2–C
6烷基羰基、C
2–C
6鹵烷基羰基、C
2–C
6烷氧基羰基、C
1–C
4烷氧基、C
1–C
4鹵烷氧基、C
2–C
6烷氧基烷基、C
2–C
6鹵烷氧基烷基、C
2–C
6氰基烷基、或-SO
nR
14。
實施例63.如實施例62之化合物,其中各R
3獨立地係鹵素、氰基、C
1–C
4烷基、或C
1–C
4鹵烷基。
實施例64.如實施例63之化合物,其中各R
3獨立地係鹵素、氰基、C
1–C
3烷基、或C
1–C
3鹵烷基。
實施例65.如實施例64之化合物,其中各R
3獨立地係鹵素、氰基、C
1–C
2烷基、或C
1–C
2鹵烷基。
實施例66.如實施例65之化合物,其中各R
3獨立地係鹵素、氰基、CH
3、CH
2CH
3、或CF
3。
實施例67.如實施例66之化合物,其中各R
3獨立地係鹵素、氰基、或CF
3。
實施例68.如實施例67之化合物,其中各R
3獨立地係F、Cl、Br、或氰基。
實施例69.如實施例68之化合物,其中各R
3獨立地係Br或氰基。
實施例70.如實施例69之化合物,其中各R
3獨立地係鹵素或氰基。
實施例71.如實施例70之化合物,其中各R
3獨立地係氰基。
實施例72.如實施例70之化合物,其中各R
3獨立地係鹵素。
實施例73.如實施例72之化合物,其中各R
3獨立地係Br。
實施例74.如式
1或實施例1至73中任一者無論單獨或組合之化合物,其中m係至少1且一個R
3係位於3位(即相鄰於-AR
1基團),由式
1D之化合物表示:
,
其中A、R
1、R
2、及Z係如發明內容或實施例1至59中任一者中所定義;
R
3a係如實施例61至73中任一者中針對R
3所定義;
R
3b係如實施例61至73中任一者中針對R
3所定義;且
p係0或1。
實施例75.如實施例74之化合物,其中p係1;R
3a係鹵素、氰基、C
1–C
3烷基、C
1–C
3鹵烷基、或C
1–C
3烷氧基;且R
3b係鹵素、氰基、C
1–C
3烷基、C
1–C
3鹵烷基、或C
1–C
3烷氧基。
實施例76.如實施例75之化合物,其中p係0且R
3a係鹵素、氰基、C
1–C
3烷基、C
1–C
3鹵烷基、或C
1–C
3烷氧基。
實施例77.如實施例76之化合物,其中R
3a係鹵素或氰基。
實施例78.如實施例77之化合物,其中R
3a係Br或氰基。
實施例79.如式
1或實施例1至28中任一者無論單獨或組合之化合物,其中R
5係H、C
1–C
6烷基、C
2–C
6烯基、C
2–C
6炔基、C
1–C
6鹵烷基、C
2–C
6鹵烯基、C
2–C
6鹵炔基、C
2–C
6烷氧基烷基、C
2–C
6鹵烷氧基烷基、C
2–C
6氰基烷基、C
3–C
7氰基烷氧基烷基、C
2–C
6烷基硫基烷基、或C
2–C
6鹵烷基硫基烷基。
實施例80.如實施例79之化合物,其中R
5係C
1–C
6烷基、或C
1–C
6鹵烷基。
實施例81.如實施例1之化合物,其中當A係A-5時,則R
3係在4、5、或6位。
實施例82.如實施例1之化合物,其中當A係A-3、B係O、R
3係3-Br時,則R
1非係3-溴丙烷。
實施例83.如實施例1之化合物,其中當A係A-3時,R
3係在3位之鹵素。
實施例84.如實施例1之化合物,其中當A係A-1時,R
3係在3位之氰基。
實施例85.如實施例1之化合物,其中R
1非係C
3–C
6環胺基。
實施例86.如實施例1之化合物,其中各R
11a獨立地係C
1–C
2烷基或C
1–C
2鹵烷基。
實施例87.如實施例1之化合物,其中各R
11b獨立地係C
1–C
2烷基或C
1–C
2鹵烷基。
實施例88.如實施例1之化合物,其中各R
12獨立地係H或C
1–C
3烷基。
實施例89.如實施例1之化合物,其中各R
14獨立地係C
1–C
3烷基或C
1–C
3鹵烷基。
實施例90.如實施例1之化合物,其中各R
14獨立地係C
1–C
3烷基。
實施例91.如實施例1之化合物,其中m係1、2、或3。
實施例92.如實施例1之化合物,其中m係1或2。
本發明之實施例(包括上述實施例1至92及任何其他本文中所述之實施例)可以任何方式組合,並且實施例中之變項描述不僅關於式
1之化合物,亦關於可用於製備式
1之化合物之起始化合物及中間化合物。此外,本發明之實施例(包括上述實施例1至92及任何其他本文中所述之實施例、以及上述者之任何組合)均關於本發明之組合物與方法。
實施例1至92之組合係說明如下:
實施例A.一種式
1之化合物,其中
A係A-1、A-2、A-3、或A-5;
R
1係C
1–C
6烷基、C
2–C
6烯基、C
2–C
6炔基、C
1–C
6鹵烷基、C
2–C
6鹵烯基、C
2–C
6鹵炔基、C
3–C
6環烷基、C
3–C
6鹵環烷基、C
3–C
6鹵環烷基烷基、C
4–C
8烷基環烷基、C
4–C
8環烷基烷基、C
1–C
6烷基胺基、C
1–C
6鹵烷基胺基、C
2–C
10二烷基胺基、C
2–C
10鹵二烷基胺基、C
1–C
6烷氧基、C
3–C
6烯基氧基、C
3–C
6炔基氧基、C
1–C
6鹵烷氧基、C
3–C
6鹵烯基氧基、C
3–C
6鹵炔基氧基、C
3–C
6環烷氧基、C
3–C
6鹵環烷氧基、C
4–C
8環烷基烷氧基、C
4–C
8鹵環烷基烷氧基、C
2–C
6烷氧基烷基、C
2–C
6鹵烷氧基烷基、C
2–C
6烷氧基鹵烷基、C
2–C
6烷氧基烷氧基、C
2–C
6氰基烷基、C
2–C
6氰基烷氧基、C
3–C
7氰基烷氧基烷基、C
1–C
6羥基烷基、C
1–C
6硝基烷基、C
1–C
6烷基硫基、C
1–C
6鹵烷基硫基、C
3–C
8環烷基硫基、C
1–C
6烯基硫基、C
1–C
6烷基亞磺醯基、C
1–C
6鹵烷基亞磺醯基、C
1–C
6烷基磺醯基、C
1–C
6鹵烷基磺醯基、C
3–C
8環烷基磺醯基、C
2–C
6烷基硫基烷基、或C
2–C
6鹵烷基硫基烷基;
R
2係鹵素、C
1–C
4烷基、或C
1–C
4鹵烷基;
各R
3獨立地係鹵素、氰基、CHO、C
1–C
4烷基、C
2–C
4烯基、C
2–C
4炔基、C
1–C
4鹵烷基、C
2–C
4鹵烯基、C
2–C
4鹵炔基、C
3–C
6環烷基、C
3–C
6鹵環烷基、C
4–C
8烷基環烷基、C
2–C
6烷基羰基、C
2–C
6鹵烷基羰基、C
2–C
6烷氧基羰基、C
1–C
4烷氧基、C
3–C
4烯基氧基、C
3–C
4炔基氧基、C
1–C
4鹵烷氧基、C
3–C
4鹵烯基氧基、C
3–C
4鹵炔基氧基、C
3–C
6環烷氧基、C
3–C
6鹵環烷氧基、C
2–C
6烷氧基烷基、C
2–C
6鹵烷氧基烷基、C
2–C
4烷基羰基氧基、C
2–C
6氰基烷基、-C(=O)N(R
11aR
11b)、-C(=NOR
12)H、或-SO
nR
14;
R
5係H、C
1–C
6烷基、C
2–C
6烯基、C
2–C
6炔基、C
1–C
6鹵烷基、C
2–C
6鹵烯基、C
2–C
6鹵炔基、C
2–C
6烷氧基烷基、C
2–C
6鹵烷氧基烷基、C
2–C
6氰基烷基、C
3–C
7氰基烷氧基烷基、C
2–C
6烷基硫基烷基、或C
2–C
6鹵烷基硫基烷基;
R
11a係C
1–C
2烷基或C
1–C
2鹵烷基;
R
11b係C
1–C
2烷基、或C
1–C
2鹵烷基;
R
12係H或C
1–C
3烷基;且
R
14係C
1–C
3烷基、或C
1–C
3鹵烷基。
實施例B.如實施例A之化合物,其中
A係A-1、A-2、或A-5;
R
1係C
1–C
6烷基、C
2–C
6烯基、C
2–C
6炔基、C
1–C
6鹵烷基、C
1–C
6烷氧基、C
3–C
6烯基氧基、C
3–C
6炔基氧基、C
1–C
6鹵烷氧基、C
3–C
6鹵烯基氧基、C
3–C
6環烷氧基、C
4–C
8環烷基烷氧基、C
2–C
6氰基烷基、C
2–C
6氰基烷氧基、C
1–C
6烷基硫基、C
1–C
6鹵烷基硫基、或C
1–C
6烯基硫基;
R
2係鹵素、或C
1–C
4烷基;
各R
3獨立地係鹵素、氰基、CHO、C
1–C
4烷基、C
2–C
4烯基、C
2–C
4炔基、C
1–C
4鹵烷基、C
2–C
4鹵烯基、C
2–C
4鹵炔基、C
3–C
6環烷基、C
3–C
6鹵環烷基、C
2–C
6烷基羰基、C
2–C
6鹵烷基羰基、C
2–C
6烷氧基羰基、C
1–C
4烷氧基、C
1–C
4鹵烷氧基、C
2–C
6烷氧基烷基、C
2–C
6鹵烷氧基烷基、C
2–C
6氰基烷基、或-SO
nR
14;
R
5係C
1–C
6烷基、或C
1–C
6鹵烷基;
各R
14獨立地係C
1–C
3烷基;且
m係0、1、或2。
實施例C.如實施例B之化合物,其中
A係A-1、或A-2;
R
1係C
1–C
6烷基、C
2–C
6烯基、C
2–C
6炔基、C
1–C
6鹵烷基、C
1–C
6烷氧基、C
3–C
6烯基氧基、C
3–C
6炔基氧基、C
1–C
6鹵烷氧基、C
3–C
6鹵烯基氧基、C
2–C
6氰基烷基、C
2–C
6氰基烷氧基、C
1–C
6烷基硫基、C
1–C
6鹵烷基硫基、或C
1–C
6烯基硫基;
R
2係鹵素、或CH
3;且
各R
3獨立地係鹵素、氰基、C
1–C
4烷基、或C
1–C
4鹵烷基。
實施例D.如實施例C之化合物,其中
A係A-1;
R
1係C
1–C
6烷基、C
2–C
6烯基、C
2–C
6炔基、C
1–C
6鹵烷基、C
1–C
6烷氧基、C
3–C
6烯基氧基、C
3–C
6炔基氧基、C
1–C
6鹵烷氧基、C
3–C
6鹵烯基氧基、C
1–C
6烷基硫基、C
1–C
6鹵烷基硫基、或C
1–C
6烯基硫基;
Z係O;
R
2係鹵素;
各R
3獨立地係鹵素、氰基、C
1–C
3烷基、或C
1–C
3鹵烷基;且
m係1或2。
實施例E.如實施例C之化合物,其中
A係A-2;
R
1係C
1–C
6烷基、C
2–C
6烯基、C
1–C
6鹵烷基、C
1–C
6烷氧基、或C
1–C
6鹵烷氧基;
Z係O;
R
2係F、Cl、或Br;
各R
3獨立地係鹵素、氰基、C
1–C
2烷基、或C
1–C
2鹵烷基;且
m係0或1。
實施例F.如實施例A之化合物,其中
A係A-3;
R
1係C
1–C
6烷基、C
2–C
6烯基、C
2–C
6炔基、C
1–C
6鹵烷基、C
1–C
6烷氧基、C
3–C
6烯基氧基、C
3–C
6炔基氧基、C
1–C
6鹵烷氧基、C
3–C
6鹵烯基氧基、C
3–C
6環烷氧基、C
4–C
8環烷基烷氧基、C
2–C
6氰基烷基、C
2–C
6氰基烷氧基、C
1–C
6烷基硫基、C
1–C
6鹵烷基硫基、或C
1–C
6烯基硫基;
R
2係鹵素、或C
1–C
4烷基;
各R
3獨立地係鹵素、氰基、C
1–C
4烷基、或C
1–C
4鹵烷基;且
m係1或2。
實施例G.如實施例F之化合物,其中
B係O;
R
1係C
1–C
6烷基、C
2–C
6烯基、C
2–C
6炔基、C
1–C
6鹵烷基、C
1–C
6烷氧基、C
3–C
6烯基氧基、C
3–C
6炔基氧基、C
1–C
6鹵烷氧基、C
3–C
6鹵烯基氧基、C
2–C
6氰基烷基、C
2–C
6氰基烷氧基、C
1–C
6烷基硫基、C
1–C
6鹵烷基硫基、或C
1–C
6烯基硫基;
Z係O;
R
2係鹵素、或CH
3;
各R
3獨立地係鹵素、氰基、C
1–C
3烷基、或C
1–C
3鹵烷基;且
m係1或2。
具體實施例包括選自由下列所組成之群組的式
1之化合物:
2-氯-6-[(5-氯-2-嘧啶基)氧基]苯甲酸3,3,3-三氟丙酯(化合物15);
2-溴-6-[(5-氯-2-嘧啶基)氧基]苯甲酸3,3,3-三氟-1-甲基丙酯(化合物16);
2-溴-6-[(5-氯-2-嘧啶基)氧基]苯甲酸丙酯(化合物13);
2-溴-6-[(5-氯-2-嘧啶基)氧基]苯甲酸4,4,4-三氟丁酯(化合物20);
2-溴-6-[(5-氯-2-嘧啶基)氧基]苯甲酸2-丙烯-1-基酯(化合物22);
2-溴-6-[(5-氯-2-嘧啶基)氧基]苯甲酸3-丁烯-1-基酯(化合物21);
2-溴-6-[(5-氯-2-嘧啶基)氧基]苯甲酸2,2,3,3,3-五氟丙酯(化合物23);
2-溴-6-[(5-氯-2-嘧啶基)氧基]苯甲酸3,3,3-三氟丙酯(化合物26);
1-[2-氯-6-[(5-氯-2-嘧啶基)氧基]苯基]-4,4,4-三氟-1-丁酮(化合物107);及
3-[(5-氯-2-嘧啶基)氧基]-2-(5,5,5-三氟戊基)苄腈(化合物73)。
如在發明內容中所述之本發明實施例包括(其中用於下列實施例之式
1P包括其
N-氧化物及鹽):
實施例P1.一種式
1P之化合物,其中A係H
2、O、S、或N(OR
5)。
實施例P2.如實施例P1之化合物,其中A係H
2、O、或N(OR
5)。
實施例P3.如實施例P2之化合物,其中A係O或N(OR
5)。
實施例P4.如實施例P3之化合物,其中A係O。
實施例P5.如實施例P3之化合物,其中A係N(OR
5)。
實施例P6.如式
1P或實施例P1至P5中任一者無論單獨或組合之化合物,其中R
1係C
1–C
6烷基、C
2–C
6烯基、C
2–C
6炔基、C
1–C
6鹵烷基、C
2–C
6鹵烯基、C
2–C
6鹵炔基、C
3–C
6環烷基、C
3–C
6鹵環烷基、C
4–C
8烷基環烷基、C
4–C
8環烷基烷基、C
1–C
6烷基胺基、C
1–C
6鹵烷基胺基、C
2–C
10二烷基胺基、C
2–C
10鹵二烷基胺基、C
3–C
6環胺基、C
1–C
6烷氧基、C
3–C
6烯基氧基、C
3–C
6炔基氧基、C
1–C
6鹵烷氧基、C
3–C
6鹵烯基氧基、C
3–C
6鹵炔基氧基、C
3–C
6環烷氧基、C
3–C
6鹵環烷氧基、C
4–C
8環烷基烷氧基、C
4–C
8鹵環烷基烷氧基、C
2–C
6烷氧基烷基、C
2–C
6鹵烷氧基烷基、C
2–C
6烷氧基鹵烷基、C
2–C
6烷氧基烷氧基、C
2–C
6氰基烷基、C
2–C
6氰基烷氧基、C
3–C
7氰基烷氧基烷基、C
1–C
6羥基烷基、C
1–C
6硝基烷基、C
1–C
6烷基硫基、C
1–C
6鹵烷基硫基、C
3–C
8環烷基硫基、C
1–C
6烷基亞磺醯基、C
1–C
6鹵烷基亞磺醯基、C
1–C
6烷基磺醯基、C
1–C
6鹵烷基磺醯基、C
3–C
8環烷基磺醯基、C
2–C
6烷基硫基烷基、C
2–C
6鹵烷基硫基烷基、苄基、-NR
7OR
8、-ON(R
9aR
9b)、或-NR
7N(R
9aR
9b)。
實施例P7.如實施例P6之化合物,其中R
1係C
1–C
6烷基、C
2–C
6烯基、C
2–C
6炔基、C
1–C
6鹵烷基、C
2–C
6鹵烯基、C
2–C
6鹵炔基、C
3–C
6環烷基、C
3–C
6鹵環烷基、C
4–C
8烷基環烷基、C
4–C
8環烷基烷基、C
1–C
6烷基胺基、C
1–C
6鹵烷基胺基、C
2–C
10二烷基胺基、C
2–C
10鹵二烷基胺基、C
3–C
6環胺基、C
1–C
6烷氧基、C
3–C
6烯基氧基、C
3–C
6炔基氧基、C
1–C
6鹵烷氧基、C
3–C
6鹵烯基氧基、C
3–C
6鹵炔基氧基、C
3–C
6環烷氧基、C
3–C
6鹵環烷氧基、C
4–C
8環烷基烷氧基、C
4–C
8鹵環烷基烷氧基、C
2–C
6烷氧基烷基、C
2–C
6鹵烷氧基烷基、C
2–C
6烷氧基鹵烷基、C
2–C
6烷氧基烷氧基、C
2–C
6氰基烷基、C
2–C
6氰基烷氧基、C
3–C
7氰基烷氧基烷基、C
1–C
6羥基烷基、C
1–C
6硝基烷基、C
1–C
6烷基硫基、C
1–C
6鹵烷基硫基、C
3–C
8環烷基硫基、C
1–C
6烷基亞磺醯基、C
1–C
6鹵烷基亞磺醯基、C
1–C
6烷基磺醯基、C
1–C
6鹵烷基磺醯基、C
3–C
8環烷基磺醯基、C
2–C
6烷基硫基烷基、或C
2–C
6鹵烷基硫基烷基。
實施例P8.如實施例P7之化合物,其中R
1係C
1–C
6烷基、C
2–C
6烯基、C
2–C
6炔基、C
1–C
6鹵烷基、C
2–C
6鹵烯基、C
2–C
6鹵炔基、C
3–C
6環烷基、C
3–C
6鹵環烷基、C
1–C
6烷氧基、C
3–C
6烯基氧基、C
3–C
6炔基氧基、C
1–C
6鹵烷氧基、C
3–C
6鹵烯基氧基、C
3–C
6鹵炔基氧基、或C
3–C
6環烷氧基。
實施例P9.如實施例P8之化合物,其中R
1係C
1–C
6烷氧基、C
3–C
6烯基氧基、C
3–C
6炔基氧基、C
1–C
6鹵烷氧基、C
3–C
6鹵烯基氧基、C
3–C
6鹵炔基氧基、或C
3–C
6環烷氧基。
實施例P10.如式
1P或實施例P1至P9中任一者無論單獨或組合之化合物,其中Z係O。
實施例P11.如式
1P或實施例P1至P10中任一者無論單獨或組合之化合物,其中R
2係鹵素、C
1–C
4烷基、或C
1–C
4鹵烷基。
實施例P12.如實施例P11之化合物,其中R
2係鹵素或C
1–C
4烷基。
實施例P13.如實施例P12之化合物,其中R
2係鹵素或CH
3。
實施例P14.如實施例P13之化合物,其中R
2係鹵素。
實施例P15.如實施例P14之化合物,其中R
2係F、Cl、或Br。
實施例P16.如式
1P或實施例P1至P15中任一者無論單獨或組合之化合物,其中m係0、1、或2。
實施例P17.如實施例P16之化合物,其中m係0或1。
實施例P18.如實施例P17之化合物,其中m係1。
實施例P19.如實施例P17之化合物,其中m係0(即3、4、5、及6位皆未經R
3取代)。
實施例P20.如式
1P或實施例P1至P19中任一者無論單獨或組合之化合物,其中各R
3獨立地係鹵素、氰基、CHO、C
1–C
4烷基、C
2–C
4烯基、C
2–C
4炔基、C
1–C
4鹵烷基、C
2–C
4鹵烯基、C
2–C
4鹵炔基、C
3–C
6環烷基、C
3–C
6鹵環烷基、C
4–C
8烷基環烷基、C
2–C
6烷基羰基、C
2–C
6鹵烷基羰基、C
2–C
6烷氧基羰基、C
1–C
4烷氧基、C
3–C
4烯基氧基、C
3–C
4炔基氧基、C
1–C
4鹵烷氧基、C
3–C
4鹵烯基氧基、C
3–C
4鹵炔基氧基、C
3–C
6環烷氧基、C
3–C
6鹵環烷氧基、C
2–C
6烷氧基烷基、C
2–C
6鹵烷氧基烷基、C
2–C
4烷基羰基氧基、C
2–C
6氰基烷基、-C(=O)N(R
11aR
11b)、-C(=NOR
12)H、或-SO
nR
14。
實施例P21.如實施例P20之化合物,其中各R
3獨立地係鹵素、氰基、CHO、C
1–C
4烷基、C
2–C
4烯基、C
2–C
4炔基、C
1–C
4鹵烷基、C
2–C
4鹵烯基、C
2–C
4鹵炔基、C
3–C
6環烷基、C
3–C
6鹵環烷基、C
2–C
6烷基羰基、C
2–C
6鹵烷基羰基、C
2–C
6烷氧基羰基、C
1–C
4烷氧基、C
1–C
4鹵烷氧基、C
2–C
6烷氧基烷基、C
2–C
6鹵烷氧基烷基、C
2–C
6氰基烷基、或-SO
nR
14。
實施例P22.如實施例P21之化合物,其中各R
3獨立地係鹵素、氰基、C
1–C
4烷基、或C
1–C
4鹵烷基。
實施例P23.如實施例P22之化合物,其中各R
3獨立地係鹵素或氰基。
實施例P24.如實施例P23之化合物,其中各R
3獨立地係氰基。
實施例P25.如實施例P23之化合物,其中各R
3獨立地係鹵素。
實施例P26.如實施例P23之化合物,其中各R
3獨立地係Br。
實施例P27.如式
1P或實施例P1至P26中任一者無論單獨或組合之化合物,其中m係1且R
3係位於3位(即相鄰於C(=A)R
1基團)。
實施例P28.如式
1P或實施例P1至P26中任一者無論單獨或組合之化合物,其中m係2且R
3係位於3位及6位(即相鄰於C(=A)R
1基團及Z(嘧啶基團))。
實施例P29.如式
1P或實施例P1至P28中任一者無論單獨或組合之化合物,其中R
5係H、C
1–C
6烷基、C
2–C
6烯基、C
2–C
6炔基、C
1–C
6鹵烷基、C
2–C
6鹵烯基、C
2–C
6鹵炔基、C
2–C
6烷氧基烷基、C
2–C
6鹵烷氧基烷基、C
2–C
6氰基烷基、C
3–C
7氰基烷氧基烷基、C
2–C
6烷基硫基烷基、或C
2–C
6鹵烷基硫基烷基。
實施例P30.如實施例P29之化合物,其中R
5係C
1–C
6烷基、或C
1–C
6鹵烷基。
本發明之實施例(包括上述實施例P1至P30及任何其他本文中所述之實施例)可以任何方式組合,並且實施例中之變項描述不僅關於式
1P之化合物,亦關於可用於製備式
1P之化合物之起始化合物及中間化合物。此外,本發明之實施例(包括上述實施例P1至P30及任何其他本文中所述之實施例、以及上述者之任何組合)均關於本發明之組合物與方法。
實施例P1至P30之組合係說明如下:
實施例PA.一種式
1P之化合物,其中
A係H
2、O、S、或N(OR
5);
R
1係C
1–C
6烷基、C
2–C
6烯基、C
2–C
6炔基、C
1–C
6鹵烷基、C
2–C
6鹵烯基、C
2–C
6鹵炔基、C
3–C
6環烷基、C
3–C
6鹵環烷基、C
4–C
8烷基環烷基、C
4–C
8環烷基烷基、C
1–C
6烷基胺基、C
1–C
6鹵烷基胺基、C
2–C
10二烷基胺基、C
2–C
10鹵二烷基胺基、C
3–C
6環胺基、C
1–C
6烷氧基、C
3–C
6烯基氧基、C
3–C
6炔基氧基、C
1–C
6鹵烷氧基、C
3–C
6鹵烯基氧基、C
3–C
6鹵炔基氧基、C
3–C
6環烷氧基、C
3–C
6鹵環烷氧基、C
4–C
8環烷基烷氧基、C
4–C
8鹵環烷基烷氧基、C
2–C
6烷氧基烷基、C
2–C
6鹵烷氧基烷基、C
2–C
6烷氧基鹵烷基、C
2–C
6烷氧基烷氧基、C
2–C
6氰基烷基、C
2–C
6氰基烷氧基、C
3–C
7氰基烷氧基烷基、C
1–C
6羥基烷基、C
1–C
6硝基烷基、C
1–C
6烷基硫基、C
1–C
6鹵烷基硫基、C
3–C
8環烷基硫基、C
1–C
6烷基亞磺醯基、C
1–C
6鹵烷基亞磺醯基、C
1–C
6烷基磺醯基、C
1–C
6鹵烷基磺醯基、C
3–C
8環烷基磺醯基、C
2–C
6烷基硫基烷基、或C
2–C
6鹵烷基硫基烷基;
Z係O;
R
2係鹵素、C
1–C
4烷基、或C
1–C
4鹵烷基;
各R
3獨立地係鹵素、氰基、CHO、C
1–C
4烷基、C
2–C
4烯基、C
2–C
4炔基、C
1–C
4鹵烷基、C
2–C
4鹵烯基、C
2–C
4鹵炔基、C
3–C
6環烷基、C
3–C
6鹵環烷基、C
2–C
6烷基羰基、C
2–C
6鹵烷基羰基、C
2–C
6烷氧基羰基、C
1–C
4烷氧基、C
1–C
4鹵烷氧基、C
2–C
6烷氧基烷基、C
2–C
6鹵烷氧基烷基、C
2–C
6氰基烷基、或-SO
nR
14;且
m係0、1、或2。
實施例PB.如實施例PA之化合物,其中
A係H
2、O、或N(OR
5);
R
1係C
1–C
6烷基、C
2–C
6烯基、C
2–C
6炔基、C
1–C
6鹵烷基、C
2–C
6鹵烯基、C
2–C
6鹵炔基、C
3–C
6環烷基、C
3–C
6鹵環烷基、C
1–C
6烷氧基、C
3–C
6烯基氧基、C
3–C
6炔基氧基、C
1–C
6鹵烷氧基、C
3–C
6鹵烯基氧基、C
3–C
6鹵炔基氧基、或C
3–C
6環烷氧基;
R
2係鹵素、或C
1–C
4烷基;
各R
3獨立地係鹵素、氰基、C
1–C
4烷基、或C
1–C
4鹵烷基;
R
5係H、C
1–C
6烷基、C
2–C
6烯基、C
2–C
6炔基、C
1–C
6鹵烷基、C
2–C
6鹵烯基、C
2–C
6鹵炔基、C
2–C
6烷氧基烷基、C
2–C
6鹵烷氧基烷基、C
2–C
6氰基烷基、C
3–C
7氰基烷氧基烷基、C
2–C
6烷基硫基烷基、或C
2–C
6鹵烷基硫基烷基;且
m係0或1。
實施例PC.如實施例PB之化合物,其中
A係O或N(OR
5);
R
1係C
1–C
6烷氧基、C
3–C
6烯基氧基、C
3–C
6炔基氧基、C
1–C
6鹵烷氧基、C
3–C
6鹵烯基氧基、C
3–C
6鹵炔基氧基、或C
3–C
6環烷氧基;
R
2係鹵素、或CH
3;
R
3獨立地係鹵素或氰基;且
R
5係C
1–C
6烷基、或C
1–C
6鹵烷基。
實施例PD.如實施例PC之化合物,其中
A係O;
R
2係鹵素;且
各R
3獨立地係鹵素。
具體實施例包括選自由下列所組成之群組的式
1之化合物:
2-氯-6-[(5-氯-2-嘧啶基)氧基]苯甲酸3,3,3-三氟丙酯(化合物15)、
2-溴-6-[(5-氯-2-嘧啶基)氧基]苯甲酸3,3,3-三氟-1-甲基丙酯(化合物16)、
2-溴-6-[(5-氯-2-嘧啶基)氧基]苯甲酸丙酯(化合物13)、
2-溴-6-[(5-氯-2-嘧啶基)氧基]苯甲酸4,4,4-三氟丁酯(化合物20)、
2-溴-6-[(5-氯-2-嘧啶基)氧基]苯甲酸2-丙烯-1-基酯(化合物22)、
2-溴-6-[(5-氯-2-嘧啶基)氧基]苯甲酸3-丁烯-1-基酯(化合物21)、
2-溴-6-[(5-氯-2-嘧啶基)氧基]苯甲酸2,2,3,3,3-五氟丙酯(化合物23)、以及
2-溴-6-[(5-氯-2-嘧啶基)氧基]苯甲酸3,3,3-三氟丙酯(化合物26)。
本發明亦關於一種用於防治非所欲植物之方法,該方法包含於植物所在地施用除草有效量之本發明化合物(例如本文中所述之組合物)。值得注意的關於使用方法之實施例是該些涉及上述實施例之化合物的實施例。本發明化合物特別適用於各式作物(諸如小麥、大麥、玉米、大豆、向日葵、棉花、油菜籽及稻米)以及特用作物(如甘蔗、柑橘、水果及核果作物)中之選擇性雜草防治。
亦值得注意的實施例係包含上述實施例之化合物的本發明之除草組合物。
本發明亦包括除草混合物,其包含(a)選自式
1、其
N-氧化物及鹽之化合物,以及(b)至少一種額外活性成分,其選自(b1)光系統II抑制劑、(b2)乙醯羥酸合成酶(AHAS)抑制劑、(b3)乙醯輔酶A羧化酶(ACCase)抑制劑、(b4)生長素(auxin)模擬物、(b5) 5‑烯醇-丙酮醯莽草酸-3-磷酸(EPSP)合成酶抑制劑、(b6)光系統I電子轉向劑(diverters)、(b7)原紫質原氧化酶(PPO)抑制劑、(b8)麩醯胺酸合成酶(GS)抑制劑、(b9)極長鏈脂肪酸(VLCFA)延長酶抑制劑、(b10)生長素傳輸抑制劑、(b11)八氫番茄紅素去飽和酶(PDS)抑制劑、(b12) 4‑羥基苯基‑丙酮酸二氧合酶(HPPD)抑制劑、(b13)黑尿酸茄尼轉移酶(HST)抑制劑、(b14)纖維素生合成抑制劑、(b15)其他除草劑,包括有絲分裂干擾劑、有機砷劑、亞速爛(asulam)、溴布泰(bromobutide)、環庚草醚(cinmethylin)、苄草隆(cumyluron)、邁隆(dazomet)、燕麥枯(difenzoquat)、汰草龍(dymron)、乙氧苯草胺(etobenzanid)、抑草丁(flurenol)、殺木膦(fosamine)、殺木膦-銨(fosamine‑ammonium)、海丹托西叮(hydantocidin)、威百畝(metam)、甲基汰草龍(methyldymron)、油酸(oleic acid)、噁嗪草酮(oxaziclomefone)、壬酸(pelargonic acid)及稗草畏(pyributicarb)、與(b16)除草劑安全劑;以及(b1)至(b16)之化合物之鹽。
「光系統II抑制劑(Photosystem II inhibitor)」(b1)是在Q
B結合位置結合至D‑1蛋白質並因而阻斷電子在葉綠體類囊膜從Q
A遷移到Q
B的化合物。經阻斷而無法穿過光系統II的電子係經由一系列的反應轉移而形成毒性化合物,其會破壞細胞膜並造成葉綠體膨潤、膜滲漏並且最後細胞破壞。Q
B結合位置具有三個不同的結合部位:結合部位A結合三𠯤如草脫淨(atrazine)、三𠯤酮(triazinone)如菲殺淨(hexazinone)、及尿嘧啶如克草(bromacil),結合部位B結合苯脲(phenylurea)如達有龍(diuron),而結合部位C結合苯並噻二唑如本達隆(bentazon)、腈如溴苯腈(bromoxynil)與苯基-嗒𠯤(phenyl-pyridazine)如必汰草(pyridate)。光系統II抑制劑之實例包括草殺淨(ametryn)、胺唑草酮(amicarbazone)、草脫淨(atrazine)、本達隆(bentazon)、克草(bromacil)、溴酚肟(bromofenoxim)、溴苯腈(bromoxynil)、滅落寧(chlorbromuron)、氯草敏(chloridazon)、綠麥隆(chlorotoluron)、枯草龍(chloroxuron)、苄草隆(cumyluron)、氰乃淨(cyanazine)、殺草隆(daimuron)、甜菜安(desmedipham)、敵草淨(desmetryn)、惡唑隆(dimefuron)、愛落殺(dimethametryn)、達有龍(diuron)、磺噻隆(ethidimuron)、非草隆(fenuron)、伏草隆(fluometuron)、菲殺淨(hexazinone)、碘苯腈(ioxynil)、異丙隆(isoproturon)、愛速隆(isouron)、環草定(lenacil)、理有龍(linuron)、苯嗪草酮(metamitron)、甲草苯隆(methabenzthiazuron)、溴谷隆(metobromuron)、甲氧隆(metoxuron)、滅必淨(metribuzin)、綠谷隆(monolinuron)、草不隆(neburon)、蔬草滅(pentanochlor)、甜菜寧(phenmedipham)、撲滅通(prometon)、撲草淨(prometryn)、除草靈(propanil)、普拔根(propazine)、啶蟲丙醚(pyridafol)、必汰草(pyridate)、環草隆(siduron)、草滅淨(simazine)、西草淨(simetryn)、丁噻隆(tebuthiuron)、特草定(terbacil)、甲氧去草净(terbumeton)、特丁津(terbuthylazine)、去草淨(terbutryn)及草達津(trietazine)。
「AHAS抑制劑」(b2)是抑制乙醯羥酸合成酶(AHAS)(亦稱為乙醯乳酸合成酶(ALS))的化合物,且因而藉由抑制支鏈脂族胺基酸(如纈胺酸、白胺酸及異白胺酸)的製造來殺死植物,前述胺基酸為蛋白質合成與細胞生長所需者。AHAS抑制劑之實例包括醯嘧磺隆(amidosulfuron)、四唑嘧磺隆(azimsulfuron)、免速隆(bensulfuron‑methyl)、雙草醚(bispyribac‑sodium)、氯酯磺草胺(cloransulam‑methyl)、氯嘧磺隆(chlorimuron‑ethyl)、氯磺隆(chlorsulfuron)、西速隆(cinosulfuron)、環磺隆(cyclosulfamuron)、雙氯磺草胺(diclosulam)、胺苯磺隆(ethametsulfuron‑methyl)、亞速隆(ethoxysulfuron)、伏速隆(flazasulfuron)、雙氟磺草胺(florasulam)、氟酮磺隆鈉(flucarbazone‑sodium)、唑嘧磺草胺(flumetsulam)、氟啶嘧磺隆(flupyrsulfuron‑methyl)、氟啶嘧磺隆鈉(flupyrsulfuron-sodium)、甲醯胺磺隆(foramsulfuron)、合速隆(halosulfuron‑methyl)、咪草酯(imazamethabenz‑methyl)、甲氧咪草煙(imazamox)、甲咪唑煙酸(imazapic)、依滅草(imazapyr)、滅草喹(imazaquin)、咪草煙(imazethapyr)、依速隆(imazosulfuron)、甲基碘磺隆(iodosulfuron‑methyl)(包括鈉鹽)、碘磺隆(iofensulfuron)(2-碘-
N-[[(4-甲氧基-6-甲基-1,3,5-三𠯤-2-基)胺基]羰基]-苯磺醯胺)、甲磺胺磺隆(mesosulfuron‑methyl)、雙醚氯吡嘧磺隆(metazosulfuron)(3-氯-4-(5,6-二氫-5-甲基-1,4,2-二噁𠯤-3-基)-
N-[[(4,6-二甲氧基-2-嘧啶基)胺基]羰基]-1-甲基-1
H-吡唑-5-磺醯胺)、磺草唑胺(metosulam)、甲磺隆(metsulfuron‑methyl)、煙嘧磺隆(nicosulfuron)、環氧嘧磺隆(oxasulfuron)、平速爛(penoxsulam)、氟嘧磺隆(primisulfuron‑methyl)、丙苯磺隆(propoxycarbazone‑sodium)、咪唑嘧磺隆(propyrisulfuron)(2-氯-
N-[[(4,6-二甲氧基-2-嘧啶基)胺基]羰基]-6-丙咪唑並[1,2-
b]嗒𠯤-3-磺醯胺)、氟磺隆(prosulfuron)、百速隆(pyrazosulfuron‑ethyl)、嘧啶肟草醚(pyribenzoxim)、環酯草醚(pyriftalid)、嘧草醚(pyriminobac‑methyl)、嘧草硫醚鈉(pyrithiobac‑sodium)、玉嘧磺隆(rimsulfuron)、甲嘧磺隆(sulfometuron‑methyl)、磺醯磺隆(sulfosulfuron)、酮脲磺草吩酯(thiencarbazone)、噻吩磺隆(thifensulfuron‑methyl)、氟酮磺草胺(triafamone) (
N-[2-[(4,6-二甲氧基-1,3,5-三𠯤-2-基)羰基]-6-氟苯基]-1,1-二氟-
N-甲基甲磺醯胺)、醚苯磺隆(triasulfuron)、苯磺隆(tribenuron‑methyl)、三氟啶磺隆(trifloxysulfuron)(包括鈉鹽)、氟胺磺隆(triflusulfuron‑methyl)及三氟甲磺隆(tritosulfuron)。
「ACCase抑制劑」(b3)是抑制乙醯輔酶A羧化酶酵素的化合物,乙醯輔酶A羧化酶酵素負責催化植物中脂質與脂肪酸合成的早期步驟。脂質是細胞膜的基本成分,沒有脂質就無法製造新的細胞。乙醯輔酶A羧化酶的抑制與隨後之脂質產生缺乏會導致細胞膜失去完整性,特別是在活性生長區域如分生組織中。最終芽體(shoot)與根莖(rhizome)會停止生長,並且芽體分生組織與根莖芽開始枯萎。ACCase抑制劑的例子包括亞汰草(alloxydim)、丁苯草酮(butroxydim)、剋草同(clethodim)、炔草酸(clodinafop)、環殺草(cycloxydim)、賽伏草(cyhalofop)、禾草靈(diclofop)、芬殺草(fenoxaprop)、伏寄普(fluazifop)、合氯氟(haloxyfop)、唑啉草酯(pinoxaden)、氯苯噻草酮(profoxydim)、普拔草(propaquizafop)、快伏草(quizalofop)、西殺草(sethoxydim)、得殺草(tepraloxydim)與肟草酮(tralkoxydim),包括解析形式如芬殺草-P (fenoxaprop-P)、伏寄普-P (fluazifop-P)、合氯氟-P (haloxyfop-P)與快伏草-P (quizalofop-P)以及酯形式如炔草酯(clodinafop-propargyl)、丁基賽伏草(cyhalofop-butyl)、甲基禾草靈(diclofop-methyl)與芬殺草-P-乙基(fenoxaprop-P-ethyl)。
生長素係一種植物激素,其調節許多植物組織中的生長。「生長素模擬物(Auxin mimic)」(b4)係模擬植物生長激素生長素的化合物,從而造成不受控制及混亂的生長,導致易感物種植物死亡。生長素模擬物之實例包括胺環吡克(aminocyclopyrachlor)(6-胺基-5-氯-2-環丙基-4-嘧啶羧酸)與其甲酯及乙酯以及其鈉鹽與鉀鹽、氯胺基吡啶酸(aminopyralid)、草除靈乙酯(benazolin‑ethyl)、克攔本(chloramben)、氯醯草膦(clacyfos)、克普草(clomeprop)、畢克草(clopyralid)、麥草畏(dicamba)、2,4‑D、2,4‑DB、滴丙酸(dichlorprop)、氟氯比(fluroxypyr)、哈洛昔芬(halauxifen) (4-胺基-3-氯-6-(4-氯-2-氟-3-甲氧苯基)-2-吡啶羧酸)、甲基哈洛昔芬(halauxifen-methyl) (4-胺基-3-氯-6-(4-氯-2-氟-3-甲氧苯基)-2-吡啶羧酸甲酯)、MCPA、MCPB、甲氯丙酸(mecoprop)、毒莠定(picloram)、快克草(quinclorac)、氯甲喹啉酸(quinmerac)、2,3,6‑TBA、三氯比(triclopyr)與4-胺基-3-氯-6-(4-氯-2-氟-3-甲氧苯基)-5-氟-2-吡啶羧酸甲酯。
「EPSP合成酶抑制劑」(b5)為抑制5-烯醇-丙酮醯莽草酸-3-磷酸合成酶(5-enol-pyruvylshikimate-3-phosphate synthase)之化合物,該酶涉及芳族胺基酸如酪胺酸、色胺酸與苯丙胺酸之合成。EPSP抑制劑除草劑係經由植物葉子迅速吸收並且在韌皮轉位至生長點。草甘膦(Glyphosate)係屬於此類之相對不具選擇性之萌後除草劑。草甘膦包括酯與鹽如銨鹽、異丙銨鹽、鉀鹽、鈉鹽(包括倍半鈉鹽(sesquisodium))與三甲基硫鹽(trimesium)(又稱為草硫膦(sulfosate))。
「光系統I電子轉向劑(Photosystem I electron diverter)」(b6)係接受來自光系統I之電子的化合物,並且會在數個循環後產生羥基自由基。這些自由基極具反應性並且會迅速破壞不飽和脂質,包括膜脂肪酸與葉綠素。此會破壞細胞膜完整性,使得細胞與胞器「滲漏」,導致葉片快速淍萎與乾化,最終造成植物死亡。此第二型光合成抑制劑的實例包括敵草快(diquat)與巴拉刈(paraquat)。
「PPO抑制劑」(b7)係抑制酵素原紫質原氧化酶之化合物,其在植物中迅速導致高度反應性化合物的生成而破壞細胞膜,造成細胞液漏失。PPO抑制劑之實例包括亞喜芬鈉(acifluorfen‑sodium)、草芬定(azafenidin)、雙苯嘧草酮(benzfendizone)、治草醚(bifenox)、布芬草(butafenacil)、唑草酮(carfentrazone)、乙唑草酮(carfentrazone‑ethyl)、甲氧基護谷(chlomethoxyfen)、吲哚酮草酯(cinidon‑ethyl)、異丙吡草酯(fluazolate)、氟噠嗪草酯(flufenpyr‑ethyl)、氟烯草酸(flumiclorac‑pentyl)、丙炔氟草胺(flumioxazin)、乙羧氟草醚(fluoroglycofen‑ethyl)、氟噻甲草酯(fluthiacet‑methyl)、氟磺胺草醚(fomesafen)、氟硝磺醯胺(halosafen)、乳氟禾草靈(lactofen)、快噁草酮(oxadiargyl)、樂滅草(oxadiazon)、復祿芬(oxyfluorfen)、環戊惡草酮(pentoxazone)、氟唑草胺(profluazol)、雙唑草腈(pyraclonil)、吡草醚(pyraflufen‑ethyl)、嘧啶肟草醚(saflufenacil)、甲磺草胺(sulfentrazone)、代森環(thidiazimin)、trifludimoxazin(二氫-1,5-二甲基-6-硫基-3-[2,2,7-三氟-3,4-二氫-3-側氧基-4-(2-丙炔-1-基)-2
H-1,4-苯並㗁𠯤-6-基]-1,3,5-三𠯤-2,4(1
H,3
H)-二酮)及氟丙嘧草酯(tiafenacil)(
N-[2-[[2-氯-5-[3,6-二氫-3-甲基-2,6-二側氧基-4-(三氟甲基)-1(2
H)-嘧啶基]-4-氟苯基]硫基]-1-側氧丙基]-β-丙胺酸甲酯)。
「GS抑制劑」(b8)係抑制麩醯胺酸合成酶酵素活性之化合物,植物利用該酶將氨轉化為麩醯胺酸。因此,氨會累積而麩醯胺酸量降低。由於氨毒性與其他代謝過程所需之胺基酸缺乏的綜合效應,可能對植物造成傷害。GS抑制劑包括草銨膦與其酯類及鹽類,諸如草銨膦-銨與其他固殺草(phosphinothricin)衍生物、草銨膦-P((2
S)-2-胺基-4-(羥甲膦基)丁酸)與畢拉草(bilanaphos)。
「VLCFA延長酶抑制劑」(b9)係具有廣泛各式化學結構之除草劑,其會抑制延長酶。延長酶係位於葉綠體中或葉綠體附近之酵素的其中一種,其涉及VLCFA的生物合成。在植物中,極長鏈脂肪酸是疏水性聚合物的主要構分,疏水性聚合物防止葉子表面乾燥並提供花粉粒安定性。此類除草劑包括乙草胺(acetochlor)、拉草(alachlor)、莎稗磷(anilofos)、丁基拉草(butachlor)、苯酮唑(cafenstrole)、二甲草胺(dimethachlor)、汰草滅(dimethenamid)、大芬滅(diphenamid)、異噁苯碸(fenoxasulfone)(3-[[(2,5-二氯-4-乙氧基苯基)甲基]磺醯基]-4,5-二氫-5,5-二甲基異㗁唑)、四唑草胺(fentrazamide)、噻草胺(flufenacet)、茚草酮(indanofan)、滅芬草(mefenacet)、滅草胺(metazachlor)、莫多草(metolachlor)、萘丙胺(naproanilide)、滅落脫(napropamide)、滅落脫-M (napropamide-M)((2R)-
N,
N-二乙基-2-(1-萘氧基)丙醯胺)、烯草胺(pethoxamid)、哌草磷(piperophos)、普拉草(pretilachlor)、雷蒙得(propachlor)、異丙草胺(propisochlor)、派羅克殺草碸(pyroxasulfone)與欣克草(thenylchlor),包括解析形式如S-莫多草與氯乙醯胺(chloroacetamide)及氧乙醯胺(oxyacetamide)。
「生長素輸送抑制劑」(b10)是抑制植物中之生長素輸送的化學物質,如藉由與生長素載體蛋白質結合。生長素輸送抑制劑的實例包括二氟吡隆(diflufenzopyr)、鈉得爛(naptalam)(亦稱為
N-(1-萘基)鄰胺甲醯苯甲酸與2-[(1-萘胺基)羰基]苯甲酸)。
「PDS抑制劑」(b11)係抑制類胡蘿蔔素生物合成途徑的八氫番茄紅素去飽和酶(phytoene desaturase)步驟之化合物。PDS抑制劑之實例包括氟丁草胺(beflubutamid)、吡氟草胺(diflufenican)、氟啶草酮(fluridone)、氟草吡酮(flurochloridone)、呋草酮(flurtamone)、氟草敏(norflurzon)與氟吡醯草胺(picolinafen)。
「HPPD抑制劑」(b12)為抑制4-羥基苯基-丙酮酸-二氧合酶合成之生物合成的化學物質。HPPD抑制劑之實例包括苯並雙環酮(benzobicyclon)、吡草酮(benzofenap)、二環吡草酮(bicyclopyrone)(4-羥基-3-[[2-[(2-甲氧基乙氧基)甲基]-6-(三氟甲基)-3-吡啶基]羰基]雙環[3.2.1]辛-3-烯-2-酮)、芬昆諾三酮(fenquinotrione)(2-[[8-氯-3,4-二氫-4-(4-甲氧基苯基)-3-側氧基-2-喹噁啉基]羰基]-1,3-環己二酮)、異噁氯草酮(isoxachlortole)、異噁唑草酮(isoxaflutole)、硝草酮(mesotrione)、磺醯草吡唑(pyrasulfotole)、苄草唑(pyrazolynate)、普芬草(pyrazoxyfen)、磺草酮(sulcotrione)、特呋三酮(tefuryltrione)、環磺酮(tembotrione)、tolpyralate(1-[[1-乙基-4-[3-(2-甲氧基乙氧基)-2-甲基-4-(甲基磺醯基)苄醯基]-1H-吡唑-5-基]氧基]乙基甲基碳酸酯)、苯吡唑草酮(topramezone)、5-氯-3-[(2-羥基-6-側氧基-1-環己烯-1-基)羰基]-1-(4-甲氧基苯基)-2(1
H)-喹噁啉酮、4-(2,6-二乙基-4-甲基苯基)-5-羥基-2,6-二甲基-3(2
H)-嗒𠯤酮、4-(4-氟苯基)-6-[(2-羥基-6-側氧基-1-環己烯-1-基)羰基]-2-甲基-1,2,4-三𠯤-3,5(2
H,4
H)-二酮、5-[(2-羥基-6-側氧基-1-環己烯-1-基)羰基]-2-(3-甲氧基苯基)-3-(3-甲氧基丙基)-4(3
H)-嘧啶酮、2-甲基-
N-(4-甲基-1,2,5-㗁二唑-3-基)-3-(甲基亞磺醯基)-4-(三氟甲基)苯甲醯胺與2-甲基-3-(甲基磺醯基)-
N-(1-甲基-1
H-四唑-5-基)-4-(三氟甲基)苯甲醯胺。
「HST抑制劑」(b13)干擾植物將黑尿酸轉化為2‑甲基‑6‑茄尼基‑1,4‑苯並醌的能力,從而干擾類胡蘿蔔素生物合成。HST抑制劑之實例包括氟啶草(haloxydine)、三氯吡啶酚(pyriclor)、環比瑞摩(cyclopyrimorate)(4-嗎啉羧酸6-氯-3-(2-環丙基-6-甲基苯氧基)-4-嗒𠯤酯)、3-(2-氯-3,6-二氟苯基)-4-羥基-1-甲基-1,5-萘啶-2(1
H)-酮、7-(3,5-二氯-4-吡啶基)-5-(2,2-二氟乙基)-8-羥基吡啶並[2,3-
b]吡𠯤-6(5
H)-酮與4-(2,6-二乙基-4-甲基苯基)-5-羥基-2,6-二甲基-3(2
H)-嗒𠯤酮。
HST抑制劑亦包括式
A與式
B之化合物。
其中R
d1係H、Cl、或CF
3;R
d2係H、Cl、或Br;R
d3係H或Cl;R
d4係H、Cl、或CF
3;R
d5係CH
3、CH
2CH
3、或CH
2CHF
2;且R
d6係OH、或‑OC(=O)‑
i‑Pr;且R
e1係H、F、Cl、CH
3、或CH
2CH
3;R
e2係H或CF
3;R
e3係H、CH
3、或CH
2CH
3;R
e4係H、F、或Br;R
e5係Cl、CH
3、CF
3、OCF
3、或CH
2CH
3;R
e6係H、CH
3、CH
2CHF
2、或C≡CH;R
e7係OH、‑OC(=O)Et、‑OC(=O)‑
i‑Pr、或‑OC(=O)‑
t‑Bu;且A
e8係N或CH。
「纖維素生物合成抑制劑」(b14)抑制某些植物中的纖維素生物合成。當它們在萌前或早期萌後施用於幼嫩或快速生長植物上時會最為有效。纖維素生物合成抑制劑的實例包括草克樂(chlorthiamid)、二氯苯腈(dichlobenil)、氟胺草唑(flupoxam)、三嗪茚草胺(indaziflam)(
N 2-[(1
R,2
S)-2,3-二氫-2,6-二甲基-1
H-茚-1-基]-6-(1-氟乙基)-1,3,5-三𠯤-2,4-二胺)、異噁草胺(isoxaben)與三唑侖(triaziflam)。
「其他除草劑」(b15)包括經由各式不同作用模式作用的除草劑,諸如有絲分裂干擾劑(例如麥草伏-M-甲酯(flamprop‑M‑methyl)與麥草伏-M-異丙酯(flamprop‑M‑isopropyl))、有機砷劑(例如DSMA與MSMA)、7,8-二氫蝶酸合成酶(7,8‑dihydropteroate synthase)抑制劑、葉綠體類異戊二烯(isoprenoid)合成抑制劑與細胞壁生物合成抑制劑。其他除草劑包括具有未知作用模式或不屬於(b1)至(b14)所列出之特定分類的除草劑,或經由上列作用模式之組合而作用的除草劑。其他除草劑之實例包括苯草醚(aclonifen)、亞速爛(asulam)、殺草強(amitrole)、溴布泰(bromobutide)、環庚草醚(cinmethylin)、可滅蹤(clomazone)、苄草隆(cumyluron)、殺草隆(daimuron)、燕麥枯(difenzoquat)、乙氧苯草胺(etobenzanid)、伏草隆(fluometuron)、抑草丁(flurenol)、殺木膦(fosamine)、殺木膦-銨(fosamine‑ammonium)、邁隆(dazomet)、汰草龍(dymron)、艾分卡斑唑(ipfencarbazone)(1-(2,4-二氯苯基)-
N-(2,4-二氟苯基)-1,5-二氫-
N-(1-甲基乙基)-5-側氧基-4
H-1,2,4-三唑-4-甲醯胺)、威百畝(metam)、甲基汰草龍(methyldymron)、油酸(oleic acid)、噁嗪草酮(oxaziclomefone)、壬酸(pelargonic acid)、稗草畏(pyributicarb)與5-[[(2,6-二氟苯基)甲氧基]甲基]-4,5-二氫-5-甲基-3-(3-甲基-2-噻吩基)異㗁唑。
「除草劑安全劑」(b16)係添加至除草劑製劑中以消除或減輕除草劑對某些作物之植物毒性效果的物質。這些化合物會保護作物免受除草劑傷害,但典型不會防止除草劑防治非所欲植物。除草劑安全劑的例子包括但不限於解草嗪(benoxacor)、解毒喹(cloquintocet‑mexyl)、苄草隆(cumyluron)、解草胺腈(cyometrinil)、啶醯菌胺(cyprosulfamide)、殺草隆(daimuron)、二氯丙烯胺(dichlormid)、大賽克農(dicyclonon)、增效磷(dietholate)、哌草丹(dimepiperate)、解草唑(fenchlorazole‑ethyl)、解草啶(fenclorim)、解草胺(flurazole)、氟草肟(fluxofenim)、解草惡唑(furilazole)、雙苯噁唑酸(isoxadifen‑ethyl)、唑解草酯(mefenpyr‑diethyl)、梅芬內(mephenate)、苯草酮(methoxyphenone)、萘二甲酸酐(naphthalic anhydride)、解草腈(oxabetrinil)、
N-(胺基羰基)-2-甲苯磺醯胺與
N-(胺基-羰基)-2-氟苯磺醯胺、1‑溴‑4‑[(氯甲基)磺醯基]苯、2‑(二氯甲基)‑2-甲基-1,3‑二氧𠷬(MG 191)、4‑(二氯乙醯基)-1‑氧雜-4‑偶氮螺-[4.5]癸烷(MON 4660)、2,2-二氯-1-(2,2,5-三甲基-3-㗁唑啶基)-乙酮、及2-甲氧基-
N-[[4-[[(甲基胺基)羰基]胺基]苯基]磺醯基]
-苯甲醯胺。
本發明之實施例係一種除草混合物,其包含(a)式1之化合物,以及(b)至少一種選自(b1)光系統II抑制劑、(b2)乙醯羥酸合成酶(AHAS)抑制劑、(b4)生長素模擬物、(b5) 5‑烯醇-丙酮醯莽草酸-3-磷酸(EPSP)合成酶抑制劑、(b7)原紫質原氧化酶(PPO)抑制劑、(b9)極長鏈脂肪酸(VLCFA)延長酶抑制劑、及(b12) 4‑羥苯基‑丙酮酸二氧合酶(HPPD)抑制劑之額外活性成分。
式
1之化合物可藉由合成有機化學技術領域中習知的一般方法製備。如方案1至10所述的一或多個以下方法及變化型可用於製備式
1之化合物。除非另有說明,否則下列式
1至
17之化合物中的(A、Z、R
1、R
2、R
3、R
4、R
5、R
6a、及R
6b)之定義係如上述發明內容中所定義。式
1a至
1b之化合物為式1之化合物的各種子集合,並且式
1a至
1b之所有取代基係如以上針對式
1所定義者,除非另有說明。
如方案1所示,式1之化合物可藉由在鹼(如碳酸鉀或碳酸銫)存在下,加熱在適當溶劑(例如乙腈、四氫呋喃、或
N,N-二甲基甲醯胺)中之式
2之化合物與式
3之化合物(其中LG係鹵素或SO
2Me)以進行親核取代來製備。反應一般係於20至110℃之範圍內的溫度下進行。
方案1
如方案2所示,式
1b之化合物(其中A係S)可藉由使式
1a之化合物(其中A係A-3且B係O)與硫化試劑諸如勞森試劑(Lawesson’s reagent)、十硫化四磷、或五硫化二磷,於諸如四氫呋喃或甲苯之溶劑中反應來製備。一般而言,反應係於0至115℃之範圍內的溫度下進行。
方案2
如方案3所示,式
2a之化合物(其中A係A-3、B係O、且Z係O)可藉由以適當去保護劑使式
4之化合物(其中R
20係CH
3或C(=O)CH
3)去保護而製備。適當的甲氧基(即當R
20係CH
3時)去保護試劑諸如在乙酸中的BBr
3、AlCl
3、及HBr,可於溶劑(諸如甲苯、二氯甲烷、及二氯乙烷)存在下在–80至120℃之溫度下使用。適當的乙氧基(即當R
20係C(=O)CH
3)去保護劑包括在室溫下之甲醇中的碳酸鉀或甲醇水溶液中的乙酸銨,可如Das, et al.,
Tetrahedron 2003,
59, 1049–1054及其中引述之方法所討論使用。或者,式
4之化合物可與甲醇中之Amberlyst 15
©組合(如Das, et al.
Tet.Lett. 2003,
44, 5465–5468中所討論)或與乙醇中之乙酸鈉組合(如Narender, T., et al.
Synthetic Communications 2009,
39(11), 1949–1956中所討論)以獲得式
2a之化合物。其他適用於製備式
2a之化合物的有用酚保護基團可見於Greene, T. W.;Wuts, P. G. M.
Protective Groups in Organic Synthesis, 4th ed.;Wiley: Hoboken, New Jersey, 1991。
方案3
如方案4所示,式
5之化合物(其中R
1a係烷基、烯基、或炔基)可藉由使有機金屬試劑,諸如式
6之有機鎂或有機鋰試劑,與式
7之醯胺反應而製備。此反應一般在溶劑諸如四氫呋喃或二乙醚中,在-78至25℃之範圍內的溫度下進行。對於所屬領域中具有通常知識者而言,諸如式
7之醯胺通常稱為「溫勒伯醯胺(Weinreb Amide)」,並且此種轉化通常稱為「溫勒伯-納姆酮合成(Weinreb-Nahm ketone synthesis)」。參見
Synthesis 2008 , 23,3707-3738及其中所引用的參考文獻。
方案4
如方案5所示,式
8之化合物可藉由使式
9之酸與式
10之烷基胺、醇、或硫醇(其中R
1b係烷氧基、烷基硫基、或烷基胺基),於脫水性耦合試劑(諸如丙基膦酸酐、二環己基碳二亞胺、
N-(3-二甲基胺基丙基)-
N'‑乙基碳二亞胺、
N,
N'-羰基二咪唑、氯化2-氯-1,3-二甲基咪唑、或碘化2-氯-1-甲基吡啶)存在下反應而製備。聚合物支撐試劑諸如聚合物支撐環己基碳二亞胺亦為合適的。此等反應通常在0至60℃之範圍內的溫度下,於諸如二氯甲烷、乙腈、
N,
N‑二甲基甲醯胺、或乙酸乙酯的溶劑中,且在諸如三乙胺、
N,
N-二異丙胺、或1,8-二氮雜雙環[5.4.0]十一-7-烯之鹼的存在下進行。採用丙基膦酸酐之耦合條件,參見
Organic Process Research & Development 2009,
13, 900–906。
方案5
在方案6中,式
11之化合物(其中R
x係R
4、OR
5、或NR
6aR
6b)可藉由使有機胺、有機羥基胺、或有機肼與式
8之化合物,一般於酸或鹼存在下縮合而輕易製備。反應一般在溶劑諸如甲醇、乙醇、二氯甲烷、或甲苯中,在20至110℃之範圍內的溫度下進行。適用於反應之酸包括但不限於無機酸(諸如氫氯酸)及有機酸(諸如乙酸及三氟乙酸)。適用於反應之鹼包括但不限於氫氧化物(諸如氫氧化鈉)、碳酸鹽(諸如碳酸鈉及碳酸鉀)、及有機鹼(諸如乙酸鈉及吡啶)。
方案6
如方案7所示,式
12之苄醇可藉由所屬技術領域中具有通常知識者所熟知之廣泛各式方法,將式
13之醛還原而製備。適用於反應之還原劑包括但不限於硼氫化鈉、鋁氫化鋰、及氫化二異丁基鋁。各式溶劑亦適用於此反應,包括但不限於甲醇、乙醇、及四氫呋喃,且反應溫度一般在-10℃至25℃之範圍內。
方案7
如方案8所示,式
14之苄基鹵化物(其中X係Cl、Br、或I)可藉由所屬技術領域中具有通常知識者所熟知之廣泛各式方法,將式
12之化合物上之醇用鹵化物取代而製備。一個此種方法採用亞硫醯氯及可選地
N,N-二甲基甲醯胺,在溶劑包括但不限於二氯甲烷、甲苯、氯仿中及無溶劑下,並且一般在介於0至80℃的溫度下進行。或者,式
14之化合物可採用磷試劑及鹵化物試劑自式
12之苄基醇製備。一般磷試劑係三苯基膦,且鹵化物試劑包括但不限於四鹵化碳、
N-鹵琥珀醯亞胺、二鹵化物、及四鹵甲烷。適用於此反應之溶劑包括但不限於二氯甲烷、四氫呋喃、及乙腈,且一般反應溫度範圍在–78至50℃。此後者之反應係所屬技術領域具有通常知識者所熟知,且稱為「阿佩爾反應(Appel Reaction)」。例如參見Smith, M. B.; March, J.
March’s Advanced Organic Chemistry, 6
thed., pages 576-580;John Wiley & Sons: Hoboken, New Jersey及其中的參考文獻。
方案8
在方案9中,含苄基雜原子之式
15之化合物(其中R
1b係烷氧基、烷基硫基、或烷基胺基)可由所屬技術領域中具有通常知識者,使用適當之式
10之雜烷基試劑(醇、烷基胺、或硫醇)且一般於鹼存在下,將式
14之化合物進行置換反應而輕易製備。適用於反應之溶劑包括但不限於四氫呋喃、
N,N‑二甲基甲醯胺、乙腈、甲苯、及二氯甲烷。適用於反應之鹼包括但不限於氫氧化物(諸如氫氧化鈉及氫氧化鉀)、氫化物鹼(諸如氫化鈉)、碳酸鹼(諸如碳酸鈉及碳酸鉀)、及有機鹼(諸如三乙胺及
N,N‑二乙基異丙基胺)。此外,此反應可選地可經碘化物取代,例如碘化鈉或碘化四丁基銨。
方案9
如方案10所示,式
16之碸(n = 1)及亞碸(n = 2)可藉由所屬技術領域中具有通常知識者所熟知之廣泛各式方法,將式
17之化合物(其中A係A-1,且R
21係烷基或鹵烷基)氧化而輕易製備。適用於此反應之試劑包括但不限於過氧化二氫、3‑氯-苯羧酸、過碘酸鈉、及Oxone。一般用於此反應之溶劑包括二氯甲烷、甲醇、四氫呋喃、及乙酸,且一般反應溫度範圍介於–78至50℃。硫會先氧化為亞碸(n = 1),接著氧化為碸(n = 2)。利用已充份建立之分析方法(即薄層層析術、核磁共振等)小心監控反應進度,得以進行亞碸或碸之選擇。
方案10
在方案11中,式
18之化合物可藉由烷基化式
19之化合物而輕易製備。此可於適當之鹼存在下使用適當烷基化試劑達成。適用於此反應之溶劑通常包括極性溶劑,包括但不限於
N,N-二甲基甲醯胺、二甲亞碸、乙腈、或四氫呋喃。合適之鹼通常包括但不限於氫化鈉、胺化鈉(sodium amide)、氫氧化鈉、及二異丙基胺化鋰(lithium diisopropyl amide)。反應溫度在0℃至100℃之範圍內,如合成實例5中所述。
方案11
如方案12所示,式
20之化合物可透過式
21之化合物之去氧來製備。一種方法利用過渡金屬催化劑,於氫化物源存在下及可選地於酸存在下利用多種溶劑包括甲醇及乙醇進行。一般過渡金屬催化劑係鈀碳(palladium on carbon),並且標準氫化物源包括在常壓或升壓下之氫氣、或甲酸銨。此反應所利用之酸可包括氫氯酸、硫酸、及對甲苯磺酸。此反應的實例可見於
J. Med.Chem. 1992,
35, 1818。第二種方法採用氫化物源與酸之組合。一般氫化物源包括三乙基矽烷及硼氫化鈉,並結合布忍斯特酸(Brönsted acid)諸如三氟乙酸及乙酸,或路易士酸(Lewis acid)諸如三氟化硼合乙醚。這些反應之溶劑可為單獨的酸,或為酸與多種其他常見溶劑(諸如二氯甲烷或乙腈)之混合物。此反應之實例可見於US 2007/0003539或合成實例6之步驟B。
方案12
如方案13所示,式
22之化合物(其中R
1a係烷基、烯基、或炔基)可藉由使有機金屬試劑(諸如有機鎂或有機鋰試劑)與式
23之醛反應而製備。此反應一般係在溶劑(諸如四氫呋喃或二乙醚)中在–78至25℃之範圍內的溫度下進行。此反應之實例可見於
Synlett,
2016,
27, 789或如合成實例6之步驟A所述。
方案13
如方案14所示,式
25之化合物可藉由使氰基與式
24之化合物(R
3a= Br或I)進行過渡金屬催化耦合來製備。此反應之條件通常包括氰化物源及銅催化劑或鈀催化劑與輔催化劑。此反應一般係由鹵化銅(I)於配位基(諸如2‑(甲基胺基)乙基胺或反-
N,N’-二甲基環己烷-1,2-二胺)存在下與金屬氰化物鹽進行。此反應可在一系列極性非質子性溶劑諸如
N,N-二甲基甲醯胺、四氫呋喃、乙腈、
N-甲基-2-吡咯啶酮、或甲苯中,在100至210℃之範圍內的溫度下進行。此反應對於所屬技術領域具有通常知識者係習知為羅森蒙德-馮布勞恩(Rosenmund-von Braun)反應。在相似條件下可採用氰化銅(I),不論有無經添加之配位基及氰化物源之存在。類似之耦合反應可藉由使用鈀催化劑(諸如肆(三苯基膦)鈀、二乙酸鈀、或參(二亞苄基乙酮)二鈀)與可選地膦配位基和輔催化劑(諸如氰化鋅)來進行。這些反應可在一系列極性非質子性溶劑諸如
N,N-二甲基甲醯胺、
N-甲基-2-吡咯啶酮、乙腈、及1,4-二㗁烷(1,4-dioxane)中,在80至150℃之範圍內的溫度下進行。或者,鈀輔催化劑(諸如鹵化銅(I))及氰化物鹽可用來取代在相似條件下之氰化鋅。此反應的實例可見於
J. Am. Chem.Soc. 2003,
125, 2890並且如合成實例6之步驟C所述。
方案14
式
24、
22、及
20之化合物可使用方案3及方案1所述之方法輕易轉化為式
1之化合物;即藉由去保護式
3之化合物的PG基團然後進行烷基化。所屬技術領域中具有通常知識者會認知到,可將各種官能基轉化成其他官能基以提供不同之式
1之化合物。關於以簡單直接方式說明官能基之相互轉化的寶貴資源,參見Larock, R. C.,
Comprehensive Organic Transformations: A Guide to Functional Group Preparations, 2nd Ed., Wiley-VCH, New York, 1999。例如,用於製備式
1之化合物的中間物可能含有芳族硝基,其可被還原成胺基,然後透過所屬技術領域所熟知的反應例如山德邁耳反應(Sandmeyer reaction)轉化成各種鹵化物,以提供式
1之化合物。上述反應在多種情況下亦可變換順序進行。
會認知到,上述用於製備式
1之化合物的一些試劑及反應條件,可能無法與某些存在於中間物中的官能性相容。在這些情況中,將保護/去保護序列或官能基相互轉化納入合成中,將有助於獲得所欲產物。保護基的使用和選擇對於具有化學合成通常知識者而言將是顯而易見的(請參見例如Greene, T. W.;Wuts, P. G. M.
Protective Groups in Organic Synthesis, 2nd ed.; Wiley: New York, 1991)。所屬技術領域中具有通常知識者將會認知到,在一些情況下,在引入給定試劑(如在任何個別方案中所述者)後,可能必須進行未詳述之額外常規合成步驟以完成式
1之化合物之合成。所屬技術領域中具有通常知識者亦將會認知到,可能必須以與所特定呈現者所意味之次序不同的次序,來執行以上方案中所說明步驟之組合以製備式
1之化合物。
所屬技術領域中具有通常知識者亦將會認知到,式
1之化合物與本文中所述之中間物可經受各式親電子、親核、自由基、有機金屬、氧化、與還原反應以加入取代基或修飾現有取代基。
即使沒有進一步的闡述,相信所屬領域中具有通常知識者使用上述說明可最大程度地利用本發明。下列非限定實例說明本發明。下列實例之步驟說明整體合成轉換之各步驟的程序,且用於每個步驟之起始材料可能不必然藉由其程序描述於其他實例或步驟中之特定製備運行來製備。百分比係以重量計,除了層析溶劑混合物或另有指明者。層析溶劑混合物之份數及百分比係以體積計,除非另有說明。
1H NMR光譜係以位於四甲基矽烷低場區之ppm來報導;「s」代表單峰,「d」代表雙重峰,「t」代表三重峰,「q」代表四重峰,「m」代表多重峰,「dd」代表雙重雙重峰,「dt」代表雙重三重峰,而「br s」代表寬單峰。質譜(MS)係以加入H+(分子量為1)至分子所形成之(M+1)或自分子損失H+(分子量為1)所形成之(M–1)的最高同位素豐度母離子分子量來記述,其藉由使用液相層析術結合質譜儀(LCMS)利用常壓化學游離法(AP+)來觀察,其中「amu」代表統一原子質量單位。
實例1
2-[(5-氯-2-嘧啶基)氧基]-
N-(2,2,2-三氟乙基)苯甲醯胺(化合物28)之製備
步驟A:2-甲氧基-
N-(2,2,2-三氟乙基)苯甲醯胺之製備
將2,2,2-三氟乙胺(1.28 g, 12.89毫莫耳)及三乙胺(4.1 mL, 29.31毫莫耳)於二氯甲烷(30 mL)中之溶液冷卻至0℃。將反應混合物用2-甲氧基苯甲醯氯(2.0 g, 11.72毫莫耳)於二氯甲烷(8 mL)中之溶液在低於5℃之溫度下處理。讓反應混合物緩慢溫熱至室溫。加入去離子水,使混合物經分配。將水相用二氯甲烷萃取。將合併之有機相用1N HCl及飽和氯化鈉水溶液洗滌並以硫酸鎂乾燥,然後於真空下濃縮為白色固體。將固體從己烷中濾出以獲得呈固體之標題化合物(2.24 g)。
1H NMR (400 MHz, CDCl
3) δ 8.20 (d, 2H), 7.49 (t, 1H), 7.10 (t, 1H), 7.00 (d, 1H), 4.10 (q, 2H), 3.99 (s, 3H).
步驟B:2-羥基-
N-(2,2,2-三氟乙基)苯甲醯胺之製備
將2-甲氧基-
N-(2,2,2-三氟乙基)苯甲醯胺(即步驟A之產物)(1.0 g, 4.28毫莫耳)於無水二氯甲烷(20 mL)中之溶液用冰水浴冷卻至0℃。將溶液用在二氯甲烷中之1 M三溴化硼溶液(4.72 mL, 4.72毫莫耳)逐滴處理並且攪拌3小時。接著將反應混合物倒入冰水中並經分配。將水相用二氯甲烷、接著用乙酸乙酯萃取。將合併之有機相用飽和氯化鈉水溶液洗滌、以硫酸鎂乾燥,然後於真空下濃縮為固體。將固體從己烷中濾出以獲得呈固體之標題化合物(475 mg)。
1H NMR (400 MHz, CDCl
3) δ 7.44 (t, 1H), 7.40 (d, 1H), 7.01 (d, 1H), 6.89 (t, 1H), 6.53 (bs, 1H), 4.13 (m,2 H).
步驟C:2-[(5-氯-2-嘧啶基)氧基]-
N-(2,2,2-三氟乙基)-苯甲醯胺之製備
於2-羥基-
N-(2,2,2-三氟乙基)苯甲醯胺(即步驟B之產物)(100 mg, 0.456毫莫耳)在乙腈(3 mL)中之溶液中加入2,5-二氯嘧啶(71 mg, 0.48毫莫耳)及碳酸鉀(190 mg, 1.37毫莫耳)。將反應混合物加熱至80℃歷時12小時。使反應在水及乙酸乙酯之間分配,將有機相分離出來、以硫酸鎂乾燥,然後在真空下濃縮。將殘餘物藉由層析術在矽凝膠上以5克Bond elut管柱純化(以20%乙酸乙酯/己烷洗提)以產出油狀之標題化合物(0.30 g),即本發明之化合物。
1H NMR (400 MHz, CDCl
3) δ 8.30 (s, 2H), 7.65 (d, 1H), 7.48 (t, 1H), 7.31 (t, 1H), 7.21 (bs, 1H), 7.00 (d, 1H), 4.75 (q, 2H).
實例2
2-溴-6-[(5-氯-2-嘧啶基)氧基]苯甲酸3-丁烯-1-基酯(化合物21)之製備
步驟A:2-溴-6-羥基苯甲酸3-丁烯基酯之製備
於2-溴-6-羥基苯甲酸(0.200 g, 0.921 mmol)在無水二氯甲烷(3 mL)中之攪拌溶液中加入草醯氯(94.8 µL, 1.11 mml)及2滴
N,N’‑二甲基甲醯胺。將反應混合物在室溫下攪拌3小時。接著將反應混合物在真空下濃縮並將殘餘物溶於無水二氯甲烷(3 mL)中,然後用3-丁烯-1-醇(86.9 µL, 1.01 mmol)及3滴三乙胺處理。將反應混合物在室溫下攪拌18小時。將反應混合物在真空下濃縮至Celite
®矽藻土助濾劑上,然後以管柱層析術在矽凝膠上純化(以0至20%在己烷中之乙酸乙酯洗提)以產出標題化合物(0.117 g)。
1H NMR (500 MHz, CDCl
3) δ 10.96 (s, 1H), 7.24–7.17 (m, 2H), 6.98–6.93 (m, 1H), 5.95–5.87 (m, 1H), 5.22–5.18 (m, 1H), 5.15–5.12 (m, 1H), 4.47 (t, 2H), 2.62–2.57 (m, 2H).
步驟B:2-溴-6[(5-氯-2-嘧啶基)氧基]苯甲酸3-丁烯-1-基酯之製備
於2-溴-6-羥基苯甲酸3-丁烯基酯(即步驟A之產物)(0.117 g, 0.431 mmol)及5-氯-2-(甲基磺醯基)-嘧啶(即5-氯-2-甲基磺醯基嘧啶)(99.8 mg, 0.518 mmol)在
N,N’‑二甲基甲醯胺(2 mL)中之攪拌溶液中加入碳酸鉀(85.9 mg, 0.646 mmol)。將反應混合物在室溫下攪拌18小時。接著使反應混合物通過Celite®矽藻助濾劑墊過濾,然後將濾液在真空下濃縮。將粗殘餘物藉由管柱層析術在矽凝膠上純化(以0至30%在己烷中之乙酸乙酯洗提),以產出呈固體之標題產物(0.104 g),即本發明之化合物。
1H NMR (500 MHz, CDCl
3) δ 8.48 (s, 2H), 7.53 (dd, 1H), 7.35 (t, 1H), 7.17 (dd, 1H), 5.75–5.65 (m, 1H), 5.11–4.99 (m, 2H), 4.29 (t, 2H), 2.39–2.34 (m, 2H).
實例3
2-溴-6-[(5-氯-2-嘧啶基)氧基]苯甲酸3,3,3-三氟丙酯(化合物26)之製備
步驟A:2-溴-6-羥基苯甲酸3,3,3-三氟丙酯之製備
於2-溴-6-羥基苯甲酸(0.500 g, 2.30 mmol)及分子篩在3,3,3-三氟丙-1-醇(15 mL)中之攪拌溶液中加入濃硫酸(0.300 mL)。將反應混合物在78℃下加熱24小時。將反應混合物冷卻至室溫然後通過小型Celite®矽藻土助濾劑墊過濾。將濾液用乙酸乙酯稀釋然後用水及飽和氯化鈉水溶液洗滌。將有機相分離、以硫酸鎂乾燥然後在真空下濃縮。將粗材料藉由管柱層析術在矽凝膠上純化(以0至20%在己烷中之乙酸乙酯洗提)以產出標題化合物(0.268 g)。
1H NMR (500 MHz, CDCl
3) δ 10.79 (s, 1H), 7.26–7.20 (m, 2H), 7.00–6.94 (m, 1H), 4.63 (t, 2H), 2.70 (m, 2H).
步驟B:2-溴-6-[(5-氯-2-嘧啶基)-氧基]苯甲酸3,3,3-三氟丙酯之製備
於2-溴-6-羥基苯甲酸3,3,3-三氟丙酯(即步驟A之產物)(0.124 g, 0.396 mmol)及5-氯-2-(甲基磺醯基)-嘧啶(即5-氯-2-甲基磺醯基嘧啶)(95.1 mg, 0.475 mmol)在
N,N’‑二甲基甲醯胺(2 mL)中之攪拌溶液中加入碳酸鉀(82.1 mg, 0.594 mmol)。將反應在室溫下攪拌18小時。使反應混合物通過Celite®矽藻助濾劑墊過濾,然後將濾液在真空下濃縮。將粗材料藉由管柱層析術在矽凝膠上純化(以0至30%在己烷中之乙酸乙酯洗提),以產出呈固體之標題產物(55.0 mg),即本發明之化合物。
1H NMR (500 MHz, CDCl
3) δ 8.49 (s, 2H), 7.54 (dd, 1H), 7.38 (t, 1H), 7.20 (dd, 1H), 4.46 (t, 2H), 2.50 (m, 2H).
實例4
1-[2-氯-6-[(5-氯-2-嘧啶基)氧基]苯基]-4,4,4-三氟-1-丁酮(化合物107)之製備
步驟A:2-氯-6-甲氧基-α-(3,3,3-三氟丙基)苯甲醇之製備
於反應燒瓶中倒入1.92 g (79.18 mmol)的鎂、催化量的碘、及50 mL的二乙醚。將混合物加熱至回流,然後將1,1,1-三氟-3-碘-丙烷(10.64 g, 47.51 mmol)在30 min內加入。讓混合物冷卻至室溫然後在–78℃下轉移至倒有2-氯-6-甲氧基-苯甲醛(6.75 g, 39.59 mmol)及75 mL四氫呋喃之第二反應燒瓶中。讓反應混合物溫熱至室溫、以1 N氫氯酸淬熄、然後在二乙醚及鹽水之間分配。將有機相以MgSO
4乾燥、過濾、然後濃縮以提供9.4 g的粗產物,其未經純化即使用於後續步驟中。
步驟B:1-(2-氯-6-甲氧基苯基)-4,4,4-三氟-1-丁酮之製備
在15 min內於2-氯-6-甲氧基-α-(3,3,3-三氟丙基)苯甲醇(即步驟A中所獲得之粗材料,9.4 g)在175 mL丙酮中之溶液中加入15.7 mL (42 mmol)的2.64 M瓊斯試劑(Jones reagent)。將反應混合物攪拌另外30 min、用0.5 mL的異丙醇淬熄、然後在二乙醚及水之間分配。將有機相以MgSO
4乾燥、過濾、然後濃縮。將粗材料藉由矽凝膠層析術純化(以己烷:乙酸乙酯梯度洗提)以提供7.0 g的標題化合物。
1H NMR (CDCl
3) δ 7.32–7.24 (m, 1H), 7.00 (d, 1H), 6.84 (d, 1H), 3.82 (s, 3H), 3.09–3.01 (m, 2H), 2.64–2.51 (m, 2H).
步驟C:1-(2-氯-6-羥基苯基)-4,4,4-三氟-1-丁酮之製備
在0℃下於1-(2-氯-6-甲氧基苯基)-4,4,4-三氟-1-丁酮(即來自步驟B之產物,3.5 g,13.2 mmol)在100 mL的二氯甲烷之溶液中加入三溴化硼(1.0 M在二氯甲烷中,15.79 mL)。將反應溶液攪拌2 h同時溫熱至室溫,接著將其倒入冰冷之稀釋氫氯酸水溶液中,然後用二氯甲烷萃取。將有機相以MgSO
4乾燥、過濾、然後濃縮。將粗材料藉由矽凝膠層析術純化(以己烷/乙酸乙酯之梯度洗提)以提供2.6 g的標題化合物。
1H NMR (CDCl
3) δ 11.88 (s, 1H), 7.35–7.30 (m, 1H), 7.01–6.98 (m, 1H), 6.96–6.92 (m, 1H), 3.55–3.49 (m, 2H), 2.65–2.53 (m, 2H).
步驟D:1-[2-氯-6-[(5-氯-2-嘧啶基)氧基]苯基]-4,4,4-三氟-1-丁酮之製備
於反應燒瓶中倒入1-(2-氯-6-羥基苯基)-4,4,4-三氟-1-丁酮(即步驟C中所獲得之產物,2.6 g,10.3 mmol)、5-氯-2-(甲基磺醯基)-嘧啶(2.7 g, 14.0 mmol)、碳酸鉀(1.7 g, 12.36 mmol)、及50 mL的異丙醇。將反應混合物加熱至50℃歷時1 h、倒入稀釋冰冷氫氯酸水溶液中、然後用二乙醚重複萃取。將合併之有機萃取物用鹽水洗滌、以MgSO
4乾燥、過濾然後濃縮。將粗材料藉由矽凝膠層析術純化(以己烷/乙酸乙酯之梯度洗提)以提供3.0 g的標題化合物,即本發明之化合物。
1H NMR (CDCl
3) δ 8.49 (s, 2H), 7.45–7.40 (m, 1H), 7.37–7.33 (m, 1H), 7.15–7.11 (m, 1H), 3.14–3.08 (m, 2H), 2.57–2.46 (m, 2H).
實例5
2-[(5-氯-2-嘧啶基)氧基]-α-戊基苯乙腈(化合物141)之製備
步驟A:2-甲氧基-α-戊基苯乙腈之製備
於2-甲氧基-苯乙腈(500 mg, 3.39 mmol)在二甲亞碸(5 mL)中之溶液中加入氫氧化鈉水溶液(50%, 0.75 mL),接著加入1-溴戊烷(559 mg, 0.458 mL, 3.76 mmol),然後在環境溫度下將反應混合物攪拌18 h。使反應混合物在乙酸乙酯及水之間分配,將有機相用水洗滌(3 ×)。將有機相以MgSO
4乾燥然後在真空下濃縮。將所得殘餘物藉由層析術在矽凝膠上純化(以0至50%在己烷中之乙酸乙酯梯度洗提)以產出定量產率之所欲產物。
1H NMR (500 MHz, CDCl
3) δ 7.38–7.41 (m, 1H), 7.27–7.31 (m, 1H), 6.96–7.01 (m, 1H), 6.87–6.91 (m, 1H), 4.15–4.20 (m, 1H), 3.85 (s, 3H), 1.77–1.90 (m, 2H), 1.41–1.58 (m, 2H), 1.27–1.37 (m, 4H), 0.84–0.94 (m, 3H).
步驟B:2-羥基-α-戊基苯乙腈之製備
在0℃下於2-甲氧基-α-戊基苯乙腈(即步驟A之產物,440 mg,2.02 mmol)在二氯甲烷(10 mL)中之溶液中加入三溴化硼(1.0 M在二氯甲烷中,10 mL,10 mmol),然後在18 h內讓反應溫熱至室溫。將反應混合物用飽和碳酸鈉溶液淬熄、將相分離、然後將有機層以MgSO
4乾燥。在真空下將溶劑移除,然後藉由層析術在矽凝膠上純化(以0至50%在己烷中之乙酸乙酯梯度洗提)以產出所欲產物(232 mg)。
1H NMR (500 MHz, CDCl
3) δ 7.35–7.39 (m, 1H), 7.15–7.20 (m, 1H), 6.93–6.98 (m, 1H), 6.76–6.79 (m, 1H), 5.28–5.40 (bs, 1H), 4.14–4.20 (m, 1H), 1.84–1.93 (m, 2H), 1.42–1.58 (m, 2H), 1.25–1.38 (m, 4H), 0.85–0.91 (m, 3H).
步驟C:2-[(5-氯-2-嘧啶基)氧基]-α-戊基苯乙腈之製備
於2-羥基-α-戊基苯乙腈(208 mg, 1.02 mmol)在
N,N’‑二甲基甲醯胺(2.0 mL)中之溶液中加入碳酸鉀(169 mg, 1.22 mmol),接著加入5-氯-2-(甲基磺醯基)-嘧啶(137 mg, 1.07 mmol),然後將反應加熱至35℃歷時5 h。使反應在乙酸乙酯及水之間分配。將有機相用水洗滌(3 ×),接著以MgSO
4乾燥然後濃縮。將所得殘餘物藉由層析術在矽凝膠上純化(以0至30%在己烷中之乙酸乙酯梯度洗提)以產出標題產物(171 mg),即本發明之化合物。
1H NMR (500 MHz, CDCl
3) δ 8.51 (s, 2H), 7.56–7.58 (m, 1H), 7.38–7.42 (m, 1H), 7.31–7.35 (m, 1H), 7.12–7.15 (m, 1H), 3.99–4.03 (m, 1H), 1.80–1.96 (m, 2H), 1.36–1.55 (m, 2H), 1.20–1.28 (m, 4H), 0.81–0.87 (m, 3H).
實例6
3-[(5-氯-2-嘧啶基)氧基]-2-(5,5,5-三氟戊基)苄腈(化合物73)之製備
步驟A:2-溴-6-甲氧基-α-(4,4,4-三氟丁基)苯甲醇之製備
於無水二乙醚(2 mL)中之鎂金屬刨片(0.254 g, 10.5 mmol, 1.5 eq.)中加入碘晶體。將混合物溫熱至35℃然後攪拌15 min。在30 min內於此混合物中加入1-溴-4,4,4-三氟丁烷(1.30 mL, 10.5 mmol, 1.5 eq.)。在35℃下將反應混合物持續攪拌直到所有鎂均消耗為止。將所生成之格任亞試劑(Grignard reagent)以針筒取出。在另外的反應小瓶中,將2‑溴-6-甲氧基-苯甲醛(1.50 g, 6.97 mmol, 1.0 eq.)溶於無水四氫呋喃(20 mL)然後冷卻至0℃。將先前製備之格任亞試劑逐滴加入醛中。將反應混合物在室溫下攪拌18 h。將反應用1 N氫氯酸淬熄然後用乙酸乙酯稀釋。將有機層分離、乾燥然後濃縮。將粗材料藉由管柱層析術純化(以0至20%在己烷中之乙酸乙酯梯度洗提)以產出所欲產物(2.15 g)。
1H NMR (500 MHz, CDCl
3) δ 7.21–7.16 (m, 1H), 7.09 (t, 1H), 6.90–6.87 (m, 1H), 5.17–5.09 (m, 1H), 3.90 (s, 3H), 3.72 (d, 1H), 2.24–2.10 (m, 2H), 2.02–1.75 (m, 3H), 1.73–1.61 (m, 1H).
步驟B:1-溴-3-甲氧基-2-(5,5,5-三氟戊基)苯之製備
於2-溴-6-甲氧基-α-(4,4,4-三氟丁基)苯甲醇(即步驟A之產物,2.15 g,6.58 mmol, 1.0 eq.)在無水二氯甲烷(22 mL)中之攪拌溶液中加入三乙基矽烷(4.20 mL, 26.3 mmol, 4.0 eq.)。在攪拌15 min之後,將三氟乙酸(2.01 mL, 26.3 mmol, 4.0 eq.)加入然後將反應加熱至40℃。在2 h之後,將另外4.0 eq.的三氟乙酸加入,然後在40℃下將反應混合物攪拌另外18 h。將反應冷卻至室溫然後濃縮至Celite
®矽藻土助濾劑上,藉由管柱層析術純化(以0至10%在己烷中之乙酸乙酯梯度洗提)以產出所欲產物(1.82 g)。
1H NMR (500 MHz, CDCl
3) δ 7.20–7.12 (m, 1H), 7.07–7.00 (m, 1H), 6.81–6.78 (m, 1H), 3.81 (s, 3H), 2.85–2.78 (m, 2H), 2.20–2.07 (m, 2H), 1.69–1.55 (m, 4H)
步驟C:3-甲氧基-2-(5,5,5-三氟戊基)苄腈之製備
將1-溴-3-甲氧基-2-(5,5,5-三氟戊基)苯(即步驟B之產物,1.82 g,5.86 mmol,1.0 eq.)在
N,N-二甲基甲醯胺(20 mL)中之溶液藉由鼓泡N
2通過反應混合物約10 min來進行去氧。於此混合物中加入氰化銅(I) (1.57 g, 17.6 mmol, 3.0 eq.)。使反應在160℃下在氮中回流18 h。將反應冷卻至環境溫度然後通過Celite
®矽藻土助濾劑墊過濾。將濾液用乙酸乙酯稀釋然後用水洗滌數次,接著用鹽水洗條一次。將有機層乾燥然後在真空中濃縮。將粗材料藉由管柱層析術純化(以0至30%在己烷中之乙酸乙酯洗提)以產出所欲產物(1.38 g)。
1H NMR (500 MHz, CDCl
3) δ 7.29–7.24 (m, 1H), 7.22–7.19 (m, 1H), 7.08–7.04 (m, 1H), 3.86 (s, 3H), 2.94–2.82 (m, 2H), 2.24–2.07 (m, 2H), 1.75–1.60 (m, 4H).
步驟D:3-羥基-2-(5,5,5-三氟戊基)苄腈之製備
將3-甲氧基-2-(5,5,5-三氟戊基)苄腈(即步驟C之產物,1.38 g,5.36 mmol,1.0 eq.)在二氯乙烷(17 mL)中之溶液用三溴化硼(1.0 M在二氯甲烷中,10.7 mL,10.7 mmol,2.0 eq.)處理。將反應混合物加熱至60℃歷時18 h。使反應冷卻至環境溫度然後用飽和碳酸氫鈉水溶液淬熄。將有機相分離、乾燥然後濃縮至Celite
®矽藻土助濾劑上,藉由管柱層析術純化(以0至30%在己烷中之乙酸乙酯梯度洗提)以產出所欲產物(1.16 g)。
1H NMR (500 MHz, CDCl
3) δ 7.25–7.21 (m, 1H), 7.19–7.15 (m, 1H), 6.98–6.95 (m, 1H), 5.05–5.01 (m, 1H), 2.92–2.86 (m, 2H), 2.20–2.08 (m, 2H), 1.78–1.62 (m, 4H).
步驟E:3-[(5-氯-2-嘧啶基)氧基]-2-(5,5,5-三氟戊基)苄腈之製備
將3-羥基-2-(5,5,5-三氟戊基)苄腈(即步驟D之產物,1.16 g,4.79 mmol,1.0 eq.)、5-氯-2-(甲基磺醯基)-嘧啶(1.11 g, 5.75 mmol, 1.2 quiv)、及碳酸鉀(0.993 g, 7.18 mmol, 1.5 eq.)在
N,
N-二甲基甲醯胺(16 mL)中之混合物在室溫下攪拌18 h。將反應混合物用乙酸乙酯大量稀釋,然後用水洗滌數次,接著用鹽水洗滌一次。將有機相乾燥然後濃縮至Celite
®矽藻助濾劑上,藉由管柱層析術純化(以0至30%在己烷中之乙酸乙酯梯度洗提)以產出所欲產物(1.65 g)。
1H NMR (500 MHz, CDCl
3) δ 8.52–8.48 (m, 2H), 7.61–7.56 (m, 1H), 7.42–7.36 (m, 1H), 7.35–7.31 (m, 1H), 2.87–2.78 (m, 2H), 2.16–2.00 (m, 2H), 1.74–1.64 (m, 2H), 1.63–1.54 (m, 2H).
藉由本文中所述程序以及所屬技術領域中之習知方法,可製備下列表1至585之化合物。以下表格中使用下列縮寫:
t意指三級,
s意指二級,
n意指正,
i意指異,
c意指環,Me意指甲基,Et意指乙基,Pr意指丙基,Bu意指丁基、
i‑Pr意指異丙基,Bu意指丁基,
c-Pr意指環丙基,Ph意指苯基,OMe意指甲氧基,OEt意指乙氧基,SMe意指甲基硫基,NHMe意指甲基胺基,-CN意指氰基,S(O)Me意指甲基亞磺醯基,及S(O)
2Me意指甲基磺醯基。
表1
R
2= F,(R
3)
m= 3-F,Z = O,且A = A-3A
、 | 、 | 、 | ||||
A-1 | A-2 | A-3A | A-3B |
R 1 | R 1 |
丁基 | 3,3,4,4,4-五氟丁氧基 |
三級丁基 | 2,2,3,3,3-五氟丙氧基 |
乙基 | 3,3,4,4-四氟丁氧基 |
己基 | 2,2,3,3-四氟丙氧基 |
異丁基 | 3,3,3-三氯丙氧基 |
異戊基 | 4,4,4-三氟丁氧基 |
甲基 | 2,2,2-三氟乙氧基 |
戊基 | 6,6,6-三氟己氧基 |
丙基 | 4,4,4-三氟-2-甲基-丁氧基 |
苄基 | 3,3,3-三氟丙氧基 |
烯丙基 | 4-溴丁-3-炔氧基 |
3-丁烯-1-基 | 4-氯丁-3-炔氧基 |
3-甲基-2-丁烯-1-基 | 3-氯丙-2-炔氧基 |
3-甲基-3-丁烯-1-基 | 4,4-二氟丁-2-炔氧基 |
4-甲基-3-戊烯-1-基 | 5,5,5-三氟戊-2-炔氧基 |
3-戊烯-1-基 | 5,5,5-三氟戊-3-炔氧基 |
3-丁炔-1-基 | 環丁基甲氧基 |
4-甲基-2-戊炔-1-基 | 環己氧基 |
3-戊炔-1-基 | 環戊氧基 |
2-丙炔-1-基 | 2-環丙基乙氧基 |
5-己炔-1-基 | 環丙基甲氧基 |
4-戊炔-1-基 | (2-溴-2-氯-環丙基)甲氧基 |
3-溴丙基 | (2,2-二溴環丙基)甲氧基 |
3-氯丁基 | (2,2-二氯-1-甲基-環丙基)甲氧基 |
3-氯丙基 | (3,3-二氟環丁基)甲氧基 |
4,4-二氟丁基 | 2-(2,2-二氟環丙基)乙氧基 |
2,2-二氟乙基 | (2,2-二氟環丙基)甲氧基 |
3,3-二氟丙基 | 2-氯乙氧基甲基 |
3,3,4,4,4-五氟丁基 | 2,3-二氯-5-甲氧基-戊基 |
2,2,3,3,3-五氟丙基 | 3,3-二氟-5-甲氧基-戊基 |
3,3,4,4-四氟丁基 | 2-異丙氧基乙基 |
2,2,3,3-四氟丙基 | 2-甲氧基乙基 |
3,3,3-三氯丙基 | 5-甲氧基戊基 |
4,4,4-三氟丁基 | 2-甲氧基丙基 |
2,2,2-三氟乙基 | 1,1,2,2-四氟乙氧基甲基 |
6,6,6-三氟己基 | 2,2,2-三氟乙氧基甲基 |
4,4,4-三氟-2-甲基-丁基 | 2-(三氟甲氧基)乙基 |
3,3,3-三氟丙基 | 2-異丙氧基乙氧基 |
4-溴-3-丁烯-1-基 | 4-甲氧基丁氧基 |
2-氯烯丙基 | 2-甲氧基乙氧基 |
3-氯烯丙基 | 2-甲氧基丙氧基 |
3-氯-3-丁烯-1-基 | 4-氰基丁基 |
4-氯-3-丁烯-1-基 | 3-氰基-1,2-二甲基-丙基 |
5,5-二氟-3-戊烯-1-基 | 2-氰基乙基 |
4,4,4-三氟-2-丁烯-1-基 | 3-氰基-2-甲基-丙基 |
5,5,5-三氟-3-甲基-2-戊烯-1-基 | 氰基甲基 |
5,5,5-三氟-3-戊烯-1-基 | 5-氰基戊基 |
4-溴-3-丁炔-1-基 | 3-氰基丙基 |
3-丁炔-1-基 | 4-氰基丁氧基 |
4-氯-3-丁炔-1-基 | 3-氰基-1,2-二甲基-丙氧基 |
3-氯-2-丙炔-1-基 | 2-氰基乙氧基 |
4,4-二氟-2-丁炔-1-基 | 氰基甲氧基 |
5,5,5-三氟-1-甲基-2-戊炔-1-基 | 3-氰基-2-甲基-丙氧基 |
5,5,5-三氟-2-戊炔-1-基 | 5-氰基戊氧基 |
5,5,5-三氟-3-戊炔-1-基 | 3-氰基丙氧基 |
2-環丁基乙基 | 2-(氰基甲氧基)乙基 |
環己基 | 3-(氰基甲氧基)-2-甲基-丙基 |
環戊基甲基 | 氰基甲氧基甲基 |
2-環丙基乙基 | 1,2-二甲基-3-硝基-丙基 |
3-環丙基丙基 | 4-羥基丁基 |
(2,2-二甲基環丙基)甲基 | 3-羥基-1,2-二甲基-丙基 |
(1-甲基環丙基)甲基 | 2-羥基乙基 |
(2-甲基環戊基)甲基 | 3-羥基-2-甲基-丙基 |
(2-溴-2-氯-環丙基)甲基 | 羥基甲基 |
(2,2-二溴環丙基)甲基 | 5-羥基戊基 |
2-(2,2-二氯-1-甲基-環丙基)乙基 | 3-羥基丙基 |
(2,2-二氯-1-甲基-環丙基)甲基 | 2-甲基-3-硝基-丙基 |
2-(3,3-二氟環丁基)乙基 | 4-硝基丁基 |
2-(2,2-二氟環丙基)乙基 | 2-硝基乙基 |
(2,2-二氟環丙基)甲基 | 硝基甲基 |
丁基(甲基)胺基 | 5-硝基戊基 |
二甲基胺基 | 3-硝基丙基 |
乙基(丙基)胺基 | 丁基硫基 |
異丙基(甲基)胺基 | 三級丁基硫基 |
異丙基(丙基)胺基 | 1,3-二甲基丁基硫基 |
甲基(丙基)胺基 | 3,3-二甲基丁基硫基 |
2-氯乙基(2,2,2-三氟乙基)胺基 | 乙基硫基 |
3-氯丙基(甲基)胺基 | 異戊基硫基 |
甲基(2,2,2-三氟乙基)胺基 | 甲基硫基 |
甲基(3,3,3-三氟丙基)胺基 | 戊基硫基 |
丁基胺基 | 丙基硫基 |
3-氯丙基胺基 | 3-溴丙基硫基 |
異戊基胺基 | 3-氯丁基硫基 |
丙基胺基 | 3-氯丙基硫基 |
3,3,3-三氟丙基胺基 | 2,2-二氟乙基硫基 |
1-哌啶基 | 3,3,3-三氯丙基硫基 |
1-吡咯啶基 | 4,4,4-三氟丁基硫基 |
丁氧基 | 2,2,2-三氟乙基硫基 |
三級丁氧基 | 6,6,6-三氟己基硫基 |
1,3-二甲基丁氧基 | 3,3,3-三氟丙基硫基 |
3,3-二甲基丁氧基 | 環丁基甲基硫基 |
乙氧基 | 環己基硫基 |
己基 | 環戊基硫基 |
異戊基氧基 | 2-環丙基乙基硫基 |
甲氧基 | 環丙基甲基硫基 |
丙氧基 | 2-氯乙基硫基甲基 |
烯丙基氧基 | 2,3-二氯-5-甲基硫基-戊基 |
3-丁烯氧基 | 3,3-二氟-5-甲基硫基-戊基 |
3-甲基-2-丁烯氧基 | 2-異丙基硫基乙基 |
3-甲基-3-丁烯氧基 | 2-甲基硫基乙基 |
4-甲基-3-戊烯氧基 | 5-甲基硫基戊基 |
4-溴-3-丁烯氧基 | 2-甲基硫基丙基 |
2-氯烯丙基氧基 | 1,1,2,2-四氟乙基硫基甲基 |
3-氯烯丙基氧基 | 2,2,2-三氟乙基硫基甲基 |
3-氯-3-丁烯氧基 | 2-(三氟甲基硫基)乙基 |
4-氯-3-丁烯氧基 | 雙(2-氯乙基)胺基氧基 |
5,5-二氟-3-戊烯氧基 | 氰基甲氧基(甲基)胺基 |
4,4,4-三氟-2-丁烯氧基 | 二乙基胺基(甲基)胺基 |
5,5,5-三氟-3-甲基-2-戊烯氧基 | 乙氧基(甲基)胺基 |
5,5,5-三氟-3-戊烯氧基 | 乙氧基(2,2,2-三氟乙基)胺基 |
3-丁炔氧基 | 乙基胺基(甲基)胺基] |
5-己炔氧基 | 乙基胺基(2,2,2-三氟乙基)胺基 |
4-甲基-2-戊炔氧基 | 乙基(甲基)胺基]-(2,2,2-三氟乙基)胺基 |
3-戊炔氧基 | 乙基(3,3,3-三氟丙基)胺基]-甲基-胺基 |
4-戊炔氧基 | 異丁基(甲基)胺基]氧基 |
2-丙炔氧基 | 2-甲氧基乙氧基(甲基)胺基 |
3-溴丙氧基 | 甲基(丙基)胺基]氧基 |
3-氯丁氧基 | 甲基(2,2,2-三氟乙氧基)胺基 |
3-氯丙氧基 | 甲基(2,2,2-三氟乙基)胺基]氧基 |
4,4-二氟丁氧基 | 甲基(3,3,3-三氟丙氧基)胺基 |
2,2-二氟乙氧基 | 甲基-(3,3,3-三氟丙基胺基)胺基 |
3,3-二氟丙氧基 |
本揭露亦包括表2至表292。各表之建構方式與上表1相同,除了表1的列標題(即「R
2= F,(R
3)
m= 3-F,Z = O,且A = A-3A」)係用以下所示之各別列標題替換。例如,表2的第一項係其中R
2係Cl,(R
3)
m係3-F,Z係O,A係A-3A,且R
1係丁基之式1之化合物。表3至表292係以類似方式建構。
表293
R
2= F,(R
3)
m= 3-F,且Z = O
標題列 | 標題列 | ||||||||
表 | R 2 | (R 3) m | Z | A | 表 | R 2 | (R 3) m | Z | A |
2 | Cl | 3-F | O | A-3A | 147 | F | 5-Cl | O | A-3B |
3 | Br | 3-F | O | A-3A | 148 | Cl | 5-Cl | O | A-3B |
4 | I | 3-F | O | A-3A | 149 | Br | 5-Cl | O | A-3B |
5 | CF 3 | 3-F | O | A-3A | 150 | I | 5-Cl | O | A-3B |
6 | OMe | 3-F | O | A-3A | 151 | CF 3 | 5-Cl | O | A-3B |
7 | Me | 3-F | O | A-3A | 152 | OMe | 5-Cl | O | A-3B |
8 | F | 3-Cl | O | A-3A | 153 | Me | 5-Cl | O | A-3B |
9 | Cl | 3-Cl | O | A-3A | 154 | F | 6-Cl | O | A-3B |
10 | Br | 3-Cl | O | A-3A | 155 | Cl | 6-Cl | O | A-3B |
11 | I | 3-Cl | O | A-3A | 156 | Br | 6-Cl | O | A-3B |
12 | CF 3 | 3-Cl | O | A-3A | 157 | I | 6-Cl | O | A-3B |
13 | OMe | 3-Cl | O | A-3A | 158 | CF 3 | 6-Cl | O | A-3B |
14 | Me | 3-Cl | O | A-3A | 159 | OMe | 6-Cl | O | A-3B |
15 | F | 3-Br | O | A-3A | 160 | Me | 6-Cl | O | A-3B |
16 | Cl | 3-Br | O | A-3A | 161 | F | 3-Br, 4-F | O | A-3B |
17 | Br | 3-Br | O | A-3A | 162 | Cl | 3-Br, 4-F | O | A-3B |
18 | I | 3-Br | O | A-3A | 163 | Br | 3-Br, 4-F | O | A-3B |
19 | CF 3 | 3-Br | O | A-3A | 164 | I | 3-Br, 4-F | O | A-3B |
20 | OMe | 3-Br | O | A-3A | 165 | CF 3 | 3-Br, 4-F | O | A-3B |
21 | Me | 3-Br | O | A-3A | 166 | OMe | 3-Br, 4-F | O | A-3B |
22 | F | 3-I | O | A-3A | 167 | Me | 3-Br, 4-F | O | A-3B |
23 | Cl | 3-I | O | A-3A | 168 | F | 3-F, 4-F | O | A-3B |
24 | Br | 3-I | O | A-3A | 169 | Cl | 3-F, 4-F | O | A-3B |
25 | I | 3-I | O | A-3A | 170 | Br | 3-F, 4-F | O | A-3B |
26 | CF 3 | 3-I | O | A-3A | 171 | I | 3-F, 4-F | O | A-3B |
27 | OMe | 3-I | O | A-3A | 172 | CF 3 | 3-F, 4-F | O | A-3B |
28 | Me | 3-I | O | A-3A | 173 | OMe | 3-F, 4-F | O | A-3B |
29 | F | 3-CN | O | A-3A | 174 | Me | 3-F, 4-F | O | A-3B |
30 | Cl | 3-CN | O | A-3A | 175 | F | 3-Cl, 4-F | O | A-3B |
31 | Br | 3-CN | O | A-3A | 176 | Cl | 3-Cl, 4-F | O | A-3B |
32 | I | 3-CN | O | A-3A | 177 | Br | 3-Cl, 4-F | O | A-3B |
33 | CF 3 | 3-CN | O | A-3A | 178 | I | 3-Cl, 4-F | O | A-3B |
34 | OMe | 3-CN | O | A-3A | 179 | CF 3 | 3-Cl, 4-F | O | A-3B |
35 | Me | 3-CN | O | A-3A | 180 | OMe | 3-Cl, 4-F | O | A-3B |
36 | F | 3-CF 3 | O | A-3A | 181 | Me | 3-Cl, 4-F | O | A-3B |
37 | Cl | 3-CF 3 | O | A-3A | 182 | F | 3-Br | S | A-3B |
38 | Br | 3-CF 3 | O | A-3A | 183 | Cl | 3-Br | S | A-3B |
39 | I | 3-CF 3 | O | A-3A | 184 | Br | 3-Br | S | A-3B |
40 | CF 3 | 3-CF 3 | O | A-3A | 185 | I | 3-Br | S | A-3B |
41 | OMe | 3-CF 3 | O | A-3A | 186 | CF 3 | 3-Br | S | A-3B |
42 | Me | 3-CF 3 | O | A-3A | 187 | OMe | 3-Br | S | A-3B |
43 | F | 4-Cl | O | A-3A | 188 | Me | 3-Br | S | A-3B |
44 | Cl | 4-Cl | O | A-3A | 189 | F | 3-Cl | S | A-3B |
45 | Br | 4-Cl | O | A-3A | 190 | Cl | 3-Cl | S | A-3B |
46 | I | 4-Cl | O | A-3A | 191 | Br | 3-Cl | S | A-3B |
47 | CF 3 | 4-Cl | O | A-3A | 192 | I | 3-Cl | S | A-3B |
48 | OMe | 4-Cl | O | A-3A | 193 | CF 3 | 3-Cl | S | A-3B |
49 | Me | 4-Cl | O | A-3A | 194 | OMe | 3-Cl | S | A-3B |
50 | F | 5-Cl | O | A-3A | 195 | Me | 3-Cl | S | A-3B |
51 | Cl | 5-Cl | O | A-3A | 196 | Cl | 3-F | O | A-1 |
52 | Br | 5-Cl | O | A-3A | 197 | Br | 3-F | O | A-1 |
53 | I | 5-Cl | O | A-3A | 198 | I | 3-F | O | A-1 |
54 | CF 3 | 5-Cl | O | A-3A | 199 | CF 3 | 3-F | O | A-1 |
55 | OMe | 5-Cl | O | A-3A | 200 | OMe | 3-F | O | A-1 |
56 | Me | 5-Cl | O | A-3A | 201 | Me | 3-F | O | A-1 |
57 | F | 6-Cl | O | A-3A | 202 | F | 3-Cl | O | A-1 |
58 | Cl | 6-Cl | O | A-3A | 203 | Cl | 3-Cl | O | A-1 |
59 | Br | 6-Cl | O | A-3A | 204 | Br | 3-Cl | O | A-1 |
60 | I | 6-Cl | O | A-3A | 205 | I | 3-Cl | O | A-1 |
61 | CF 3 | 6-Cl | O | A-3A | 206 | CF 3 | 3-Cl | O | A-1 |
62 | OMe | 6-Cl | O | A-3A | 207 | OMe | 3-Cl | O | A-1 |
63 | Me | 6-Cl | O | A-3A | 208 | Me | 3-Cl | O | A-1 |
64 | F | 3-Br, 4-F | O | A-3A | 209 | F | 3-Br | O | A-1 |
65 | Cl | 3-Br, 4-F | O | A-3A | 210 | Cl | 3-Br | O | A-1 |
66 | Br | 3-Br, 4-F | O | A-3A | 211 | Br | 3-Br | O | A-1 |
67 | I | 3-Br, 4-F | O | A-3A | 212 | I | 3-Br | O | A-1 |
68 | CF 3 | 3-Br, 4-F | O | A-3A | 213 | CF 3 | 3-Br | O | A-1 |
69 | OMe | 3-Br, 4-F | O | A-3A | 214 | OMe | 3-Br | O | A-1 |
70 | Me | 3-Br, 4-F | O | A-3A | 215 | Me | 3-Br | O | A-1 |
71 | F | 3-F, 4-F | O | A-3A | 216 | F | 3-I | O | A-1 |
72 | Cl | 3-F, 4-F | O | A-3A | 217 | Cl | 3-I | O | A-1 |
73 | Br | 3-F, 4-F | O | A-3A | 218 | Br | 3-I | O | A-1 |
74 | I | 3-F, 4-F | O | A-3A | 219 | I | 3-I | O | A-1 |
75 | CF 3 | 3-F, 4-F | O | A-3A | 220 | CF 3 | 3-I | O | A-1 |
76 | OMe | 3-F, 4-F | O | A-3A | 221 | OMe | 3-I | O | A-1 |
77 | Me | 3-F, 4-F | O | A-3A | 222 | Me | 3-I | O | A-1 |
78 | F | 3-Cl, 4-F | O | A-3A | 223 | F | 3-CN | O | A-1 |
79 | Cl | 3-Cl, 4-F | O | A-3A | 224 | Cl | 3-CN | O | A-1 |
80 | Br | 3-Cl, 4-F | O | A-3A | 225 | Br | 3-CN | O | A-1 |
81 | I | 3-Cl, 4-F | O | A-3A | 226 | I | 3-CN | O | A-1 |
82 | CF 3 | 3-Cl, 4-F | O | A-3A | 227 | CF 3 | 3-CN | O | A-1 |
83 | OMe | 3-Cl, 4-F | O | A-3A | 228 | OMe | 3-CN | O | A-1 |
84 | Me | 3-Cl, 4-F | O | A-3A | 229 | Me | 3-CN | O | A-1 |
85 | F | 3-Br | S | A-3A | 230 | F | 3-CF 3 | O | A-1 |
86 | Cl | 3-Br | S | A-3A | 231 | Cl | 3-CF 3 | O | A-1 |
87 | Br | 3-Br | S | A-3A | 232 | Br | 3-CF 3 | O | A-1 |
88 | I | 3-Br | S | A-3A | 233 | I | 3-CF 3 | O | A-1 |
89 | CF 3 | 3-Br | S | A-3A | 234 | CF 3 | 3-CF 3 | O | A-1 |
90 | OMe | 3-Br | S | A-3A | 235 | OMe | 3-CF 3 | O | A-1 |
91 | Me | 3-Br | S | A-3A | 236 | Me | 3-CF 3 | O | A-1 |
92 | F | 3-Cl | S | A-3A | 237 | F | 4-Cl | O | A-1 |
93 | Cl | 3-Cl | S | A-3A | 238 | Cl | 4-Cl | O | A-1 |
94 | Br | 3-Cl | S | A-3A | 239 | Br | 4-Cl | O | A-1 |
95 | I | 3-Cl | S | A-3A | 240 | I | 4-Cl | O | A-1 |
96 | CF 3 | 3-Cl | S | A-3A | 241 | CF 3 | 4-Cl | O | A-1 |
97 | OMe | 3-Cl | S | A-3A | 242 | OMe | 4-Cl | O | A-1 |
98 | Me | 3-Cl | S | A-3A | 243 | Me | 4-Cl | O | A-1 |
99 | Cl | 3-F | O | A-3B | 244 | F | 5-Cl | O | A-1 |
100 | Br | 3-F | O | A-3B | 245 | Cl | 5-Cl | O | A-1 |
101 | I | 3-F | O | A-3B | 246 | Br | 5-Cl | O | A-1 |
102 | CF 3 | 3-F | O | A-3B | 247 | I | 5-Cl | O | A-1 |
103 | OMe | 3-F | O | A-3B | 248 | CF 3 | 5-Cl | O | A-1 |
104 | Me | 3-F | O | A-3B | 249 | OMe | 5-Cl | O | A-1 |
105 | F | 3-Cl | O | A-3B | 250 | Me | 5-Cl | O | A-1 |
106 | Cl | 3-Cl | O | A-3B | 251 | F | 6-Cl | O | A-1 |
107 | Br | 3-Cl | O | A-3B | 252 | Cl | 6-Cl | O | A-1 |
108 | I | 3-Cl | O | A-3B | 253 | Br | 6-Cl | O | A-1 |
109 | CF 3 | 3-Cl | O | A-3B | 254 | I | 6-Cl | O | A-1 |
110 | OMe | 3-Cl | O | A-3B | 255 | CF 3 | 6-Cl | O | A-1 |
111 | Me | 3-Cl | O | A-3B | 256 | OMe | 6-Cl | O | A-1 |
112 | F | 3-Br | O | A-3B | 257 | Me | 6-Cl | O | A-1 |
113 | Cl | 3-Br | O | A-3B | 258 | F | 3-Br, 4-F | O | A-1 |
114 | Br | 3-Br | O | A-3B | 259 | Cl | 3-Br, 4-F | O | A-1 |
115 | I | 3-Br | O | A-3B | 260 | Br | 3-Br, 4-F | O | A-1 |
116 | CF 3 | 3-Br | O | A-3B | 261 | I | 3-Br, 4-F | O | A-1 |
117 | OMe | 3-Br | O | A-3B | 262 | CF 3 | 3-Br, 4-F | O | A-1 |
118 | Me | 3-Br | O | A-3B | 263 | OMe | 3-Br, 4-F | O | A-1 |
119 | F | 3-I | O | A-3B | 264 | Me | 3-Br, 4-F | O | A-1 |
120 | Cl | 3-I | O | A-3B | 265 | F | 3-F, 4-F | O | A-1 |
121 | Br | 3-I | O | A-3B | 266 | Cl | 3-F, 4-F | O | A-1 |
122 | I | 3-I | O | A-3B | 267 | Br | 3-F, 4-F | O | A-1 |
123 | CF 3 | 3-I | O | A-3B | 268 | I | 3-F, 4-F | O | A-1 |
124 | OMe | 3-I | O | A-3B | 269 | CF 3 | 3-F, 4-F | O | A-1 |
125 | Me | 3-I | O | A-3B | 270 | OMe | 3-F, 4-F | O | A-1 |
126 | F | 3-CN | O | A-3B | 271 | Me | 3-F, 4-F | O | A-1 |
127 | Cl | 3-CN | O | A-3B | 272 | F | 3-Cl, 4-F | O | A-1 |
128 | Br | 3-CN | O | A-3B | 273 | Cl | 3-Cl, 4-F | O | A-1 |
129 | I | 3-CN | O | A-3B | 274 | Br | 3-Cl, 4-F | O | A-1 |
130 | CF 3 | 3-CN | O | A-3B | 275 | I | 3-Cl, 4-F | O | A-1 |
131 | OMe | 3-CN | O | A-3B | 276 | CF 3 | 3-Cl, 4-F | O | A-1 |
132 | Me | 3-CN | O | A-3B | 277 | OMe | 3-Cl, 4-F | O | A-1 |
133 | F | 3-CF 3 | O | A-3B | 278 | Me | 3-Cl, 4-F | O | A-1 |
134 | Cl | 3-CF 3 | O | A-3B | 279 | F | 3-Br | S | A-1 |
135 | Br | 3-CF 3 | O | A-3B | 280 | Cl | 3-Br | S | A-1 |
136 | I | 3-CF 3 | O | A-3B | 281 | Br | 3-Br | S | A-1 |
137 | CF 3 | 3-CF 3 | O | A-3B | 282 | I | 3-Br | S | A-1 |
138 | OMe | 3-CF 3 | O | A-3B | 283 | CF 3 | 3-Br | S | A-1 |
139 | Me | 3-CF 3 | O | A-3B | 284 | OMe | 3-Br | S | A-1 |
140 | F | 4-Cl | O | A-3B | 285 | Me | 3-Br | S | A-1 |
141 | Cl | 4-Cl | O | A-3B | 286 | F | 3-Cl | S | A-1 |
142 | Br | 4-Cl | O | A-3B | 287 | Cl | 3-Cl | S | A-1 |
143 | I | 4-Cl | O | A-3B | 288 | Br | 3-Cl | S | A-1 |
144 | CF 3 | 4-Cl | O | A-3B | 289 | I | 3-Cl | S | A-1 |
145 | OMe | 4-Cl | O | A-3B | 290 | CF 3 | 3-Cl | S | A-1 |
146 | Me | 4-Cl | O | A-3B | 291 | OMe | 3-Cl | S | A-1 |
292 | Me | 3-Cl | S | A-1 |
R 1 | R 1 |
丁基亞磺醯基 | 3,3-二氟丙氧基 |
三級丁基亞磺醯基 | 乙基磺醯基 |
1,3-二甲基丁基亞磺醯基 | 異戊基磺醯基 |
3,3-二甲基丁基亞磺醯基 | 甲基磺醯基 |
乙基亞磺醯基 | 戊基磺醯基 |
異戊基亞磺醯基 | 丙基磺醯基 |
甲基亞磺醯基 | 3-溴丙基磺醯基 |
戊基亞磺醯基 | 3-氯丁基磺醯基 |
丙基亞磺醯基 | 3-氯丙基磺醯基 |
3-溴丙基亞磺醯基 | 2,2-二氟乙基磺醯基 |
3-氯丁基亞磺醯基 | 3,3,3-三氟丙基磺醯基 |
3-氯丙基亞磺醯基 | 3,3,3-三氯丙基磺醯基 |
2,2-二氟乙基亞磺醯基 | 4,4,4-三氟丁基磺醯基 |
3,3,3-三氟丙基亞磺醯基 | 2,2,2-三氟乙基磺醯基 |
3,3,3-三氯丙基亞磺醯基 | 6,6,6-三氟己基磺醯基 |
4,4,4-三氟丁基亞磺醯基 | 環丁基甲基磺醯基 |
2,2,2-三氟乙基亞磺醯基 | 環己基磺醯基 |
6,6,6-三氟己基亞磺醯基 | 環戊基磺醯基 |
1,3-二甲基丁基磺醯基 | 2-環丙基乙基磺醯基 |
3,3-二甲基丁基磺醯基 | 環丙基甲基磺醯基 |
本揭露亦包括表294至表390。各表之建構方式與上表293相同,除了表293的列標題(即「R
2= F,(R
3)
m= 3-F,且Z = O」)係用以下所示之各別列標題替換。例如,表294之標題列係「R
2= Cl,(R
3)
m= 3-F,且Z = O」,且表294之第一項係其中R
1=丁基亞磺醯基,R
2= Cl,(R
3)
m= 3-F,且Z = O之式1之化合物。表295至表390係以類似方式建構。
表391
R
2= F,(R
3)
m= 3-F,且Z = O
標題列 | 標題列 | ||||||
表 | R 2 | (R 3) m | Z | 表 | R 2 | (R 3) m | Z |
294 | Cl | 3-F | O | 343 | Cl | 5-Cl | O |
295 | Br | 3-F | O | 344 | Br | 5-Cl | O |
296 | I | 3-F | O | 345 | I | 5-Cl | O |
297 | CF 3 | 3-F | O | 346 | CF 3 | 5-Cl | O |
298 | OMe | 3-F | O | 347 | OMe | 5-Cl | O |
299 | Me | 3-F | O | 348 | Me | 5-Cl | O |
300 | F | 3-Cl | O | 349 | F | 6-Cl | O |
301 | Cl | 3-Cl | O | 350 | Cl | 6-Cl | O |
302 | Br | 3-Cl | O | 351 | Br | 6-Cl | O |
303 | I | 3-Cl | O | 352 | I | 6-Cl | O |
304 | CF 3 | 3-Cl | O | 353 | CF 3 | 6-Cl | O |
305 | OMe | 3-Cl | O | 354 | OMe | 6-Cl | O |
306 | Me | 3-Cl | O | 355 | Me | 6-Cl | O |
307 | F | 3-Br | O | 356 | F | 3-Br, 4-F | O |
308 | Cl | 3-Br | O | 357 | Cl | 3-Br, 4-F | O |
309 | Br | 3-Br | O | 358 | Br | 3-Br, 4-F | O |
310 | I | 3-Br | O | 359 | I | 3-Br, 4-F | O |
311 | CF 3 | 3-Br | O | 360 | CF 3 | 3-Br, 4-F | O |
312 | OMe | 3-Br | O | 361 | OMe | 3-Br, 4-F | O |
313 | Me | 3-Br | O | 362 | Me | 3-Br, 4-F | O |
314 | F | 3-I | O | 363 | F | 3-F, 4-F | O |
315 | Cl | 3-I | O | 364 | Cl | 3-F, 4-F | O |
316 | Br | 3-I | O | 365 | Br | 3-F, 4-F | O |
317 | I | 3-I | O | 366 | I | 3-F, 4-F | O |
318 | CF 3 | 3-I | O | 367 | CF 3 | 3-F, 4-F | O |
319 | OMe | 3-I | O | 368 | OMe | 3-F, 4-F | O |
320 | Me | 3-I | O | 369 | Me | 3-F, 4-F | O |
321 | F | 3-CN | O | 370 | F | 3-Cl, 4-F | O |
322 | Cl | 3-CN | O | 371 | Cl | 3-Cl, 4-F | O |
323 | Br | 3-CN | O | 372 | Br | 3-Cl, 4-F | O |
324 | I | 3-CN | O | 373 | I | 3-Cl, 4-F | O |
325 | CF 3 | 3-CN | O | 374 | CF 3 | 3-Cl, 4-F | O |
326 | OMe | 3-CN | O | 375 | OMe | 3-Cl, 4-F | O |
327 | Me | 3-CN | O | 376 | Me | 3-Cl, 4-F | O |
328 | F | 3-CF 3 | O | 377 | F | 3-Br | S |
329 | Cl | 3-CF 3 | O | 378 | Cl | 3-Br | S |
330 | Br | 3-CF 3 | O | 379 | Br | 3-Br | S |
331 | I | 3-CF 3 | O | 380 | I | 3-Br | S |
332 | CF 3 | 3-CF 3 | O | 381 | CF 3 | 3-Br | S |
333 | OMe | 3-CF 3 | O | 382 | OMe | 3-Br | S |
334 | Me | 3-CF 3 | O | 383 | Me | 3-Br | S |
335 | F | 4-Cl | O | 384 | F | 3-Cl | S |
336 | Cl | 4-Cl | O | 385 | Cl | 3-Cl | S |
337 | Br | 4-Cl | O | 386 | Br | 3-Cl | S |
338 | I | 4-Cl | O | 387 | I | 3-Cl | S |
339 | CF 3 | 4-Cl | O | 388 | CF 3 | 3-Cl | S |
340 | OMe | 4-Cl | O | 389 | OMe | 3-Cl | S |
341 | Me | 4-Cl | O | 390 | Me | 3-Cl | S |
342 | F | 5-Cl | O |
、 | 、 | ||||
A-4 | A-5 | A-6 | A-7 |
A | A |
A = A-4;R 4= 3-溴丙基 | A = A-5;R 5= 4-氯-3-丁炔-1-基 |
A = A-4;R 4=三級丁基 | A = A-5;R 5= 3-氯-2-丙炔-1-基 |
A = A-4;R 4= 3-氯丁基 | A = A-5;R 5= 4,4-二氟-2-丁炔-1-基 |
A = A-4;R 4= 3-氯丙基 | A = A-5;R 5= 5,5,5-三氟-1-甲基-2-戊炔-1-基 |
A = A-4;R 4= 4,4-二氟丁基 | A = A-5;R 5= 5,5,5-三氟-2-戊炔-1-基 |
A = A-4;R 4= 2,2-二氟乙基 | A = A-5;R 5= 5,5,5-三氟-3-戊炔-1-基 |
A = A-4;R 4= 3,3-二氟丙基 | A = A-5;R 5= 2-環丁基乙基 |
A = A-4;R 4=乙基 | A = A-5;R 5=環己基 |
A = A-4;R 4=己基 | A = A-5;R 5=環戊基甲基 |
A = A-4;R 4=異丁基 | A = A-5;R 5= 2-環丙基乙基 |
A = A-4;R 4=異戊基 | A = A-5;R 5= 3-環丙基丙基 |
A = A-4;R 4=甲基 | A = A-5;R 5= (2,2-二甲基環丙基)甲基 |
A = A-4;R 4= 3,3,4,4,4-五氟丁基 | A = A-5;R 5= (1-甲基環丙基)甲基 |
A = A-4;R 4= 2,2,3,3,3-五氟丙基 | A = A-5;R 5= (2-甲基環戊基)甲基 |
A = A-4;R 4=戊基 | A = A-5;R 5= (2-溴-2-氯-環丙基)甲基 |
A = A-4;R 4=丙基 | A = A-5;R 5= (2,2-二溴環丙基)甲基 |
A = A-4;R 4= 3,3,4,4-四氟丁基 | A = A-5;R 5= 2-(2,2-二氯-1-甲基-環丙基)乙基 |
A = A-4;R 4= 2,2,3,3-四氟丙基 | A = A-5;R 5= (2,2-二氯-1-甲基-環丙基)甲基 |
A = A-4;R 4= 3,3,3-三氯丙基 | A = A-5;R 5= 2-(3,3-二氟環丁基)乙基 |
A = A-4;R 4= 4,4,4-三氟丁基 | A = A-5;R 5= 2-(2,2-二氟環丙基)乙基 |
A = A-4;R 4= 2,2,2-三氟乙基 | A = A-5;R 5= (2,2-二氟環丙基)甲基 |
A = A-4;R 4= 6,6,6-三氟己基 | A = A-5;R 5= 2-氯乙氧基甲基 |
A = A-4;R 4= 4,4,4-三氟-2-甲基-丁基 | A = A-5;R 5= 2,3-二氯-5-甲氧基-戊基 |
A = A-4;R 4= 3,3,3-三氟丙基 | A = A-5;R 5= 3,3-二氟-5-甲氧基-戊基 |
A = A-4;R 4= 3-溴丙基 | A = A-5;R 5= 2-異丙氧基乙基 |
A = A-5;R 5=丁基 | A = A-5;R 5= 2-甲氧基乙基 |
A = A-5;R 5=三級丁基 | A = A-5;R 5= 5-甲氧基戊基 |
A = A-5;R 5=乙基 | A = A-5;R 5= 2-甲氧基丙基 |
A = A-5;R 5=己基 | A = A-5;R 5= 1,1,2,2-四氟乙氧基甲基 |
A = A-5;R 5=異丁基 | A = A-5;R 5= 2,2,2-三氟乙氧基甲基 |
A = A-5;R 5=異戊基 | A = A-5;R 5= 2-(三氟甲氧基)乙基 |
A = A-5;R 5=戊基 | A = A-5;R 5= 4-氰基丁基 |
A = A-5;R 5=丙基 | A = A-5;R 5= 3-氰基-1,2-二甲基-丙基 |
A = A-5;R 5=苄基 | A = A-5;R 5= 2-氰基乙基 |
A = A-5;R 5=烯丙基 | A = A-5;R 5= 3-氰基-2-甲基-丙基 |
A = A-5;R 5= 3-丁烯-1-基 | A = A-5;R 5=氰基甲基 |
A = A-5;R 5= 3-甲基-2-丁烯-1-基 | A = A-5;R 5= 5-氰基戊基 |
A = A-5;R 5= 3-甲基-3-丁烯-1-基 | A = A-5;R 5= 3-氰基丙基 |
A = A-5;R 5= 4-甲基-3-戊烯-1-基 | A = A-5;R 5= 2-(氰基甲氧基)乙基 |
A = A-5;R 5= 3-戊烯-1-基 | A = A-5;R 5= 3-(氰基甲氧基)-2-甲基-丙基 |
A = A-5;R 5= 3-丁炔-1-基 | A = A-5;R 5=氰基甲氧基甲基 |
A = A-5;R 5= 4-甲基-2-戊炔-1-基 | A = A-5;R 5= 1,2-二甲基-3-硝基-丙基 |
A = A-5;R 5= 3-戊炔-1-基 | A = A-5;R 5= 4-羥基丁基 |
A = A-5;R 5= 2-丙炔-1-基 | A = A-5;R 5= 3-羥基-1,2-二甲基-丙基 |
A = A-5;R 5= 5-己炔-1-基 | A = A-5;R 5= 3-羥基-2-甲基-丙基 |
A = A-5;R 5= 4-戊炔-1-基 | A = A-5;R 5=羥基甲基 |
A = A-5;R 5= 3-溴丙基 | A = A-5;R 5= 5-羥基戊基 |
A = A-5;R 5= 3-氯丁基 | A = A-5;R 5= 3-羥基丙基 |
A = A-5;R 5= 3-氯丙基 | A = A-5;R 5= 2-甲基-3-硝基-丙基 |
A = A-5;R 5= 4,4-二氟丁基 | A = A-5;R 5= 4-硝基丁基 |
A = A-5;R 5= 2,2-二氟乙基 | A = A-5;R 5= 2-硝基乙基 |
A = A-5;R 5= 3,3-二氟丙基 | A = A-5;R 5=硝基甲基 |
A = A-5;R 5= 3,3,4,4,4-五氟丁基 | A = A-5;R 5= 5-硝基戊基 |
A = A-5;R 5= 2,2,3,3,3-五氟丙基 | A = A-5;R 5= 3-硝基丙基 |
A = A-5;R 5= 3,3,4,4-四氟丁基 | A = A-5;R 5= 2-氯乙基硫基甲基 |
A = A-5;R 5= 2,2,3,3-四氟丙基 | A = A-5;R 5= 2,3-二氯-5-甲基硫基-戊基 |
A = A-5;R 5= 3,3,3-三氯丙基 | A = A-5;R 5= 3,3-二氟-5-甲基硫基-戊基 |
A = A-5;R 5= 4,4,4-三氟丁基 | A = A-5;R 5= 2-異丙基硫基乙基 |
A = A-5;R 5= 2,2,2-三氟乙基 | A = A-5;R 5= 2-甲基硫基乙基 |
A = A-5;R 5= 6,6,6-三氟己基 | A = A-5;R 5= 5-甲基硫基戊基 |
A = A-5;R 5= 4,4,4-三氟-2-甲基-丁基 | A = A-5;R 5= 2-甲基硫基丙基 |
A = A-5;R 5= 3,3,3-三氟丙基 | A = A-5;R 5= 1,1,2,2-四氟乙基硫基甲基 |
A = A-5;R 5= 4-溴-3-丁烯-1-基 | A = A-5;R 5= 2,2,2-三氟乙基硫基甲基 |
A = A-5;R 5= 2-氯烯丙基 | A = A-5;R 5= 2-(三氟甲基硫基)乙基 |
A = A-5;R 5= 3-氯烯丙基 | A = A-6;R 6a= Me;R 6b=丁基 |
A = A-5;R 5= 3-氯-3-丁烯-1-基 | A = A-6;R 6a= Me;R 6b=三級丁基 |
A = A-5;R 5= 4-氯-3-丁烯-1-基 | A = A-6;R 6a= Me;R 6b=乙基 |
A = A-5;R 5= 5,5-二氟-3-戊烯-1-基 | A = A-6;R 6a= Me;R 6b=異丁基 |
A = A-5;R 5= 4,4,4-三氟-2-丁烯-1-基 | A = A-6;R 6a= Me;R 6b=丙基 |
A = A-5;R 5= 5,5,5-三氟-3-甲基-2-戊烯-1-基 | A = A-6;R 6a=乙基;R 6b=乙基 |
A = A-5;R 5= 5,5,5-三氟-3-戊烯-1-基 | A = A-6;R 6a= Me;R 6b= 3,3,3-三氟丙基 |
A = A-5;R 5= 4-溴-3-丁炔-1-基 | A = A-6;R 6a= Me;R 6b= 2,2,3,3,3-五氟丙基 |
A = A-5;R 5= 3-丁炔-1-基 | A = A-6;R 6a= 3,3,3-三氟丙基;R 6b= 3,3,3-三氟丙基 |
A = A-7;R 15=異戊基 | A = A-7;R 15=乙基 |
A = A-7;R 15=戊基 | A = A-7;R 15=己基 |
A = A-7;R 15=丙基 | A = A-7;R 15=異丁基 |
A = A-7;R 15= H | A = A-7;R 15=甲基 |
本揭露亦包括表392至表585。各表之建構方式與上表391相同,除了表391的列標題(即「R
2= F,(R
3)
m= 3-F,且Z = O」)係用以下所示之各別列標題替換。例如,表392之標題列係「R
2= Cl,(R
3)
m= 3-F,且Z = O」,且表392之第一項係其中R
1= 3‑溴丙基,R
2= Cl,(R
3)
m= 3-F,且Z = O之式
1之化合物。表392至表585係以類似方式建構。
標題列 | 標題列 | ||||||
表 | R 2 | (R 3) m | Z | 表 | R 2 | (R 3) m | Z |
392 | Cl | 3-F | O | 489 | Cl | 3-F | O |
393 | Br | 3-F | O | 490 | Br | 3-F | O |
394 | I | 3-F | O | 491 | I | 3-F | O |
395 | CF 3 | 3-F | O | 492 | CF 3 | 3-F | O |
396 | OMe | 3-F | O | 493 | OMe | 3-F | O |
397 | Me | 3-F | O | 494 | Me | 3-F | O |
398 | F | 3-Cl | O | 495 | F | 3-Cl | O |
399 | Cl | 3-Cl | O | 496 | Cl | 3-Cl | O |
400 | Br | 3-Cl | O | 497 | Br | 3-Cl | O |
401 | I | 3-Cl | O | 498 | I | 3-Cl | O |
402 | CF 3 | 3-Cl | O | 499 | CF 3 | 3-Cl | O |
403 | OMe | 3-Cl | O | 500 | OMe | 3-Cl | O |
404 | Me | 3-Cl | O | 501 | Me | 3-Cl | O |
405 | F | 3-Br | O | 502 | F | 3-Br | O |
406 | Cl | 3-Br | O | 503 | Cl | 3-Br | O |
407 | Br | 3-Br | O | 504 | Br | 3-Br | O |
408 | I | 3-Br | O | 505 | I | 3-Br | O |
409 | CF 3 | 3-Br | O | 506 | CF 3 | 3-Br | O |
410 | OMe | 3-Br | O | 507 | OMe | 3-Br | O |
411 | Me | 3-Br | O | 508 | Me | 3-Br | O |
412 | F | 3-I | O | 509 | F | 3-I | O |
413 | Cl | 3-I | O | 510 | Cl | 3-I | O |
414 | Br | 3-I | O | 511 | Br | 3-I | O |
415 | I | 3-I | O | 512 | I | 3-I | O |
416 | CF 3 | 3-I | O | 513 | CF 3 | 3-I | O |
417 | OMe | 3-I | O | 514 | OMe | 3-I | O |
418 | Me | 3-I | O | 515 | Me | 3-I | O |
419 | F | 3-CN | O | 516 | F | 3-CN | O |
420 | Cl | 3-CN | O | 517 | Cl | 3-CN | O |
421 | Br | 3-CN | O | 518 | Br | 3-CN | O |
422 | I | 3-CN | O | 519 | I | 3-CN | O |
423 | CF 3 | 3-CN | O | 520 | CF 3 | 3-CN | O |
424 | OMe | 3-CN | O | 521 | OMe | 3-CN | O |
425 | Me | 3-CN | O | 522 | Me | 3-CN | O |
426 | F | 3-CF 3 | O | 523 | F | 3-CF 3 | O |
427 | Cl | 3-CF 3 | O | 524 | Cl | 3-CF 3 | O |
428 | Br | 3-CF 3 | O | 525 | Br | 3-CF 3 | O |
429 | I | 3-CF 3 | O | 526 | I | 3-CF 3 | O |
430 | CF 3 | 3-CF 3 | O | 527 | CF 3 | 3-CF 3 | O |
431 | OMe | 3-CF 3 | O | 528 | OMe | 3-CF 3 | O |
432 | Me | 3-CF 3 | O | 529 | Me | 3-CF 3 | O |
433 | F | 4-Cl | O | 530 | F | 4-Cl | O |
434 | Cl | 4-Cl | O | 531 | Cl | 4-Cl | O |
435 | Br | 4-Cl | O | 532 | Br | 4-Cl | O |
436 | I | 4-Cl | O | 533 | I | 4-Cl | O |
437 | CF 3 | 4-Cl | O | 534 | CF 3 | 4-Cl | O |
438 | OMe | 4-Cl | O | 535 | OMe | 4-Cl | O |
439 | Me | 4-Cl | O | 536 | Me | 4-Cl | O |
440 | F | 5-Cl | O | 537 | F | 5-Cl | O |
441 | Cl | 5-Cl | O | 538 | Cl | 5-Cl | O |
442 | Br | 5-Cl | O | 539 | Br | 5-Cl | O |
443 | I | 5-Cl | O | 540 | I | 5-Cl | O |
444 | CF 3 | 5-Cl | O | 541 | CF 3 | 5-Cl | O |
445 | OMe | 5-Cl | O | 542 | OMe | 5-Cl | O |
446 | Me | 5-Cl | O | 543 | Me | 5-Cl | O |
447 | F | 6-Cl | O | 544 | F | 6-Cl | O |
448 | Cl | 6-Cl | O | 545 | Cl | 6-Cl | O |
449 | Br | 6-Cl | O | 546 | Br | 6-Cl | O |
450 | I | 6-Cl | O | 547 | I | 6-Cl | O |
451 | CF 3 | 6-Cl | O | 548 | CF 3 | 6-Cl | O |
452 | OMe | 6-Cl | O | 549 | OMe | 6-Cl | O |
453 | Me | 6-Cl | O | 550 | Me | 6-Cl | O |
454 | F | 3-Br, 4-F | O | 551 | F | 3-Br, 4-F | O |
455 | Cl | 3-Br, 4-F | O | 552 | Cl | 3-Br, 4-F | O |
456 | Br | 3-Br, 4-F | O | 553 | Br | 3-Br, 4-F | O |
457 | I | 3-Br, 4-F | O | 554 | I | 3-Br, 4-F | O |
458 | CF 3 | 3-Br, 4-F | O | 555 | CF 3 | 3-Br, 4-F | O |
459 | OMe | 3-Br, 4-F | O | 556 | OMe | 3-Br, 4-F | O |
460 | Me | 3-Br, 4-F | O | 557 | Me | 3-Br, 4-F | O |
461 | F | 3-F, 4-F | O | 558 | F | 3-F, 4-F | O |
462 | Cl | 3-F, 4-F | O | 559 | Cl | 3-F, 4-F | O |
463 | Br | 3-F, 4-F | O | 560 | Br | 3-F, 4-F | O |
464 | I | 3-F, 4-F | O | 561 | I | 3-F, 4-F | O |
465 | CF 3 | 3-F, 4-F | O | 562 | CF 3 | 3-F, 4-F | O |
466 | OMe | 3-F, 4-F | O | 563 | OMe | 3-F, 4-F | O |
467 | Me | 3-F, 4-F | O | 564 | Me | 3-F, 4-F | O |
468 | F | 3-Cl, 4-F | O | 565 | F | 3-Cl, 4-F | O |
469 | Cl | 3-Cl, 4-F | O | 566 | Cl | 3-Cl, 4-F | O |
470 | Br | 3-Cl, 4-F | O | 567 | Br | 3-Cl, 4-F | O |
471 | I | 3-Cl, 4-F | O | 568 | I | 3-Cl, 4-F | O |
472 | CF 3 | 3-Cl, 4-F | O | 569 | CF 3 | 3-Cl, 4-F | O |
473 | OMe | 3-Cl, 4-F | O | 570 | OMe | 3-Cl, 4-F | O |
474 | Me | 3-Cl, 4-F | O | 571 | Me | 3-Cl, 4-F | O |
475 | F | 3-Br | S | 572 | F | 3-Br | S |
476 | Cl | 3-Br | S | 573 | Cl | 3-Br | S |
477 | Br | 3-Br | S | 574 | Br | 3-Br | S |
478 | I | 3-Br | S | 575 | I | 3-Br | S |
479 | CF 3 | 3-Br | S | 576 | CF 3 | 3-Br | S |
480 | OMe | 3-Br | S | 577 | OMe | 3-Br | S |
481 | Me | 3-Br | S | 578 | Me | 3-Br | S |
482 | F | 3-Cl | S | 579 | F | 3-Cl | S |
483 | Cl | 3-Cl | S | 580 | Cl | 3-Cl | S |
484 | Br | 3-Cl | S | 581 | Br | 3-Cl | S |
485 | I | 3-Cl | S | 582 | I | 3-Cl | S |
486 | CF 3 | 3-Cl | S | 583 | CF 3 | 3-Cl | S |
487 | OMe | 3-Cl | S | 584 | OMe | 3-Cl | S |
488 | Me | 3-Cl | S | 585 | Me | 3-Cl | S |
本揭露亦包括表586至表684。各表之建構方式與上表1相同,除了表1的列標題(即「R
2= F,(R
3)
m= 3-F,Z = O,且A = A-4」)係用以下所示之各別列標題替換。例如,表586的第一項係其中R
2係Cl,(R
3)
m係3-F,Z係O,A係A-3A,且R
1係丁基之式1之化合物。表587至表684係以類似方式建構。
標題列
表 | R 2 | (R 3) m | Z | A |
586 | F | 3-F | O | A-4 |
587 | F | 3-F | O | A-1 |
588 | F | 3-F | O | A-2 |
589 | Cl | 3-F | O | A-2 |
590 | Br | 3-F | O | A-2 |
591 | I | 3-F | O | A-2 |
592 | CF 3 | 3-F | O | A-2 |
593 | OMe | 3-F | O | A-2 |
594 | Me | 3-F | O | A-2 |
595 | F | 3-Cl | O | A-2 |
596 | Cl | 3-Cl | O | A-2 |
597 | Br | 3-Cl | O | A-2 |
598 | I | 3-Cl | O | A-2 |
599 | CF 3 | 3-Cl | O | A-2 |
600 | OMe | 3-Cl | O | A-2 |
601 | Me | 3-Cl | O | A-2 |
602 | F | 3-Br | O | A-2 |
603 | Cl | 3-Br | O | A-2 |
604 | Br | 3-Br | O | A-2 |
605 | I | 3-Br | O | A-2 |
606 | CF 3 | 3-Br | O | A-2 |
607 | OMe | 3-Br | O | A-2 |
608 | Me | 3-Br | O | A-2 |
609 | F | 3-I | O | A-2 |
610 | Cl | 3-I | O | A-2 |
611 | Br | 3-I | O | A-2 |
612 | I | 3-I | O | A-2 |
613 | CF 3 | 3-I | O | A-2 |
614 | OMe | 3-I | O | A-2 |
615 | Me | 3-I | O | A-2 |
616 | F | 3-CN | O | A-2 |
617 | Cl | 3-CN | O | A-2 |
618 | Br | 3-CN | O | A-2 |
619 | I | 3-CN | O | A-2 |
620 | CF 3 | 3-CN | O | A-2 |
621 | OMe | 3-CN | O | A-2 |
622 | Me | 3-CN | O | A-2 |
623 | F | 3-CF 3 | O | A-2 |
624 | Cl | 3-CF 3 | O | A-2 |
625 | Br | 3-CF 3 | O | A-2 |
626 | I | 3-CF 3 | O | A-2 |
627 | CF 3 | 3-CF 3 | O | A-2 |
628 | OMe | 3-CF 3 | O | A-2 |
629 | Me | 3-CF 3 | O | A-2 |
630 | F | 4-Cl | O | A-2 |
631 | Cl | 4-Cl | O | A-2 |
632 | Br | 4-Cl | O | A-2 |
633 | I | 4-Cl | O | A-2 |
634 | CF 3 | 4-Cl | O | A-2 |
635 | OMe | 4-Cl | O | A-2 |
636 | Me | 4-Cl | O | A-2 |
637 | F | 5-Cl | O | A-2 |
638 | Cl | 5-Cl | O | A-2 |
639 | Br | 5-Cl | O | A-2 |
640 | I | 5-Cl | O | A-2 |
641 | CF 3 | 5-Cl | O | A-2 |
642 | OMe | 5-Cl | O | A-2 |
643 | Me | 5-Cl | O | A-2 |
644 | F | 6-Cl | O | A-2 |
645 | Cl | 6-Cl | O | A-2 |
646 | Br | 6-Cl | O | A-2 |
647 | I | 6-Cl | O | A-2 |
648 | CF 3 | 6-Cl | O | A-2 |
649 | OMe | 6-Cl | O | A-2 |
650 | Me | 6-Cl | O | A-2 |
651 | F | 3-Br, 4-F | O | A-2 |
652 | Cl | 3-Br, 4-F | O | A-2 |
653 | Br | 3-Br, 4-F | O | A-2 |
654 | I | 3-Br, 4-F | O | A-2 |
655 | CF 3 | 3-Br, 4-F | O | A-2 |
656 | OMe | 3-Br, 4-F | O | A-2 |
657 | Me | 3-Br, 4-F | O | A-2 |
658 | F | 3-F, 4-F | O | A-2 |
659 | Cl | 3-F, 4-F | O | A-2 |
660 | Br | 3-F, 4-F | O | A-2 |
661 | I | 3-F, 4-F | O | A-2 |
662 | CF 3 | 3-F, 4-F | O | A-2 |
663 | OMe | 3-F, 4-F | O | A-2 |
664 | Me | 3-F, 4-F | O | A-2 |
665 | F | 3-Cl, 4-F | O | A-2 |
666 | Cl | 3-Cl, 4-F | O | A-2 |
667 | Br | 3-Cl, 4-F | O | A-2 |
668 | I | 3-Cl, 4-F | O | A-2 |
669 | CF 3 | 3-Cl, 4-F | O | A-2 |
670 | OMe | 3-Cl, 4-F | O | A-2 |
671 | Me | 3-Cl, 4-F | O | A-2 |
672 | F | 3-Br | S | A-2 |
673 | Cl | 3-Br | S | A-2 |
674 | Br | 3-Br | S | A-2 |
675 | I | 3-Br | S | A-2 |
676 | CF 3 | 3-Br | S | A-2 |
677 | OMe | 3-Br | S | A-2 |
678 | Me | 3-Br | S | A-2 |
679 | F | 3-Cl | S | A-2 |
680 | Cl | 3-Cl | S | A-2 |
681 | Br | 3-Cl | S | A-2 |
682 | I | 3-Cl | S | A-2 |
683 | CF 3 | 3-Cl | S | A-2 |
684 | OMe | 3-Cl | S | A-2 |
本發明之化合物將通常用作為組合物(即配方)中之除草活性成分,並伴隨有至少一種選自由界面活性劑、固體稀釋劑及液體稀釋劑所組成之群組的額外組分以作為載體之用。配方或組合物成分係經選擇,以配合活性成分之物理性質、施用型態及環境因素(諸如土壤種類、濕度和溫度)。
有用之配方包括液體及固體組合物。液體組合物包括溶液(包括可乳化濃縮物)、懸浮液、乳液(包括微乳液、油在水中乳液、可流動濃縮物及/或懸浮乳液(suspoemulsion))及類似者,並選擇性地可增稠成凝膠。水性液體組合物的一般類型係可溶濃縮物(soluble concentrate)、懸浮濃縮物(suspension concentrate)、膠囊懸浮液(capsule suspension)、濃縮乳液、微乳液、油在水中乳液、可流動濃縮物及懸浮乳液。非水性液體組合物的一般類型係可乳化濃縮物、可微乳化濃縮物、可分散濃縮物(dispersible concentrate)及油分散液(oil dispersion)。
固體組合物的一般類型為塵粉(dusts)、粉劑、粒劑、丸劑(pellets)、珠劑(prills)、錠劑(pastilles)、片劑、包膜(filled films)(包括種子塗層)等等,其可為水分散性(「可濕性」)或水溶性。由成膜溶液或可流動懸浮液形成的膜和塗層在種子處理上特別有用。可將活性成分(微)囊封((micro)encapsulated),並使其進一步形成懸浮物或固體配方;或者可將整個活性成分之配方囊封(或「包覆(overcoated)」)。封裝可以控制或減緩活性成分的釋放。可乳化粒劑結合了可乳化濃縮物配方與乾粒狀配方的優點。高強度組合物主要用作進一步配方的中間物。
可噴灑配方通常在噴灑前會先在適合的介質中擴展。此等液體及固體配方係經配製以迅速稀釋於噴灑介質中,此介質通常係水,但有時係另一種合適介質,像是芳烴或烷烴或植物油。噴灑量可在每公頃約一至數千公升的範圍,但更典型係在每公頃約十到數百公升的範圍。可噴灑配方可在桶中與水或其他適合的介質混合,藉由空中或地面施用而運用於葉處理,或施用於植物的生長介質。液體配方及乾配方可在栽植期間直接計量加入滴流灌溉系統或犁溝。
配方通常將含有下列近似範圍內之有效量的活性成分、稀釋劑和界面活性劑,其等之重量加起來等於百分之百。
重量百分比 | |||
活性 成分 | 稀釋劑 | 界面活性劑 | |
水分散性及水溶性粒劑、片劑及粉劑 | 0.001–90 | 0–99.999 | 0–15 |
油分散液、懸浮液、乳液、溶液(包括可乳化濃縮物) | 1–50 | 40–99 | 0–50 |
塵粉 | 1–25 | 70–99 | 0–5 |
粒劑及丸劑 | 0.001–99 | 5–99.999 | 0–15 |
高強度組合物 | 90–99 | 0–10 | 0–2 |
固體稀釋劑包括例如,黏土如膨土、微晶高嶺石、厄帖浦石與高嶺土、石膏、纖維素、二氧化鈦、氧化鋅、澱粉、糊精、糖(例如乳糖、蔗糖)、二氧化矽、滑石、雲母、矽藻土、尿素、碳酸鈣、碳酸鈉、碳酸氫鈉及硫酸鈉。典型固體稀釋劑係描述於Watkins et al.,
Handbook of Insecticide Dust Diluents and Carriers, 2nd Ed., Dorland Books, Caldwell, New Jersey中。
液體稀釋劑包括例如水、
N,
N-二甲基烷醯胺(例如
N,
N-二甲基甲醯胺)、薴烯、二甲亞碸、
N-烷基吡咯啶酮(例如,
N-甲基吡咯啶酮)、磷酸烷酯(例如磷酸三乙酯)、乙二醇、三甘醇、丙二醇、二丙二醇、聚丙二醇、碳酸伸丙酯、碳酸伸丁酯、石蠟(例如,白礦油、正烷烴、異烷烴)、烷基苯、烷基萘、甘油、三乙酸甘油酯(glycerol triacetate)、山梨糖醇、芳烴、脫芳脂族、烷基苯、烷基萘、酮類(諸如環己酮、2-庚酮、異佛酮及4-羥基-4-甲基-2-戊酮)、乙酸酯(諸如乙酸異戊酯、乙酸己酯、乙酸庚酯、乙酸辛酯、乙酸壬酯、乙酸十三酯及乙酸異莰酯)、其他酯類(諸如烷化乳酸酯、二元酯、苯甲酸烷酯、苯甲酸芳酯及γ-丁內酯)、以及醇類(其可為線性、分支、飽和或不飽和,諸如甲醇、乙醇、正丙醇、異丙醇、正丁醇、異丁醇、正己醇、2-乙基己醇、正辛醇、癸醇、異癸醇、異十八醇、鯨蠟醇、月桂醇、十三醇、油醇、環已醇、四氫糠醇、二丙酮醇、甲酚及苯甲醇)。液體稀釋劑亦包括飽和及不飽和脂肪酸的甘油酯(典型係C
6–C
22),諸如植物種子和水果油(例如橄欖、蓖麻、亞麻仁、芝麻、玉米、花生、向日葵、葡萄籽、紅花、棉籽、大豆、油菜籽、椰子及棕櫚仁之油)、動物來源脂肪(例如牛肉脂、豬肉脂、豬油、鱈魚肝油、魚油)及上述者之混合物。液體稀釋劑亦包括烷化(例如,甲基化、乙基化、丁基化)脂肪酸,其中脂肪酸可藉由水解來自植物和動物來源的甘油酯而獲得,並可藉由蒸餾純化。典型的液體稀釋劑係描述於Marsden,
Solvents Guide, 2nd Ed., Interscience, New York, 1950中。
本發明之固體及液體組合物常包括一或多種界面活性劑。當加至液體中時,界面活性劑(也稱為「界面活性劑」)通常會改變(最常的是減少)液體的表面張力。取決於界面活性劑分子中親水性和親油性基的性質,界面活性劑可用作為潤濕劑、分散劑、乳化劑或消泡劑。
界面活性劑可分為非離子性、陰離子性或陽離子性。可用於本發明組合物的非離子性界面活性劑包括但不限於:醇烷氧化物(alcohol alkoxylate),諸如基於天然及合成醇(其可為分枝或線性)並從該等醇與環氧乙烷、環氧丙烷、環氧丁烷與上述者之混合物所製備出的醇烷氧化物;胺乙氧基化物、烷醇醯胺、及乙氧基化烷醇醯胺;烷氧基化三酸甘油酯,如乙氧基化大豆油、蓖麻油、和油菜籽油;烷基酚烷氧化物,如辛苯酚乙氧化物(octylphenol ethoxylate)、壬苯酚乙氧化物、二壬苯酚乙氧化物、及十二烷苯酚乙氧化物(由苯酚及環氧乙烷、環氧丙烷、環氧丁烷或上述者混合物所製備);由環氧乙烷或環氧丙烷所製備的嵌段聚合物以及其中的末端嵌段由環氧丙烷所製備的反向嵌段聚合物;乙氧基化脂肪酸;乙氧基化脂肪酯和油;乙氧基化甲基酯;乙氧基化三苯乙烯苯酚(包括由環氧乙烷、環氧丙烷、環氧丁烷、或其混合物所製備者);脂肪酸酯、甘油酯、羊毛脂為基礎的衍生物、聚乙氧基化酯如聚乙氧基化山梨醇酐脂肪酸酯、聚乙氧基化山梨糖醇脂肪酸酯、及聚乙氧基化甘油脂肪酸酯;其他山梨醇酐衍生物,如山梨醇酐酯;聚合界面活性劑,如隨機共聚物、嵌段共聚物、醇酸peg(聚乙二醇)樹脂、接枝或梳形聚合物、及星形聚合物;聚乙二醇(peg);聚乙二醇脂肪酸酯;基於聚矽氧之界面活性劑;以及糖衍生物,如蔗糖酯、烷基聚葡萄糖苷、及烷基多醣。
有用的陰離子界面活性劑包括但不限於:烷芳基磺酸及其鹽;羧基化醇或烷基酚乙氧化物;二苯磺酸鹽衍生物;木質素以及木質素衍生物,例如木質磺酸鹽;順丁烯二酸或琥珀酸或其酐;烯烴磺酸鹽;磷酸酯,如醇烷氧化物之磷酸酯、烷基苯酚烷氧化物之磷酸酯、及苯乙烯基苯酚乙氧化物之磷酸酯;基於蛋白質之界面活性劑;肌胺酸衍生物;苯乙烯基酚醚硫酸鹽;油及脂肪酸之硫酸鹽及磺酸鹽;乙氧基化烷基酚之硫酸鹽及磺酸鹽;醇之硫酸鹽;乙氧基化醇之硫酸鹽;胺及醯胺之磺酸鹽,如
N,
N-烷基牛磺酸鹽;苯、異丙苯、甲苯、二甲苯、十二苯、及十三苯之磺酸鹽;縮合萘之磺酸鹽;萘及烷基萘之磺酸鹽;分餾石油之磺酸鹽;磺琥珀醯胺酸鹽(sulfosuccinamate);及磺琥珀酸鹽(sulfosuccinate)及其衍生物,如二烷基磺琥珀酸鹽。
有用的陽離子界面活性劑包括但不限於:醯胺及乙氧基化醯胺;胺,如
N-烷基丙二胺、三伸丙三胺、及二伸丙四胺,以及乙氧基化胺、乙氧基化二胺、及丙氧基化胺(從胺與環氧乙烷、環氧丙烷、環氧丁烷或上述者之混合物所製備者);胺鹽,如胺乙酸鹽及二胺鹽;四級銨鹽,如四級鹽、乙氧基化四級鹽、及雙四級鹽;以及胺氧化物,如烷基二甲基胺氧化物及雙-(2-羥乙基)-烷基胺氧化物。
亦可用於本發明組合物者係非離子界面活性劑與陰離子界面活性劑之混合物,或非離子界面活性劑與陽離子界面活性劑之混合物。非離子、陰離子、及陽離子界面活性劑及其建議用法係揭示於各式公開參考文獻,包括
McCutcheon’s Emulsifiers and Detergents, annual American and International Editions published by McCutcheon’s Division, The Manufacturing Confectioner Publishing Co.;Sisely and Wood,
Encyclopedia of Surface Active Agents, Chemical Publ.Co., Inc., New York, 1964;以及A. S. Davidson and B. Milwidsky,
Synthetic Detergents, Seventh Edition, John Wiley and Sons, New York, 1987。
本發明組合物亦可含有配方輔助劑及添加劑,所屬領域中具有通常知識者稱之為配方助劑(部分該等助劑可視為亦具有固體稀釋劑、液體稀釋劑或界面活性劑之功能)。此等配方輔助劑及添加劑可控制:pH(緩衝溶液)、處理期間的發泡(抗發泡劑如聚有機矽氧烷)、活性成份的沉降(懸浮劑)、黏度(觸變增稠劑)、容器中之微生物生長(抗微生物劑)、產物凍結(抗凍劑)、顏色(染料/顏料分散液)、洗除(成膜劑或黏著劑)、蒸發(蒸發阻滯劑)以及其他配方特性。成膜劑包括例如聚乙酸乙烯酯、聚乙酸乙烯酯共聚物、聚乙烯吡咯啶酮-乙酸乙烯酯共聚物、聚乙烯醇、聚乙烯醇共聚物及蠟。配方輔助劑及添加劑之實例包括列示於以下文獻者:
McCutcheon’s Volume 2: Functional Materials, annual International and North American editions published by McCutcheon’s Division, The Manufacturing Confectioner Publishing Co.;以及PCT公開WO 03/024222號。
式
1之化合物及任何其他活性成分一般係藉由將活性成分溶於溶劑中或藉由在液體或乾式稀釋劑中磨碎而併入本發明組合物中。溶液(包括可乳化濃縮物)可藉由簡單混合成分來製備。若意欲用作為可乳化濃縮物之液體組合物的溶劑與水不互溶,則典型會加入乳化劑以在用水稀釋時乳化該含活性成分之溶劑。粒徑最高達2,000 µm的活性成分漿液可使用介質研磨機來濕磨,以獲得平均直徑在3 µm以下的粒子。水性漿液可製成為成品懸浮液濃縮物(請參見例如U.S. 3,060,084)或藉由噴霧乾燥進一步加工以形成水分散性粒劑。乾式配方通常需要乾磨製程,其產生的平均粒徑在2到10 µm的範圍。塵粉及粉劑可藉由摻合、通常加上研磨(如以錘磨或流能研磨機)來製備。粒劑及丸劑可藉由將活性物質噴灑於預成形之粒狀載體或以黏聚技術來製備。參見Browning, 「Agglomeration」,
Chemical Engineering, December 4, 1967, pp 147–48、
Perry’s Chemical Engineer’s Handbook, 4th Ed., McGraw-Hill, New York, 1963, pages 8–57與後文、以及WO 91/13546。丸劑可如U.S. 4,172,714中所述製備。水分散性粒劑及水溶性粒劑可如U.S. 4,144,050、U.S. 3,920,442及DE 3,246,493中所教示者製備。片劑可如U.S. 5,180,587、U.S. 5,232,701及U.S. 5,208,030中所教示者製備。膜可如GB 2,095,558及U.S. 3,299,566中所教示者製備。
關於配方技術領域的進一步資訊,請參見T. S. Woods, 「The Formulator’s Toolbox – Product Forms for Modern Agriculture」 in
Pesticide Chemistry and Bioscience, The Food–Environment Challenge, T. Brooks and T. R. Roberts, Eds., Proceedings of the 9th International Congress on Pesticide Chemistry, The Royal Society of Chemistry, Cambridge, 1999, pp. 120–133。亦請參見U.S. 3,235,361第6欄第16行至第7欄第19行及實例10至41;U.S. 3,309,192第5欄第43行至第7欄第62行及實例8、12、15、39、41、52、53、58、132、138至140、162至164、166、167、及169至182;U.S. 2,891,855第3欄第66行至第5欄第17行及實例1至4;Klingman,
Weed Control as a Science, John Wiley and Sons, Inc., New York, 1961, pp 81–96;Hance等人,
Weed Control Handbook, 8th Ed., Blackwell Scientific Publications, Oxford, 1989;以及
Developments in formulation technology, PJB Publications, Richmond, UK, 2000。
在下列實例中,所有的百分比皆以重量計且所有配方皆以習用方式製備。化合物編號參照索引表A中的化合物。即使沒有進一步的闡述,相信所屬領域中具有通常知識者使用上述說明可最大程度地利用本發明。因此,以下實例僅為說明之用,而絕非以任何方式限制本發明之揭示內容。除非另有說明,否則百分比皆以重量計。
實例A
實例B
實例C
實例D
實例E
實例F
實例G
實例H
實例I
高強度濃縮物 | |
化合物1 | 98.5% |
矽氣凝膠 | 0.5% |
合成非晶細二氧化矽 | 1.0% |
可濕性粉劑 | |
化合物1 | 65.0% |
十二烷基酚聚乙二醇醚 | 2.0% |
木質磺酸鈉 | 4.0% |
矽鋁酸鈉 | 6.0% |
蒙脫土(經煅燒) | 23.0% |
粒劑 | |
化合物1 | 10.0% |
厄帖浦石粒劑(低揮發性物質,0.71/0.30 mm;U.S.S.25–50號篩) | 90.0% |
擠製丸劑 | |
化合物1 | 25.0% |
無水硫酸鈉 | 10.0% |
粗木質磺酸鈣 | 5.0% |
烷基萘磺酸鈉 | 1.0% |
鈣/鎂膨土 | 59.0% |
可乳化濃縮物 | |
化合物1 | 10.0% |
聚氧乙烯山梨糖醇己油酸酯(polyoxyethylene sorbitol hexoleate) | 20.0% |
C 6-C 10脂肪酸甲酯 | 70.0% |
微乳液 | |
化合物1 | 5.0% |
聚乙烯吡咯啶酮-乙酸乙烯酯共聚物 | 30.0% |
烷基聚葡萄糖苷 | 30.0% |
甘油單油酸酯 | 15.0% |
水 | 20.0% |
懸浮濃縮物 | |
化合物1 | 35% |
丁基聚氧乙烯/聚丙烯嵌段共聚物 | 4.0% |
硬脂酸/聚乙二醇共聚物 | 1.0% |
苯乙烯丙烯酸聚合物 | 1.0% |
三仙膠 | 0.1% |
丙二醇 | 5.0% |
聚矽氧基底消泡劑 | 0.1% |
1,2-苯並異噻唑啉-3-酮(1,2-benzisothiazolin-3-one) | 0.1% |
水 | 53.7% |
水乳液 | ||
化合物1 | 10.0% | |
丁基聚氧乙烯/聚丙烯嵌段共聚物 | 4.0% | |
硬脂酸/聚乙二醇共聚物 | 1.0% | |
苯乙烯丙烯酸聚合物 | 1.0% | |
三仙膠 | 0.1% | |
丙二醇 | 5.0% | |
聚矽氧基底消泡劑 | 0.1% | |
1,2-苯並異噻唑啉-3-酮(1,2-benzisothiazolin-3-one) | 0.1% | |
芳族石油基底烴 | 20.0 | |
水 | 58.7% | |
油分散液 | |
化合物1 | 25% |
聚氧乙烯山梨糖醇己油酸酯 | 15% |
有機修飾膨土 | 2.5% |
脂肪酸甲酯 | 57.5% |
本揭露亦包括如上述惟「化合物1」係經下列置換之實例A至實例I:「化合物2」、「化合物3」、「化合物4」、「化合物5」、「化合物6」、「化合物7」、「化合物8」、「化合物9」、「化合物10」、「化合物11」、「化合物12」、「化合物13」、「化合物14」、「化合物15」、「化合物16」、「化合物17」、「化合物18」、「化合物19」、「化合物20」、「化合物21」、「化合物22」、「化合物23」、「化合物24」、「化合物25」、「化合物26」、「化合物27」、「化合物28」、「化合物29」、「化合物30」、「化合物31」、「化合物32」、「化合物33」、「化合物34」、「化合物35」、「化合物36」、「化合物37」、「化合物38」、「化合物39」、「化合物40」、「化合物41」、「化合物42」、「化合物43」、「化合物44」、「化合物45」、「化合物46」、「化合物47」、「化合物48」、「化合物49」、「化合物50」、「化合物51」、「化合物52」、「化合物53」、「化合物54」、「化合物55」、「化合物56」、「化合物57」、「化合物58」、「化合物59」、「化合物60」、「化合物61」、「化合物62」、「化合物63」、「化合物64」、「化合物65」、「化合物66」、「化合物67」、「化合物68」、「化合物69」、「化合物70」、「化合物71」、「化合物72」、「化合物73」、「化合物74」、「化合物75」、「化合物76」、「化合物77」、「化合物78」、「化合物79」、「化合物80」、「化合物81」、「化合物82」、「化合物83」、「化合物84」、「化合物85」、「化合物86」、「化合物87」、「化合物88」、「化合物89」、「化合物90」、「化合物91」、「化合物92」、「化合物93」、「化合物94」、「化合物95」、「化合物96」、「化合物97」、「化合物98」、「化合物99」、「化合物100」、「化合物101」、「化合物102」、「化合物103」、「化合物104」、「化合物104」、「化合物106」、「化合物107」、「化合物108」、「化合物109」、「化合物110」、「化合物111」、「化合物112」、「化合物113」、「化合物114」、「化合物115」、「化合物116」、「化合物117」、「化合物118」、「化合物119」、「化合物120」、「化合物121」、「化合物122」、「化合物123」、「化合物124」、「化合物125」、「化合物126」、「化合物127」、「化合物128」、「化合物129」、「化合物130」、「化合物131」、「化合物132」、「化合物133」、「化合物134」、「化合物135」、「化合物136」、「化合物137」、「化合物138」、「化合物139」、「化合物140」、「化合物141」、「化合物142」、「化合物143」、「化合物144」、「化合物145」、或「化合物146」。
試驗結果指出,本發明化合物係高活性之萌前及/或萌後除草劑及/或植物生長調節劑。本發明化合物通常對於萌後雜草防治(即在雜草幼苖從土壤萌發後施用)與萌前雜草防治(即在雜草幼苖從土壤萌發前施用)顯示出最高活性。在想要完全防治所有植物的區域,諸如在燃料儲槽、工業倉儲區域、停車場、露天汽車電影院、機場、河岸、灌溉與其他水道、看板與高速公路及鐵路設施周圍,許多這些化合物對於廣大範圍之萌前或萌後雜草防治具有效用。許多本發明化合物經由下列方式而可用於選擇性防治作物/雜草混生中的禾草與闊葉雜草,包括在作物與雜草中進行選擇性代謝,或者對於作物與雜草中的生理抑制位點具有選擇性活性,或者在作物與雜草混生的環境之上或之中進行選擇性施放。所屬領域中具有通常知識者會認知到,化合物或化合物群組內之這些選擇性因子的較佳組合可藉由實施常規生物與/或生化檢定而輕易決定。重要農藝作物可對於本發明化合物顯示耐受性,包括但不限於苜蓿草、大麥、棉花、小麥、油菜、甜菜、玉米、高粱、大豆、稻米、燕麥、花生、蔬菜、番茄、馬鈴薯、多年生栽植作物包括咖啡、可可、油棕櫚、橡膠、甘蔗、柑橘、葡萄、果樹、堅果樹、香蕉、芭蕉、鳳梨、乾啤酒花、茶與林木如桉樹及針葉樹(例如火炬松)與草坪物種(例如肯塔基藍草、聖奧古斯丁草、肯德基菲斯克草與百慕達草)。本發明化合物可用於經基因轉殖或育種以引進除草劑抗性、表現對無脊椎動物害蟲具有毒性之蛋白質(諸如蘇力菌(
Bacillus thuringiensis)毒素)及/或表現其他有用性狀的作物。所屬領域中具有通常知識者會瞭解到,並非所有化合物對所有雜草皆同樣有效。或者,本化合物可用於修飾植物生長。
由於本發明化合物同時具有萌前與萌後除草活性,以藉由殺滅或毒傷非所欲植物或降低其生長以防治該植物,該等化合物可藉由各式方法有用地施用,該等方法涉及使除草有效量之本發明化合物(或包含該化合物與至少一種界面活性劑、固體稀釋劑、或液體稀釋劑之組合物)接觸非所欲植物之葉子或其他部位或非所欲植物之環境,如非所欲植物生長其中或圍繞非所欲植物之種子或其他繁殖體(propagule)之土壤或水。
本發明化合物之除草有效量係考慮多種因素而決定。這些因素包括:所選用之配方、施用方法、存在之植物的數量與種類、生長條件等。一般而言,本發明化合物之除草有效量係約0.001至20 kg/ha,而較佳範圍係約0.004至1 kg/ha。所屬領域中具有通常知識者可輕易決定要達到所欲雜草防治程度所需之除草有效量。
在一個常見實施例中,本發明化合物(典型以經配製組合物)係施用至包含所欲植物(例如作物)及非所欲植物(即雜草)的所在地而與生長介質(例如土壤)接觸,上述兩者可為種子、幼苖及/或較大植物。在此所在地中,包含本發明化合物之組合物可直接施用至植物或其部分(尤其是非所欲植物)及/或施用至與植物接觸之生長介質。
在經本發明化合物處理之所在地中的所欲植物的品種及栽培品種可藉由習用繁殖及育種方法或藉由基因工程方法來獲得。基因改造植物(基因轉殖植物)係異源基因(轉殖基因)已穩定整合至該植物基因體中者。藉由其在植物基因體中之特定位置來定義之轉殖基因稱為轉化或基因轉殖事件。
可依據本發明處理之所在地中的基因改造植物栽培品種包括對於一或多種生物壓力(害蟲如線蟲、昆蟲、蟎、真菌等)或非生物壓力(乾旱、寒冷溫度、土壤鹽度等)具有抗性者或者含有其他理想特徵者。植物可經基因改造以展現例如下列性狀:耐除草劑、抗昆蟲、油輪廓(oil profile)改變、或耐乾旱。含有單一基因轉化事件或多個轉化事件之組合的有用基因改造植物係列示於展示C中。關於展示C中所列示之基因改造的額外資訊可得自公開可用之資料庫,例如由美國農業部(U.S. Department of Agriculture)所維護者。
下列縮寫(T1至T37)係用於展示C中以表示性狀。「-」意指無此項目;「tol.」意指「耐受性(tolerance)」;且「res.」意指抗性。
展示C
*阿根廷油菜(
Brassica napus),**波蘭白菜(
B. rapa),#茄子
性狀 | 說明 | 性狀 | 說明 | 性狀 | 說明 |
T1 | 耐草甘膦 | T15 | 耐寒冷 | T27 | 高色胺酸 |
T2 | 高月桂酸油 | T16 | 耐咪唑啉酮除草劑 | T28 | 直立葉半矮生 |
T3 | 耐草銨膦 | T17 | α-澱粉酶改變 | T29 | 半矮生 |
T4 | 植酸鹽分解 | T18 | 授粉控制 | T30 | 耐低鐵 |
T5 | 耐苯腈(Oxynil) | T19 | 耐2,4-D | T31 | 油/脂肪酸改變 |
T6 | 耐疫病 | T20 | 離胺酸提高 | T32 | 耐HPPD |
T7 | 抗昆蟲 | T21 | 耐乾旱 | T33 | 高油 |
T9 | 花色改變 | T22 | 成熟/衰老延緩 | T34 | 耐芳基氧基烷酸鹽 |
T11 | 耐ALS除草劑 | T23 | 產物品質改變 | T35 | 耐硝草酮 |
T12 | 耐麥草畏 | T24 | 高纖維素 | T36 | 菸鹼減少 |
T13 | 抗過敏 | T25 | 澱粉/碳水化合物改變 | T37 | 產物改變 |
T14 | 耐鹽 | T26 | 抗昆蟲及疫病 |
作物 | 事件名稱 | 事件代碼 | 性狀 | 基因 |
苜蓿草 | J101 | MON-00101-8 | T1 | cp4 epsps (aroA:CP4) |
苜蓿草 | J163 | MON-ØØ163-7 | T1 | cp4 epsps (aroA:CP4) |
芥花* | 23-18-17(事件18) | CGN-89465-2 | T2 | te |
芥花* | 23-198(事件23) | CGN-89465-2 | T2 | te |
芥花* | 61061 | DP-Ø61Ø61-7 | T1 | gat4621 |
芥花* | 73496 | DP-Ø73496-4 | T1 | gat4621 |
芥花* | GT200 (RT200) | MON-89249-2 | T1 | cp4 epsps (aroA:CP4);goxv247 |
芥花* | GT73 (RT73) | MON-ØØØ73-7 | T1 | cp4 epsps (aroA:CP4);goxv247 |
芥花* | HCN10 (Topas 19/2) | - | T3 | bar |
芥花* | HCN28 (T45) | ACS-BNØØ8-2 | T3 | pat (syn) |
芥花* | HCN92 (Topas 19/2) | ACS-BNØØ7-1 | T3 | bar |
芥花* | MON88302 | MON-883Ø2-9 | T1 | cp4 epsps (aroA:CP4) |
芥花* | MPS961 | - | T4 | phyA |
芥花* | MPS962 | - | T4 | phyA |
芥花* | MPS963 | - | T4 | phyA |
芥花* | MPS964 | - | T4 | phyA |
芥花* | MPS965 | - | T4 | phyA |
芥花* | MS1 (B91-4) | ACS-BNØØ4-7 | T3 | bar |
芥花* | MS8 | ACS-BNØØ5-8 | T3 | bar |
芥花* | OXY-235 | ACS-BNØ11-5 | T5 | bxn |
芥花* | PHY14 | - | T3 | bar |
芥花* | PHY23 | - | T3 | bar |
芥花* | PHY35 | - | T3 | bar |
芥花* | PHY36 | - | T3 | bar |
芥花* | RF1 (B93-101) | ACS-BNØØ1-4 | T3 | bar |
芥花* | RF2 (B94-2) | ACS-BNØØ2-5 | T3 | bar |
芥花* | RF3 | ACS-BNØØ3-6 | T3 | bar |
豆類 | EMBRAPA 5.1 | EMB-PV051-1 | T6 | ac1(正義及反義) |
茄子# | EE-1 | - | T7 | cry1Ac |
棉花 | 19-51a | DD-Ø1951A-7 | T11 | S4-HrA |
棉花 | 281-24-236 | DAS-24236-5 | T3,T7 | pat (syn);cry1F |
棉花 | 3006-210-23 | DAS-21Ø23-5 | T3,T7 | pat (syn);cry1Ac |
棉花 | 31707 | - | T5,T7 | bxn;cry1Ac |
棉花 | 31803 | - | T5,T7 | bxn;cry1Ac |
棉花 | 31807 | - | T5,T7 | bxn;cry1Ac |
棉花 | 31808 | - | T5,T7 | bxn;cry1Ac |
棉花 | 42317 | - | T5,T7 | bxn;cry1Ac |
棉花 | BNLA-601 | - | T7 | cry1Ac |
棉花 | BXN10211 | BXN10211-9 | T5 | bxn;cry1Ac |
棉花 | BXN10215 | BXN10215-4 | T5 | bxn;cry1Ac |
棉花 | BXN10222 | BXN10222-2 | T5 | bxn;cry1Ac |
棉花 | BXN10224 | BXN10224-4 | T5 | bxn;cry1Ac |
棉花 | COT102 | SYN-IR102-7 | T7 | vip3A(a) |
棉花 | COT67B | SYN-IR67B-1 | T7 | cry1Ab |
棉花 | COT202 | - | T7 | vip3A |
棉花 | 事件1 | - | T7 | cry1Ac |
棉花 | GMF Cry1A | GTL-GMF311-7 | T7 | cry1Ab-Ac |
棉花 | GHB119 | BCS-GH005-8 | T7 | cry2Ae |
棉花 | GHB614 | BCS-GH002-5 | T1 | 2mepsps |
棉花 | GK12 | - | T7 | cry1Ab-Ac |
棉花 | LLCotton25 | ACS-GH001-3 | T3 | bar |
棉花 | MLS 9124 | - | T7 | cry1C |
棉花 | MON1076 | MON-89924-2 | T7 | cry1Ac |
棉花 | MON1445 | MON-01445-2 | T1 | cp4 epsps (aroA:CP4) |
棉花 | MON15985 | MON-15985-7 | T7 | cry1Ac;cry2Ab2 |
棉花 | MON1698 | MON-89383-1 | T7 | cp4 epsps (aroA:CP4) |
棉花 | MON531 | MON-00531-6 | T7 | cry1Ac |
棉花 | MON757 | MON-00757-7 | T7 | cry1Ac |
棉花 | MON88913 | MON-88913-8 | T1 | cp4 epsps (aroA:CP4) |
棉花 | Nqwe Chi 6 Bt | - | T7 | - |
棉花 | SKG321 | - | T7 | cry1A;CpTI |
棉花 | T303-3 | BCS-GH003-6 | T3,T7 | cry1Ab;bar |
棉花 | T304-40 | BCS-GH004-7 | T3,T7 | cry1Ab;bar |
棉花 | CE43-67B | - | T7 | cry1Ab |
棉花 | CE46-02A | - | T7 | cry1Ab |
棉花 | CE44-69D | - | T7 | cry1Ab |
棉花 | 1143-14A | - | T7 | cry1Ab |
棉花 | 1143-51B | - | T7 | cry1Ab |
棉花 | T342-142 | - | T7 | cry1Ab |
棉花 | PV-GHGT07 (1445) | - | T1 | cp4 epsps (aroA:CP4) |
棉花 | EE-GH3 | - | T1 | mepsps |
棉花 | EE-GH5 | - | T7 | cry1Ab |
棉花 | MON88701 | MON-88701-3 | T3,T12 | 經修改dmo;bar |
棉花 | OsCr11 | - | T13 | 經修改Cry j |
亞麻 | FP967 | CDC-FL001-2 | T11 | als |
扁豆 | RH44 | - | T16 | als |
玉米 | 3272 | SYN-E3272-5 | T17 | amy797E |
玉米 | 5307 | SYN-05307-1 | T7 | ecry3.1Ab |
玉米 | 59122 | DAS-59122-7 | T3,T7 | cry34Ab1;cry35Ab1;pat |
玉米 | 676 | PH-000676-7 | T3,T18 | pat;dam |
玉米 | 678 | PH-000678-9 | T3,T18 | pat;dam |
玉米 | 680 | PH-000680-2 | T3,T18 | pat;dam |
玉米 | 98140 | DP-098140-6 | T1,T11 | gat4621;zm-hra |
玉米 | Bt10 | - | T3,T7 | cry1Ab;pat |
玉米 | Bt176 (176) | SYN-EV176-9 | T3,T7 | cry1Ab;bar |
玉米 | BVLA430101 | - | T4 | phyA2 |
玉米 | CBH-351 | ACS-ZM004-3 | T3,T7 | cry9C;bar |
玉米 | DAS40278-9 | DAS40278-9 | T19 | aad-1 |
玉米 | DBT418 | DKB-89614-9 | T3,T7 | cry1Ac;pinII;bar |
玉米 | DLL25 (B16) | DKB-89790-5 | T3 | bar |
玉米 | GA21 | MON-00021-9 | T1 | mepsps |
玉米 | GG25 | - | T1 | mepsps |
玉米 | GJ11 | - | T1 | mepsps |
玉米 | Fl117 | - | T1 | mepsps |
玉米 | GAT-ZM1 | - | T3 | pat |
玉米 | LY038 | REN-00038-3 | T20 | cordapA |
玉米 | MIR162 | SYN-IR162-4 | T7 | vip3Aa20 |
玉米 | MIR604 | SYN-IR604-5 | T7 | mcry3A |
玉米 | MON801 (MON80100) | MON801 | T1,T7 | cry1Ab;cp4 epsps (aroA:CP4);goxv247 |
玉米 | MON802 | MON-80200-7 | T1,T7 | cry1Ab;cp4 epsps (aroA:CP4);goxv247 |
玉米 | MON809 | PH-MON-809-2 | T1,T7 | cry1Ab;cp4 epsps (aroA:CP4);goxv247 |
玉米 | MON810 | MON-00810-6 | T1,T7 | cry1Ab;cp4 epsps (aroA:CP4);goxv247 |
玉米 | MON832 | - | T1 | cp4 epsps (aroA:CP4);goxv247 |
玉米 | MON863 | MON-00863-5 | T7 | cry3Bb1 |
玉米 | MON87427 | MON-87427-7 | T1 | cp4 epsps (aroA:CP4) |
玉米 | MON87460 | MON-87460-4 | T21 | cspB |
玉米 | MON88017 | MON-88017-3 | T1,T7 | cry3Bb1;cp4 epsps (aroA:CP4) |
玉米 | MON89034 | MON-89034-3 | T7 | cry2Ab2;cry1A.105 |
玉米 | MS3 | ACS-ZM001-9 | T3,T18 | bar;細菌核糖核酸酶(barnase) |
玉米 | MS6 | ACS-ZM005-4 | T3,T18 | bar;細菌核糖核酸酶(barnase) |
玉米 | NK603 | MON-00603-6 | T1 | cp4 epsps (aroA:CP4) |
玉米 | T14 | ACS-ZM002-1 | T3 | pat (syn) |
玉米 | T25 | ACS-ZM003-2 | T3 | pat (syn) |
玉米 | TC1507 | DAS-01507-1 | T3,T7 | cry1Fa2;pat |
玉米 | TC6275 | DAS-06275-8 | T3,T7 | mocry1F;bar |
玉米 | VIP1034 | - | T3,T7 | vip3A;pat |
玉米 | 43A47 | DP-043A47-3 | T3,T7 | cry1F;cry34Ab1;cry35Ab1;pat |
玉米 | 40416 | DP-040416-8 | T3,T7 | cry1F;cry34Ab1;cry35Ab1;pat |
玉米 | 32316 | DP-032316-8 | T3,T7 | cry1F;cry34Ab1;cry35Ab1;pat |
玉米 | 4114 | DP-004114-3 | T3,T7 | cry1F;cry34Ab1;cry35Ab1;pat |
甜瓜 | 甜瓜A | - | T22 | sam-k |
甜瓜 | 甜瓜B | - | T22 | sam-k |
木瓜 | 55-1 | CUH-CP551-8 | T6 | prsv cp |
木瓜 | 63-1 | CUH-CP631-7 | T6 | prsv cp |
木瓜 | 華農1號(Huanong No. 1) | - | T6 | prsv rep |
木瓜 | X17-2 | UFL-X17CP-6 | T6 | prsv cp |
李子 | C-5 | ARS-PLMC5-6 | T6 | ppv cp |
芥花** | ZSR500 | - | T1 | cp4 epsps (aroA:CP4);goxv247 |
芥花** | ZSR502 | - | T1 | cp4 epsps (aroA:CP4);goxv247 |
芥花** | ZSR503 | - | T1 | cp4 epsps (aroA:CP4);goxv247 |
稻米 | 7Crp#242-95-7 | - | T13 | 7crp |
稻米 | 7Crp#10 | - | T13 | 7crp |
稻米 | GM Shanyou 63 | - | T7 | cry1Ab;cry1Ac |
稻米 | Huahui-1/TT51-1 | - | T7 | cry1Ab;cry1Ac |
稻米 | LLRICE06 | ACS-OS001-4 | T3 | bar |
稻米 | LLRICE601 | BCS-OS003-7 | T3 | bar |
稻米 | LLRICE62 | ACS-OS002-5 | T3 | bar |
稻米 | Tarom molaii + cry1Ab | - | T7 | cry1Ab(截短) |
稻米 | GAT-OS2 | - | T3 | bar |
稻米 | GAT-OS3 | - | T3 | bar |
稻米 | PE-7 | - | T7 | Cry1Ac |
稻米 | 7Crp#10 | - | T13 | 7crp |
稻米 | KPD627-8 | - | T27 | OASA1D |
稻米 | KPD722-4 | - | T27 | OASA1D |
稻米 | KA317 | - | T27 | OASA1D |
稻米 | HW5 | - | T27 | OASA1D |
稻米 | HW1 | - | T27 | OASA1D |
稻米 | B-4-1-18 | - | T28 | Δ OsBRI1 |
稻米 | G-3-3-22 | - | T29 | OSGA2ox1 |
稻米 | AD77 | - | T6 | DEF |
稻米 | AD51 | - | T6 | DEF |
稻米 | AD48 | - | T6 | DEF |
稻米 | AD41 | - | T6 | DEF |
稻米 | 13pNasNa800725atAprt1 | - | T30 | HvNAS1;HvNAAT-A;APRT |
稻米 | 13pAprt1 | - | T30 | APRT |
稻米 | gHvNAS1-gHvNAAT-1 | - | T30 | HvNAS1;HvNAAT-A;HvNAAT-B |
稻米 | gHvIDS3-1 | - | T30 | HvIDS3 |
稻米 | gHvNAAT1 | - | T30 | HvNAAT-A;HvNAAT-B |
稻米 | gHvNAS1-1 | - | T30 | HvNAS1 |
稻米 | NIA-OS006-4 | - | T6 | WRKY45 |
稻米 | NIA-OS005-3 | - | T6 | WRKY45 |
稻米 | NIA-OS004-2 | - | T6 | WRKY45 |
稻米 | NIA-OS003-1 | - | T6 | WRKY45 |
稻米 | NIA-OS002-9 | - | T6 | WRKY45 |
稻米 | NIA-OS001-8 | - | T6 | WRKY45 |
稻米 | OsCr11 | - | T13 | 經修改Cry j |
稻米 | 17053 | - | T1 | cp4 epsps (aroA:CP4) |
稻米 | 17314 | - | T1 | cp4 epsps (aroA:CP4) |
玫瑰 | WKS82 / 130-4-1 | IFD-52401-4 | T9 | 5AT;bp40 (f3'5'h) |
玫瑰 | WKS92 / 130-9-1 | IFD-52901-9 | T9 | 5AT;bp40 (f3'5'h) |
大豆 | 260-05 (G94-1, G94-19, G168) | - | T9 | gm-fad2-1(靜默基因座) |
大豆 | A2704-12 | ACS-GM005-3 | T3 | pat |
大豆 | A2704-21 | ACS-GM004-2 | T3 | pat |
大豆 | A5547-127 | ACS-GM006-4 | T3 | pat |
大豆 | A5547-35 | ACS-GM008-6 | T3 | pat |
大豆 | CV127 | BPS-CV127-9 | T16 | csr1-2 |
大豆 | DAS68416-4 | DAS68416-4 | T3 | pat |
大豆 | DP305423 | DP-305423-1 | T11,T31 | gm-fad2-1(靜默基因座);gm-hra |
大豆 | DP356043 | DP-356043-5 | T1,T31 | gm-fad2-1(靜默基因座);gat4601 |
大豆 | FG72 | MST-FG072-3 | T32,T1 | 2mepsps;hppdPF W336 |
大豆 | GTS 40-3-2 (40-3-2) | MON-04032-6 | T1 | cp4 epsps (aroA:CP4) |
大豆 | GU262 | ACS-GM003-1 | T3 | pat |
大豆 | MON87701 | MON-87701-2 | T7 | cry1Ac |
大豆 | MON87705 | MON-87705-6 | T1,T31 | fatb1-A(正義及反義);fad2-1A(正義及反義);cp4 epsps (aroA:CP4) |
大豆 | MON87708 | MON-87708-9 | T1,T12 | dmo;cp4 epsps (aroA:CP4) |
大豆 | MON87769 | MON-87769-7 | T1,T31 | Pj.D6D;Nc.Fad3;cp4 epsps (aroA:CP4) |
大豆 | MON89788 | MON-89788-1 | T1 | cp4 epsps (aroA:CP4) |
大豆 | W62 | ACS-GM002-9 | T3 | bar |
大豆 | W98 | ACS-GM001-8 | T3 | bar |
大豆 | MON87754 | MON-87754-1 | T33 | dgat2A |
大豆 | DAS21606 | DAS-21606 | T34,T3 | 經修改aad-12;pat |
大豆 | DAS44406 | DAS-44406-6 | T1,T3,T34 | 經修改aad-12;2mepsps;pat |
大豆 | SYHT04R | SYN-0004R-8 | T35 | 經修改avhppd |
大豆 | 9582.814.19.1 | - | T3,T7 | cry1Ac, cry1F, PAT |
南瓜 | CZW3 | SEM-ØCZW3-2 | T6 | cmv cp, zymv cp, wmv cp |
南瓜 | ZW20 | SEM-0ZW20-7 | T6 | zymv cp, wmv cp |
甜菜 | GTSB77 (T9100152) | SY-GTSB77-8 | T1 | cp4 epsps (aroA:CP4);goxv247 |
甜菜 | H7-1 | KM-000H71-4 | T1 | cp4 epsps (aroA:CP4) |
甜菜 | T120-7 | ACS-BV001-3 | T3 | pat |
甜菜 | T227-1 | - | T1 | cp4 epsps (aroA:CP4) |
甘蔗 | NXI-1T | - | T21 | EcbetA |
向日葵 | X81359 | - | T16 | als |
胡椒 | PK-SP01 | - | T6 | cmv cp |
菸草 | C/F/93/08-02 | - | T5 | bxn |
菸草 | 載體21-41 | - | T36 | NtQPT1(反義) |
向日葵 | X81359 | - | T16 | als |
小麥 | MON71800 | MON-718ØØ-3 | T1 | cp4 epsps (aroA:CP4) |
雖然最典型而言,本發明化合物係用以防治非所欲植物,然而使經處理所在地中之所欲植物與本發明化合物接觸,可能對於所欲植物之基因性狀導致超加成或協同效果,包括透過基因改造所導入之性狀。舉例而言,對於植食性昆蟲害蟲或植物疫病之抵抗性、對於生物性/非生物性壓力之耐受性或儲存穩定性可能會高於預期來自所欲植物中之基因性狀。
本發明之一實施例係一種防治非所欲植物在基因改造植物中生長之方法,該等基因改造植物展現草甘膦耐受性、草銨膦耐受性、ALS除草劑耐受性、麥草畏耐受性、咪唑啉酮除草劑耐受性、2,4-D耐受性、HPPD耐受性、及硝草酮耐受性的性狀,該方法包含使該植物或其環境與除草有效量的式1之化合物接觸。
本發明化合物亦可與一或多種其他生物活性化合物或藥劑包括除草劑、除草劑安全劑、殺真菌劑、殺蟲劑、殺線蟲劑、殺菌劑、殺蟎劑、生長調節素如昆蟲蛻皮抑制劑與生根刺激劑、化學滅菌劑、化學傳訊素、驅蟲劑、誘引劑、費洛蒙、激食因子、植物營養素、其他生物活性化合物或蟲生細菌、病毒或真菌混合以形成多組分殺蟲劑,從而提供更廣泛的農業保護範圍。本發明化合物與其他除草劑之混合物可擴展對抗額外雜草物種的活性範圍,並且壓抑任何抗性生物型的增生。因此本發明亦關於包含式
1之化合物(以除草有效量)以及至少一種額外生物活性化合物或藥劑(以生物有效量)之組合物,並可進一步包含界面活性劑、固體稀釋劑或液體稀釋劑之至少一者。其他生物活性化合物或藥劑可配製於包含界面活性劑、固體稀釋劑或液體稀釋劑之至少一者之組合物中。對於本發明之混合物而言,一或多種其他生物活性化合物或藥劑可與式
1之化合物一起配製以形成預混物,或一或多種其他生物活性化合物或藥劑可與式
1之化合物分開配製,並且在施用前將該等配方組合在一起(例如於噴灑桶中),或者是接連施用。
一或多種以下除草劑與本發明化合物之混合物對於雜草防治尤為有用:乙草胺(acetochlor)、亞喜芬(acifluorfen)與其鈉鹽、苯草醚(aclonifen)、丙烯醛(acrolein, 2‑propenal)、拉草(alachlor)、亞汰草(alloxydim)、草殺淨(ametryn)、胺唑草酮(amicarbazone)、醯嘧磺隆(amidosulfuron)、胺環吡克(aminocyclopyrachlor)與其酯(例如甲酯、乙酯)及鹽(例如鈉鹽、鉀鹽)、氯胺基吡啶酸(aminopyralid)、殺草強(amitrole)、胺磺酸銨(ammonium sulfamate)、莎稗磷(anilofos)、亞速爛(asulam)、草脫淨(atrazine)、四唑嘧磺隆(azimsulfuron)、氟丁草胺(beflubutamid)、草除靈(benazolin)、草除靈乙酯(benazolin‑ethyl)、醯苯草酮(bencarbazone)、倍尼芬(benfluralin)、呋草黃(benfuresate)、免速隆(bensulfuron‑methyl)、地散磷(bensulide)、本達隆(bentazone)、苯並雙環酮(benzobicyclon)、吡草酮(benzofenap)、二環吡草酮(bicyclopyrone)、治草醚(bifenox)、畢拉草(bilanafos)、雙草醚(bispyribac)與其鈉鹽、克草(bromacil)、溴布泰(bromobutide)、溴酚肟(bromofenoxim)、溴苯腈(bromoxynil)、溴苯腈辛酸酯(bromoxynil octanoate)、丁基拉草(butachlor)、布芬草(butafenacil)、抑草磷(butamifos)、比達寧(butralin)、丁苯草酮(butroxydim)、拔敵草(butylate)、苯酮唑(cafenstrole)、草長滅(carbetamide)、乙唑草酮(carfentrazone‑ethyl)、兒茶素(catechin)、甲氧基護谷(chlomethoxyfen)、克攔本(chloramben)、滅落寧(chlorbromuron)、氯甲丹(chlorflurenol-methyl)、氯草敏(chloridazon)、氯嘧磺隆(chlorimuron‑ethyl)、綠麥隆(chlorotoluron)、克普芬(chlorpropham)、氯磺隆(chlorsulfuron)、大克草(chlorthal‑dimethyl)、草克樂(chlorthiamid)、吲哚酮草酯(cinidon-ethyl)、環庚草醚(cinmethylin)、西速隆(cinosulfuron)、氯醯草膦(clacyfos)、環苯草酮(clefoxydim)、剋草同(clethodim)、炔草酯(clodinafop-propargyl)、可滅蹤(clomazone)、克普草(clomeprop)、畢克草(clopyralid)、畢克草醇胺(clopyralid‑olamine)、氯酯磺草胺(cloransulam-methyl)、苄草隆(cumyluron)、氰乃淨(cyanazine)、草滅特(cycloate)、環比瑞摩(cyclopyrimorate)、環磺隆(cyclosulfamuron)、環殺草(cycloxydim)、丁基賽伏草(cyhalofop-butyl)、2,4‑D與其丁氧乙酯(butotyl ester)、丁酯、異辛酯(isoctyl ester)與異丙酯及其二甲銨鹽、二乙醇胺(diolamine)鹽與三乙醇胺(trolamine)鹽、殺草隆(daimuron)、得拉本(dalapon)、得拉本鈉(dalapon‑sodium)、邁隆(dazomet)、2,4‑DB與其二甲銨鹽、鉀鹽及鈉鹽、甜菜安(desmedipham)、敵草淨(desmetryn)、麥草畏(dicamba)與其二乙二醇銨(diglycolammonium)鹽、二甲銨鹽、鉀鹽及鈉鹽、二氯苯腈(dichlobenil)、滴丙酸(dichlorprop)、甲基禾草靈(diclofop‑methyl)、雙氯磺草胺(diclosulam)、燕麥枯硫酸甲酯(difenzoquat metilsulfate)、吡氟草胺(diflufenican)、二氟吡隆(diflufenzopyr)、惡唑隆(dimefuron)、哌草丹(dimepiperate)、二甲草胺(dimethachlor)、愛落殺(dimethametryn)、汰草滅(dimethenamid)、汰草滅-P、穫萎得(dimethipin)、二甲胂酸(dimethylarsinic acid)與其鈉鹽、敵樂胺(dinitramine)、特樂酚(dinoterb)、大芬滅(diphenamid)、敵草快二溴化物(diquat dibromide)、汰硫草(dithiopyr)、達有龍(diuron)、DNOC、茵多酸(endothal)、EPTC、戊草丹(esprocarb)、乙丁烯氟靈(ethalfluralin)、胺苯磺隆(ethametsulfuron‑methyl)、乙嗪草酮(ethiozin)、乙氧呋草黃(ethofumesate)、氯氟草醚(ethoxyfen)、亞速隆(ethoxysulfuron)、乙氧苯草胺(etobenzanid)、乙基芬殺草(fenoxaprop‑ethyl)、乙基芬殺草-P (fenoxaprop‑P-ethyl)、異噁苯碸(fenoxasulfone)、芬昆諾三酮(fenquinotrione)、四唑草胺(fentrazamide)、非草隆(fenuron)、非草隆-TCA (fenuron‑TCA)、麥草伏-甲酯(flamprop‑methyl)、麥草伏-M-異丙酯(flamprop‑M‑isopropyl)、麥草伏-M-甲酯(flamprop‑M‑methyl)、伏速隆(flazasulfuron)、雙氟磺草胺(florasulam)、伏寄普丁酯(fluazifop‑butyl)、伏寄普-P-丁酯(fluazifop‑P‑butyl)、異丙吡草酯(fluazolate)、氟酮磺隆(flucarbazone)、氟吡磺隆(flucetosulfuron)、氟消草(fluchloralin)、噻草胺(flufenacet)、氟噠嗪草(flufenpyr)、氟噠嗪草酯(flufenpyr-ethyl)、唑嘧磺草胺(flumetsulam)、氟烯草酸(flumiclorac‑pentyl)、丙炔氟草胺(flumioxazin)、伏草隆(fluometuron)、乙羧氟草醚(fluoroglycofen‑ethyl)、氟胺草唑(flupoxam)、氟啶嘧磺隆(flupyrsulfuron‑methyl)與其鈉鹽、抑草丁(flurenol)、芴丁酯(flurenol-butyl)、氟啶草酮(fluridone)、氟草吡酮(flurochloridone)、氟氯比(fluroxypyr)、呋草酮(flurtamone)、氟噻甲草酯(fluthiacet‑methyl)、氟磺胺草醚(fomesafen)、甲醯胺磺隆(foramsulfuron)、殺木膦銨(fosamine‑ammonium)、草銨膦(glufosinate)、草銨膦銨(glufosinate‑ammonium)、草銨膦-P (glufosinate-P)、草甘膦(glyphosate)與其鹽如銨鹽、異丙銨鹽、鉀鹽、鈉鹽(包括倍半鈉鹽)及三甲基硫鹽(亦稱為草硫膦(sulfosate))、哈洛昔芬(halauxifen)、甲基哈洛昔芬(halauxifen-methyl)、合速隆(halosulfuron‑methyl)、合氯氟伊托酯(haloxyfop‑etotyl)、甲基合氯氟(haloxyfop-methyl)、菲殺淨(hexazinone)、海丹托西叮(hydantocidin)、咪草酯(imazamethabenz‑methyl)、甲氧咪草煙(imazamox)、甲咪唑煙酸(imazapic)、依滅草(imazapyr)、滅草喹(imazaquin)、滅草喹銨(imazaquin‑ammonium)、咪草煙(imazethapyr)、咪草煙銨(imazethapyr‑ammonium)、依速隆(imazosulfuron)、茚草酮(indanofan)、三嗪茚草胺(indaziflam)、依歐芬速隆(iofensulfuron)、甲基碘磺隆(iodosulfuron-methyl)、碘苯腈(ioxynil)、碘苯腈辛酸酯(ioxynil octanoate)、碘苯腈鈉(ioxynil‑sodium)、艾分卡斑唑(ipfencarbazone)、異丙隆(isoproturon)、愛速隆(isouron)、異噁草胺(isoxaben)、異噁唑草酮(isoxaflutole)、異噁氯草酮(isoxachlortole)、乳氟禾草靈(lactofen)、環草定(lenacil)、理有龍(linuron)、順丁烯二醯肼(maleic hydrazide)、MCPA與其鹽(例如MCPA-二甲銨鹽、MCPA-鉀鹽與MCPA-鈉鹽)、酯(例如MCPA-2‑乙基己酯、MCPA-丁氧乙酯)與硫酯(例如MCPA-硫乙酯)、MCPB與其鹽(例如MCPB-鈉鹽)及酯(例如MCPB-乙酯)、甲氯丙酸(mecoprop)、甲氯丙酸-P (mecoprop‑P)、滅芬草(mefenacet)、美福泰(mefluidide)、甲磺胺磺隆(mesosulfuron-methyl)、硝草酮(mesotrione)、威百畝(metam‑sodium)、惡唑醯草胺(metamifop)、苯嗪草酮(metamitron)、滅草胺(metazachlor)、雙醚氯吡嘧磺隆(metazosulfuron)、甲草苯隆(methabenzthiazuron)、甲胂酸(methylarsonic acid)與其鈣鹽、單銨鹽、單鈉鹽及二鈉鹽、甲基汰草龍(methyldymron)、吡喃隆(metobenzuron)、溴谷隆(metobromuron)、莫多草(metolachlor)、S-莫多草(S-metolachlor)、磺草唑胺(metosulam)、甲氧隆(metoxuron)、滅必淨(metribuzin)、甲磺隆(metsulfuron‑methyl)、稻得壯(molinate)、綠谷隆(monolinuron)、萘丙胺(naproanilide)、滅落脫(napropamide)、滅落脫-M (napropamide-M)、鈉得爛(naptalam)、草不隆(neburon)、煙嘧磺隆(nicosulfuron)、氟草敏(norflurazon)、坪草丹(orbencarb)、嘧苯胺磺隆(orthosulfamuron)、胺磺樂靈(oryzalin)、快噁草酮(oxadiargyl)、樂滅草(oxadiazon)、環氧嘧磺隆(oxasulfuron)、噁嗪草酮(oxaziclomefone)、復祿芬(oxyfluorfen)、巴拉刈二氯鹽(paraquat dichloride)、克草蜢(pebulate)、壬酸(pelargonic acid)、施得圃(pendimethalin)、平速爛(penoxsulam)、蔬草滅(pentanochlor)、環戊惡草酮(pentoxazone)、佈福松(perfluidone)、烯草胺(pethoxamid)、百特胺(pethoxyamid)、甜菜寧(phenmedipham)、毒莠定(picloram)、毒莠定鉀(picloram‑potassium)、氟吡醯草胺(picolinafen)、唑啉草酯(pinoxaden)、哌草磷(piperophos)、普拉草(pretilachlor)、氟嘧磺隆(primisulfuron‑methyl)、胺氟樂靈(prodiamine)、氯苯噻草酮(profoxydim)、撲滅通(prometon)、撲草凈(prometryn)、雷蒙得(propachlor)、除草靈(propanil)、普拔草(propaquizafop)、普拔根(propazine)、苯胺靈(propham)、異丙草胺(propisochlor)、丙苯磺隆(propoxycarbazone)、咪唑嘧磺隆(propyrisulfuron)、戊炔草胺(propyzamide)、芐草丹(prosulfocarb)、氟磺隆(prosulfuron)、雙唑草腈(pyraclonil)、吡草醚(pyraflufen-ethyl)、磺醯草吡唑(pyrasulfotole)、雙唑草晴(pyrazogyl)、苄草唑(pyrazolynate)、普芬草(pyrazoxyfen)、百速隆(pyrazosulfuron‑ethyl)、嘧啶肟草醚(pyribenzoxim)、稗草畏(pyributicarb)、必汰草(pyridate)、環酯草醚(pyriftalid)、嘧草醚(pyriminobac‑methyl)、嘧啶硫蕃(pyrimisulfan)、嘧草硫醚(pyrithiobac)、嘧草硫醚鈉(pyrithiobac‑sodium)、派羅克殺草碸(pyroxasulfone)、啶磺草胺(pyroxsulam)、快克草(quinclorac)、氯甲喹啉酸(quinmerac)、莫克草(quinoclamine)、乙基快伏草(quizalofop‑ethyl)、乙基快伏草-P (quizalofop‑P‑ethyl)、喹禾糠酯(quizalofop‑P‑tefuryl)、玉嘧磺隆(rimsulfuron)、嘧啶肟草醚(saflufenacil)、西殺草(sethoxydim)、環草隆(siduron)、草滅淨(simazine)、西草淨(simetryn)、磺草酮(sulcotrione)、甲磺草胺(sulfentrazone)、甲嘧磺隆(sulfometuron‑methyl)、磺醯磺隆(sulfosulfuron)、2,3,6-TBA、TCA、TCA‑鈉、牧草胺(tebutam)、丁噻隆(tebuthiuron)、特呋三酮(tefuryltrione)、環磺酮(tembotrione)、得殺草(tepraloxydim)、特草定(terbacil)、甲氧去草淨(terbumeton)、特丁津(terbuthylazine)、去草淨(terbutryn)、欣克草(thenylchlor)、噻草定(thiazopyr)、酮脲磺草吩酯(thiencarbazone)、噻吩磺隆(thifensulfuron‑methyl)、殺丹(thiobencarb)、氟丙嘧草酯(tiafenacil)、仲草丹(tiocarbazil)、托派拉雷(tolpyralate)、苯吡唑草酮(topramezone)、肟草酮(tralkoxydim)、野燕畏(tri‑allate)、氟酮磺草胺(triafamone)、醚苯磺隆(triasulfuron)、三唑侖(triaziflam)、苯磺隆(tribenuron‑methyl)、三氯比(triclopyr)、丁氧乙基三氯比(triclopyr‑butotyl)、三氯比三乙銨(triclopyr-triethylammonium)、三地芬(tridiphane)、草達津(trietazine)、三氟啶磺隆(trifloxysulfuron)、三氟草嗪(trifludimoxazin)、三福林(trifluralin)、氟胺磺隆(triflusulfuron‑methyl)、三氟甲磺隆(tritosulfuron)、萬隆(vernolate)、3-(2-氯-3,6-二氟苯基)-4-羥基-1-甲基-1,5-萘啶-2(1
H)-酮、5-氯-3-[(2-羥基-6-氧-1-環己烯-1-基)羰基]-1-(4-甲氧苯基)-2(1
H)-喹㗁啉酮、2-氯-
N-(1-甲基-1
H-四唑-5-基)-6-(三氟甲基)-3-吡啶甲醯胺、7-(3,5-二氯-4-吡啶基)-5-(2,2-二氟乙基)-8-羥基吡啶並[2,3-
b]吡嗪-6(5
H-酮)、4-(2,6-二乙基-4-甲基苯基)-5-羥基-2,6-二甲基-3(2
H)-嗒𠯤酮)、5-[[(2,6-二氟苯基)甲氧基]甲基]-4,5-二氫-5-甲基-3-(3-甲基-2-噻吩基)異㗁唑(先前為methioxolin)、4-(4-氟苯基)-6-[(2-羥基-6-氧-1-環己烯-1-基)羰基]-2-甲基-1,2,4-三𠯤-3,5(2
H,4
H)-二酮、4-胺基-3-氯-6-(4-氯-2-氟-3-甲氧苯基)-5-氟-2-吡啶羧酸甲酯、2-甲基-3-(甲基磺醯基)-
N-(1-甲基-1
H-四唑-5-基)-4-(三氟甲基)苯甲醯胺、以及2-甲基-
N-(4-甲基-1,2,5-㗁二唑-3-基)-3-(甲基亞磺醯基)-4-(三氟甲基)苯甲醯胺。其他除草劑亦包括生物除草劑如損毀鏈格孢菌(
Alternaria destruensSimmons)、刺盤孢炭疽菌(
Colletotrichum gloeosporiodes(Penz.)Penz.& Sacc.)、稗內臍蠕孢菌(
Drechsiera monoceras, MTB-951)、疣孢漆斑菌(
Myrothecium verrucaria(Albertini & Schweinitz) Ditmar: Fries)、棕櫚疫病菌(
Phytophthora palmivora(Butl.)Butl.)及遏藍菜柄鏽菌(
Puccinia thlaspeosSchub.)。
本發明化合物亦可與植物生長調節素(諸如艾維激素(aviglycine)、
N-(苯基甲基)-1
H-嘌呤-6-胺、丙醯芸苔素內酯(epocholeone)、吉貝素(gibberellic acid)、吉貝素(gibberellin) A
4及A
7、超敏蛋白(harpin protein)、縮節胺(mepiquat chloride)、調環酸鈣(prohexadione calcium)、茉莉酸丙酯(prohydrojasmon)、復硝酚鈉(sodium nitrophenolate)與抗倒酯(trinexapac-methyl))及植物生長修改生物(諸如仙人掌桿菌(
Bacillus cereus)菌株BP01)組合使用。
農業保護劑(即除草劑、除草劑安全劑、殺蟲劑、殺真菌劑、殺線蟲劑、殺蟎劑與生物劑)的一般參考文獻包括
The Pesticide Manual, 13th Edition, C. D. S. Tomlin, Ed., British Crop Protection Council, Farnham, Surrey, U.K., 2003及
The BioPesticide Manual,
2nd Edition, L. G. Copping, Ed., British Crop Protection Council, Farnham, Surrey, U.K., 2001。
對於使用一或多種這些各式混合伙伴藥劑之實施例而言,混合伙伴藥劑之典型用量類似於混合物伙伴藥劑單獨使用時之慣常量。更具體在混合物中,活性成分通常以產品標籤上指明單獨使用活性成分之施用率的二分之一到全部來施用。這些量係列示於參考文獻如
The Pesticide Manual及
The BioPesticide Manual中。這些各式混合伴(總計)對式
1之化合物的重量比例一般介於約1:3000與約3000:1之間。值得注意的是介於約1:300與約300:1之間的重量百分比(例如介於約1:30與約30:1之間的比例)。所屬技術領域具有通常知識者可透過簡單實驗,輕易決定活性成分要達成所欲生物活性範圍所需之生物有效量。將為顯而易見的是,包括這些額外組分可擴展雜草防治的範圍,使其超出單獨使用式
1之化合物所防治的範圍。
在某些情況中,本發明化合物與其他生物活性(尤其是除草性)化合物或藥劑(即活性成分)的組合物對於雜草可造成大於相加(即協同)之效果,及/或對於作物或其他所欲植物可造成小於相加(即安全化)之效果。減少釋放至環境中之活性成分的量,同時確保有效的害蟲防治總是為理想者。能夠使用較大量的活性成分以提供更有效之雜草防治且不會造成過度作物傷害亦為理想者。當除草活性成分以達成農藝上令人滿意之雜草防治程度的施用率對雜草產生協同作用時,該等組合可有利地降低作物生產成本及減少環境負荷。當除草活性成分之安全化發生於作物上時,該等組合可有利地藉由減少雜草競爭而提高作物保護。
值得注意的是本發明化合物與至少一種其他除草活性成分之組合。特別值得注意的組合是其中之其他除草活性成分具有與本發明化合物不同的作用位置。在某些情況中,與至少一種其他具有相似防治範圍但不同作用位置之除草活性成分的組合將特別有利於抗性管理。因此,本發明組合物可進一步包含具有相似防治範圍但不同作用位置之(除草有效量的)至少一種額外除草活性成分。
本發明化合物亦可與除草劑安全劑組合使用,諸如草毒死(allidochlor)、解草嗪(benoxacor)、解毒喹(cloquintocet-mexyl)、苄草隆(cumyluron)、解草胺腈(cyometrinil)、環丙磺醯胺(cyprosulfonamide)、殺草隆(daimuron)、二氯丙烯胺(dichlormid)、大賽克農(dicyclonon)、增效磷(dietholate)、哌草丹(dimepiperate)、解草唑(fenchlorazole-ethyl)、解草啶(fenclorim)、解草胺(flurazole)、氟草肟(fluxofenim)、解草惡唑(furilazole)、雙苯噁唑酸(isoxadifen-ethyl)、唑解草酯(mefenpyr-diethyl)、梅芬內(mephenate)、苯草酮(methoxyphenone)、萘二甲酸酐(1,8-naphthalic anhydride)、解草腈(oxabetrinil)、
N-(胺基羰基)-2‑甲苯磺醯胺、
N-(胺基羰基)-2‑氟苯磺醯胺、1-溴-4-[(氯甲基)磺醯基]苯(BCS)、4-(二氯乙醯基)-1-氧雜-4‑偶氮螺[4.5]癸烷(MON 4660)、2-(二氯甲基)-2‑甲基-1,3-二氧𠷬(MG 191)、1,6-二氫-1-(2-甲氧苯基)-6-側氧基-2-苯基-5-嘧啶羧酸乙酯、2‑羥基-
N,
N-二甲基-6-(三氟甲基)吡啶-3-羧醯胺、及1-(3,4-二甲基苯基)-1,6-二氫-6-側氧基-2-苯基-5-嘧啶羧酸3‑側氧基-1-環己烯-1-基酯、2,2
-二氯-1-(2,2,5-三甲基-3-㗁唑啶基)-乙酮以及2-甲氧基-N-[[4-[[(甲基胺基)羰基]胺基]苯基]磺醯基]-苯甲醯胺,以增進對於某些作物之安全性。解毒有效量之除草劑安全劑可與本發明化合物同時施用,或作為種子處理施用。因此,本發明之一態樣涉及一種除草混合物,其包含本發明化合物與解毒有效量之除草劑安全劑。種子處理對於雜草之選擇性防治尤為有用,因為其將解毒作用實體限制在作物植物上。因此,本發明之特別有用的實施例係一種用於選擇性防治非所欲植物在作物中生長之方法,其包含使該作物之所在地接觸除草有效量的本發明化合物,其中該作物之種子(作物係自其生長)係經解毒有效量的安全劑處理。安全劑的解毒有效量可由所屬技術領域具有通常知識者透過簡單實驗而輕易決定。
本發明化合物亦可與下列混合:(1)提供除草效果之聚核苷酸,包括但不限於DNA、RNA、及/或透過下調、干擾、抑制、或靜默基因衍生轉錄本而影響特定標靶之量的化學修飾核苷酸;或(2)提供安全化效果之聚核苷酸,包括但不限於DNA、RNA、及/或透過下調、干擾、抑制、或靜默基因衍生轉錄本而影響特定標靶之量的化學修飾核苷酸。
值得注意的是包含下列者之組合物:(除草有效量之)本發明化合物、(有效量之)至少一種選自由其他除草劑與除草劑安全劑所組成之群組的額外活性成分、以及至少一種選自由界面活性劑、固體稀釋劑、與液體稀釋劑所組成之群組的組分。
對於更佳防治非所欲植物(例如諸如協同作用造成的較低使用率、更廣泛的雜草防治範圍或增進作物安全性)或防止抗性雜草之發展而言,較佳者為本發明化合物與選自由2,4-D、乙草胺(acetochlor)、拉草(alachlor)、草脫淨(atrazine)、溴苯腈(bromoxynil)、本達隆(bentazon)、二環吡草酮(bicyclopyrone)、乙唑草酮(carfentrazone-ethyl)、氯酯磺草胺(cloransulam-methyl)、麥草畏(dicamba)、汰草滅-p (dimethenamid-p)、雙氟磺草胺(florasulam)、噻草胺(flufenacet)、丙炔氟草胺(flumioxazin)、氟啶嘧磺隆甲酯(flupyrsulfuron-methyl)、氟氯比(fluroxypyr-meptyl)、草甘膦(glyphosate)、甲基哈洛昔芬(halauxifen-methyl)、異噁唑草酮(isoxaflutole)、MCPA、硝草酮(mesotrione)、莫多草(metolachlor)、甲磺隆(metsulfuron-methyl)、煙嘧磺隆(nicosulfuron)、磺醯草吡唑(pyrasulfotole)、派羅克殺草碸(pyroxasulfone)、啶磺草胺(pyroxsulam)、玉嘧磺隆(rimsulfuron)、嘧啶肟草醚(saflufenacil)、環磺酮(tembotrione)、噻吩磺隆(thifensulfuron-methyl)、苯吡唑草酮(topramazone)及苯磺隆(tribenuron)所組成之群組的除草劑之混合物。
表A1列出說明本發明之混合物、組合物、及方法的組分(a)與組分(b)之具體組合。組分(a)欄中之化合物13係標示於索引表A中。表A1之第二欄列出特定組分(b)之化合物(例如第一行中的「2,4‑D」)。表A1之第三、四及五欄列出在典型施用於田間生長作物時,組分(a)相對於組分(b)(即(a):(b))的重量比例範圍。因此,例如表A1第一行具體揭示組分(a)(即索引表A中之化合物13)與2,4‑D之組合一般係以介於1:192至6:1的重量比例施用。表A1之其餘行係以類似方式架構。
表A1
組分 (a) (化合物 13 ) | 組分 (b) | 典型 重量比例 | 更典型 重量比例 | 最典型 重量比例 |
13 | 2,4-D | 1:192 – 6:1 | 1:64 – 2:1 | 1:24 – 1:3 |
13 | 乙草胺(Acetochlor) | 1:768 – 2:1 | 1:256 – 1:2 | 1:96 – 1:11 |
13 | 亞喜芬(Acifluorfen) | 1:96 – 12:1 | 1:32 – 4:1 | 1:12 – 1:2 |
13 | 苯草醚(Aclonifen) | 1:857 – 2:1 | 1:285 – 1:3 | 1:107 – 1:12 |
13 | 拉草(Alachlor) | 1:768 – 2:1 | 1:256 – 1:2 | 1:96 – 1:11 |
13 | 草殺淨(Ametryn) | 1:384 – 3:1 | 1:128 – 1:1 | 1:48 – 1:6 |
13 | 胺唑草酮(Amicarbazone) | 1:192 – 6:1 | 1:64 – 2:1 | 1:24 – 1:3 |
13 | 醯嘧磺隆(Amidosulfuron) | 1:6 – 168:1 | 1:2 – 56:1 | 1:1 – 11:1 |
13 | 胺環吡克(Aminocyclopyrachlor) | 1:48 – 24:1 | 1:16 – 8:1 | 1:6 – 2:1 |
13 | 氯胺基吡啶酸(Aminopyralid) | 1:20 – 56:1 | 1:6 – 19:1 | 1:2 – 4:1 |
13 | 殺草強(Amitrole) | 1:768 – 2:1 | 1:256 – 1:2 | 1:96 – 1:11 |
13 | 莎稗磷(Anilofos) | 1:96 – 12:1 | 1:32 – 4:1 | 1:12 – 1:2 |
13 | 亞速爛(Asulam) | 1:960 – 2:1 | 1:320 – 1:3 | 1:120 – 1:14 |
13 | 草脫淨(Atrazine) | 1:192 – 6:1 | 1:64 – 2:1 | 1:24 – 1:3 |
13 | 四唑嘧磺隆(Azimsulfuron) | 1:6 – 168:1 | 1:2 – 56:1 | 1:1 – 11:1 |
13 | 氟丁草胺(Beflubutamid) | 1:342 – 4:1 | 1:114 – 2:1 | 1:42 – 1:5 |
13 | 呋草黃(Benfuresate) | 1:617 – 2:1 | 1:205 – 1:2 | 1:77 – 1:9 |
13 | 免速隆(Bensulfuron-methyl) | 1:25 – 45:1 | 1:8 – 15:1 | 1:3 – 3:1 |
13 | 本達隆(Bentazone) | 1:192 – 6:1 | 1:64 – 2:1 | 1:24 – 1:3 |
13 | 苯並雙環酮(Benzobicyclon) | 1:85 – 14:1 | 1:28 – 5:1 | 1:10 – 1:2 |
13 | 吡草酮(Benzofenap) | 1:257 – 5:1 | 1:85 – 2:1 | 1:32 – 1:4 |
13 | 二環吡草酮(Bicyclopyrone) | 1:42 – 27:1 | 1:14 – 9:1 | 1:5 – 2:1 |
13 | 治草醚(Bifenox) | 1:257 – 5:1 | 1:85 – 2:1 | 1:32 – 1:4 |
13 | 雙草醚(Bispyribac-sodium) | 1:10 – 112:1 | 1:3 – 38:1 | 1:1 – 7:1 |
13 | 克草(Bromacil) | 1:384 – 3:1 | 1:128 – 1:1 | 1:48 – 1:6 |
13 | 溴布泰(Bromobutide) | 1:384 – 3:1 | 1:128 – 1:1 | 1:48 – 1:6 |
13 | 溴苯腈(Bromoxynil) | 1:96 – 12:1 | 1:32 – 4:1 | 1:12 – 1:2 |
13 | 丁基拉草(Butachlor) | 1:768 – 2:1 | 1:256 – 1:2 | 1:96 – 1:11 |
13 | 布芬草(Butafenacil) | 1:42 – 27:1 | 1:14 – 9:1 | 1:5 – 2:1 |
13 | 拔敵草(Butylate) | 1:1542 – 1:2 | 1:514 – 1:5 | 1:192 – 1:22 |
13 | 苯酮唑(Carfenstrole) | 1:192 – 6:1 | 1:64 – 2:1 | 1:24 – 1:3 |
13 | 乙唑草酮(Carfentrazone-ethyl) | 1:128 – 9:1 | 1:42 – 3:1 | 1:16 – 1:2 |
13 | 氯嘧磺隆(Chlorimuron-ethyl) | 1:8 – 135:1 | 1:2 – 45:1 | 1:1 – 9:1 |
13 | 綠麥隆(Chlorotoluron) | 1:768 – 2:1 | 1:256 – 1:2 | 1:96 – 1:11 |
13 | 氯磺隆(Chlorsulfuron) | 1:6 – 168:1 | 1:2 – 56:1 | 1:1 – 11:1 |
13 | 西速隆(Cincosulfuron) | 1:17 – 68:1 | 1:5 – 23:1 | 1:2 – 5:1 |
13 | 吲哚酮草酯(Cinidon-ethyl) | 1:384 – 3:1 | 1:128 – 1:1 | 1:48 – 1:6 |
13 | 環庚草醚(Cinmethylin) | 1:34 – 34:1 | 1:11 – 12:1 | 1:4 – 3:1 |
13 | 氯醯草膦(Clacyfos) | 1:34 – 34:1 | 1:11 – 12:1 | 1:4 – 3:1 |
13 | 剋草同(Clethodim) | 1:48 – 24:1 | 1:16 – 8:1 | 1:6 – 2:1 |
13 | 炔草酯(Clodinafop-propargyl) | 1:20 – 56:1 | 1:6 – 19:1 | 1:2 – 4:1 |
13 | 可滅蹤(Clomazone) | 1:384 – 3:1 | 1:128 – 1:1 | 1:48 – 1:6 |
13 | 克普草(Clomeprop) | 1:171 – 7:1 | 1:57 – 3:1 | 1:21 – 1:3 |
13 | 畢克草(Clopyralid) | 1:192 – 6:1 | 1:64 – 2:1 | 1:24 – 1:3 |
13 | 氯酯磺草胺(Cloransulam-methyl) | 1:12 – 96:1 | 1:4 – 32:1 | 1:1 – 6:1 |
13 | 苄草隆(Cumyluron) | 1:384 – 3:1 | 1:128 – 1:1 | 1:48 – 1:6 |
13 | 氰乃淨(Cyanazine) | 1:384 – 3:1 | 1:128 – 1:1 | 1:48 – 1:6 |
13 | 環比瑞摩(Cyclopyrimorate) | 1:17 – 68:1 | 1:5 – 23:1 | 1:2 – 5:1 |
13 | 環磺隆(Cyclosulfamuron) | 1:17 – 68:1 | 1:5 – 23:1 | 1:2 – 5:1 |
13 | 環殺草(Cycloxydim) | 1:96 – 12:1 | 1:32 – 4:1 | 1:12 – 1:2 |
13 | 賽伏草(Cyhalofop) | 1:25 – 45:1 | 1:8 – 15:1 | 1:3 – 3:1 |
13 | 殺草隆(Daimuron) | 1:192 – 6:1 | 1:64 – 2:1 | 1:24 – 1:3 |
13 | 甜菜安(Desmedipham) | 1:322 – 4:1 | 1:107 – 2:1 | 1:40 – 1:5 |
13 | 麥草畏(Dicamba) | 1:192 – 6:1 | 1:64 – 2:1 | 1:24 – 1:3 |
13 | 二氯苯腈(Dichlobenil) | 1:1371 – 1:2 | 1:457 – 1:4 | 1:171 – 1:20 |
13 | 滴丙酸(Dichlorprop) | 1:925 – 2:1 | 1:308 – 1:3 | 1:115 – 1:13 |
13 | 甲基禾草靈(Diclofop-methyl) | 1:384 – 3:1 | 1:128 – 1:1 | 1:48 – 1:6 |
13 | 雙氯磺草胺(Diclosulam) | 1:10 – 112:1 | 1:3 – 38:1 | 1:1 – 7:1 |
13 | 燕麥枯(Difenzoquat) | 1:288 – 4:1 | 1:96 – 2:1 | 1:36 – 1:4 |
13 | 吡氟草胺(Diflufenican) | 1:857 – 2:1 | 1:285 – 1:3 | 1:107 – 1:12 |
13 | 二氟吡隆(Diflufenzopyr) | 1:12 – 96:1 | 1:4 – 32:1 | 1:1 – 6:1 |
13 | 二甲草胺(Dimethachlor) | 1:768 – 2:1 | 1:256 – 1:2 | 1:96 – 1:11 |
13 | 愛落殺(Dimethametryn) | 1:192 – 6:1 | 1:64 – 2:1 | 1:24 – 1:3 |
13 | 汰草滅-P (Dimethenamid-P) | 1:384 – 3:1 | 1:128 – 1:1 | 1:48 – 1:6 |
13 | 汰硫草(Dithiopyr) | 1:192 – 6:1 | 1:64 – 2:1 | 1:24 – 1:3 |
13 | 達有龍(Diuron) | 1:384 – 3:1 | 1:128 – 1:1 | 1:48 – 1:6 |
13 | EPTC | 1:768 – 2:1 | 1:256 – 1:2 | 1:96 – 1:11 |
13 | 戊草丹(Esprocarb) | 1:1371 – 1:2 | 1:457 – 1:4 | 1:171 – 1:20 |
13 | 乙丁烯氟靈(Ethalfluralin) | 1:384 – 3:1 | 1:128 – 1:1 | 1:48 – 1:6 |
13 | 胺苯磺隆(Ethametsulfuron-methyl) | 1:17 – 68:1 | 1:5 – 23:1 | 1:2 – 5:1 |
13 | 氯氟草醚(Ethoxyfen) | 1:8 – 135:1 | 1:2 – 45:1 | 1:1 – 9:1 |
13 | 亞速隆(Ethoxysulfuron) | 1:20 – 56:1 | 1:6 – 19:1 | 1:2 – 4:1 |
13 | 乙氧苯草胺(Etobenzanid) | 1:257 – 5:1 | 1:85 – 2:1 | 1:32 – 1:4 |
13 | 乙基芬殺草(Fenoxaprop-ethyl) | 1:120 – 10:1 | 1:40 – 4:1 | 1:15 – 1:2 |
13 | 異噁苯碸(Fenoxasulfone) | 1:85 – 14:1 | 1:28 – 5:1 | 1:10 – 1:2 |
13 | 芬昆諾三酮(Fenquinotrione) | 1:17 – 68:1 | 1:5 – 23:1 | 1:2 – 5:1 |
13 | 四唑草胺(Fentrazamide) | 1:17 – 68:1 | 1:5 – 23:1 | 1:2 – 5:1 |
13 | 伏速隆(Flazasulfuron) | 1:17 – 68:1 | 1:5 – 23:1 | 1:2 – 5:1 |
13 | 雙氟磺草胺(Florasulam) | 1:2 – 420:1 | 1:1 – 140:1 | 2:1 – 27:1 |
13 | 丁基伏寄普(Fluazifop-butyl) | 1:192 – 6:1 | 1:64 – 2:1 | 1:24 – 1:3 |
13 | 氟酮磺隆(Flucarbazone) | 1:8 – 135:1 | 1:2 – 45:1 | 1:1 – 9:1 |
13 | 氟吡磺隆(Flucetosulfuron) | 1:8 – 135:1 | 1:2 – 45:1 | 1:1 – 9:1 |
13 | 噻草胺(Flufenacet) | 1:257 – 5:1 | 1:85 – 2:1 | 1:32 – 1:4 |
13 | 唑嘧磺草胺(Flumetsulam) | 1:24 – 48:1 | 1:8 – 16:1 | 1:3 – 3:1 |
13 | 氟烯草酸(Flumiclorac-pentyl) | 1:10 – 112:1 | 1:3 – 38:1 | 1:1 – 7:1 |
13 | 丙炔氟草胺(Flumioxazin) | 1:25 – 45:1 | 1:8 – 15:1 | 1:3 – 3:1 |
13 | 伏草隆(Fluometuron) | 1:384 – 3:1 | 1:128 – 1:1 | 1:48 – 1:6 |
13 | 氟啶嘧磺隆甲酯(Flupyrsulfuron-methyl) | 1:3 – 336:1 | 1:1 – 112:1 | 2:1 – 21:1 |
13 | 氟啶草酮(Fluridone) | 1:384 – 3:1 | 1:128 – 1:1 | 1:48 – 1:6 |
13 | 氟氯比(Fluroxypyr) | 1:96 – 12:1 | 1:32 – 4:1 | 1:12 – 1:2 |
13 | 呋草酮(Flurtamone) | 1:857 – 2:1 | 1:285 – 1:3 | 1:107 – 1:12 |
13 | 氟噻甲草酯(Fluthiacet-methyl) | 1:48 – 42:1 | 1:16 – 14:1 | 1:3 – 3:1 |
13 | 氟磺胺草醚(Fomesafen) | 1:96 – 12:1 | 1:32 – 4:1 | 1:12 – 1:2 |
13 | 甲醯胺磺隆(Foramsulfuron) | 1:13 – 84:1 | 1:4 – 28:1 | 1:1 – 6:1 |
13 | 草銨膦(Glufosinate) | 1:288 – 4:1 | 1:96 – 2:1 | 1:36 – 1:4 |
13 | 草甘膦(Glyphosate) | 1:288 – 4:1 | 1:96 – 2:1 | 1:36 – 1:4 |
13 | 合速隆(Halosulfuron-methyl) | 1:17 – 68:1 | 1:5 – 23:1 | 1:2 – 5:1 |
13 | 哈洛昔芬(Halauxifen) | 1:20 – 56:1 | 1:6 – 19:1 | 1:2 – 4:1 |
13 | 甲基哈洛昔芬(Halauxifen-methyl) | 1:20 – 56:1 | 1:6 – 19:1 | 1:2 – 4:1 |
13 | 甲基合氯氟(Haloxyfop-methyl) | 1:34 – 34:1 | 1:11 – 12:1 | 1:4 – 3:1 |
13 | 菲殺淨(Hexazinone) | 1:192 – 6:1 | 1:64 – 2:1 | 1:24 – 1:3 |
13 | 海丹托西叮(hydantocidin) | 1:1100 – 16:1 | 1:385 – 8:1 | 1:144 – 4:1 |
13 | 甲氧咪草煙(Imazamox) | 1:13 – 84:1 | 1:4 – 28:1 | 1:1 – 6:1 |
13 | 甲咪唑煙酸(Imazapic) | 1:20 – 56:1 | 1:6 – 19:1 | 1:2 – 4:1 |
13 | 依滅草(Imazapyr) | 1:85 – 14:1 | 1:28 – 5:1 | 1:10 – 1:2 |
13 | 滅草喹(Imazaquin) | 1:34 – 34:1 | 1:11 – 12:1 | 1:4 – 3:1 |
13 | 咪草酯(Imazethabenz-methyl) | 1:171 – 7:1 | 1:57 – 3:1 | 1:21 – 1:3 |
13 | 咪草煙(Imazethapyr) | 1:24 – 48:1 | 1:8 – 16:1 | 1:3 – 3:1 |
13 | 依速隆(Imazosulfuron) | 1:27 – 42:1 | 1:9 – 14:1 | 1:3 – 3:1 |
13 | 茚草酮(Indanofan) | 1:342 – 4:1 | 1:114 – 2:1 | 1:42 – 1:5 |
13 | 三嗪茚草胺(Indaziflam) | 1:25 – 45:1 | 1:8 – 15:1 | 1:3 – 3:1 |
13 | 甲基碘磺隆(Iodosulfuron-methyl) | 1:3 – 336:1 | 1:1 – 112:1 | 2:1 – 21:1 |
13 | 碘苯腈(Ioxynil) | 1:192 – 6:1 | 1:64 – 2:1 | 1:24 – 1:3 |
13 | 艾分卡斑唑(Ipfencarbazone) | 1:85 – 14:1 | 1:28 – 5:1 | 1:10 – 1:2 |
13 | 異丙隆(Isoproturon) | 1:384 – 3:1 | 1:128 – 1:1 | 1:48 – 1:6 |
13 | 異噁草胺(Isoxaben) | 1:288 – 4:1 | 1:96 – 2:1 | 1:36 – 1:4 |
13 | 異噁唑草酮(Isoxaflutole) | 1:60 – 20:1 | 1:20 – 7:1 | 1:7 – 2:1 |
13 | 乳氟禾草靈(Lactofen) | 1:42 – 27:1 | 1:14 – 9:1 | 1:5 – 2:1 |
13 | 環草定(Lenacil) | 1:384 – 3:1 | 1:128 – 1:1 | 1:48 – 1:6 |
13 | 理有龍(Linuron) | 1:384 – 3:1 | 1:128 – 1:1 | 1:48 – 1:6 |
13 | MCPA | 1:192 – 6:1 | 1:64 – 2:1 | 1:24 – 1:3 |
13 | MCPB | 1:288 – 4:1 | 1:96 – 2:1 | 1:36 – 1:4 |
13 | 甲氯丙酸(Mecoprop) | 1:768 – 2:1 | 1:256 – 1:2 | 1:96 – 1:11 |
13 | 滅芬草(Mefenacet) | 1:384 – 3:1 | 1:128 – 1:1 | 1:48 – 1:6 |
13 | 美福泰(Mefluidide) | 1:192 – 6:1 | 1:64 – 2:1 | 1:24 – 1:3 |
13 | 甲磺胺磺隆(Mesosulfuron-methyl) | 1:5 – 224:1 | 1:1 – 75:1 | 1:1 – 14:1 |
13 | 硝草酮(Mesotrione) | 1:42 – 27:1 | 1:14 – 9:1 | 1:5 – 2:1 |
13 | 惡唑醯草胺(Metamifop) | 1:42 – 27:1 | 1:14 – 9:1 | 1:5 – 2:1 |
13 | 滅草胺(Metazachlor) | 1:384 – 3:1 | 1:128 – 1:1 | 1:48 – 1:6 |
13 | 雙醚氯吡嘧磺隆(Metazosulfuron) | 1:25 – 45:1 | 1:8 – 15:1 | 1:3 – 3:1 |
13 | 甲草苯隆(Methabenzthiazuron) | 1:768 – 2:1 | 1:256 – 1:2 | 1:96 – 1:11 |
13 | 莫多草(Metolachlor) | 1:768 – 2:1 | 1:256 – 1:2 | 1:96 – 1:11 |
13 | 磺草唑胺(Metosulam) | 1:8 – 135:1 | 1:2 – 45:1 | 1:1 – 9:1 |
13 | 滅必淨(Metribuzin) | 1:192 – 6:1 | 1:64 – 2:1 | 1:24 – 1:3 |
13 | 甲磺隆(Metsulfuron-methyl) | 1:2 – 560:1 | 1:1 – 187:1 | 3:1 – 35:1 |
13 | 稻得壯(Molinate) | 1:1028 – 2:1 | 1:342 – 1:3 | 1:128 – 1:15 |
13 | 滅落脫(Napropamide) | 1:384 – 3:1 | 1:128 – 1:1 | 1:48 – 1:6 |
13 | 滅落脫-M (Napropamide-M) | 1:192 – 6:1 | 1:64 – 2:1 | 1:24 – 1:3 |
13 | 鈉得爛(Naptalam) | 1:192 – 6:1 | 1:64 – 2:1 | 1:24 – 1:3 |
13 | 煙嘧磺隆(Nicosulfuron) | 1:12 – 96:1 | 1:4 – 32:1 | 1:1 – 6:1 |
13 | 氟草敏(Norflurazon) | 1:1152 – 1:1 | 1:384 – 1:3 | 1:144 – 1:16 |
13 | 坪草丹(Orbencarb) | 1:1371 – 1:2 | 1:457 – 1:4 | 1:171 – 1:20 |
13 | 嘧苯胺磺隆(Orthosulfamuron) | 1:20 – 56:1 | 1:6 – 19:1 | 1:2 – 4:1 |
13 | 胺磺樂靈(Oryzalin) | 1:514 – 3:1 | 1:171 – 1:2 | 1:64 – 1:8 |
13 | 快噁草酮(Oxadiargyl) | 1:384 – 3:1 | 1:128 – 1:1 | 1:48 – 1:6 |
13 | 樂滅草(Oxadiazon) | 1:548 – 3:1 | 1:182 – 1:2 | 1:68 – 1:8 |
13 | 環氧嘧磺隆(Oxasulfuron) | 1:27 – 42:1 | 1:9 – 14:1 | 1:3 – 3:1 |
13 | 噁嗪草酮(Oxaziclomefone) | 1:42 – 27:1 | 1:14 – 9:1 | 1:5 – 2:1 |
13 | 復祿芬(Oxyfluorfen) | 1:384 – 3:1 | 1:128 – 1:1 | 1:48 – 1:6 |
13 | 巴拉刈(Paraquat) | 1:192 – 6:1 | 1:64 – 2:1 | 1:24 – 1:3 |
13 | 施得圃(Pendimethalin) | 1:384 – 3:1 | 1:128 – 1:1 | 1:48 – 1:6 |
13 | 平速爛(Penoxsulam) | 1:10 – 112:1 | 1:3 – 38:1 | 1:1 – 7:1 |
13 | 烯草胺(Penthoxamid) | 1:384 – 3:1 | 1:128 – 1:1 | 1:48 – 1:6 |
13 | 環戊惡草酮(Pentoxazone) | 1:102 – 12:1 | 1:34 – 4:1 | 1:12 – 1:2 |
13 | 甜菜寧(Phenmedipham) | 1:102 – 12:1 | 1:34 – 4:1 | 1:12 – 1:2 |
13 | 毒莠定(Picloram) | 1:96 – 12:1 | 1:32 – 4:1 | 1:12 – 1:2 |
13 | 氟吡醯草胺(Picolinafen) | 1:34 – 34:1 | 1:11 – 12:1 | 1:4 – 3:1 |
13 | 唑啉草酯(Pinoxaden) | 1:25 – 45:1 | 1:8 – 15:1 | 1:3 – 3:1 |
13 | 普拉草(Pretilachlor) | 1:192 – 6:1 | 1:64 – 2:1 | 1:24 – 1:3 |
13 | 氟嘧磺隆(Primisulfuron-methyl) | 1:8 – 135:1 | 1:2 – 45:1 | 1:1 – 9:1 |
13 | 胺氟樂靈(Prodiamine) | 1:384 – 3:1 | 1:128 – 1:1 | 1:48 – 1:6 |
13 | 氯苯噻草酮(Profoxydim) | 1:42 – 27:1 | 1:14 – 9:1 | 1:5 – 2:1 |
13 | 撲草凈(Prometryn) | 1:384 – 3:1 | 1:128 – 1:1 | 1:48 – 1:6 |
13 | 雷蒙得(Propachlor) | 1:1152 – 1:1 | 1:384 – 1:3 | 1:144 – 1:16 |
13 | 除草靈(Propanil) | 1:384 – 3:1 | 1:128 – 1:1 | 1:48 – 1:6 |
13 | 普拔草(Propaquizafop) | 1:48 – 24:1 | 1:16 – 8:1 | 1:6 – 2:1 |
13 | 丙苯磺隆(Propoxycarbazone) | 1:17 – 68:1 | 1:5 – 23:1 | 1:2 – 5:1 |
13 | 咪唑嘧磺隆(Propyrisulfuron) | 1:17 – 68:1 | 1:5 – 23:1 | 1:2 – 5:1 |
13 | 戊炔草胺(Propyzamide) | 1:384 – 3:1 | 1:128 – 1:1 | 1:48 – 1:6 |
13 | 芐草丹(Prosulfocarb) | 1:1200 – 1:2 | 1:400 – 1:4 | 1:150 – 1:17 |
13 | 氟磺隆(Prosulfuron) | 1:6 – 168:1 | 1:2 – 56:1 | 1:1 – 11:1 |
13 | 雙唑草腈(Pyraclonil) | 1:42 – 27:1 | 1:14 – 9:1 | 1:5 – 2:1 |
13 | 吡草醚(Pyraflufen-ethyl) | 1:5 – 224:1 | 1:1 – 75:1 | 1:1 – 14:1 |
13 | 磺醯草吡唑(Pyrasulfotole) | 1:13 – 84:1 | 1:4 – 28:1 | 1:1 – 6:1 |
13 | 苄草唑(Pyrazolynate) | 1:857 – 2:1 | 1:285 – 1:3 | 1:107 – 1:12 |
13 | 百速隆(Pyrazosulfuron-ethyl) | 1:10 – 112:1 | 1:3 – 38:1 | 1:1 – 7:1 |
13 | 普芬草(Pyrazoxyfen) | 1:5 – 224:1 | 1:1 – 75:1 | 1:1 – 14:1 |
13 | 嘧啶肟草醚(Pyribenzoxim) | 1:10 – 112:1 | 1:3 – 38:1 | 1:1 – 7:1 |
13 | 稗草畏(Pyributicarb) | 1:384 – 3:1 | 1:128 – 1:1 | 1:48 – 1:6 |
13 | 必汰草(Pyridate) | 1:288 – 4:1 | 1:96 – 2:1 | 1:36 – 1:4 |
13 | 環酯草醚(Pyriftalid) | 1:10 – 112:1 | 1:3 – 38:1 | 1:1 – 7:1 |
13 | 嘧草醚(Pyriminobac-methyl) | 1:20 – 56:1 | 1:6 – 19:1 | 1:2 – 4:1 |
13 | 嘧啶硫蕃(Pyrimisulfan) | 1:17 – 68:1 | 1:5 – 23:1 | 1:2 – 5:1 |
13 | 嘧草硫醚(Pyrithiobac) | 1:24 – 48:1 | 1:8 – 16:1 | 1:3 – 3:1 |
13 | 派羅克殺草碸(Pyroxasulfone) | 1:85 – 14:1 | 1:28 – 5:1 | 1:10 – 1:2 |
13 | 啶磺草胺(Pyroxsulam) | 1:5 – 224:1 | 1:1 – 75:1 | 1:1 – 14:1 |
13 | 快克草(Quinclorac) | 1:192 – 6:1 | 1:64 – 2:1 | 1:24 – 1:3 |
13 | 乙基快伏草(Quizalofop-ethyl) | 1:42 – 27:1 | 1:14 – 9:1 | 1:5 – 2:1 |
13 | 玉嘧磺隆(Rimsulfuron) | 1:13 – 84:1 | 1:4 – 28:1 | 1:1 – 6:1 |
13 | 嘧啶肟草醚(Saflufenacil) | 1:25 – 45:1 | 1:8 – 15:1 | 1:3 – 3:1 |
13 | 西殺草(Sethoxydim) | 1:96 – 12:1 | 1:32 – 4:1 | 1:12 – 1:2 |
13 | 草滅淨(Simazine) | 1:384 – 3:1 | 1:128 – 1:1 | 1:48 – 1:6 |
13 | 磺草酮(Sulcotrione) | 1:120 – 10:1 | 1:40 – 4:1 | 1:15 – 1:2 |
13 | 甲磺草胺(Sulfentrazone) | 1:147 – 8:1 | 1:49 – 3:1 | 1:18 – 1:3 |
13 | 甲嘧磺隆(Sulfometuron-methyl) | 1:34 – 34:1 | 1:11 – 12:1 | 1:4 – 3:1 |
13 | 磺醯磺隆(Sulfosulfuron) | 1:8 – 135:1 | 1:2 – 45:1 | 1:1 – 9:1 |
13 | 丁噻隆(Tebuthiuron) | 1:384 – 3:1 | 1:128 – 1:1 | 1:48 – 1:6 |
13 | 特呋三酮(Tefuryltrione) | 1:42 – 27:1 | 1:14 – 9:1 | 1:5 – 2:1 |
13 | 環磺酮(Tembotrione) | 1:31 – 37:1 | 1:10 – 13:1 | 1:3 – 3:1 |
13 | 得殺草(Tepraloxydim) | 1:25 – 45:1 | 1:8 – 15:1 | 1:3 – 3:1 |
13 | 特草定(Terbacil) | 1:288 – 4:1 | 1:96 – 2:1 | 1:36 – 1:4 |
13 | 特丁津(Terbuthylazine) | 1:857 – 2:1 | 1:285 – 1:3 | 1:107 – 1:12 |
13 | 去草淨(Terbutryn) | 1:192 – 6:1 | 1:64 – 2:1 | 1:24 – 1:3 |
13 | 欣克草(Thenylchlor) | 1:85 – 14:1 | 1:28 – 5:1 | 1:10 – 1:2 |
13 | 噻草定(Thiazopyr) | 1:384 – 3:1 | 1:128 – 1:1 | 1:48 – 1:6 |
13 | 酮脲磺草吩酯(Thiencarbazone) | 1:3 – 336:1 | 1:1 – 112:1 | 2:1 – 21:1 |
13 | 噻吩磺隆(Thifensulfuron-methyl) | 1:5 – 224:1 | 1:1 – 75:1 | 1:1 – 14:1 |
13 | 氟丙嘧草酯(Tiafenacil) | 1:17 – 68:1 | 1:5 – 23:1 | 1:2 – 5:1 |
13 | 殺丹(Thiobencarb) | 1:768 – 2:1 | 1:256 – 1:2 | 1:96 – 1:11 |
13 | 托派拉雷(Tolpyralate) | 1:31 – 37:1 | 1:10 – 13:1 | 1:3 – 3:1 |
13 | 苯吡唑草酮(Topramezone) | 1:6 – 168:1 | 1:2 – 56:1 | 1:1 – 11:1 |
13 | 肟草酮(Tralkoxydim) | 1:68 – 17:1 | 1:22 – 6:1 | 1:8 – 2:1 |
13 | 氟酮磺草胺(Triafamone) | 1:2 – 420:1 | 1:1 – 140:1 | 2:1 – 27:1 |
13 | 野燕畏(Triallate) | 1:768 – 2:1 | 1:256 – 1:2 | 1:96 – 1:11 |
13 | 醚苯磺隆(Triasulfuron) | 1:5 – 224:1 | 1:1 – 75:1 | 1:1 – 14:1 |
13 | 三唑侖(Triaziflam) | 1:171 – 7:1 | 1:57 – 3:1 | 1:21 – 1:3 |
13 | 苯磺隆-甲酯(Tribenuron-methyl) | 1:3 – 336:1 | 1:1 – 112:1 | 2:1 – 21:1 |
13 | 三氯比(Triclopyr) | 1:192 – 6:1 | 1:64 – 2:1 | 1:24 – 1:3 |
13 | 三氟啶磺隆(Trifloxysulfuron) | 1:2 – 420:1 | 1:1 – 140:1 | 2:1 – 27:1 |
13 | 三氟草嗪(Trifludimoxazin) | 1:25 – 45:1 | 1:8 – 15:1 | 1:3 – 3:1 |
13 | 三福林(Trifluralin) | 1:288 – 4:1 | 1:96 – 2:1 | 1:36 – 1:4 |
13 | 氟胺磺隆(Triflusulfuron-methyl) | 1:17 – 68:1 | 1:5 – 23:1 | 1:2 – 5:1 |
13 | 三氟甲磺隆(Tritosulfuron) | 1:13 – 84:1 | 1:4 – 28:1 | 1:1 – 6:1 |
表A2之建構方式如同上表A1,惟「組分(a)」欄標題下方的項目係用以下所示之各別組分(a)欄項目替換。組分(a)欄中之化合物15係標示於索引表A中。因此,舉例而言在表A2中,「組分(a)」欄標題下方之所有項目皆敘述「化合物15」(即索引表A中所標示之化合物15),並且表A2中之欄標題下方的第一行具體揭示化合物15與2,4‑D之混合物。表A3至表A146係以類似方式建構。
表編號 | 組分 (a) 欄項目 |
A2 | 化合物15 |
A3 | 化合物16 |
A4 | 化合物21 |
A5 | 化合物22 |
A6 | 化合物23 |
A7 | 化合物24 |
A8 | 化合物27 |
A9 | 化合物1 |
A10 | 化合物2 |
A11 | 化合物3 |
A12 | 化合物4 |
A13 | 化合物5 |
A14 | 化合物6 |
A15 | 化合物7 |
A16 | 化合物8 |
A17 | 化合物9 |
A18 | 化合物10 |
A19 | 化合物11 |
A20 | 化合物12 |
A21 | 化合物14 |
A22 | 化合物17 |
A23 | 化合物18 |
A24 | 化合物19 |
A25 | 化合物20 |
A26 | 化合物25 |
A27 | 化合物26 |
A28 | 化合物28 |
A29 | 化合物29 |
A30 | 化合物30 |
A31 | 化合物31 |
A32 | 化合物32 |
A33 | 化合物33 |
A34 | 化合物34 |
A35 | 化合物35 |
A36 | 化合物36 |
A37 | 化合物37 |
A38 | 化合物38 |
A39 | 化合物39 |
A40 | 化合物40 |
A41 | 化合物41 |
A42 | 化合物42 |
A43 | 化合物43 |
A44 | 化合物44 |
A45 | 化合物45 |
A46 | 化合物46 |
A47 | 化合物47 |
A48 | 化合物48 |
A49 | 化合物49 |
A50 | 化合物50 |
A51 | 化合物51 |
A52 | 化合物52 |
A53 | 化合物53 |
A54 | 化合物54 |
A55 | 化合物55 |
A56 | 化合物56 |
A57 | 化合物57 |
A58 | 化合物58 |
A59 | 化合物59 |
A60 | 化合物60 |
A61 | 化合物61 |
A62 | 化合物62 |
A63 | 化合物63 |
A64 | 化合物64 |
A65 | 化合物65 |
A66 | 化合物66 |
A67 | 化合物67 |
A68 | 化合物68 |
A69 | 化合物69 |
A70 | 化合物70 |
A71 | 化合物71 |
A72 | 化合物72 |
A73 | 化合物73 |
A74 | 化合物74 |
A75 | 化合物75 |
A76 | 化合物76 |
A77 | 化合物77 |
A78 | 化合物78 |
A79 | 化合物79 |
A80 | 化合物80 |
A81 | 化合物81 |
A82 | 化合物82 |
A83 | 化合物83 |
A84 | 化合物84 |
A85 | 化合物85 |
A86 | 化合物86 |
A87 | 化合物87 |
A88 | 化合物88 |
A89 | 化合物89 |
A90 | 化合物90 |
A91 | 化合物91 |
A92 | 化合物92 |
A93 | 化合物93 |
A94 | 化合物94 |
A95 | 化合物95 |
A96 | 化合物96 |
A97 | 化合物97 |
A98 | 化合物98 |
A99 | 化合物99 |
A100 | 化合物100 |
A101 | 化合物101 |
A102 | 化合物102 |
A103 | 化合物103 |
A104 | 化合物104 |
A105 | 化合物104 |
A106 | 化合物106 |
A107 | 化合物107 |
A108 | 化合物108 |
A109 | 化合物109 |
A110 | 化合物110 |
A111 | 化合物111 |
A112 | 化合物112 |
A113 | 化合物113 |
A114 | 化合物114 |
A115 | 化合物115 |
A116 | 化合物116 |
A117 | 化合物117 |
A118 | 化合物118 |
A119 | 化合物119 |
A120 | 化合物120 |
A121 | 化合物121 |
A122 | 化合物122 |
A123 | 化合物123 |
A124 | 化合物124 |
A125 | 化合物125 |
A126 | 化合物126 |
A127 | 化合物127 |
A128 | 化合物128 |
A129 | 化合物129 |
A130 | 化合物130 |
A131 | 化合物131 |
A132 | 化合物132 |
A133 | 化合物133 |
A134 | 化合物134 |
A135 | 化合物135 |
A136 | 化合物136 |
A137 | 化合物137 |
A138 | 化合物138 |
A139 | 化合物139 |
A140 | 化合物140 |
A141 | 化合物141 |
A142 | 化合物142 |
A143 | 化合物143 |
A144 | 化合物144 |
A145 | 化合物145 |
A146 | 化合物146 |
本發明化合物可用於防治對具有AHAS抑制劑或(b2) [抑制乙醯羥酸合成酶(AHAS)亦稱為乙醯乳酸合成酶(ALS)之化學化合物]作用模式之除草劑有抗性的雜草物種。
以下試驗展示本發明化合物對抗特定雜草之防治效能。然而,該化合物提供之雜草防治未限於這些物種。請參見索引表A至C以取得化合物說明。以下索引表中使用下列縮寫:
t係三級,
s係二級,
n係正,
i係異,
c係環,Me係甲基,Et係乙基,Pr係丙基,
i‑Pr係異丙基,Bu係丁基,
c‑Pr係環丙基,
t-Bu係三級丁基,Ph係苯基,OMe係甲氧基,OEt係乙氧基,SMe係甲基硫基,TFP係三氟丙基(即–CH
2CH
2CF
3),Bn係苄基,及-CN係氰基。縮寫「Cmpd.No.」代表「化合物編號」。縮寫「Ex.」表示「實例」,且其後之數字意指該化合物係於該實例中製備。質譜係以估計精確度在±0.5 Da內之最高同位素豐度母離子(M+1)之分子量記述,該母離子係藉由將H
+(分子量係1)加入至分子形成。含有較低豐度之一或多種較高原子量同位素(例如
37Cl、
81Br)的分子離子之存在並未記述。發生於含有多個鹵素之化合物的替代分子離子峰(例如M+2或M+4)亦未記述。所記述之M+1峰係藉由使用大氣壓力化學離子化(AP
+)或電噴灑離子化(ESI)之質譜測定法觀察。
索引表A
Z=O
*
1H NMR數據請參見索引表C。
**
1H NMR數據請參見合成實例。
E表示雙鍵的E立體化學。
索引表B
索引表C
1H NMR數據係以位於四甲基矽烷低場區之ppm來表示。耦合係以(s)‑單峰、(d)‑雙重峰、(t)‑三重峰、(m)‑多重峰、(dd)‑雙重雙重峰、(dt)‑雙重三重峰、(br s)‑寬單峰標明。
本發明之生物實例
試驗A
、 | 、 | 、 | 、 | |||||
A-1 | A-2 | A-3A | A-5 | A-7 |
Cmpd.No. | A | R 1 | R 2 | R 3 | M.S. (AP+) 或m.p. |
4 | A-3A | OCH 2CF 2CF 3 | Br | 3-F | 447 |
5 | A-3A | OCH 2CF 2CF 3 | Cl | 3-F | 401 |
6 | A-3A | OCH 2(環-戊基) | Cl | 3-Br | 411 |
7 | A-3A | OCH 2CH 2CN | Cl | 3-Br | 382 |
8 | A-3A | OCH 2(環-丁基) | Cl | 3-Br | 397 |
9 | A-3A | OCH 2(環-丙基) | Cl | 3-Br | 393 |
10 | A-3A | OCH 2(2,2-二-F-環-丙基) | Cl | 3-Br | 419 |
11 | A-3A | OCH 2CH=C(CH 3) 2 | Cl | 3-Br | 397 |
13 | A-3A | OCH 2CH 2CH 3 | Cl | 3-Br | * |
15 | A-3A | OCH 2CH 2CF 3 | Cl | 3-Cl | 381 |
16 | A-3A | OCH(CH 3)CH 2CF 3 | Cl | 3-Br | 439 |
17 | A-3A | OCH 2CH 2CF 3 | Cl | (m = 0) | 347 |
18 | A-3A | N(CH 3)CH 2CH(CH 3)(CF 3) | Cl | 3-Br | 452 |
19 | A-3A | N(CH 3)CH 2CH 2CF 3 | Cl | 3-Br | 438 |
20 | A-3A | OCH 2CH 2CH 2CF 3 | Cl | 3-Br | * |
21 (Ex.2) | A-3A | OCH 2CH 2CH=CH 2 | Cl | 3-Br | * |
22 | A-3A | OCH 2CH=CH 2 | Cl | 3-Br | 369 |
23 | A-3A | OCH 2CF 2CF 3 | Cl | 3-Br | 461 |
24 | A-3A | N(CH 3)OCH 2CF 3 | Br | 3-Br | 484 |
25 | A-3A | N(CH 3)OCH 2CF 3 | Cl | 3-Br | 440 |
26 (Ex.3) | A-3A | OCH 2CH 2CF 3 | Cl | 3-Br | 425 |
28 (Ex.1) | A-3A | NHCH 2CF 3 | Cl | (m = 0) | * |
29 | A-3A | CH 2Cl | Cl | (m = 0) | 283 (65–70) |
30 | A-3A | OCH 2CH 2CF 3 | Cl | 3-CN | 372 |
32 | A-3A | OCH 2CF 3 | Cl | 3-CN | 358 |
33 | A-3A | OCH 2CH 2CF 3 | Br | 3-Br | 467 |
34 | A-3A | OCH 2CF 3 | Br | 3-Br | 455 |
35 | A-3A | OCH 2CF 3 | Cl | 3-Br | 411 |
36 | A-3A | OCH(CH 2Cl) 2 | Cl | 3-Br | 439 |
37 | A-3A | OCH 2CH(CH 3)CH=CH 2 | Cl | 3-Br | 397 |
38 | A-3A | OCH 2CH 2C≡CH | Cl | 3-Br | 381 |
39 | A-3A | OCH 2CN | Cl | 3-CN | 315 |
41 | A-3A | OCH 2CH 2CF 3 | Br | 3-F | 409 |
42 | A-3A | OCH 2CH 2CF 3 | Cl | 3-F | 365 |
43 | A-3A | OC(CH 3) 3 | Cl | 3-F | 325 |
44 | A-3A | O(環-戊基) | Cl | 3-Br | 397 |
45 | A-3A | OCH 2CCl 3 | Cl | 3-Br | 459 |
46 | A-3A | OCH 2CH 2Cl | Cl | 3-Br | 391 |
47 | A-3A | OCH 2CF 3 | Br | 3-F | 396 |
48 | A-3A | OCH 2CF 3 | Cl | 3-F | 351 |
49 | A-3A | OCH 2CN | Cl | 3-F | 308 (80–83) |
50 | A-3A | E-OCH 2CH=CHCF 3 | Cl | 3-Br | 437 |
51 | A-3A | CH 3 | Cl | 3-OMe | 279 |
52 | A-3A | CH 3 | Cl | (m = 0) | 249 |
55 | A-5;R 5係Me | CH 3 | Cl | (m = 0) | 278 |
56 | A-5;R 5係 i-Pr | CH 3 | Cl | (m = 0) | 306 |
57 | A-5;R 5係 i-Pr | H | Cl | (m = 0) | 292 |
58 | A-5;R 5係Bn | CH 3 | Cl | (m = 0) | 354 |
59 | A-5;R 5係 t-Bu | CH 3 | Cl | (m = 0) | 320 |
60 | A-5;R 5係H | CH 3 | Cl | (m = 0) | 264 |
61 | A-3A | OCH 2C(Br)=CH 2 | Cl | 3-Br | 87–91 |
62 | A-1 | OCH 2CF 3 | Cl | 3-Br | 63–66 |
63 | A-1 | OCH 2CF 2CF 3 | Cl | 3-Br | 49–53 |
64 | A-3A | OCH 2CH 2CF 3 | Cl | 4-CN | 117–120 |
65 | A-3A | OCH 2CH 2CH 2CF 3 | Cl | 3-CF 3 | 429 |
66 | A-1 | OCH 2CH 2CF 3 | Cl | 3-Br | 63–67 |
67 | A-3A | CH 2CH 2CH 3 | Cl | 3-CN | 85–88 |
68 | A-3A | CH 2CH 2CH 2CH 3 | Cl | 3-CN | 98–102 |
69 | A-5;R 5係 i-Pr | CH 3 | Cl | 3-CN | 80–84 |
70 | A-3A | SCH 2CH 2CH 3 | Cl | 3-Br | 387 |
71 | A-3A | SCH 2CH 2CF 3 | Cl | 3-Br | 121–125 |
72 | A-1 | CH 2CH 2CF 3 | Cl | 3-CN | 342 |
73 | A-1 | (CH 2) 3CF 3 | Cl | 3-CN | 356 |
74 | A-1 | O(CH 2) 3CF 3 | Cl | 3-Br | 425 |
75 | A-3A | CH 2CH 2CH 3 | Cl | 3-Br | 88–92 |
76 | A-5;R 5係 i-Pr | CH 3 | Cl | 3-F | 62–66 |
77 | A-3A | (CH 2) 3CF 3 | Cl | 3-Br | 423 |
78 | A-3A | O( c-Bu) | Cl | 3-Br | 100–103 |
79 | A-3A | (CH 2) 3CH 3 | Cl | 3-Br | 77–81 |
80 | A-1 | O(CH 2) 2CF 3 | Cl | 3-CN | 358 |
81 | A-1 | O(CH 2) 3CF 3 | Cl | 3-CN | 372 |
82 | A-3A | (CH 2) 4CF 3 | Cl | 3-Br | 437 |
83 | A-3A | SCH 2CH 3 | Cl | 3-Br | 373 |
84 | A-3A | OCH(CH 3)CH 2CH 3 | Cl | 3-Br | 385 |
85 | A-3A | SCH 2CF 3 | Cl | 3-Br | 90–93 |
86 | A-1 | (CH 2) 2CH 3 | Cl | 3-CN | 288 |
87 | A-1 | (CH 2) 3CH 3 | Cl | 3-CN | 302 |
88 | A-3A | O(CH 2) 2CF 3 | Cl | 4-Cl | 87–90 |
89 | A-1 | (CH 2) 2CF 3 | Cl | 3-Br | 395 |
90 | A-3A | OCH 2CH 2C(=CH 2)CH 3 | Cl | 3-Br | 397 |
91 | A-3A | SCH 2CH=CH 2 | Cl | 3-Br | 385 |
92 | A-3A | (CH 2) 2CF 3 | Cl | 3-Br | 409 |
93 | A-3A | NH(CH 2) 2CF 3 | Cl | 3-Br | 424 |
94 | A-3A | O(CH 2) 2CF 3 | Cl | 4-Br | 88–91 |
95 | A-5;R 5係Et | CH 3 | Cl | 3-Br | 370 |
96 | A-3A | O(CH 2) 2C(CH 3) 3 | Cl | 3-Br | 413 |
97 | A-3A | OCH 2CHClCH 2Cl | Cl | 3-Br | 439 |
99 | A-3A | O(CH 2) 2CF 3 | Cl | 3-CH 3 | 51–53 |
100 | A-3A | O(CH 2) 3CH 3 | Cl | 3-Br | 385 |
101 | A-3A | O(CH 2) 4CH 3 | Cl | 3-Br | 399 |
102 | A-3A | OCH 2CH 2CH 2CH 2Br | Cl | 3-Br | 449 |
103 | A-3A | OCH 2CF 2CHF 2 | Cl | 3-Br | 443 |
104 | A-5;R 5係 i-Pr | CH 3 | Cl | 3-Cl | 340 |
105 | A-5;R 5係 i-Pr | CH 3 | Cl | 3-Br | 384 |
106 | A-1 | OCH 2CH 3 | Cl | 3-Br | 343 |
107 (Ex.4) | A-3A | (CH 2) 2CF 3 | Cl | 3-Cl | ** |
108 | A-3A | OCH 2C≡CH | Cl | 3-Br | 108–112 |
109 | A-3A | (CH 2) 4CF 3 | Cl | 3-CN | 384 |
110 | A-3A | CH 2CH 2CF 2CF 3 | Cl | 3-Br | 459 |
111 | A-3A | CH 2CH 2CF 2CF 3 | Cl | 3-CN | 406 |
112 | A-3A | O(CH 2) 2CF 3 | Cl | 3-OCH 3 | 109–113 |
113 | A-3A | O(CH 2) 2CF 3 | Cl | 3-CF 3 | 415 |
114 | A-2 | (CH 2) 3CH 3 | Cl | 3-Br | 380 |
115 | A-3A | O(CH 2) 2CF 3 | Cl | 3-O- i-Pr | 405 |
116 | A-3A | O(CH 2) 2CF 3 | Cl | 3-OCH 2CH 3 | 391 |
117 | A-3A | O(CH 2) 2CF 3 | Cl | 3-OCH 2CF 3 | 445 |
118 | A-2 | (CH 2) 2CH 3 | Cl | 3-Br | 366 |
119 | A-3A | 順-OCH 2CCl=CCl | Cl | 3-Br | 114–117 |
120 | A-3A | 反-OCH 2CCl=CCl | Cl | 3-Br | 84–88 |
121 | A-1 | (CH 2) 4CF 3 | Cl | 3-Br | 423 |
122 | A-1 | (CH 2) 2CF 3 | Cl | 3-Cl | 351 |
123 | A-3A | O(CH 2) 2 c-Pr | Cl | 3-Br | 397 |
124 | A-1 | (CH 2) 4CF 3 | Cl | 3-Cl | 379 |
125 | A-3A | (CH 2) 3CF 3 | Cl | 3-CF 3 | 413 |
126 | A-7;R 15係Me | (CH 2) 3CF 3 | Cl | 3-CN | 371 |
127 | A-3A | 順-OCH 2C=C(CH 3)Cl | Cl | 3-Br | 59–63 |
128 | A-3A | 反-OCH 2C=C(CH 3)Cl | Cl | 3-Br | 82–86 |
129 | A-2 | (CH 2) 3CH 3 | Cl | (m = 0) | 302 |
130 | A-3A | (CH 2) 3CH 3 | Cl | 3-CF 3 | 359 |
131 | A-1 | OCH 2CF 3 | Cl | 3-CN | 344 |
132 | A-1 | OCH 2CF 2CF 3 | Cl | 3-CN | 70–73 |
133 | A-3A | (CH 2) 3CF 3 | Cl | 3-CN | 94–96 |
134 | A-1 | (CH 2) 3CF 3 | Cl | 3-CH 2CH 3 | 359 |
135 | A-1 | (CH 2) 3CF 3 | Cl | 3- c-Pr | 371 |
136 | A-3A | (CH 2) 2CH 3 | Cl | 3-CF 3 | 345 |
137 | A-1 | (CH 2) 3CF 3 | Cl | 3-Cl | 365 |
138 | A-1 | (CH 2) 3CF 3 | Cl | 3-Br | 409 |
141 (Ex.5) | A-2 | (CH 2) 4CH 3 | Cl | (m = 0) | ** |
142 | A-3A | (CH 2) 2CF 3 | Cl | 3-CN | 354 |
143 | A-3A | (CH 2) 3CF 3 | Cl | 3-Cl | 379 |
144 | A-2 | (CH 2) 3CF 3 | Cl | (m = 0) | 356 |
145 | A-2 | (CH 2) 4CF 3 | Cl | (m = 0) | 370 |
146 | A-7;R 15係H | (CH 2) 3CF 3 | Cl | 3-CN | 358 |
INCode | Cmpd | 結構 | M.S. (AP+) 或m.p. |
TLU08 | 53 | 415 (80–83) | |
TKV38 | 54 | 361 (78-81) |
Cmpd | 1H NMR(CDCl 3溶液,除非另有指明) |
1 | 8.48 (s, 2H), 7.53 (dd, 1H), 7.35 (t, 1H), 7.18 (dd, 1H), 4.02 (d, 2H), 1.98–1.83 (m, 1H), 0.89 (d, 6H). |
2 | 8.48 (m, 2H), 7.55 (dd, 1H), 7.38 (t, 1H), 7.26 (s, 1H), 7.20 (dd, 1H), 5.55–5.46 (m, 1H), 5.38 (m, 1H), 4.80-4.78 (m, 2H). |
3 | 8.47 (s, 2H), 7.54 (dd, 1H), 7.36 (t, 1H), 7.19 (dd, 1H), 4.99–4.93 (m, 1H), 4.91–4.89 (m, 1H), 4.63 (s, 2H), 1.71 (s, 3H). |
12 | 8.48 (s, 2H), 7.51 (dd, 1H), 7.32 (t, 1H), 7.15 (dd, 1H), 2.55 (s, 3H). |
13 | 8.49 (s, 2H), 7.53 (dd, 1H), 7.35 (t, 1H), 7.18 (dd, 1H), 4.20 (t, 2H), 1.58–1.67 (m, 2H), 0.82–0.93 (m, 3H). |
14 | 8.49 (s, 2H), 7.51 (dd, 0.95 Hz, 1H), 7.32 (t, 1H), 7.16 (dd, 1H), 1.43 (s, 9 H). |
20 | 8.49 (s, 2H), 7.54 (dd, 1H), 7.37 (t, 1H), 7.20 (dd, 1H), 4.31 (t, 2H), 2.20–2.04 (m, 2H), 1.93–1.85 (m, 2H). |
21 | 8.48 (s, 2H), 7.53 (dd, 1H), 7.35 (t, 1H), 7.17 (dd, 1H), 5.75–5.67 (m, 1H), 5.09–5.05 (m, 1H), 5.03–5.00 (m, 1H), 4.29 (t, 2H), 2.39–2.34 (m, 2H). |
27 | 8.37 (s, 2H), 7.64 (d, 1H), 7.46 (t, 1H), 7.32 (t, 1H), 7.19 (bs, 1H), 7.00 (d, 1H), 4.75 (q, 2H). |
28 | 8.30 (s, 2H), 7.65 (d, 1H), 7.48 (t, 1H), 7.31 (t, 1H), 7.21 (bs, 1H), 7.00 (d, 1H), 4.75 (q, 2H). |
31 | 8.81 (s, 2H), 7.63 (dd, 1H), 7.45 (t, 1H), 7.22 (dd, 1H), 4.58 (q, 2H). |
40 | 8.50 (s, 2H), 7.57 (dd, 1H), 7.43 (t, 1H), 7.24 (dd, 1H), 4.87 (s, 2H). |
99 | 500 MHz) 8.47 (s, 2H) 7.53–7.56 (m, 1H) 7.29–7.33 (m, 1H) 7.14–7.18 (m, 1H) 4.19 (t, 2H) 2.26–2.36 (m, 2H) 2.09 (s, 3H). |
139 | 10.39 (s, 1H), 8.46 (s, 2H), 7.62–7.56 (m, 1H), 7.47–7.42 (m, 1H), 7.22–7.17 (m, 1H). |
140 | (500 MHz) 8.49 (s, 2H), 7.54–7.58 (m, 1H), 7.40–7.45 (m, 1H), 7.30–7.36 (m, 1H), 7.16–7.20 (m, 1H), 3.72 (s, 2H). |
將選自稗草(
Echinochloa crus-galli)、地膚(
Kochia scoparia)、豬草(common ragweed,
Ambrosia elatior)、義大利黑麥草(
Lolium multiflorum)、大馬唐草(
Digitaria sanguinalis)、大狐尾草(
Setaria faberii)、牽牛花(
Ipomoeaspp.)、反枝莧(
Amaranthus retroflexus)、苘麻(
Abutilon theophrasti)、小麥(
Triticum aestivum)、及玉米(
Zea mays)之植物物種的種子栽植於壤土與砂之摻合物中,並且用定向土壤噴灑來進行萌前處理,該處理係使用配製於不具植物毒性之溶劑混合物中的試驗化學物質,且該混合物包括界面活性劑。
同時,將選自這些作物與雜草物種以及黑草(
Alopecurus myosuroides)、及豬殃殃(catchweed bedstraw,
Galium aparine)之植物栽植於含有相同壤土與砂之摻合物的罐中,並且以試驗化學物質(以相同方式配製)進行萌後施用處理。使用高度範圍在2至10 cm且在一葉至二葉階段的植物來進行萌後處理。將經處理的植物與未經處理的對照組維持於溫室中約10天,之後將所有經處理的植物與未經處理的對照組比較,並目視評估其損害。歸納於表A中之植物反應評級係基於0至100的標度,其中0係無效果而100係完全防治。顯示為破折號(–)之反應意指無試驗結果。
試驗B
表A | 化合物 | |||||||||||||
1000 g ai/ha | 12 | 55 | 56 | 57 | 58 | 59 | ||||||||
萌後 | ||||||||||||||
稗草 | 80 | 0 | 50 | 20 | 40 | 0 | ||||||||
黑草 | 50 | - | - | - | - | - | ||||||||
玉米 | 20 | 0 | 30 | 20 | 30 | 20 | ||||||||
大馬唐草 | - | 0 | 40 | 30 | 80 | 10 | ||||||||
大狐尾草 | 70 | 10 | 70 | 20 | 60 | 10 | ||||||||
豬殃殃 | 80 | - | - | - | - | - | ||||||||
地膚 | 80 | - | - | - | - | - | ||||||||
牽牛花 | - | - | - | 10 | 30 | 0 | ||||||||
反枝莧 | 100 | 0 | 60 | 40 | 100 | 30 | ||||||||
豬草 | 60 | - | - | - | - | - | ||||||||
義大利黑麥草 | 50 | - | - | - | - | - | ||||||||
苘麻 | - | 10 | 100 | - | 90 | - | ||||||||
小麥 | 0 | 0 | 10 | 20 | 20 | 30 | ||||||||
表A | 化合物 | |||||||||||||
500 g ai/ha | 6 | 7 | 8 | 9 | 10 | 11 | 13 | 14 | 15 | 16 | 17 | 18 | 20 | 21 |
萌後 | ||||||||||||||
稗草 | 40 | 90 | 40 | 90 | 100 | 20 | 100 | 40 | 100 | 90 | 0 | 0 | 100 | 100 |
黑草 | 30 | 80 | 20 | 80 | 90 | 20 | 70 | 70 | 100 | 90 | 0 | 0 | 50 | 80 |
玉米 | 10 | 70 | 20 | 50 | 60 | 10 | 90 | 10 | 90 | 60 | 20 | 0 | 40 | 60 |
大馬唐草 | - | - | - | - | - | - | - | - | - | - | - | - | - | - |
大狐尾草 | 50 | 100 | 60 | 90 | 100 | 20 | 100 | 60 | 100 | 90 | 0 | 0 | 100 | 100 |
豬殃殃 | 90 | 100 | 90 | 100 | 100 | 20 | 100 | 100 | 100 | 100 | 0 | 0 | 90 | 90 |
地膚 | 90 | 100 | 80 | 90 | 100 | 40 | 100 | 70 | 100 | 100 | 0 | 10 | 100 | 100 |
牽牛花 | - | - | - | - | - | - | - | - | - | - | - | - | - | - |
反枝莧 | 90 | 100 | 90 | 100 | 100 | 60 | 100 | 100 | 100 | 100 | 40 | 20 | 100 | 100 |
豬草 | 30 | 90 | 40 | 10 | 50 | 0 | 20 | 0 | 40 | 30 | 0 | 0 | 40 | 40 |
義大利黑麥草 | 40 | 70 | 30 | 50 | 60 | 0 | 100 | 70 | 90 | 30 | 0 | 0 | 40 | 90 |
苘麻 | - | - | - | - | - | - | - | - | - | - | - | - | - | - |
小麥 | 10 | 20 | 0 | 50 | 40 | 0 | 30 | 40 | 100 | 20 | 0 | 0 | 20 | 40 |
表A | 化合物 | |||||||||||||
500 g ai/ha | 22 | 23 | 24 | 25 | 26 | 27 | 28 | 30 | 31 | 32 | 33 | 34 | 35 | 39 |
萌後 | ||||||||||||||
稗草 | 100 | 50 | 10 | 10 | 100 | 0 | 20 | 20 | 0 | 0 | 100 | 20 | 80 | 0 |
黑草 | 90 | 50 | 0 | 30 | 100 | - | - | 30 | 0 | 0 | 90 | 70 | 80 | 0 |
玉米 | 50 | 20 | 0 | 20 | 100 | 0 | 0 | 70 | 0 | 0 | 90 | 30 | 30 | 0 |
大馬唐草 | - | - | - | - | - | 0 | 0 | - | - | - | - | - | - | - |
大狐尾草 | 100 | 80 | 0 | 10 | 100 | 0 | 0 | 100 | 0 | 0 | 100 | 80 | 100 | 0 |
豬殃殃 | 90 | 100 | 20 | 50 | 100 | - | - | 100 | 0 | 0 | 100 | 100 | 100 | 0 |
地膚 | 100 | 100 | 0 | 50 | 100 | - | - | 100 | 0 | 0 | 100 | 90 | 100 | 0 |
牽牛花 | - | - | - | - | - | 0 | 0 | - | - | - | - | - | - | - |
反枝莧 | 100 | 100 | 10 | 60 | 100 | 0 | 20 | 100 | 0 | 30 | 100 | 100 | 100 | 0 |
豬草 | 30 | 10 | 0 | 20 | 60 | - | - | 0 | 0 | 0 | 40 | 0 | 0 | 0 |
義大利黑麥草 | 60 | 70 | 0 | 0 | 80 | - | - | 0 | 0 | 0 | 80 | 0 | 40 | 0 |
苘麻 | - | - | - | - | - | 0 | 30 | - | - | - | - | - | - | - |
小麥 | 30 | 10 | 0 | 10 | 90 | 0 | 0 | 30 | 0 | 0 | 60 | 0 | 20 | 0 |
表A | 化合物 | |||||||||||||
500 g ai/ha | 40 | 41 | 42 | 47 | 48 | 49 | 61 | 64 | 65 | 72 | 73 | 75 | 78 | 79 |
萌後 | ||||||||||||||
稗草 | 20 | 0 | 0 | 0 | 30 | 0 | 100 | 0 | 70 | 100 | 100 | 100 | 100 | 100 |
黑草 | 20 | 0 | 0 | 0 | 20 | 0 | 100 | 0 | 40 | 50 | 100 | 60 | 60 | 90 |
玉米 | 20 | 0 | 30 | 0 | 0 | 0 | 40 | 0 | 20 | 60 | 60 | 90 | 60 | 90 |
大馬唐草 | - | - | - | - | - | - | - | - | - | - | - | - | - | - |
大狐尾草 | 40 | 0 | 0 | 0 | 20 | 0 | 100 | 0 | 90 | 100 | 100 | 100 | 80 | 80 |
豬殃殃 | 40 | 0 | 0 | 0 | 10 | 0 | 100 | 0 | 70 | 100 | 100 | 100 | 100 | 100 |
地膚 | 100 | 60 | 60 | 0 | 0 | 0 | - | 0 | - | 100 | 100 | 100 | 100 | 100 |
牽牛花 | - | - | - | - | - | - | - | - | - | - | - | - | - | - |
反枝莧 | 100 | 90 | 90 | 0 | 40 | 0 | 100 | 0 | 100 | 100 | 100 | 100 | 90 | 100 |
豬草 | 0 | 10 | 0 | 0 | 0 | 0 | 30 | 0 | 30 | 30 | 30 | 40 | 30 | 40 |
義大利黑麥草 | 0 | 0 | 0 | 0 | 0 | 0 | 80 | 0 | 0 | 40 | 100 | 70 | 30 | 90 |
苘麻 | - | - | - | - | - | - | - | - | - | - | - | - | - | - |
小麥 | 20 | 0 | 0 | 0 | 0 | 0 | 30 | 0 | 0 | 40 | 90 | 70 | 30 | 30 |
表A | 化合物 | |||||||||||||
500 g ai/ha | 83 | 84 | 85 | 91 | 106 | 125 | 130 | 136 | 139 | |||||
萌後 | ||||||||||||||
稗草 | 90 | 40 | 20 | 100 | 100 | 90 | 100 | 80 | 0 | |||||
黑草 | 40 | 0 | 0 | 30 | 20 | 90 | 90 | 100 | 0 | |||||
玉米 | 30 | 40 | 40 | 50 | 10 | 30 | 50 | 50 | 0 | |||||
大馬唐草 | - | - | - | - | - | - | - | - | - | |||||
大狐尾草 | 80 | 60 | 60 | 100 | 70 | 90 | 90 | 90 | 0 | |||||
豬殃殃 | 20 | 40 | 90 | 90 | 10 | 100 | 100 | 100 | 0 | |||||
地膚 | 90 | 70 | 80 | 100 | - | 100 | 100 | 100 | 0 | |||||
牽牛花 | - | - | - | - | - | - | - | - | - | |||||
反枝莧 | 70 | 70 | 70 | 100 | 20 | 100 | 100 | 100 | 0 | |||||
豬草 | 0 | 0 | 0 | 20 | 0 | 40 | 60 | 60 | 0 | |||||
義大利黑麥草 | 0 | 0 | 0 | 30 | 0 | 90 | 90 | 70 | 20 | |||||
苘麻 | - | - | - | - | - | - | - | - | - | |||||
小麥 | 0 | 20 | 20 | 30 | 0 | 30 | 30 | 20 | 0 | |||||
表A | 化合物 | |||||||||||||
125 g ai/ha | 1 | 2 | 3 | 4 | 5 | 6 | 7 | 8 | 9 | 10 | 11 | 13 | 15 | 16 |
萌後 | ||||||||||||||
稗草 | 30 | 40 | 60 | 0 | 0 | 10 | 30 | 10 | 20 | 20 | 10 | 80 | 90 | 10 |
黑草 | 20 | 30 | 30 | 0 | 0 | 10 | 30 | 0 | 30 | 20 | 0 | 30 | 90 | 20 |
玉米 | 20 | 20 | 30 | 0 | 0 | 0 | 10 | 0 | 20 | 10 | 0 | 30 | 50 | 20 |
大狐尾草 | 60 | 60 | 80 | 0 | 0 | 10 | 50 | 30 | 20 | 30 | 20 | 80 | 90 | 20 |
豬殃殃 | 70 | 90 | 70 | 0 | 0 | 60 | 100 | 60 | 70 | 100 | 10 | 100 | 100 | 90 |
地膚 | 30 | 90 | 40 | 0 | 0 | 40 | 100 | 40 | 50 | 90 | 0 | 100 | 100 | 80 |
反枝莧 | 70 | 80 | 100 | 0 | 0 | 60 | 100 | 50 | 100 | 90 | 10 | 90 | 100 | 90 |
豬草 | 10 | 0 | 0 | 0 | 0 | 10 | 40 | 10 | 0 | 10 | 0 | 0 | 20 | 10 |
義大利黑麥草 | 0 | 20 | 30 | 0 | 0 | 0 | 20 | 0 | 0 | 10 | 0 | 0 | 60 | 10 |
小麥 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 10 | 0 | 0 | 20 | 20 | 20 |
表A | 化合物 | |||||||||||||
125 g ai/ha | 17 | 18 | 19 | 20 | 21 | 22 | 23 | 24 | 25 | 26 | 30 | 31 | 32 | 33 |
萌後 | ||||||||||||||
稗草 | 0 | 0 | 0 | 30 | 70 | 60 | 10 | 0 | 0 | 100 | 0 | 0 | 0 | 80 |
黑草 | 0 | 0 | 0 | 30 | 60 | 60 | 10 | 0 | 0 | 100 | 10 | 0 | 0 | 60 |
玉米 | 0 | 0 | 0 | 30 | 30 | 30 | 10 | 0 | 0 | 60 | 30 | 0 | 0 | 30 |
大狐尾草 | 0 | 0 | 0 | 50 | 70 | 80 | 30 | 0 | 0 | 100 | 60 | 0 | 0 | 100 |
豬殃殃 | 0 | 0 | 0 | 10 | 80 | 30 | 90 | 10 | 20 | 100 | 60 | 0 | 0 | 100 |
地膚 | 0 | 0 | 0 | 90 | 90 | 90 | 80 | 0 | 10 | 100 | 100 | 0 | 0 | 100 |
反枝莧 | 20 | 10 | 10 | 100 | 80 | 100 | 100 | 0 | 30 | 100 | 100 | 0 | 20 | 100 |
豬草 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 10 | 30 | 0 | 0 | 0 | 30 |
義大利黑麥草 | 0 | 0 | 0 | 0 | 0 | 0 | 10 | 0 | 0 | 70 | 0 | 0 | 0 | 30 |
小麥 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 40 | 0 | 0 | 0 | 20 |
表A | 化合物 | |||||||||||||
125 g ai/ha | 34 | 35 | 36 | 37 | 38 | 39 | 40 | 41 | 42 | 43 | 44 | 45 | 46 | 47 |
萌後 | ||||||||||||||
稗草 | 0 | 10 | 0 | 30 | 60 | 0 | 0 | 0 | 0 | 10 | 0 | 20 | 30 | 0 |
黑草 | 10 | 40 | 0 | 30 | 0 | 0 | 10 | 0 | 0 | 0 | 0 | 0 | 0 | 0 |
玉米 | 30 | 20 | 0 | 10 | 10 | 0 | 20 | 0 | 20 | 0 | 0 | 20 | 10 | 0 |
大狐尾草 | 20 | 40 | 0 | 40 | 90 | 0 | 10 | 0 | 0 | 0 | 0 | 20 | 40 | 0 |
豬殃殃 | 50 | 60 | 0 | 40 | 80 | 0 | 30 | 0 | 0 | 40 | 0 | 100 | 70 | 0 |
地膚 | 60 | 90 | 0 | 40 | 60 | 0 | 70 | 20 | 30 | 10 | 0 | 50 | 90 | 0 |
反枝莧 | 100 | 100 | 60 | 80 | 100 | 0 | 70 | 90 | 80 | 40 | 0 | 100 | 100 | 0 |
豬草 | 0 | 0 | 0 | 0 | 10 | 0 | 0 | 0 | 0 | 0 | 0 | 10 | 0 | 0 |
義大利黑麥草 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 |
小麥 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 |
表A | 化合物 | |||||||||||||
125 g ai/ha | 48 | 49 | 50 | 51 | 53 | 54 | 61 | 62 | 63 | 64 | 65 | 66 | 67 | 68 |
萌後 | ||||||||||||||
稗草 | 0 | 0 | 20 | 0 | 0 | 0 | 100 | 40 | 10 | 0 | 30 | 100 | 0 | 30 |
黑草 | 0 | 0 | 20 | 0 | 0 | 0 | 30 | 40 | 0 | 0 | 20 | 100 | 0 | 30 |
玉米 | 0 | 0 | 10 | 0 | 0 | 0 | 20 | 30 | 30 | 0 | 10 | 70 | 0 | 20 |
大狐尾草 | 0 | 0 | 70 | 0 | 0 | 0 | 60 | 40 | 30 | 0 | 40 | 100 | 0 | 30 |
豬殃殃 | 0 | 0 | 90 | 10 | 0 | 0 | 60 | 80 | 30 | 0 | 20 | 100 | 0 | 60 |
地膚 | 0 | 0 | 90 | 0 | 0 | 0 | - | 100 | 50 | 0 | - | 50 | 0 | 40 |
反枝莧 | 20 | 0 | 100 | 0 | 0 | 0 | 40 | 90 | 60 | 0 | 90 | 100 | 0 | 90 |
豬草 | 0 | 0 | 0 | 0 | 0 | 0 | 10 | 0 | 0 | 0 | 10 | 20 | 0 | 20 |
義大利黑麥草 | 0 | 0 | 20 | 0 | 0 | 0 | 20 | 0 | 0 | 0 | 0 | 50 | 0 | 0 |
小麥 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 30 | 0 | 0 |
表A | 化合物 | |||||||||||||
125 g ai/ha | 69 | 70 | 71 | 72 | 73 | 74 | 75 | 76 | 77 | 78 | 79 | 80 | 81 | 82 |
萌後 | ||||||||||||||
稗草 | 70 | 30 | 40 | 80 | 90 | 40 | 90 | 0 | 90 | 60 | 90 | 90 | 50 | 100 |
黑草 | 30 | 20 | 30 | 30 | 50 | 30 | 40 | 0 | 50 | 20 | 50 | 90 | 40 | 40 |
玉米 | 20 | 10 | 20 | 50 | 30 | 20 | 80 | 0 | 30 | 40 | 80 | 60 | 40 | 30 |
大狐尾草 | 30 | 30 | 40 | 70 | 100 | 70 | 90 | 0 | 90 | 50 | 80 | 90 | 70 | 100 |
豬殃殃 | 60 | 70 | 90 | 80 | 100 | 80 | 80 | 90 | 100 | 70 | 90 | 90 | 80 | 100 |
地膚 | 40 | 70 | 50 | 100 | 100 | 40 | 100 | 0 | 100 | 70 | 100 | 70 | 50 | 100 |
反枝莧 | 80 | 20 | 70 | 100 | 100 | 100 | 100 | 30 | 100 | 80 | 100 | 100 | 100 | 100 |
豬草 | 0 | 20 | 20 | 10 | 20 | 10 | 30 | 0 | 0 | 0 | 30 | 30 | 10 | 40 |
義大利黑麥草 | 0 | 20 | 20 | 10 | 80 | 20 | 40 | 0 | 60 | 0 | 90 | 50 | 10 | 60 |
小麥 | 0 | 0 | 0 | 10 | 20 | 10 | 20 | 0 | 10 | 20 | 20 | 40 | 0 | 30 |
表A | 化合物 | |||||||||||||
125 g ai/ha | 83 | 84 | 85 | 86 | 87 | 88 | 89 | 90 | 91 | 92 | 93 | 94 | 95 | 96 |
萌後 | ||||||||||||||
稗草 | 0 | 0 | 0 | 40 | 100 | 0 | 90 | 30 | 30 | 100 | 0 | 0 | 30 | 10 |
黑草 | 0 | 0 | 0 | 20 | 70 | 0 | 60 | 0 | 20 | 50 | 0 | 0 | 10 | 10 |
玉米 | 20 | 10 | 10 | 30 | 50 | 0 | 20 | 10 | 20 | 40 | 0 | 0 | 10 | 20 |
大狐尾草 | 0 | 0 | 0 | 30 | 90 | 0 | 50 | 60 | 30 | 100 | 0 | 0 | 60 | 10 |
豬殃殃 | 30 | 30 | 30 | 70 | 70 | 0 | 80 | 20 | 70 | 100 | 0 | 0 | 40 | 20 |
地膚 | 30 | 30 | 30 | 100 | 100 | 0 | 90 | 50 | 60 | 100 | 0 | 0 | 0 | 0 |
反枝莧 | 30 | 30 | 30 | 40 | 60 | 0 | 90 | 50 | 100 | 100 | 0 | 0 | 20 | 10 |
豬草 | 0 | 0 | 0 | 0 | 0 | 0 | 10 | 0 | 0 | 20 | 0 | 0 | 0 | 0 |
義大利黑麥草 | 0 | 0 | 0 | 20 | 30 | 0 | 30 | 0 | 0 | 50 | 0 | 0 | 0 | 0 |
小麥 | 0 | 0 | 0 | 40 | 30 | 0 | 20 | 0 | 20 | 20 | 0 | 0 | 0 | 0 |
表A | 化合物 | |||||||||||||
125 g ai/ha | 97 | 98 | 99 | 100 | 101 | 102 | 103 | 104 | 105 | 106 | 107 | 108 | 109 | 110 |
萌後 | ||||||||||||||
稗草 | 20 | 10 | 80 | 50 | 20 | 0 | 30 | 0 | 0 | 40 | 90 | 10 | 0 | 60 |
黑草 | 20 | 10 | 80 | 40 | 0 | 0 | 10 | 20 | 10 | 0 | 90 | 0 | 0 | 50 |
玉米 | 10 | 10 | 50 | 10 | 0 | 0 | 20 | 10 | 0 | 0 | 60 | 20 | 20 | 50 |
大狐尾草 | 60 | 20 | 90 | 70 | 20 | 0 | 70 | 10 | 0 | 10 | 90 | 10 | 0 | 90 |
豬殃殃 | 100 | 50 | 70 | 70 | 40 | 0 | 100 | 30 | 20 | 0 | 90 | 40 | 30 | 100 |
地膚 | 40 | 0 | 40 | 80 | 20 | 0 | 100 | 10 | 10 | - | 90 | 40 | 20 | 100 |
反枝莧 | 50 | 90 | 40 | 70 | 60 | 0 | 100 | 40 | 30 | 10 | 100 | 50 | 60 | 100 |
豬草 | 20 | 10 | 30 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 30 | 0 | 20 | 0 |
義大利黑麥草 | 30 | 0 | 50 | 20 | 10 | 0 | 0 | 0 | 0 | 0 | 80 | 0 | 0 | 20 |
小麥 | 0 | 10 | 30 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 30 | 0 | 0 | 20 |
表A | 化合物 | |||||||||||||
125 g ai/ha | 111 | 112 | 113 | 114 | 115 | 116 | 117 | 118 | 119 | 120 | 121 | 122 | 123 | 124 |
萌後 | ||||||||||||||
稗草 | 0 | 10 | 40 | 10 | 0 | 10 | 10 | 10 | 0 | 0 | 40 | 50 | 50 | 60 |
黑草 | 0 | 30 | 40 | 10 | 20 | 0 | 10 | 0 | 0 | 0 | 30 | 60 | 50 | 60 |
玉米 | 0 | 0 | 20 | 20 | 10 | 10 | 10 | 10 | 20 | 0 | 10 | 20 | 10 | 20 |
大狐尾草 | 0 | 30 | 50 | 20 | 0 | 20 | 10 | 10 | 0 | 0 | 70 | 40 | 50 | 70 |
豬殃殃 | 0 | 80 | 80 | 80 | 20 | 60 | 100 | 30 | 90 | 30 | 80 | 60 | 100 | 90 |
地膚 | 0 | 30 | 100 | 80 | 0 | 10 | 50 | 60 | 30 | 0 | 80 | 80 | 90 | 80 |
反枝莧 | 0 | 70 | 100 | 100 | 40 | 50 | 70 | 60 | 100 | 20 | 100 | 100 | 100 | 100 |
豬草 | 0 | 40 | 20 | 20 | 0 | 0 | 20 | 10 | 10 | 0 | 50 | 10 | 10 | 20 |
義大利黑麥草 | 0 | 0 | 30 | 10 | 0 | 0 | 0 | 0 | 0 | 0 | 20 | 20 | 20 | 20 |
小麥 | 0 | 0 | 20 | 10 | 0 | 0 | 0 | 0 | 0 | 0 | 10 | 0 | 0 | 10 |
表A | 化合物 | |||||||||||||
125 g ai/ha | 125 | 126 | 127 | 128 | 129 | 130 | 131 | 132 | 133 | 134 | 135 | 136 | 137 | 138 |
萌後 | ||||||||||||||
稗草 | 30 | 0 | 30 | 20 | 100 | 90 | 10 | 50 | 30 | 20 | 10 | 30 | 60 | 90 |
黑草 | 30 | 0 | 20 | 20 | 80 | 50 | 0 | 30 | 0 | 20 | 20 | 50 | 30 | 90 |
玉米 | 10 | 0 | 20 | 10 | 20 | 20 | 30 | 30 | 20 | 10 | 20 | 20 | 10 | 60 |
大狐尾草 | 50 | 0 | 50 | 20 | 100 | 40 | 20 | 50 | 30 | 20 | 20 | 30 | 60 | 90 |
豬殃殃 | 100 | 0 | 90 | 80 | 90 | 100 | 50 | 60 | 50 | 40 | 80 | 40 | 100 | 100 |
地膚 | 100 | 0 | 60 | 60 | 100 | 100 | 90 | 70 | 20 | 60 | 60 | 80 | 100 | 100 |
反枝莧 | 100 | 10 | 30 | 50 | 70 | 100 | 80 | 90 | 50 | 80 | 90 | 100 | 100 | 100 |
豬草 | 30 | 0 | 0 | 0 | 0 | 30 | 0 | 0 | 0 | 10 | 10 | 20 | 40 | 60 |
義大利黑麥草 | 20 | 0 | 0 | 0 | 60 | 20 | 20 | 0 | 0 | 10 | 10 | 10 | 30 | 100 |
小麥 | 20 | 0 | 10 | 10 | 10 | 30 | 20 | 20 | 0 | 10 | 0 | 10 | 10 | 40 |
表A | 化合物 | |||||||||||||
125 g ai/ha | 139 | 140 | 141 | 142 | 143 | 144 | 145 | 146 | ||||||
萌後 | ||||||||||||||
稗草 | 0 | 0 | 20 | 0 | 70 | 90 | 80 | 90 | ||||||
黑草 | 0 | 0 | 10 | 0 | 80 | 90 | 60 | 90 | ||||||
玉米 | 0 | 0 | 20 | 10 | 30 | 80 | 50 | 80 | ||||||
大狐尾草 | 0 | 0 | 40 | 0 | 70 | 90 | 70 | 90 | ||||||
豬殃殃 | 0 | 0 | 60 | 20 | 100 | 100 | 80 | 100 | ||||||
地膚 | 0 | 30 | 60 | 10 | 100 | 100 | 90 | 100 | ||||||
反枝莧 | 0 | 20 | 70 | 20 | 100 | 100 | 100 | 70 | ||||||
豬草 | 0 | 0 | 20 | 20 | 50 | 10 | 20 | 30 | ||||||
義大利黑麥草 | 0 | 0 | 10 | 0 | 80 | 80 | 40 | 70 | ||||||
小麥 | 0 | 0 | 0 | 0 | 20 | 60 | 30 | 20 | ||||||
表A | 化合物 | |||||||||||||
31 g ai/ha | 1 | 2 | 3 | 4 | 5 | 19 | 36 | 37 | 38 | 43 | 44 | 45 | 46 | 50 |
萌後 | ||||||||||||||
稗草 | 20 | 30 | 20 | 0 | 0 | 0 | 0 | 0 | 10 | 0 | 0 | 20 | 0 | 0 |
黑草 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 |
玉米 | 0 | 10 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 10 |
大狐尾草 | 30 | 30 | 30 | 0 | 0 | 0 | 0 | 0 | 40 | 0 | 0 | 20 | 0 | 20 |
豬殃殃 | 50 | 60 | 40 | 0 | 0 | 0 | 0 | 10 | 50 | 20 | 0 | 50 | 50 | 60 |
地膚 | 20 | 50 | 0 | 0 | 0 | 0 | 0 | 0 | 30 | 0 | 0 | 20 | 30 | 60 |
反枝莧 | 40 | 60 | 70 | 0 | 0 | 10 | 0 | 20 | 80 | 10 | 0 | 80 | 60 | 80 |
豬草 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 10 | 0 | 0 |
義大利黑麥草 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 |
小麥 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 |
表A | 化合物 | |||||||||||||
31 g ai/ha | 51 | 53 | 54 | 62 | 63 | 66 | 67 | 68 | 69 | 70 | 71 | 74 | 76 | 77 |
萌後 | ||||||||||||||
稗草 | 0 | 0 | 0 | 20 | 0 | 40 | 0 | 10 | 10 | 0 | 0 | 10 | 0 | 30 |
黑草 | 0 | 0 | 0 | 0 | 0 | 10 | 0 | 10 | 10 | 0 | 10 | 10 | 0 | 20 |
玉米 | 0 | 0 | 0 | 0 | 10 | 20 | 0 | 10 | 0 | 10 | 10 | 10 | 0 | 10 |
大狐尾草 | 0 | 0 | 0 | 0 | 0 | 30 | 0 | 20 | 20 | 0 | 10 | 20 | 0 | 30 |
豬殃殃 | 0 | 0 | 0 | 30 | 0 | 30 | 0 | 20 | 40 | 30 | 30 | 20 | 0 | 90 |
地膚 | 0 | 0 | 0 | 60 | 20 | 20 | 0 | 20 | 20 | 20 | 10 | 20 | 0 | 100 |
反枝莧 | 0 | 0 | 0 | 50 | 20 | 40 | 0 | 20 | 40 | 10 | 30 | 60 | 0 | 100 |
豬草 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 |
義大利黑麥草 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 20 |
小麥 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 |
表A | 化合物 | |||||||||||||
31 g ai/ha | 80 | 81 | 82 | 86 | 87 | 88 | 89 | 90 | 92 | 93 | 94 | 95 | 96 | 97 |
萌後 | ||||||||||||||
稗草 | 30 | 10 | 30 | 20 | 40 | 0 | 30 | 0 | 40 | 0 | 0 | 0 | 0 | 10 |
黑草 | 30 | 10 | 40 | 0 | 10 | 0 | 20 | 0 | 10 | 0 | 0 | 0 | 0 | 0 |
玉米 | 10 | 10 | 20 | 30 | 40 | 0 | 10 | 0 | 10 | 0 | 0 | 0 | 0 | 10 |
大狐尾草 | 30 | 20 | 30 | 10 | 40 | 0 | 20 | 10 | 50 | 0 | 0 | 0 | 0 | 10 |
豬殃殃 | 60 | 30 | 90 | 30 | 30 | 0 | 30 | 0 | 90 | 0 | 0 | 10 | 0 | 100 |
地膚 | 50 | 30 | 80 | 90 | 100 | 0 | 80 | 30 | 100 | 0 | 0 | 0 | 0 | - |
反枝莧 | 80 | 50 | 100 | 30 | 40 | 0 | 90 | 10 | 100 | 0 | 0 | 10 | 0 | 20 |
豬草 | 10 | 0 | 40 | 0 | 0 | 0 | 10 | 0 | 0 | 0 | 0 | 0 | 0 | 10 |
義大利黑麥草 | 0 | 0 | 40 | 0 | 0 | 0 | 10 | 0 | 0 | 0 | 0 | 0 | 0 | 20 |
小麥 | 0 | 0 | 10 | 30 | 20 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 |
表A | 化合物 | |||||||||||||
31 g ai/ha | 98 | 99 | 100 | 101 | 102 | 103 | 104 | 105 | 107 | 108 | 109 | 110 | 111 | 112 |
萌後 | ||||||||||||||
稗草 | 0 | 30 | 10 | 10 | 0 | 0 | 0 | 0 | 40 | 0 | 0 | 30 | 0 | 0 |
黑草 | 0 | 30 | 0 | 0 | 0 | 0 | 0 | 0 | 50 | 0 | 0 | 0 | 0 | 0 |
玉米 | 0 | 0 | 10 | 0 | 0 | 20 | 0 | 0 | 30 | 10 | 10 | 20 | 0 | 0 |
大狐尾草 | 0 | 50 | 20 | 0 | 0 | 10 | 0 | 0 | 70 | 0 | 0 | 30 | 0 | 0 |
豬殃殃 | 10 | 20 | 20 | 10 | 0 | 70 | 10 | 10 | 90 | 20 | 0 | 70 | 0 | 60 |
地膚 | 0 | 20 | 60 | 0 | 0 | 70 | 0 | 0 | 90 | 20 | 0 | 100 | 0 | 0 |
反枝莧 | 30 | 10 | 30 | 20 | 0 | 90 | 10 | 10 | 100 | 20 | 20 | 90 | 0 | 40 |
豬草 | 0 | 10 | 0 | 0 | 0 | 0 | 0 | 0 | 20 | 0 | 0 | 0 | 0 | 20 |
義大利黑麥草 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 20 | 0 | 0 | 0 | 0 | 0 |
小麥 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 |
表A | 化合物 | |||||||||||||
31 g ai/ha | 113 | 114 | 115 | 116 | 117 | 118 | 119 | 120 | 121 | 122 | 123 | 124 | 126 | 127 |
萌後 | ||||||||||||||
稗草 | 10 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 20 | 10 | 10 | 10 | 0 | 10 |
黑草 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 20 | 20 | 10 | 20 | 0 | 10 |
玉米 | 10 | 10 | 0 | 0 | 10 | 0 | 10 | 0 | 10 | 10 | 10 | 10 | 0 | 10 |
大狐尾草 | 10 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 10 | 10 | 20 | 30 | 0 | 10 |
豬殃殃 | 40 | 50 | 20 | 30 | 60 | 10 | 10 | 0 | 70 | 30 | 90 | 70 | 0 | 60 |
地膚 | 80 | 20 | 0 | 0 | 20 | 30 | 30 | 0 | 20 | 80 | 50 | 50 | 0 | 10 |
反枝莧 | 90 | 50 | 10 | 40 | 30 | 40 | 70 | 0 | 80 | 70 | 70 | 70 | 0 | 20 |
豬草 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 20 | 0 | 0 | 10 | 0 | 0 |
義大利黑麥草 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 10 | 0 | 0 | 0 | 0 | 0 |
小麥 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 10 | 0 | 0 | 10 | 0 | 0 |
表A | 化合物 | |||||||||||||
31 g ai/ha | 128 | 129 | 131 | 132 | 133 | 134 | 135 | 137 | 138 | 140 | 141 | 142 | 143 | 144 |
萌後 | ||||||||||||||
稗草 | 0 | 20 | 0 | 30 | 10 | 0 | 0 | 20 | 90 | 0 | 10 | 0 | 20 | 40 |
黑草 | 0 | 20 | 0 | 0 | 0 | 10 | 0 | 10 | 40 | 0 | 0 | 0 | 30 | 50 |
玉米 | 10 | 20 | 20 | 20 | 0 | 10 | 10 | 10 | 30 | 0 | 10 | 0 | 10 | 20 |
大狐尾草 | 10 | 20 | 0 | 30 | 10 | 10 | 10 | 10 | 90 | 0 | 20 | 0 | 30 | 60 |
豬殃殃 | 20 | 30 | 20 | 20 | 30 | 10 | 50 | 40 | 70 | 0 | 40 | 0 | 90 | 40 |
地膚 | 10 | 40 | 40 | 40 | 0 | 20 | 10 | 90 | 90 | 0 | 50 | 0 | 90 | 90 |
反枝莧 | 20 | 20 | 50 | 60 | 30 | 40 | 40 | 80 | 100 | 0 | 40 | 0 | 100 | 90 |
豬草 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 10 | 30 | 0 | 0 | 0 | 20 | 10 |
義大利黑麥草 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 10 | 30 | 0 | 0 | 0 | 20 | 30 |
小麥 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 20 | 0 | 0 | 0 | 10 | 10 |
表A | 化合物 | 表A | 化合物 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
31 g ai/ha | 145 | 146 | 1000 g ai/ha | 12 | 55 | 56 | 57 | 58 | 59 | |||||||||||||||||||||||||||||||||||||||||||||||||||||
萌後 | 萌前 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
稗草 | 30 | 30 | 稗草 | 80 | 0 | 90 | 50 | 90 | 20 | |||||||||||||||||||||||||||||||||||||||||||||||||||||
黑草 | 40 | 30 | 玉米 | - | 0 | 0 | 0 | 20 | 0 | |||||||||||||||||||||||||||||||||||||||||||||||||||||
玉米 | 30 | 20 | 大馬唐草 | - | 0 | 100 | 100 | 100 | 80 | |||||||||||||||||||||||||||||||||||||||||||||||||||||
大狐尾草 | 50 | 30 | 大狐尾草 | 100 | 0 | 100 | 90 | 100 | 30 | |||||||||||||||||||||||||||||||||||||||||||||||||||||
豬殃殃 | 40 | 70 | 地膚 | 0 | - | - | - | - | - | |||||||||||||||||||||||||||||||||||||||||||||||||||||
地膚 | 70 | 70 | 牽牛花 | - | - | - | 0 | 0 | 0 | |||||||||||||||||||||||||||||||||||||||||||||||||||||
反枝莧 | 90 | 60 | 反枝莧 | 100 | 0 | 100 | 60 | 50 | 30 | |||||||||||||||||||||||||||||||||||||||||||||||||||||
豬草 | 10 | 0 | 豬草 | 80 | - | - | - | - | - | |||||||||||||||||||||||||||||||||||||||||||||||||||||
義大利黑麥草 | 10 | 0 | 義大利黑麥草 | 40 | - | - | - | - | - | |||||||||||||||||||||||||||||||||||||||||||||||||||||
小麥 | 10 | 20 | 苘麻 | - | 0 | 90 | 20 | 20 | 0 | |||||||||||||||||||||||||||||||||||||||||||||||||||||
小麥 | - | 0 | 0 | 0 | 20 | 0 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||
表A | 化合物 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
500 g ai/ha | 6 | 7 | 8 | 9 | 10 | 11 | 13 | 14 | 15 | 16 | 17 | 18 | 20 | 21 | ||||||||||||||||||||||||||||||||||||||||||||||||
萌前 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
稗草 | 60 | 100 | 100 | 90 | 100 | 30 | 100 | 60 | 100 | 100 | 0 | 0 | 100 | 100 | ||||||||||||||||||||||||||||||||||||||||||||||||
玉米 | - | - | - | - | - | - | - | - | - | - | - | - | - | - | ||||||||||||||||||||||||||||||||||||||||||||||||
大馬唐草 | - | - | - | - | - | - | - | - | - | - | - | - | - | - | ||||||||||||||||||||||||||||||||||||||||||||||||
大狐尾草 | 100 | 100 | 100 | 100 | 100 | 100 | 100 | 100 | 100 | 100 | 0 | 0 | 100 | 100 | ||||||||||||||||||||||||||||||||||||||||||||||||
地膚 | 0 | 100 | 0 | 100 | 100 | 0 | 100 | 70 | 100 | 80 | 0 | 10 | 100 | 100 | ||||||||||||||||||||||||||||||||||||||||||||||||
牽牛花 | - | - | - | - | - | - | - | - | - | - | - | - | - | - | ||||||||||||||||||||||||||||||||||||||||||||||||
反枝莧 | 70 | 100 | 60 | 100 | 100 | 20 | 100 | 100 | 100 | 100 | 10 | 40 | 100 | 100 | ||||||||||||||||||||||||||||||||||||||||||||||||
豬草 | 0 | 50 | 0 | 0 | 0 | 0 | 0 | 10 | 10 | 0 | 0 | 0 | 0 | 0 | ||||||||||||||||||||||||||||||||||||||||||||||||
義大利黑麥草 | 70 | 30 | 30 | 30 | 30 | 0 | 90 | 20 | 90 | 20 | 0 | 0 | 90 | 90 | ||||||||||||||||||||||||||||||||||||||||||||||||
苘麻 | - | - | - | - | - | - | - | - | - | - | - | - | - | - | ||||||||||||||||||||||||||||||||||||||||||||||||
小麥 | - | - | - | - | - | - | - | - | - | - | - | - | - | - | ||||||||||||||||||||||||||||||||||||||||||||||||
表A | 化合物 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
500 g ai/ha | 22 | 23 | 24 | 25 | 26 | 27 | 28 | 30 | 31 | 32 | 33 | 34 | 35 | 39 | ||||||||||||||||||||||||||||||||||||||||||||||||
萌前 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
稗草 | 100 | 70 | 30 | 30 | 100 | 0 | 20 | 0 | 0 | 0 | 100 | 90 | 90 | 0 | ||||||||||||||||||||||||||||||||||||||||||||||||
玉米 | - | - | - | - | - | 0 | 0 | - | - | - | - | - | - | - | ||||||||||||||||||||||||||||||||||||||||||||||||
大馬唐草 | - | - | - | - | - | 0 | 50 | - | - | - | - | - | - | - | ||||||||||||||||||||||||||||||||||||||||||||||||
大狐尾草 | 100 | 100 | 20 | 60 | 100 | 0 | 20 | 100 | 0 | 0 | 100 | 100 | 100 | 0 | ||||||||||||||||||||||||||||||||||||||||||||||||
地膚 | 100 | 50 | 0 | 50 | 100 | - | - | 100 | 0 | 0 | 100 | 40 | 80 | 0 | ||||||||||||||||||||||||||||||||||||||||||||||||
牽牛花 | - | - | - | - | - | 0 | 0 | - | - | - | - | - | - | - | ||||||||||||||||||||||||||||||||||||||||||||||||
反枝莧 | 100 | 100 | 90 | 80 | 100 | 0 | 80 | 100 | 0 | 30 | 100 | 100 | 100 | 0 | ||||||||||||||||||||||||||||||||||||||||||||||||
豬草 | 0 | 10 | 0 | 0 | 20 | - | - | 0 | 0 | 0 | 20 | 0 | 0 | 0 | ||||||||||||||||||||||||||||||||||||||||||||||||
義大利黑麥草 | 90 | 40 | 0 | 0 | 100 | - | - | 0 | 0 | 0 | 100 | 0 | 30 | 0 | ||||||||||||||||||||||||||||||||||||||||||||||||
苘麻 | - | - | - | - | - | 0 | 20 | - | - | - | - | - | - | - | ||||||||||||||||||||||||||||||||||||||||||||||||
小麥 | - | - | - | - | - | 0 | 0 | - | - | - | - | - | - | - | ||||||||||||||||||||||||||||||||||||||||||||||||
表A | 化合物 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
500 g ai/ha | 40 | 41 | 42 | 47 | 48 | 49 | 61 | 64 | 65 | 72 | 73 | 75 | 78 | 79 | ||||||||||||||||||||||||||||||||||||||||||||||||
萌前 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
稗草 | 50 | 0 | 0 | 0 | 10 | 0 | 100 | 0 | 100 | 100 | 100 | 100 | 100 | 100 | ||||||||||||||||||||||||||||||||||||||||||||||||
玉米 | - | - | - | - | - | - | - | - | - | - | - | - | - | - | ||||||||||||||||||||||||||||||||||||||||||||||||
大馬唐草 | - | - | - | - | - | - | - | - | - | - | - | - | - | - | ||||||||||||||||||||||||||||||||||||||||||||||||
大狐尾草 | 100 | 0 | 0 | 0 | 10 | 0 | 100 | 0 | 100 | 100 | 100 | 100 | 100 | 100 | ||||||||||||||||||||||||||||||||||||||||||||||||
地膚 | 90 | 30 | 0 | 0 | 0 | 0 | 100 | 0 | 90 | 100 | 100 | 100 | 60 | 100 | ||||||||||||||||||||||||||||||||||||||||||||||||
牽牛花 | - | - | - | - | - | - | - | - | - | - | - | - | - | - | ||||||||||||||||||||||||||||||||||||||||||||||||
反枝莧 | 100 | 40 | 30 | 0 | 0 | 0 | 100 | 0 | 100 | 100 | 100 | 100 | 100 | 100 | ||||||||||||||||||||||||||||||||||||||||||||||||
豬草 | 0 | 80 | 0 | 0 | 0 | 0 | 20 | 0 | 80 | 10 | 50 | 10 | 0 | 90 | ||||||||||||||||||||||||||||||||||||||||||||||||
義大利黑麥草 | 0 | 0 | 0 | 0 | 0 | 0 | 80 | 0 | 30 | 30 | 90 | 100 | 20 | 100 | ||||||||||||||||||||||||||||||||||||||||||||||||
苘麻 | - | - | - | - | - | - | - | - | - | - | - | - | - | - | ||||||||||||||||||||||||||||||||||||||||||||||||
小麥 | - | - | - | - | - | - | - | - | - | - | - | - | - | - | ||||||||||||||||||||||||||||||||||||||||||||||||
表A | 化合物 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
500 g ai/ha | 83 | 84 | 85 | 91 | 106 | 125 | 130 | 136 | 139 | |||||||||||||||||||||||||||||||||||||||||||||||||||||
萌前 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
稗草 | 90 | 90 | 10 | 100 | 100 | 100 | 100 | 100 | 0 | |||||||||||||||||||||||||||||||||||||||||||||||||||||
玉米 | - | - | - | - | - | - | - | - | - | |||||||||||||||||||||||||||||||||||||||||||||||||||||
大馬唐草 | - | - | - | - | - | - | - | - | - | |||||||||||||||||||||||||||||||||||||||||||||||||||||
大狐尾草 | 100 | 100 | 70 | 100 | 100 | 100 | 100 | 100 | 0 | |||||||||||||||||||||||||||||||||||||||||||||||||||||
地膚 | 0 | 0 | 0 | 100 | 90 | 100 | 100 | 100 | 0 | |||||||||||||||||||||||||||||||||||||||||||||||||||||
牽牛花 | - | - | - | - | - | - | - | - | - | |||||||||||||||||||||||||||||||||||||||||||||||||||||
反枝莧 | 90 | 100 | 60 | 100 | 70 | 100 | 100 | 100 | 0 | |||||||||||||||||||||||||||||||||||||||||||||||||||||
豬草 | 0 | 0 | 0 | 0 | 0 | 40 | 90 | 80 | 0 | |||||||||||||||||||||||||||||||||||||||||||||||||||||
義大利黑麥草 | 0 | 0 | 0 | 80 | 10 | 100 | 100 | 100 | 0 | |||||||||||||||||||||||||||||||||||||||||||||||||||||
苘麻 | - | - | - | - | - | - | - | - | - | |||||||||||||||||||||||||||||||||||||||||||||||||||||
小麥 | - | - | - | - | - | - | - | - | - | |||||||||||||||||||||||||||||||||||||||||||||||||||||
表A | 化合物 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
125 g ai/ha | 1 | 2 | 3 | 4 | 5 | 6 | 7 | 8 | 9 | 10 | 11 | 13 | 15 | 16 | ||||||||||||||||||||||||||||||||||||||||||||||||
萌前 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
稗草 | 30 | 50 | 80 | 0 | 0 | 10 | 50 | 30 | 40 | 40 | 0 | 100 | 100 | 30 | ||||||||||||||||||||||||||||||||||||||||||||||||
大狐尾草 | 70 | 100 | 100 | 0 | 0 | 60 | 90 | 100 | 100 | 100 | 40 | 100 | 100 | 90 | ||||||||||||||||||||||||||||||||||||||||||||||||
地膚 | 40 | 70 | 40 | 0 | 0 | 0 | 50 | 0 | 70 | 90 | 0 | 90 | 100 | 90 | ||||||||||||||||||||||||||||||||||||||||||||||||
反枝莧 | 70 | 90 | 100 | 0 | 0 | 10 | 100 | 10 | 100 | 100 | 0 | 100 | 100 | 90 | ||||||||||||||||||||||||||||||||||||||||||||||||
豬草 | 0 | 0 | 0 | 0 | 0 | 0 | - | 0 | 0 | 0 | 0 | 0 | 0 | 0 | ||||||||||||||||||||||||||||||||||||||||||||||||
義大利黑麥草 | 0 | 10 | 30 | 0 | 0 | 0 | 0 | 0 | 10 | 10 | 0 | 10 | 40 | 0 | ||||||||||||||||||||||||||||||||||||||||||||||||
表A | 化合物 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
125 g ai/ha | 17 | 18 | 19 | 20 | 21 | 22 | 23 | 24 | 25 | 26 | 30 | 31 | 32 | 33 | ||||||||||||||||||||||||||||||||||||||||||||||||
萌前 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
稗草 | 0 | 0 | 0 | 100 | 100 | 40 | 20 | 0 | 0 | 100 | 0 | 0 | 0 | 100 | ||||||||||||||||||||||||||||||||||||||||||||||||
大狐尾草 | 0 | 0 | 0 | 100 | 100 | 100 | 70 | 0 | 10 | 100 | 100 | 0 | 0 | 100 | ||||||||||||||||||||||||||||||||||||||||||||||||
地膚 | 0 | 0 | 20 | 30 | 40 | 30 | 0 | 0 | 0 | 100 | 90 | 0 | 0 | 60 | ||||||||||||||||||||||||||||||||||||||||||||||||
反枝莧 | 0 | 10 | 20 | 100 | 100 | 100 | 100 | 0 | 40 | 100 | 100 | 0 | 30 | 100 | ||||||||||||||||||||||||||||||||||||||||||||||||
豬草 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 20 | 0 | 0 | 0 | 0 | ||||||||||||||||||||||||||||||||||||||||||||||||
義大利黑麥草 | 0 | 0 | 0 | 30 | 30 | 30 | 0 | 0 | 0 | 70 | 0 | 0 | 0 | 40 | ||||||||||||||||||||||||||||||||||||||||||||||||
表A | 化合物 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
125 g ai/ha | 34 | 35 | 36 | 37 | 38 | 39 | 40 | 41 | 42 | 43 | 44 | 45 | 46 | 47 | ||||||||||||||||||||||||||||||||||||||||||||||||
萌前 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
稗草 | 0 | 70 | 0 | 30 | 90 | 0 | 0 | 0 | 0 | 40 | 0 | 0 | 20 | 0 | ||||||||||||||||||||||||||||||||||||||||||||||||
大狐尾草 | 70 | 100 | 0 | 70 | 100 | 0 | 20 | 0 | 0 | 60 | 40 | 10 | 100 | 0 | ||||||||||||||||||||||||||||||||||||||||||||||||
地膚 | 20 | 30 | 0 | 0 | 40 | 0 | 60 | 30 | 0 | 100 | 0 | 0 | 70 | 0 | ||||||||||||||||||||||||||||||||||||||||||||||||
反枝莧 | 40 | 100 | 0 | 0 | 100 | 0 | 40 | 30 | 0 | 90 | 0 | 70 | 100 | 0 | ||||||||||||||||||||||||||||||||||||||||||||||||
豬草 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 50 | 0 | 0 | 0 | 0 | 0 | 0 | ||||||||||||||||||||||||||||||||||||||||||||||||
義大利黑麥草 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | ||||||||||||||||||||||||||||||||||||||||||||||||
表A | 化合物 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
125 g ai/ha | 48 | 49 | 50 | 51 | 53 | 54 | 61 | 62 | 63 | 64 | 65 | 66 | 67 | 68 | ||||||||||||||||||||||||||||||||||||||||||||||||
萌前 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
稗草 | 0 | 0 | 10 | 0 | 0 | 0 | 50 | 70 | 100 | 0 | 30 | 100 | 0 | 70 | ||||||||||||||||||||||||||||||||||||||||||||||||
大狐尾草 | 0 | 0 | 100 | 0 | 0 | 0 | 100 | 100 | 90 | 0 | 100 | 100 | 0 | 80 | ||||||||||||||||||||||||||||||||||||||||||||||||
地膚 | 0 | 0 | 0 | 0 | 0 | 0 | 90 | 70 | 0 | 0 | 60 | 40 | 0 | 30 | ||||||||||||||||||||||||||||||||||||||||||||||||
反枝莧 | 0 | 0 | 90 | 0 | 0 | 0 | 100 | 90 | 90 | 0 | 100 | 100 | 0 | 80 | ||||||||||||||||||||||||||||||||||||||||||||||||
豬草 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 100 | 0 | 0 | ||||||||||||||||||||||||||||||||||||||||||||||||
義大利黑麥草 | 0 | 0 | 0 | 0 | 0 | 0 | 30 | 10 | 0 | 0 | 10 | 30 | 0 | 0 | ||||||||||||||||||||||||||||||||||||||||||||||||
表A | 化合物 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
125 g ai/ha | 69 | 70 | 71 | 72 | 73 | 74 | 75 | 76 | 77 | 78 | 79 | 80 | 81 | 82 | ||||||||||||||||||||||||||||||||||||||||||||||||
萌前 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
稗草 | 90 | 20 | 10 | 90 | 100 | 60 | 100 | 70 | 100 | 60 | 100 | 100 | 90 | 100 | ||||||||||||||||||||||||||||||||||||||||||||||||
大狐尾草 | 70 | 60 | 100 | 90 | 100 | 100 | 100 | 70 | 100 | 90 | 100 | 100 | 100 | 100 | ||||||||||||||||||||||||||||||||||||||||||||||||
地膚 | 30 | 0 | 0 | 90 | 100 | 100 | 80 | 0 | 100 | 20 | 80 | 100 | 90 | 80 | ||||||||||||||||||||||||||||||||||||||||||||||||
反枝莧 | 100 | 0 | 40 | 100 | 100 | 90 | 100 | 50 | 100 | 80 | 100 | 100 | 100 | 100 | ||||||||||||||||||||||||||||||||||||||||||||||||
豬草 | 0 | 0 | 0 | 0 | 10 | 0 | 0 | 0 | 0 | 0 | 30 | 20 | 0 | 60 | ||||||||||||||||||||||||||||||||||||||||||||||||
義大利黑麥草 | 0 | 0 | 0 | 10 | 50 | 20 | 80 | 0 | 70 | 0 | 90 | 50 | 20 | 80 | ||||||||||||||||||||||||||||||||||||||||||||||||
表A | 化合物 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
125 g ai/ha | 83 | 84 | 85 | 86 | 87 | 88 | 89 | 90 | 91 | 92 | 93 | 94 | 95 | 96 | ||||||||||||||||||||||||||||||||||||||||||||||||
萌前 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
稗草 | 30 | 0 | 0 | 90 | 100 | 0 | 90 | 40 | 90 | 100 | 0 | 0 | 70 | 0 | ||||||||||||||||||||||||||||||||||||||||||||||||
大狐尾草 | 90 | 0 | 0 | 50 | 100 | 0 | 50 | 70 | 70 | 100 | 0 | 0 | 50 | 0 | ||||||||||||||||||||||||||||||||||||||||||||||||
地膚 | 0 | 0 | 0 | 100 | 90 | 0 | 50 | 0 | 20 | 90 | 0 | 0 | 0 | 0 | ||||||||||||||||||||||||||||||||||||||||||||||||
反枝莧 | 30 | 0 | 0 | 100 | 100 | 0 | 100 | 0 | 40 | 100 | 0 | 0 | 40 | 0 | ||||||||||||||||||||||||||||||||||||||||||||||||
豬草 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | ||||||||||||||||||||||||||||||||||||||||||||||||
義大利黑麥草 | 0 | 0 | 0 | 20 | 20 | 0 | 20 | 0 | 0 | 80 | 0 | 0 | 0 | 0 | ||||||||||||||||||||||||||||||||||||||||||||||||
表A | 化合物 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
125 g ai/ha | 97 | 98 | 99 | 100 | 101 | 102 | 103 | 104 | 105 | 106 | 107 | 108 | 109 | 110 | ||||||||||||||||||||||||||||||||||||||||||||||||
萌前 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
稗草 | 10 | 30 | 100 | 100 | 10 | 0 | 50 | 30 | 30 | 0 | 100 | 30 | 20 | 100 | ||||||||||||||||||||||||||||||||||||||||||||||||
大狐尾草 | 70 | 40 | 100 | 100 | 40 | 0 | 60 | 40 | 20 | 80 | 100 | 80 | 40 | 100 | ||||||||||||||||||||||||||||||||||||||||||||||||
地膚 | 0 | 0 | 80 | 0 | 0 | 0 | 70 | 0 | 0 | 30 | 100 | 10 | 0 | 100 | ||||||||||||||||||||||||||||||||||||||||||||||||
反枝莧 | 20 | 0 | 90 | 60 | 0 | 0 | 100 | 40 | 20 | 30 | 100 | 70 | 60 | 100 | ||||||||||||||||||||||||||||||||||||||||||||||||
豬草 | 0 | 0 | 10 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 20 | 0 | 0 | 0 | ||||||||||||||||||||||||||||||||||||||||||||||||
義大利黑麥草 | 0 | 0 | 30 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 80 | 0 | 0 | 70 | ||||||||||||||||||||||||||||||||||||||||||||||||
表A | 化合物 | |||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
125 g ai/ha | 111 | 112 | 113 | 114 | 115 | 116 | 117 | 118 | 119 | 120 | 121 | 122 | 123 | 124 | ||||||||||||||||||||||||||||||||||||||||||||||||
萌前 | ||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||||
稗草 | 0 | 80 | 90 | 20 | 0 | 0 | 0 | 0 | 20 | 0 | 30 | 90 | 70 | 80 | ||||||||||||||||||||||||||||||||||||||||||||||||
大狐尾草 | 0 | 70 | 100 | 90 | 0 | 30 | 20 | 20 | 90 | 0 | 100 | 40 | 100 | 100 | ||||||||||||||||||||||||||||||||||||||||||||||||
地膚 | 0 | 50 | 60 | 10 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 70 | 10 | 10 | ||||||||||||||||||||||||||||||||||||||||||||||||
反枝莧 | 0 | 100 | 100 | 30 | 0 | 70 | 30 | 50 | 100 | 0 | 0 | 90 | 80 | 100 | ||||||||||||||||||||||||||||||||||||||||||||||||
豬草 | 0 | 0 | 0 | 80 | 0 | 0 | 0 | 50 | 0 | 0 | 0 | 0 | 0 | 0 | ||||||||||||||||||||||||||||||||||||||||||||||||
義大利黑麥草 | 0 | 0 | 40 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 30 | 20 | 20 | ||||||||||||||||||||||||||||||||||||||||||||||||
表A | 化合物 | |||||||||||||||||||||||||||||||
125 g ai/ha | 125 | 126 | 127 | 128 | 129 | 130 | 131 | 132 | 133 | 134 | 135 | 136 | 137 | 138 | ||||||||||||||||||
萌前 | ||||||||||||||||||||||||||||||||
稗草 | 100 | 0 | 60 | 50 | 100 | 100 | 100 | 100 | 30 | 80 | 40 | 100 | 90 | 100 | ||||||||||||||||||
大狐尾草 | 100 | 0 | 100 | 100 | 100 | 100 | 90 | 100 | 90 | 90 | 50 | 100 | 100 | 100 | ||||||||||||||||||
地膚 | 100 | 0 | 30 | 0 | 100 | 100 | 100 | 60 | 10 | 10 | 0 | 100 | 70 | 100 | ||||||||||||||||||
反枝莧 | 100 | 0 | 70 | 30 | 100 | 100 | 100 | 100 | 100 | 50 | 20 | 100 | 100 | 100 | ||||||||||||||||||
豬草 | 20 | 0 | 0 | 0 | 0 | 20 | 0 | 0 | 0 | 0 | 0 | 80 | 0 | 0 | ||||||||||||||||||
義大利黑麥草 | 70 | 0 | 10 | 10 | 60 | 80 | 20 | 30 | 0 | 20 | 10 | 20 | 20 | 100 | ||||||||||||||||||
表A | 化合物 | 表A | 化合物 | |||||||||||||||||||||||||||||
125 g ai/ha | 139 | 140 | 141 | 142 | 143 | 144 | 145 | 146 | 31 g ai/ha | 145 | 146 | |||||||||||||||||||||
萌前 | 萌前 | |||||||||||||||||||||||||||||||
稗草 | 0 | 0 | 60 | 0 | 100 | 100 | 80 | 100 | 稗草 | 40 | 20 | |||||||||||||||||||||
大狐尾草 | 0 | 0 | 100 | 0 | 100 | 100 | 100 | 100 | 大狐尾草 | 90 | 80 | |||||||||||||||||||||
地膚 | 0 | 40 | 20 | 0 | 100 | 100 | 40 | 80 | 地膚 | 0 | 60 | |||||||||||||||||||||
反枝莧 | 0 | 10 | 90 | 0 | - | 100 | 100 | 100 | 反枝莧 | 100 | 60 | |||||||||||||||||||||
豬草 | 50 | 0 | 30 | 0 | 0 | 10 | 30 | 0 | 豬草 | 0 | 0 | |||||||||||||||||||||
義大利黑麥草 | 0 | 10 | 10 | 0 | 70 | 70 | 50 | 50 | 義大利黑麥草 | 10 | 0 | |||||||||||||||||||||
表A | 化合物 | |||||||||||||
31 g ai/ha | 1 | 2 | 3 | 4 | 5 | 19 | 36 | 37 | 38 | 43 | 44 | 45 | 46 | 50 |
萌前 | ||||||||||||||
稗草 | 20 | 10 | 60 | 0 | 0 | 0 | 0 | 0 | 20 | 0 | 0 | 0 | 0 | 0 |
大狐尾草 | 30 | 70 | 70 | 0 | 0 | 0 | 0 | 20 | 30 | 0 | 0 | 0 | 40 | 50 |
地膚 | 0 | 30 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 100 | 0 | 0 | 0 | 0 |
反枝莧 | 20 | 40 | 50 | 0 | 0 | 0 | 0 | 0 | 60 | 30 | 0 | 0 | 50 | 0 |
豬草 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 |
義大利黑麥草 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 |
表A | 化合物 | |||||||||||||
31 g ai/ha | 51 | 53 | 54 | 62 | 63 | 66 | 67 | 68 | 69 | 70 | 71 | 74 | 76 | 77 |
萌前 | ||||||||||||||
稗草 | 0 | 0 | 0 | 30 | 40 | 90 | 0 | 10 | 70 | 0 | 0 | 10 | 0 | 20 |
大狐尾草 | 0 | 0 | 0 | 30 | 10 | 70 | 0 | 10 | 40 | 0 | 40 | 40 | 0 | 100 |
地膚 | 0 | 0 | 0 | 20 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 80 |
反枝莧 | 0 | 0 | 0 | 60 | 0 | 20 | 0 | 20 | 40 | 0 | 0 | 20 | 0 | 100 |
豬草 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 |
義大利黑麥草 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 |
表A | 化合物 | |||||||||||||
31 g ai/ha | 80 | 81 | 82 | 86 | 87 | 88 | 89 | 90 | 92 | 93 | 94 | 95 | 96 | 97 |
萌前 | ||||||||||||||
稗草 | 60 | 10 | 50 | 0 | 70 | 0 | 20 | 0 | 70 | 0 | 0 | 10 | 0 | 0 |
大狐尾草 | 90 | 30 | 90 | 0 | 60 | 0 | 10 | 10 | 100 | 0 | 0 | 0 | 0 | 40 |
地膚 | 100 | 0 | 70 | 10 | 30 | 0 | 10 | 0 | 90 | 0 | 0 | 0 | 0 | 0 |
反枝莧 | 100 | 100 | 90 | 20 | 40 | 0 | 10 | 0 | 100 | 0 | 0 | 0 | 0 | 0 |
豬草 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 |
義大利黑麥草 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 30 | 0 | 0 | 0 | 0 | 0 |
表A | 化合物 | |||||||||||||
31 g ai/ha | 98 | 99 | 100 | 101 | 102 | 103 | 104 | 105 | 107 | 108 | 109 | 110 | 111 | 112 |
萌前 | ||||||||||||||
稗草 | 0 | 70 | 40 | 0 | 0 | 0 | 0 | 0 | 90 | 10 | 0 | 40 | 0 | 0 |
大狐尾草 | 0 | 90 | 50 | 0 | 0 | 10 | 0 | 0 | 100 | 10 | 0 | 80 | 0 | 0 |
地膚 | 0 | 40 | 0 | 0 | 0 | 0 | 0 | 0 | 90 | 0 | 0 | 10 | 0 | 0 |
反枝莧 | 0 | 50 | 0 | 0 | 0 | 40 | 0 | 0 | 100 | 0 | 0 | 40 | 0 | 60 |
豬草 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 |
義大利黑麥草 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 30 | 0 | 0 | 0 | 0 | 10 |
表A | 化合物 | |||||||||||||
31 g ai/ha | 113 | 114 | 115 | 116 | 117 | 118 | 119 | 120 | 121 | 122 | 123 | 124 | 126 | 127 |
萌前 | ||||||||||||||
稗草 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 30 | 20 | 10 | 0 | 20 |
大狐尾草 | 60 | 10 | 0 | 0 | 0 | 0 | 50 | 0 | 30 | 0 | 40 | 60 | 0 | 30 |
地膚 | 10 | 0 | 70 | 0 | 0 | 0 | 0 | 0 | 20 | 10 | 0 | 0 | 0 | 0 |
反枝莧 | 100 | 0 | 0 | 50 | 0 | 20 | 20 | 0 | 0 | 40 | 0 | 40 | 0 | 0 |
豬草 | 0 | 20 | 20 | 30 | 0 | 100 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 |
義大利黑麥草 | 10 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 10 | 0 | 0 | 0 | 0 | 0 |
表A | 化合物 | |||||||||||||
31 g ai/ha | 128 | 129 | 131 | 132 | 133 | 134 | 135 | 137 | 138 | 140 | 141 | 142 | 143 | 144 |
萌前 | ||||||||||||||
稗草 | 20 | 70 | 0 | 30 | 0 | 0 | 0 | 0 | 70 | 0 | 0 | 0 | 20 | 80 |
大狐尾草 | 30 | 100 | 0 | 40 | 0 | 10 | 0 | 70 | 90 | 0 | 10 | 0 | 100 | 100 |
地膚 | 0 | 30 | 10 | 10 | 0 | 0 | 0 | 0 | 50 | 0 | 10 | 0 | 100 | 90 |
反枝莧 | 0 | 90 | 90 | 70 | 70 | 0 | 0 | 10 | 80 | 0 | 0 | 0 | - | 100 |
豬草 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 |
義大利黑麥草 | 0 | 20 | 0 | 0 | 0 | 0 | 0 | 0 | 10 | 10 | 0 | 0 | 20 | 20 |
在淹沒式水田試驗中使選自稻米(
Oryza sativa)、小花輪傘草(small-flower umbrella sedge,
Cyperus difformis)、異藥花(
Heteranthera limosa)、及稗草(
Echinochloa crus-galli)之植物物種生長至2葉階段以供測試。在處理時,將試驗罐淹沒至高於土壤表面3 cm、藉由直接施用試驗化合物至稻田水中來處理、然後於試驗期間保持於該水深。將經處理的植物與對照組維持於溫室中13至15天,之後將所有物種與對照組比較並目視評估。歸納於表B中之植物反應評級係基於0至100的標度,其中0係無效果而100係完全防治。顯示為破折號(–)之反應意指無試驗結果。
試驗C
表B | 化合物 | |||||||||||||
250 g ai/ha | 1 | 2 | 3 | 4 | 5 | 6 | 7 | 8 | 9 | 10 | 11 | 12 | 13 | 18 |
淹沒 | ||||||||||||||
稗草 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 20 | 0 | 0 | 0 | 0 | 0 |
異藥花 | 20 | 30 | 30 | 0 | 0 | 0 | 0 | 0 | 75 | 80 | 0 | 0 | 70 | 0 |
稻米 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 30 | 0 |
輪傘草 | 80 | 100 | 100 | 0 | 0 | 0 | 0 | 70 | 75 | 80 | 0 | 0 | 75 | 0 |
表B | 化合物 | |||||||||||||
250 g ai/ha | 19 | 20 | 21 | 22 | 23 | 24 | 25 | 26 | 30 | 33 | 35 | 36 | 37 | 38 |
淹沒 | ||||||||||||||
稗草 | 0 | 0 | 30 | 0 | 0 | 0 | 0 | 60 | 0 | 0 | 0 | 0 | 0 | 0 |
異藥花 | 0 | 30 | 70 | 40 | 30 | 0 | 0 | 100 | 40 | 80 | 50 | 0 | 0 | 40 |
稻米 | 0 | 0 | 0 | 0 | 15 | 0 | 0 | 20 | 0 | 0 | 0 | 0 | 0 | 0 |
輪傘草 | 0 | 40 | 100 | 50 | 95 | 0 | 0 | 100 | 0 | 95 | 60 | 0 | 0 | 30 |
表B | 化合物 | |||||||||||||
250 g ai/ha | 43 | 44 | 45 | 46 | 47 | 48 | 49 | 50 | 51 | 53 | 54 | 56 | 57 | 58 |
淹沒 | ||||||||||||||
稗草 | 0 | 0 | 0 | 0 | 0 | 20 | 20 | 0 | 15 | 0 | 0 | 0 | 0 | 0 |
異藥花 | 0 | 0 | 0 | 75 | 0 | 0 | 0 | 65 | 0 | 0 | 0 | 0 | 0 | 0 |
稻米 | 0 | 0 | 0 | 10 | 0 | 20 | 20 | 0 | 15 | 0 | 0 | 0 | 0 | 0 |
輪傘草 | 0 | 30 | 0 | 80 | 0 | 0 | 0 | 80 | 0 | 0 | 0 | 0 | 0 | 0 |
表B | 化合物 | |||||||||||||
250 g ai/ha | 61 | 62 | 63 | 64 | 65 | 66 | 67 | 68 | 69 | 70 | 71 | 74 | 75 | 76 |
淹沒 | ||||||||||||||
稗草 | 20 | 40 | 45 | 0 | 0 | 30 | 0 | 0 | 0 | 0 | 0 | 40 | 40 | 0 |
異藥花 | 100 | 100 | 100 | 0 | 70 | 100 | 0 | 0 | 75 | 70 | 90 | 100 | 95 | 85 |
稻米 | 0 | 0 | 25 | 0 | 0 | 0 | 0 | 0 | 20 | 0 | 0 | 0 | 35 | 10 |
輪傘草 | 100 | 90 | 100 | 0 | 85 | 95 | 0 | 0 | 80 | 80 | 95 | 100 | 95 | 70 |
表B | 化合物 | |||||||||||||
250 g ai/ha | 77 | 78 | 79 | 80 | 81 | 82 | 83 | 84 | 85 | 86 | 87 | 88 | 89 | 90 |
淹沒 | ||||||||||||||
稗草 | 15 | 20 | 60 | 75 | 45 | 35 | 0 | 0 | 0 | 40 | 50 | 0 | 40 | 0 |
異藥花 | 85 | 70 | 90 | 100 | 100 | 100 | 80 | 0 | 0 | 100 | 100 | 0 | 95 | 30 |
稻米 | 0 | 15 | 45 | 55 | 0 | 30 | 0 | 0 | 0 | 20 | 35 | 20 | 40 | 0 |
輪傘草 | 100 | 80 | 100 | 100 | 100 | 95 | 80 | 0 | 0 | 100 | 100 | 0 | 95 | 60 |
表B | 化合物 | |||||||||||||
250 g ai/ha | 91 | 92 | 93 | 94 | 95 | 96 | 97 | 98 | 99 | 100 | 101 | 102 | 103 | 104 |
淹沒 | ||||||||||||||
稗草 | 0 | 25 | 0 | 0 | 0 | 0 | 0 | 0 | 60 | 40 | 0 | 0 | 0 | 0 |
異藥花 | 100 | 100 | 0 | 0 | 30 | 0 | 70 | 0 | 100 | 90 | 0 | 80 | 95 | 75 |
稻米 | 20 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 40 | 0 | 0 | 0 | 20 | 0 |
輪傘草 | 95 | 100 | 0 | 0 | 0 | 0 | 75 | 0 | 90 | 70 | 0 | 80 | 95 | 75 |
表B | 化合物 | |||||||||||||
250 g ai/ha | 105 | 106 | 107 | 108 | 109 | 110 | 111 | 112 | 113 | 114 | 115 | 116 | 117 | 118 |
淹沒 | ||||||||||||||
稗草 | 0 | 0 | 50 | 0 | 0 | 25 | 0 | 20 | 65 | 0 | 0 | 30 | 0 | 0 |
異藥花 | 40 | 0 | 95 | 80 | 0 | 75 | 0 | 100 | 80 | 40 | 0 | 75 | 20 | 0 |
稻米 | 0 | 0 | 35 | 0 | 0 | 25 | 0 | 40 | 20 | 0 | 0 | 70 | 0 | 0 |
輪傘草 | 0 | 0 | 95 | 60 | 0 | 90 | 0 | 100 | 90 | 90 | 0 | 90 | 60 | 50 |
表B | 化合物 | |||||||||||||
250 g ai/ha | 119 | 120 | 121 | 122 | 123 | 124 | 125 | 126 | 127 | 128 | 129 | 130 | 131 | 132 |
淹沒 | ||||||||||||||
稗草 | 0 | 0 | 50 | 80 | 40 | 45 | 45 | 90 | 40 | 20 | 45 | 55 | 15 | 45 |
異藥花 | 100 | 0 | 0 | 100 | 95 | 100 | 70 | 0 | 90 | 90 | 90 | 40 | 80 | 90 |
稻米 | 0 | 0 | 35 | 40 | 35 | 40 | 35 | 0 | 15 | 15 | 40 | 35 | 15 | 45 |
輪傘草 | 90 | 0 | 70 | 100 | 95 | 100 | 90 | 0 | 90 | 85 | 80 | 98 | 90 | 80 |
表B | 化合物 | |||||||||||||
250 g ai/ha | 133 | 134 | 135 | 136 | 137 | 138 | 139 | 140 | 141 | 142 | 143 | 144 | 145 | 146 |
淹沒 | ||||||||||||||
稗草 | 0 | 0 | 0 | 45 | 75 | 50 | 0 | 0 | 20 | 0 | 50 | 70 | 50 | 40 |
異藥花 | 0 | 95 | 85 | 60 | 95 | 100 | 30 | 0 | 70 | 0 | 90 | 100 | 100 | 100 |
稻米 | 30 | 20 | 20 | 35 | 50 | 45 | 0 | 0 | 10 | 0 | 40 | 35 | 30 | 35 |
輪傘草 | 0 | 95 | 85 | 80 | 95 | 85 | 0 | 0 | 50 | 0 | 90 | 100 | 100 | 85 |
將選自黑草(
Alopecurus myosuroides)、義大利黑麥草(Italian ryegrass,
Lolium multiflorum)、小麥(winter wheat,
Triticum aestivum)、豬殃殃(catchweed bedstraw,
Galium aparine)、玉米(
Zea mays)、大馬唐草(large crabgrass,
Digitaria sanguinalis)、大狐尾草(giant foxtail,
Setaria faberii)、強生草(
Sorghum halepense)、藜(
Chenopodium album)、牽牛花(
Ipomoea coccinea)、油莎草(yellow nutsedge,
Cyperus esculentus)、反枝莧(
Amaranthus retroflexus)、豬草(common ragweed,
Ambrosia elatior)、大豆(
Glycine max)、稗草(
Echinochloa crus-galli)、油菜籽(
Brassica napus)、長芒莧(palmer pigweed,
Amaranthus palmeri)、莧菜藤子(common waterhemp,
Amaranthus rudis)、苘麻(
Abutilon theophrasti)、地膚(
Kochia scoparia)、蘇利南草(
Brachiaria decumbens)、顛茄(eastern black nightshade,
Solanum ptycanthum)、猩猩草(
Euphorbia heterophylla)、風剪草(
Apera spica-venti)、及野生燕麥(wild oat
Avena fatua)之植物物種的種子栽植於壤土與砂之摻合物或粉質壤土中,並且以配製於不具植物毒性溶劑混合物中之試驗化學物質進行萌前處理,該混合物包括界面活性劑。
同時,將選自這些作物與雜草物種以及繁縷(common chickweed,
Stellaria media)、野生蕎麥(wild buckwheat,
Polygonum convolvulus)、野生芥菜(
Sinapis arvensis)、原野鬼罌粟(
Papaver rhoeas)、原野紫羅蘭(
Viola arvensis)、裂葉老鸛草(cutleaf geranium,
Geranium dissectum)、加拿大薊(
Cirsium arvense)、及婆婆納(bird’s-eye speedwell,
Veronica persica)之植物栽植於含Sunshine Redi-Earth
®栽植介質之罐中,該栽植介質含泥炭蘚(spaghnum peat moss)、蛭石、起始營養素及白雲石灰石,並且以試驗化學物質(以相同方式配製)進行萌後施用處理。使用高度範圍在2至18 cm(1至4葉階段)的植物來進行萌後處理。將經處理的植物與對照組維持於溫室中13至15天,之後將所有物種與對照組比較並目視評估。歸納於表C中之植物反應評級係基於0至100的標度,其中0係無效果而100係完全防治。顯示為破折號(–)之反應意指無試驗結果。
在淹沒式水田試驗中使由稻米(
Oryza sativa)、小花輪傘草(small-flower umbrella sedge,
Cyperus difformis)、異藥花(
Heteranthera limosa)、及稗草(
Echinochloa crus-galli)所組成之植物物種生長至2葉階段以供測試。在處理時,將試驗罐淹沒至高於土壤表面3 cm、藉由直接施用試驗化合物至稻田水中來處理、然後於試驗期間保持於該水深。
表C | 化合物 | ||||||||||||||||||||||||||||||
125 g ai/ha | 7 | 15 | 16 | 20 | 21 | 22 | 23 | 26 | 33 | 35 | 72 | 73 | 75 | 77 | |||||||||||||||||
萌後 | |||||||||||||||||||||||||||||||
稗草 | 10 | 20 | 20 | 20 | 20 | 10 | 20 | 30 | 25 | 15 | 10 | 30 | - | 30 | |||||||||||||||||
黑草 | 5 | 10 | 5 | 10 | 5 | 5 | 20 | 35 | 20 | 10 | 30 | 35 | 30 | 25 | |||||||||||||||||
野生蕎麥 | - | - | - | - | - | - | - | - | - | - | - | - | 85 | - | |||||||||||||||||
加拿大薊 | - | - | - | - | - | - | - | - | - | - | - | - | 100 | - | |||||||||||||||||
繁縷 | 50 | 90 | 80 | 75 | 80 | 60 | 85 | 98 | 85 | 50 | 98 | 85 | 98 | 100 | |||||||||||||||||
玉米 | 15 | 20 | 20 | 20 | 20 | 15 | 10 | 25 | 30 | 20 | 20 | 15 | 20 | 25 | |||||||||||||||||
大馬唐草 | 15 | 25 | 25 | 15 | 35 | 25 | 25 | 65 | 15 | 10 | 50 | 60 | 25 | 30 | |||||||||||||||||
原野鬼罌粟 | - | - | - | - | - | - | - | - | - | - | - | - | 100 | - | |||||||||||||||||
原野紫羅蘭 | - | - | - | - | - | - | - | - | - | - | - | - | 100 | - | |||||||||||||||||
大狐尾草 | 15 | 35 | 35 | 25 | 15 | 25 | 30 | 25 | 20 | 20 | 20 | 25 | 25 | 70 | |||||||||||||||||
豬殃殃 | 40 | 95 | 55 | 98 | 80 | 70 | 80 | 95 | 85 | 60 | 98 | 98 | 80 | 98 | |||||||||||||||||
裂葉老鸛草 | - | - | - | - | - | - | - | - | - | - | - | - | 65 | - | |||||||||||||||||
強生草 | - | - | - | - | - | - | 20 | 25 | 20 | 10 | 10 | 20 | 70 | - | |||||||||||||||||
地膚 | 20 | 95 | 90 | 100 | 90 | 50 | 85 | 95 | 95 | 90 | 100 | 100 | 98 | 100 | |||||||||||||||||
藜 | 55 | 95 | 60 | 85 | 85 | 75 | 80 | 98 | 90 | 70 | 85 | 98 | 90 | 90 | |||||||||||||||||
牽牛花 | 55 | 90 | 75 | 70 | 70 | 50 | 35 | 85 | 65 | 60 | 70 | 75 | 65 | 80 | |||||||||||||||||
野生芥菜 | - | - | - | - | - | - | - | - | - | - | - | - | - | - | |||||||||||||||||
顛茄 | - | - | - | - | - | - | - | - | - | - | - | - | 98 | - | |||||||||||||||||
油莎草 | 5 | 20 | 20 | 10 | 10 | 5 | 10 | 10 | 10 | 5 | 15 | 30 | 5 | 15 | |||||||||||||||||
野生燕麥 | 5 | 10 | 10 | 5 | 5 | 5 | 5 | 35 | 30 | 0 | 10 | 10 | 35 | 15 | |||||||||||||||||
油菜籽 | 5 | 0 | 70 | 60 | 30 | 80 | 35 | 80 | 95 | 65 | 65 | 50 | 95 | 85 | |||||||||||||||||
反枝莧 | 70 | 98 | 50 | 95 | 90 | 95 | 85 | 100 | 100 | 98 | 100 | 100 | - | 100 | |||||||||||||||||
長芒莧 | - | - | - | - | - | - | - | - | - | - | - | - | 85 | - | |||||||||||||||||
猩猩草 | - | - | - | - | - | - | - | - | - | - | - | - | 80 | - | |||||||||||||||||
豬草 | 25 | 65 | 40 | 60 | 55 | 50 | 50 | 90 | 60 | 20 | 75 | 65 | 60 | 70 | |||||||||||||||||
義大利黑麥草 | 30 | 5 | 5 | 5 | 15 | 5 | 5 | 10 | 30 | 5 | 15 | 20 | 5 | 10 | |||||||||||||||||
大豆 | 70 | 90 | 50 | 60 | 60 | 75 | 35 | 75 | 55 | 35 | 70 | 60 | 85 | 65 | |||||||||||||||||
婆婆納 | - | - | - | - | - | - | - | - | - | - | - | - | 100 | - | |||||||||||||||||
蘇利南草 | - | - | - | - | - | - | - | - | - | - | - | - | 20 | - | |||||||||||||||||
苘麻 | 40 | 85 | 50 | 70 | 70 | 85 | 40 | 80 | 75 | 40 | 70 | 75 | 75 | 65 | |||||||||||||||||
莧菜藤子 | 65 | - | - | 98 | 85 | 80 | 95 | 100 | 100 | 95 | 90 | 100 | 95 | 100 | |||||||||||||||||
小麥 | 5 | 0 | 0 | 5 | 0 | 0 | 0 | 10 | 5 | 0 | 5 | 5 | 10 | 30 | |||||||||||||||||
風剪草 | - | - | - | - | - | - | - | - | - | - | - | - | 5 | - | |||||||||||||||||
表C | 化合物 | ||||||||||||||||||||||||||||||
125 g ai/ha | 79 | 80 | 82 | 89 | 92 | 107 | 110 | 125 | 130 | 136 | 137 | 138 | 143 | 144 | |||||||||||||||||
萌後 | |||||||||||||||||||||||||||||||
稗草 | - | - | 60 | - | 20 | - | 30 | 10 | 20 | 10 | 40 | - | 20 | 10 | |||||||||||||||||
黑草 | 30 | 25 | 45 | 45 | 20 | 60 | 25 | 30 | 30 | 15 | 40 | 65 | 40 | 15 | |||||||||||||||||
野生蕎麥 | 90 | 95 | 100 | 85 | - | 100 | 80 | 98 | 80 | 80 | 90 | 100 | 100 | 95 | |||||||||||||||||
加拿大薊 | 100 | 85 | 98 | 85 | - | 90 | 95 | 90 | 98 | 85 | 100 | 95 | 100 | 90 | |||||||||||||||||
繁縷 | 98 | 90 | 90 | 100 | 100 | 100 | 90 | 98 | 90 | 80 | 100 | 100 | 100 | 85 | |||||||||||||||||
玉米 | 20 | 25 | 25 | 20 | 20 | 30 | 15 | 20 | 20 | 20 | 25 | 30 | 30 | 25 | |||||||||||||||||
大馬唐草 | 65 | 30 | 20 | 90 | 35 | 60 | 60 | 20 | 20 | 30 | 70 | 95 | 30 | 25 | |||||||||||||||||
原野鬼罌粟 | 100 | 85 | 100 | 100 | - | 100 | 100 | 100 | 100 | 90 | 100 | 100 | 100 | 100 | |||||||||||||||||
原野紫羅蘭 | 90 | 95 | 90 | 100 | - | 100 | 100 | 98 | 100 | 100 | 85 | 100 | 100 | 90 | |||||||||||||||||
大狐尾草 | 40 | 15 | 20 | 20 | 50 | 25 | 25 | 25 | 30 | 25 | 35 | 65 | 25 | 40 | |||||||||||||||||
豬殃殃 | 95 | 90 | 90 | 90 | 100 | 95 | 90 | 90 | 80 | 75 | 85 | 85 | 95 | 90 | |||||||||||||||||
裂葉老鸛草 | 65 | 60 | 60 | 55 | - | 75 | 60 | 55 | 60 | 45 | 35 | 60 | 75 | 40 | |||||||||||||||||
強生草 | 85 | 5 | 30 | 85 | - | 98 | 15 | 25 | 15 | 15 | 25 | 90 | 20 | 5 | |||||||||||||||||
地膚 | 98 | 80 | 95 | 95 | 100 | 98 | 100 | 98 | 98 | 90 | 98 | 98 | 100 | 90 | |||||||||||||||||
藜 | 100 | 85 | 90 | 100 | 85 | 100 | 98 | 100 | 95 | 80 | 90 | 100 | 95 | 85 | |||||||||||||||||
牽牛花 | 30 | 60 | 75 | 55 | 85 | 95 | 50 | 75 | 55 | 35 | 20 | 65 | 65 | 60 | |||||||||||||||||
野生芥菜 | - | 90 | 100 | - | - | 100 | 100 | 100 | 100 | 100 | 100 | 100 | 100 | 95 | |||||||||||||||||
顛茄 | 100 | 75 | 100 | 95 | - | 100 | 98 | 90 | 90 | 80 | 90 | 98 | 90 | 90 | |||||||||||||||||
油莎草 | 5 | 5 | 10 | 5 | 20 | 5 | 5 | 10 | 5 | 5 | 5 | 30 | 25 | 10 | |||||||||||||||||
野生燕麥 | 35 | 5 | 50 | 30 | 5 | 45 | 55 | 15 | 15 | 10 | 10 | 70 | 20 | 35 | |||||||||||||||||
油菜籽 | 100 | 70 | 95 | 100 | 70 | 98 | 95 | 95 | 98 | 80 | 100 | 100 | 100 | 85 | |||||||||||||||||
反枝莧 | - | - | - | - | 100 | - | - | - | - | - | - | - | - | - | |||||||||||||||||
長芒莧 | 85 | 60 | 98 | 85 | - | 100 | 95 | 85 | 65 | 70 | 70 | 98 | 100 | 80 | |||||||||||||||||
猩猩草 | 85 | 75 | 75 | 90 | - | 90 | 90 | 85 | 75 | 75 | 75 | 90 | 75 | 60 | |||||||||||||||||
豬草 | 65 | 35 | 55 | 25 | 70 | 45 | 60 | 55 | 50 | 35 | 30 | 75 | 55 | 15 | |||||||||||||||||
義大利黑麥草 | 30 | 5 | 25 | 10 | 30 | 50 | 20 | 15 | 15 | 10 | 10 | 35 | 20 | 20 | |||||||||||||||||
大豆 | 65 | 95 | 40 | 70 | 75 | 95 | 35 | 70 | 95 | 40 | 40 | 55 | 65 | 65 | |||||||||||||||||
婆婆納 | 100 | 100 | 95 | 100 | - | 100 | 95 | 98 | 98 | 85 | 100 | 100 | 100 | 95 | |||||||||||||||||
蘇利南草 | 35 | 25 | 25 | 20 | - | 35 | 25 | 20 | 20 | 10 | 20 | 35 | 20 | 25 | |||||||||||||||||
苘麻 | 90 | 55 | 75 | 70 | 85 | 90 | 75 | 30 | 75 | 70 | 70 | 75 | 70 | 65 | |||||||||||||||||
莧菜藤子 | 98 | 90 | 95 | 95 | 100 | 100 | 95 | 90 | 85 | 75 | 75 | 100 | 90 | 75 | |||||||||||||||||
小麥 | 15 | 15 | 30 | 15 | 10 | 30 | 15 | 25 | 30 | 5 | 20 | 35 | 30 | 15 | |||||||||||||||||
風剪草 | 30 | 30 | 35 | 35 | - | 50 | 30 | 35 | 35 | 30 | 45 | 50 | 40 | 30 | |||||||||||||||||
表C | 化合物 | ||||||||||||||||||||||||||||||
62 g ai/ha | 7 | 15 | 16 | 20 | 21 | 22 | 23 | 26 | 33 | 35 | 72 | 73 | 75 | 77 | |||||||||||||||||
萌後 | |||||||||||||||||||||||||||||||
稗草 | 15 | 20 | 20 | 10 | 20 | 10 | 10 | 20 | 10 | 10 | 10 | 20 | - | 25 | |||||||||||||||||
黑草 | 0 | 10 | 0 | 5 | 5 | 0 | 15 | 15 | 10 | 10 | 10 | 40 | 10 | 20 | |||||||||||||||||
野生蕎麥 | - | - | - | - | - | - | - | - | - | - | - | - | 80 | - | |||||||||||||||||
加拿大薊 | - | - | - | - | - | - | - | - | - | - | - | - | 75 | - | |||||||||||||||||
繁縷 | 30 | 90 | 50 | 65 | 50 | 65 | 50 | 85 | 85 | 45 | 90 | 90 | 90 | 100 | |||||||||||||||||
玉米 | 10 | 20 | 15 | 10 | 15 | 5 | 5 | 20 | 25 | 20 | 10 | 15 | 15 | 20 | |||||||||||||||||
大馬唐草 | 20 | 25 | 25 | 15 | 25 | 25 | 20 | 25 | 10 | 15 | 10 | 25 | 15 | 30 | |||||||||||||||||
原野鬼罌粟 | - | - | - | - | - | - | - | - | - | - | - | - | 80 | - | |||||||||||||||||
原野紫羅蘭 | - | - | - | - | - | - | - | - | - | - | - | - | 98 | - | |||||||||||||||||
大狐尾草 | 10 | 20 | 30 | 10 | 20 | 15 | 25 | 10 | 10 | 10 | 20 | 20 | 10 | 25 | |||||||||||||||||
豬殃殃 | 10 | 95 | 55 | 80 | 75 | 60 | 55 | 95 | 80 | 55 | 5 | 75 | 70 | 95 | |||||||||||||||||
裂葉老鸛草 | - | - | - | - | - | - | - | - | - | - | - | - | 35 | - | |||||||||||||||||
強生草 | - | - | - | - | - | - | 15 | 20 | 20 | 10 | 10 | 20 | 10 | - | |||||||||||||||||
地膚 | 25 | 95 | 80 | 100 | 90 | 85 | 55 | 90 | 95 | 60 | 100 | 100 | 90 | 100 | |||||||||||||||||
藜 | 30 | 75 | 40 | 70 | 65 | 70 | 65 | 98 | 80 | 65 | 75 | 90 | 70 | 70 | |||||||||||||||||
牽牛花 | 40 | 85 | 40 | 70 | 40 | 35 | 60 | 65 | 75 | 60 | 40 | 85 | 20 | 90 | |||||||||||||||||
野生芥菜 | - | - | - | - | - | - | - | - | - | - | - | - | - | - | |||||||||||||||||
顛茄 | - | - | - | - | - | - | - | - | - | - | - | - | 85 | - | |||||||||||||||||
油莎草 | 5 | 5 | 10 | 5 | 5 | 5 | 5 | 10 | 5 | 0 | 10 | 20 | 0 | 15 | |||||||||||||||||
野生燕麥 | 5 | 5 | 5 | 5 | 5 | 0 | 10 | 15 | 25 | 0 | 5 | 5 | 40 | 10 | |||||||||||||||||
油菜籽 | 0 | 100 | 60 | 50 | 50 | 55 | 50 | 75 | 55 | 50 | 0 | 98 | 80 | 70 | |||||||||||||||||
反枝莧 | 60 | 95 | 85 | 98 | 90 | 70 | 70 | 98 | 98 | 90 | 85 | 100 | - | 100 | |||||||||||||||||
長芒莧 | - | - | - | - | - | - | - | - | - | - | - | - | 95 | - | |||||||||||||||||
猩猩草 | - | - | - | - | - | - | - | - | - | - | - | - | 80 | - | |||||||||||||||||
豬草 | 20 | 50 | 10 | 55 | 45 | 50 | 40 | 55 | 50 | 10 | 40 | 60 | 50 | 35 | |||||||||||||||||
義大利黑麥草 | 30 | 10 | 0 | 10 | 0 | 0 | 5 | 10 | 5 | 5 | 10 | 10 | 10 | 10 | |||||||||||||||||
大豆 | 40 | 80 | 50 | 55 | 60 | 35 | 70 | 65 | 30 | 35 | 40 | 75 | 85 | 70 | |||||||||||||||||
婆婆納 | - | - | - | - | - | - | - | - | - | - | - | - | 100 | - | |||||||||||||||||
蘇利南草 | - | - | - | - | - | - | - | - | - | - | - | - | 20 | - | |||||||||||||||||
苘麻 | 35 | 60 | 30 | 40 | 60 | 55 | 35 | 75 | 65 | 35 | 40 | 70 | 70 | 55 | |||||||||||||||||
莧菜藤子 | 60 | - | - | 90 | 90 | 85 | 85 | 98 | 100 | 90 | 90 | 100 | 90 | 100 | |||||||||||||||||
小麥 | 5 | 0 | 0 | 5 | 0 | 0 | 0 | 5 | 0 | 0 | 0 | 5 | 0 | 10 | |||||||||||||||||
風剪草 | - | - | - | - | - | - | - | - | - | - | - | - | 10 | - | |||||||||||||||||
表C | 化合物 | ||||||||||||||||||||||||||||||
62 g ai/ha | 79 | 80 | 82 | 89 | 92 | 107 | 110 | 125 | 130 | 136 | 137 | 138 | 143 | 144 | |||||||||||||||||
萌後 | |||||||||||||||||||||||||||||||
稗草 | - | - | 10 | - | 15 | - | 20 | 5 | 10 | 10 | 20 | - | 10 | 10 | |||||||||||||||||
黑草 | 20 | 5 | 40 | 30 | 5 | 20 | 20 | 15 | 20 | 10 | 15 | 10 | 15 | 15 | |||||||||||||||||
野生蕎麥 | 85 | 75 | 100 | 75 | - | 75 | 95 | 75 | 75 | 90 | 98 | 100 | 100 | 80 | |||||||||||||||||
加拿大薊 | 70 | 75 | 85 | 85 | - | 90 | 98 | 90 | 98 | 85 | 98 | 90 | 90 | 90 | |||||||||||||||||
繁縷 | 95 | 75 | 90 | 85 | 100 | 98 | 95 | 90 | 80 | 75 | 90 | 100 | 85 | 85 | |||||||||||||||||
玉米 | 20 | 15 | 25 | 15 | 15 | 20 | 20 | 15 | 15 | 20 | 15 | 25 | 20 | 20 | |||||||||||||||||
大馬唐草 | 70 | 10 | 30 | 85 | 25 | 30 | 25 | 15 | 10 | 10 | 40 | 85 | 15 | 20 | |||||||||||||||||
原野鬼罌粟 | 100 | 85 | 100 | 100 | - | 98 | 100 | 100 | 100 | 80 | 100 | 100 | 90 | 90 | |||||||||||||||||
原野紫羅蘭 | 85 | 90 | 90 | 100 | - | 98 | 95 | 98 | 95 | 95 | 85 | 100 | 98 | 80 | |||||||||||||||||
大狐尾草 | 25 | 10 | 10 | 10 | 25 | 20 | 25 | 10 | 10 | 10 | 40 | 30 | 10 | 30 | |||||||||||||||||
豬殃殃 | 85 | 85 | 85 | 80 | 100 | 90 | 75 | 80 | 85 | 60 | 75 | 80 | 80 | 85 | |||||||||||||||||
裂葉老鸛草 | 55 | 35 | 40 | 50 | - | 60 | 40 | 55 | 45 | 50 | 30 | 55 | 60 | 35 | |||||||||||||||||
強生草 | 60 | 5 | 10 | 10 | - | 35 | 10 | 10 | 10 | 10 | 10 | 80 | 10 | 5 | |||||||||||||||||
地膚 | 90 | 80 | 95 | 80 | 100 | 95 | 100 | 95 | 95 | 85 | 98 | 95 | 100 | 90 | |||||||||||||||||
藜 | 90 | 80 | 85 | 100 | 50 | 100 | 95 | 95 | 85 | 80 | 85 | 95 | 90 | 70 | |||||||||||||||||
牽牛花 | 30 | 55 | 30 | 25 | 65 | 80 | 60 | 50 | 65 | 20 | 20 | 65 | 50 | 50 | |||||||||||||||||
野生芥菜 | - | 80 | 100 | 100 | - | 95 | 100 | 98 | 100 | 85 | 100 | 100 | 100 | 80 | |||||||||||||||||
顛茄 | 95 | 70 | 95 | 95 | - | 98 | 95 | 85 | 85 | 70 | 90 | 100 | 90 | 75 | |||||||||||||||||
油莎草 | 5 | 5 | 20 | 0 | 10 | 5 | 5 | 5 | 5 | 0 | 10 | 10 | 5 | 10 | |||||||||||||||||
野生燕麥 | 45 | 10 | 40 | 40 | 5 | 35 | 45 | 15 | 15 | 10 | 10 | 50 | 10 | 30 | |||||||||||||||||
油菜籽 | 98 | 65 | 95 | 90 | 50 | 95 | 85 | 90 | 95 | 80 | 90 | 95 | 95 | 70 | |||||||||||||||||
反枝莧 | - | - | - | - | 98 | - | - | - | - | - | - | - | - | - | |||||||||||||||||
長芒莧 | 70 | 70 | 98 | 80 | - | 100 | 98 | 80 | 45 | 70 | 50 | 90 | 80 | 40 | |||||||||||||||||
猩猩草 | 80 | 70 | 85 | 80 | - | 90 | 80 | 75 | 60 | 70 | 65 | 75 | 70 | 50 | |||||||||||||||||
豬草 | 75 | 15 | 60 | 10 | 60 | 35 | 60 | 45 | 55 | 30 | 30 | 35 | 55 | 25 | |||||||||||||||||
義大利黑麥草 | 25 | 5 | 20 | 5 | 10 | 20 | 15 | 10 | 10 | 5 | 5 | 30 | 10 | 15 | |||||||||||||||||
大豆 | 65 | 90 | 35 | 65 | 70 | 95 | 50 | 65 | 75 | 50 | 45 | 60 | 55 | 50 | |||||||||||||||||
婆婆納 | 98 | 100 | 95 | 100 | - | 100 | 90 | 98 | 98 | 80 | 100 | 100 | 85 | 95 | |||||||||||||||||
蘇利南草 | 30 | 15 | 25 | 20 | - | 20 | 15 | 10 | 15 | 10 | 10 | 25 | 10 | 20 | |||||||||||||||||
苘麻 | 80 | 30 | 50 | 40 | 60 | 75 | 70 | 60 | 65 | 35 | 15 | 50 | 65 | 50 | |||||||||||||||||
莧菜藤子 | 95 | 85 | 98 | 90 | 90 | 100 | 90 | 75 | 75 | 55 | 70 | 100 | 75 | 75 | |||||||||||||||||
小麥 | 10 | 0 | 10 | 10 | 5 | 10 | 15 | 20 | 15 | 5 | 10 | 20 | 15 | 10 | |||||||||||||||||
風剪草 | 30 | 20 | 30 | 50 | - | 50 | 35 | 10 | 35 | 30 | 30 | 35 | 35 | 15 | |||||||||||||||||
表C | 化合物 | ||||||||||||||||||||||||||||||
31 g ai/ha | 7 | 13 | 15 | 16 | 20 | 21 | 22 | 23 | 26 | 33 | 35 | 72 | 73 | 75 | |||||||||||||||||
萌後 | |||||||||||||||||||||||||||||||
稗草 | 5 | 10 | 15 | 10 | 10 | 10 | 5 | 10 | 10 | 5 | 5 | 5 | 15 | - | |||||||||||||||||
黑草 | 0 | 5 | 5 | 0 | 5 | 0 | 0 | 5 | 15 | 5 | 0 | 10 | 5 | 5 | |||||||||||||||||
野生蕎麥 | - | - | - | - | - | - | - | - | - | - | - | - | - | 60 | |||||||||||||||||
加拿大薊 | - | - | - | - | - | - | - | - | - | - | - | - | - | 75 | |||||||||||||||||
繁縷 | 5 | 70 | 80 | 20 | 60 | 50 | 60 | 50 | 80 | 55 | 40 | 85 | 80 | 85 | |||||||||||||||||
玉米 | 10 | 5 | 10 | 15 | 10 | 5 | 5 | 5 | 25 | 25 | 10 | 15 | 20 | 15 | |||||||||||||||||
大馬唐草 | 5 | 15 | 20 | 15 | 10 | 20 | 15 | 10 | 20 | 5 | 10 | 10 | 10 | 10 | |||||||||||||||||
原野鬼罌粟 | - | - | - | - | - | - | - | - | - | - | - | - | - | 80 | |||||||||||||||||
原野紫羅蘭 | - | - | - | - | - | - | - | - | - | - | - | - | - | 98 | |||||||||||||||||
大狐尾草 | 5 | 25 | 30 | 20 | 10 | 10 | 10 | 35 | 10 | 10 | 10 | 30 | 25 | 10 | |||||||||||||||||
豬殃殃 | 0 | 50 | 60 | 50 | 60 | 80 | 25 | 55 | 80 | 70 | 35 | 80 | 70 | 70 | |||||||||||||||||
裂葉老鸛草 | - | - | - | - | - | - | - | - | - | - | - | - | - | 40 | |||||||||||||||||
強生草 | - | - | - | - | - | - | - | 15 | 20 | 10 | 5 | 10 | 10 | 10 | |||||||||||||||||
地膚 | 30 | 30 | 95 | 50 | 95 | 50 | 80 | 50 | 90 | 95 | 40 | 100 | 100 | 85 | |||||||||||||||||
藜 | 25 | 55 | 75 | 50 | 80 | 60 | 70 | 55 | 90 | 70 | 40 | 85 | 80 | 55 | |||||||||||||||||
牽牛花 | 25 | 30 | 75 | 30 | 65 | 25 | 10 | 55 | 60 | 65 | 50 | 65 | 75 | 15 | |||||||||||||||||
野生芥菜 | - | - | - | - | - | - | - | - | - | - | - | - | - | - | |||||||||||||||||
顛茄 | - | - | - | - | - | - | - | - | - | - | - | - | - | 80 | |||||||||||||||||
油莎草 | 0 | 5 | 0 | 5 | 5 | 0 | 0 | 0 | 10 | 5 | 0 | 10 | 15 | 0 | |||||||||||||||||
野生燕麥 | 0 | 5 | 5 | 5 | 0 | 0 | 0 | 5 | 10 | 10 | 0 | 5 | 5 | 35 | |||||||||||||||||
油菜籽 | 0 | 35 | 95 | 35 | 50 | 40 | 40 | 5 | 75 | 45 | 30 | 60 | 80 | 80 | |||||||||||||||||
反枝莧 | 40 | 70 | 90 | 75 | 95 | 75 | 70 | 75 | 98 | 95 | 70 | 85 | 85 | - | |||||||||||||||||
長芒莧 | - | - | - | - | - | - | - | - | - | - | - | - | - | 90 | |||||||||||||||||
猩猩草 | - | - | - | - | - | - | - | - | - | - | - | - | - | 70 | |||||||||||||||||
豬草 | 20 | 5 | 40 | 10 | 50 | 10 | 35 | 35 | 55 | 30 | 5 | 50 | 55 | 10 | |||||||||||||||||
義大利黑麥草 | 0 | 0 | 5 | 0 | 5 | 0 | 0 | 0 | 5 | 5 | 0 | 5 | 5 | 10 | |||||||||||||||||
大豆 | 25 | 35 | 45 | 35 | 65 | 40 | 40 | 30 | 55 | 65 | 25 | 70 | 70 | 65 | |||||||||||||||||
婆婆納 | - | - | - | - | - | - | - | - | - | - | - | - | - | 95 | |||||||||||||||||
蘇利南草 | - | - | - | - | - | - | - | - | - | - | - | - | - | 15 | |||||||||||||||||
苘麻 | 20 | 25 | 50 | 25 | 50 | 60 | 40 | 35 | 55 | 50 | 30 | 50 | 60 | 35 | |||||||||||||||||
莧菜藤子 | 70 | - | - | - | 95 | 85 | 75 | 90 | 98 | 80 | 80 | 80 | 98 | 90 | |||||||||||||||||
小麥 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 5 | 5 | |||||||||||||||||
風剪草 | - | - | - | - | - | - | - | - | - | - | - | - | - | 5 | |||||||||||||||||
表C | 化合物 | ||||||||||||||||||||||||||||||
31 g ai/ha | 77 | 79 | 80 | 82 | 89 | 92 | 107 | 110 | 125 | 130 | 136 | 137 | 138 | 143 | |||||||||||||||||
萌後 | |||||||||||||||||||||||||||||||
稗草 | 25 | - | - | 10 | - | 10 | - | 10 | 5 | 5 | 5 | 10 | - | 10 | |||||||||||||||||
黑草 | 20 | 10 | 5 | 35 | 15 | 10 | 20 | 15 | 20 | 5 | 10 | 10 | 35 | 15 | |||||||||||||||||
野生蕎麥 | - | 80 | 70 | 70 | 75 | - | 75 | 85 | 65 | 90 | 60 | 75 | 80 | 85 | |||||||||||||||||
加拿大薊 | - | 65 | 75 | 85 | 80 | - | 85 | 90 | 85 | 75 | 75 | 85 | 80 | 85 | |||||||||||||||||
繁縷 | 80 | 90 | 75 | 85 | 95 | 100 | 90 | 95 | 75 | 75 | 65 | 55 | 85 | 80 | |||||||||||||||||
玉米 | 15 | 25 | 10 | 20 | 15 | 20 | 20 | 20 | 10 | 20 | 10 | 15 | 20 | 20 | |||||||||||||||||
大馬唐草 | 25 | 25 | 15 | 30 | 60 | 10 | 10 | 20 | 10 | 10 | 5 | 20 | 65 | 5 | |||||||||||||||||
原野鬼罌粟 | - | 98 | 75 | 85 | 95 | - | 98 | 100 | 95 | 100 | 85 | 95 | 100 | 90 | |||||||||||||||||
原野紫羅蘭 | - | 75 | 85 | 70 | 100 | - | 98 | 95 | 98 | 85 | 90 | 70 | 95 | 80 | |||||||||||||||||
大狐尾草 | 20 | 20 | 10 | 10 | 10 | 20 | 10 | 10 | 10 | 10 | 20 | 20 | 20 | 10 | |||||||||||||||||
豬殃殃 | 98 | 80 | 75 | 75 | 75 | 85 | 80 | 75 | 70 | 80 | 65 | 70 | 80 | 85 | |||||||||||||||||
裂葉老鸛草 | - | 50 | 35 | 30 | 35 | - | 35 | 30 | 30 | 35 | 25 | 25 | 35 | 50 | |||||||||||||||||
強生草 | - | 65 | 5 | 20 | 10 | - | 10 | 10 | 5 | 5 | 5 | 10 | 25 | 5 | |||||||||||||||||
地膚 | 100 | 80 | 75 | 95 | 75 | 100 | 85 | 100 | 90 | 85 | 80 | 90 | 85 | 100 | |||||||||||||||||
藜 | 75 | 85 | 75 | 75 | 75 | 60 | 85 | 90 | 98 | 90 | 75 | 75 | 90 | 90 | |||||||||||||||||
牽牛花 | 85 | 20 | 35 | 40 | 15 | 85 | 60 | 50 | 45 | 25 | 15 | 15 | 55 | 70 | |||||||||||||||||
野生芥菜 | - | - | 80 | 95 | - | - | 90 | 90 | 95 | 90 | 95 | 85 | 100 | 100 | |||||||||||||||||
顛茄 | - | 95 | 65 | 80 | 90 | - | 90 | 85 | 75 | 80 | 75 | 80 | 80 | 85 | |||||||||||||||||
油莎草 | 10 | 5 | 0 | 10 | 0 | 10 | 5 | 5 | 5 | 0 | 0 | 0 | 0 | 5 | |||||||||||||||||
野生燕麥 | 5 | 60 | 0 | 40 | 10 | 5 | 40 | 30 | 10 | 10 | 5 | 10 | 55 | 10 | |||||||||||||||||
油菜籽 | 70 | 98 | 60 | 95 | 95 | 50 | 80 | 60 | 85 | 85 | 80 | 95 | 85 | 80 | |||||||||||||||||
反枝莧 | 98 | - | - | - | - | 90 | - | - | - | - | - | - | - | - | |||||||||||||||||
長芒莧 | - | 80 | 35 | 80 | 75 | - | 95 | 95 | 85 | 65 | 55 | 45 | 80 | 75 | |||||||||||||||||
猩猩草 | - | 75 | 65 | 65 | 60 | - | 75 | 65 | 65 | 70 | 65 | 65 | 60 | 65 | |||||||||||||||||
豬草 | 40 | 20 | 10 | 35 | 5 | 40 | 35 | 50 | 35 | 45 | 20 | 35 | 30 | 50 | |||||||||||||||||
義大利黑麥草 | 5 | 30 | 0 | 15 | 5 | 15 | 35 | 10 | 5 | 10 | 5 | 5 | 5 | 10 | |||||||||||||||||
大豆 | 50 | 70 | 75 | 60 | 40 | 40 | 40 | 40 | 60 | 55 | 40 | 30 | 55 | 40 | |||||||||||||||||
婆婆納 | - | 90 | 100 | 85 | 100 | - | 100 | 95 | 70 | 85 | 80 | 80 | 100 | 80 | |||||||||||||||||
蘇利南草 | - | 25 | 10 | 20 | 10 | - | 25 | 20 | 10 | 10 | 5 | 10 | 20 | 10 | |||||||||||||||||
苘麻 | 50 | 75 | 35 | 45 | 35 | 50 | 65 | 40 | 35 | 45 | 50 | 15 | 35 | 55 | |||||||||||||||||
莧菜藤子 | 98 | 95 | 80 | 95 | 70 | 85 | 98 | 90 | 80 | 75 | 70 | 60 | 98 | 80 | |||||||||||||||||
小麥 | 0 | 5 | 0 | 10 | 10 | 0 | 5 | 5 | 5 | 5 | 5 | 5 | 5 | 10 | |||||||||||||||||
風剪草 | - | 35 | 5 | 35 | 10 | - | 15 | 25 | 15 | 15 | 10 | 10 | 15 | 35 | |||||||||||||||||
表C | 化合物 | 表C | 化合物 | ||||||||||||||||||||||||||||||
31 g ai/ha | 144 | 31 g ai/ha | 144 | ||||||||||||||||||||||||||||||
萌後 | 萌後 | ||||||||||||||||||||||||||||||||
稗草 | 5 | 顛茄 | 75 | ||||||||||||||||||||||||||||||
黑草 | 10 | 油莎草 | 0 | ||||||||||||||||||||||||||||||
野生蕎麥 | 55 | 野生燕麥 | 30 | ||||||||||||||||||||||||||||||
加拿大薊 | 60 | 油菜籽 | 35 | ||||||||||||||||||||||||||||||
繁縷 | 55 | 反枝莧 | - | ||||||||||||||||||||||||||||||
玉米 | 15 | 長芒莧 | 35 | ||||||||||||||||||||||||||||||
大馬唐草 | 25 | 猩猩草 | 35 | ||||||||||||||||||||||||||||||
原野鬼罌粟 | 80 | 豬草 | 15 | ||||||||||||||||||||||||||||||
原野紫羅蘭 | 65 | 義大利黑麥草 | 10 | ||||||||||||||||||||||||||||||
大狐尾草 | 10 | 大豆 | 30 | ||||||||||||||||||||||||||||||
豬殃殃 | 70 | 婆婆納 | 70 | ||||||||||||||||||||||||||||||
裂葉老鸛草 | 20 | 蘇利南草 | 20 | ||||||||||||||||||||||||||||||
強生草 | 5 | 苘麻 | 30 | ||||||||||||||||||||||||||||||
地膚 | 90 | 莧菜藤子 | 60 | ||||||||||||||||||||||||||||||
藜 | 75 | 小麥 | 5 | ||||||||||||||||||||||||||||||
牽牛花 | 20 | 風剪草 | 10 | ||||||||||||||||||||||||||||||
野生芥菜 | 70 | ||||||||||||||||||||||||||||||||
表C | 化合物 | ||||||||||||||||||||||||||||||||
16 g ai/ha | 7 | 13 | 15 | 16 | 20 | 21 | 22 | 23 | 26 | 33 | 35 | 72 | 73 | 75 | |||||||||||||||||||
萌後 | |||||||||||||||||||||||||||||||||
稗草 | 5 | 10 | 20 | 5 | 10 | 10 | 5 | 10 | 10 | 5 | 5 | 5 | 10 | - | |||||||||||||||||||
黑草 | 0 | 0 | 0 | 0 | 5 | 0 | 0 | 0 | 10 | 5 | 0 | 5 | 10 | 0 | |||||||||||||||||||
野生蕎麥 | - | - | - | - | - | - | - | - | - | - | - | - | - | 45 | |||||||||||||||||||
加拿大薊 | - | - | - | - | - | - | - | - | - | - | - | - | - | 70 | |||||||||||||||||||
繁縷 | 5 | 40 | 35 | 20 | 60 | 40 | 20 | 5 | 55 | 50 | 5 | 65 | 80 | 60 | |||||||||||||||||||
玉米 | 5 | 10 | 15 | 5 | 5 | 5 | 5 | 5 | 20 | 20 | 5 | 10 | 10 | 10 | |||||||||||||||||||
大馬唐草 | 5 | 5 | 30 | 10 | 10 | 10 | 10 | 10 | 10 | 5 | 10 | 10 | 15 | 10 | |||||||||||||||||||
原野鬼罌粟 | - | - | - | - | - | - | - | - | - | - | - | - | - | 70 | |||||||||||||||||||
原野紫羅蘭 | - | - | - | - | - | - | - | - | - | - | - | - | - | 80 | |||||||||||||||||||
大狐尾草 | 5 | 10 | 25 | 10 | 10 | 10 | 10 | 10 | 10 | 5 | 5 | 30 | 15 | 10 | |||||||||||||||||||
豬殃殃 | 0 | 65 | 70 | 45 | 70 | 55 | 10 | 50 | 55 | 50 | 35 | 80 | 70 | 40 | |||||||||||||||||||
裂葉老鸛草 | - | - | - | - | - | - | - | - | - | - | - | - | - | 30 | |||||||||||||||||||
強生草 | - | - | - | - | - | - | - | 0 | 10 | 10 | 0 | 5 | 5 | 5 | |||||||||||||||||||
地膚 | 0 | 30 | 90 | 40 | 95 | 60 | 50 | 5 | 90 | 90 | 5 | 100 | 98 | 75 | |||||||||||||||||||
藜 | 5 | 50 | 70 | 40 | 65 | 65 | 65 | 25 | 75 | 60 | 50 | 75 | 75 | 50 | |||||||||||||||||||
牽牛花 | 5 | 20 | 65 | 5 | 75 | 10 | 5 | 10 | 65 | 55 | 40 | 75 | 70 | 5 | |||||||||||||||||||
野生芥菜 | - | - | - | - | - | - | - | - | - | - | - | - | - | - | |||||||||||||||||||
顛茄 | - | - | - | - | - | - | - | - | - | - | - | - | - | 75 | |||||||||||||||||||
油莎草 | 0 | 5 | 0 | 0 | 0 | 0 | 0 | 0 | 5 | 5 | 0 | 5 | 5 | 0 | |||||||||||||||||||
野生燕麥 | 0 | 0 | 5 | 0 | 0 | 0 | 0 | 5 | 10 | 5 | 0 | 5 | 5 | 5 | |||||||||||||||||||
油菜籽 | 0 | 0 | 45 | 15 | 50 | 30 | 35 | 5 | 40 | 35 | 20 | 50 | 5 | 60 | |||||||||||||||||||
反枝莧 | 35 | 75 | 90 | 50 | 85 | 85 | 60 | 60 | 75 | 95 | 80 | 80 | 90 | - | |||||||||||||||||||
長芒莧 | - | - | - | - | - | - | - | - | - | - | - | - | - | 75 | |||||||||||||||||||
猩猩草 | - | - | - | - | - | - | - | - | - | - | - | - | - | 65 | |||||||||||||||||||
豬草 | 10 | 5 | 30 | 20 | 30 | 10 | 5 | 15 | 40 | 40 | 0 | 35 | 50 | 5 | |||||||||||||||||||
義大利黑麥草 | 10 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 5 | 0 | 0 | 5 | 5 | 0 | |||||||||||||||||||
大豆 | 25 | 30 | 45 | 15 | 25 | 30 | 40 | 20 | 65 | 25 | 25 | 60 | 45 | 50 | |||||||||||||||||||
婆婆納 | - | - | - | - | - | - | - | - | - | - | - | - | - | 90 | |||||||||||||||||||
蘇利南草 | - | - | - | - | - | - | - | - | - | - | - | - | - | 10 | |||||||||||||||||||
苘麻 | 5 | 20 | 50 | 20 | 20 | 40 | 50 | 10 | 30 | 25 | 40 | 40 | 40 | 30 | |||||||||||||||||||
莧菜藤子 | 35 | - | - | - | 75 | 75 | 75 | 80 | 95 | 90 | 65 | 85 | 85 | 85 | |||||||||||||||||||
小麥 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | |||||||||||||||||||
風剪草 | - | - | - | - | - | - | - | - | - | - | - | - | - | 0 | |||||||||||||||||||
表C | 化合物 | ||||||||||||||||||||||||||||||||
16 g ai/ha | 77 | 79 | 80 | 82 | 89 | 92 | 107 | 110 | 125 | 130 | 136 | 137 | 138 | 143 | |||||||||||||||||||
萌後 | |||||||||||||||||||||||||||||||||
稗草 | 15 | - | - | 10 | - | 10 | - | 10 | 5 | 5 | 5 | 10 | - | 5 | |||||||||||||||||||
黑草 | 5 | 20 | 0 | 30 | 10 | 5 | 5 | 10 | 10 | 5 | 5 | 5 | 5 | 10 | |||||||||||||||||||
野生蕎麥 | - | 75 | 70 | 80 | 70 | - | 45 | 85 | 70 | 35 | 50 | 70 | 70 | 75 | |||||||||||||||||||
加拿大薊 | - | 55 | 75 | 85 | 80 | - | 80 | 65 | 80 | 75 | 65 | 75 | 80 | 85 | |||||||||||||||||||
繁縷 | 80 | 95 | 60 | 55 | 65 | 100 | 80 | 60 | 70 | 75 | 55 | 70 | 75 | 80 | |||||||||||||||||||
玉米 | 15 | 15 | 15 | 20 | 15 | 10 | 10 | 10 | 10 | 10 | 5 | 10 | 15 | 15 | |||||||||||||||||||
大馬唐草 | 10 | 10 | 10 | 10 | 55 | 20 | 10 | 10 | 10 | 5 | 5 | 10 | 35 | 5 | |||||||||||||||||||
原野鬼罌粟 | - | 85 | 70 | 50 | 90 | - | 80 | 85 | 90 | 100 | 65 | 85 | 100 | 80 | |||||||||||||||||||
原野紫羅蘭 | - | 70 | 75 | 60 | 100 | - | 95 | 80 | 90 | 80 | 85 | 65 | 90 | 75 | |||||||||||||||||||
大狐尾草 | 10 | 10 | 5 | 10 | 10 | 10 | 10 | 10 | 10 | 10 | 10 | 20 | 10 | 20 | |||||||||||||||||||
豬殃殃 | 75 | 75 | 70 | 50 | 75 | 80 | 75 | 60 | 65 | 75 | 50 | 55 | 65 | 75 | |||||||||||||||||||
裂葉老鸛草 | - | 45 | 30 | 30 | 35 | - | 25 | 5 | 25 | 25 | 15 | 10 | 30 | 30 | |||||||||||||||||||
強生草 | - | 40 | 5 | 5 | 5 | - | 20 | 5 | 5 | 5 | 5 | 5 | 10 | 5 | |||||||||||||||||||
地膚 | 95 | 75 | 55 | 80 | 70 | 100 | 80 | 95 | 85 | 80 | 80 | 85 | 75 | 98 | |||||||||||||||||||
藜 | 55 | 75 | 50 | 70 | 70 | 40 | 80 | 75 | 70 | 75 | 55 | 55 | 65 | 75 | |||||||||||||||||||
牽牛花 | 50 | 10 | 25 | 25 | 5 | 20 | 20 | 30 | 20 | 10 | 10 | 10 | 10 | 15 | |||||||||||||||||||
野生芥菜 | - | - | 75 | 95 | 100 | - | 85 | 90 | 90 | 98 | 85 | 100 | 100 | 100 | |||||||||||||||||||
顛茄 | - | 90 | 60 | 85 | 75 | - | 75 | 75 | 50 | 75 | 70 | 60 | 75 | 65 | |||||||||||||||||||
油莎草 | 5 | 0 | 0 | 10 | 0 | 0 | 5 | 0 | 5 | 0 | 0 | 0 | 0 | 0 | |||||||||||||||||||
野生燕麥 | 0 | 15 | 0 | 25 | 15 | 5 | 5 | 20 | 5 | 5 | 5 | 5 | 10 | 10 | |||||||||||||||||||
油菜籽 | 10 | 80 | 50 | 70 | 60 | 5 | 65 | 60 | 80 | 70 | 65 | 90 | 70 | 85 | |||||||||||||||||||
反枝莧 | 95 | - | - | - | - | 85 | - | - | - | - | - | - | - | - | |||||||||||||||||||
長芒莧 | - | 60 | 30 | 75 | 55 | - | 90 | 75 | 40 | 35 | 50 | 20 | 75 | 45 | |||||||||||||||||||
猩猩草 | - | 30 | 65 | 40 | 55 | - | 70 | 40 | 65 | 55 | 40 | 15 | 30 | 55 | |||||||||||||||||||
豬草 | 40 | 30 | 5 | 40 | 0 | 35 | 25 | 40 | 5 | 25 | 20 | 20 | 0 | 20 | |||||||||||||||||||
義大利黑麥草 | 0 | 5 | 0 | 5 | 5 | 10 | 5 | 5 | 5 | 5 | 0 | 5 | 5 | 5 | |||||||||||||||||||
大豆 | 25 | 60 | 60 | 25 | 35 | 30 | 50 | 40 | 25 | 40 | 30 | 20 | 35 | 30 | |||||||||||||||||||
婆婆納 | - | 85 | 90 | 75 | 95 | - | 100 | 60 | 55 | 80 | 75 | 75 | 95 | 80 | |||||||||||||||||||
蘇利南草 | - | 25 | 10 | 20 | 10 | - | 10 | 15 | 5 | 10 | 5 | 5 | 20 | 5 | |||||||||||||||||||
苘麻 | 35 | 30 | 30 | 35 | 20 | 35 | 60 | 50 | 20 | 25 | 20 | 10 | 10 | 35 | |||||||||||||||||||
莧菜藤子 | 95 | 95 | 80 | 65 | 70 | 80 | 95 | 85 | 75 | 65 | 70 | 40 | 98 | 75 | |||||||||||||||||||
小麥 | 0 | 5 | 0 | 5 | 0 | 0 | 5 | 5 | 5 | 10 | 0 | 5 | 5 | 5 | |||||||||||||||||||
風剪草 | - | 20 | 0 | 10 | 10 | - | 5 | 20 | 10 | 10 | 5 | 10 | 0 | 30 | |||||||||||||||||||
表C | 化合物 | 表C | 化合物 |
16 g ai/ha | 144 | 16 g ai/ha | 144 |
萌後 | 萌後 | ||
稗草 | 5 | 顛茄 | 65 |
黑草 | 10 | 油莎草 | 0 |
野生蕎麥 | 70 | 野生燕麥 | 20 |
加拿大薊 | 90 | 油菜籽 | 35 |
繁縷 | 50 | 反枝莧 | - |
玉米 | 15 | 長芒莧 | 25 |
大馬唐草 | 10 | 猩猩草 | 30 |
原野鬼罌粟 | 60 | 豬草 | 10 |
原野紫羅蘭 | 60 | 義大利黑麥草 | 5 |
大狐尾草 | 5 | 大豆 | 30 |
豬殃殃 | 50 | 婆婆納 | 60 |
裂葉老鸛草 | 15 | 蘇利南草 | 10 |
強生草 | 5 | 苘麻 | 25 |
地膚 | 85 | 莧菜藤子 | 35 |
藜 | 40 | 小麥 | 5 |
牽牛花 | 30 | 風剪草 | 10 |
野生芥菜 | 70 | ||
表C | 化合物 | 表C | 化合物 |
8 g ai/ha | 13 | 4 g ai/ha | 13 |
萌後 | 萌後 | ||
稗草 | 5 | 稗草 | 5 |
黑草 | 0 | 黑草 | 0 |
繁縷 | 5 | 繁縷 | 5 |
玉米 | 5 | 玉米 | 5 |
大馬唐草 | 5 | 大馬唐草 | 5 |
大狐尾草 | 5 | 大狐尾草 | 5 |
豬殃殃 | 5 | 豬殃殃 | 10 |
地膚 | 5 | 地膚 | 0 |
藜 | 60 | 藜 | 30 |
牽牛花 | 5 | 牽牛花 | 5 |
油莎草 | 0 | 油莎草 | 0 |
野生燕麥 | 0 | 野生燕麥 | 0 |
油菜籽 | 0 | 油菜籽 | 0 |
反枝莧 | 60 | 反枝莧 | 30 |
豬草 | 5 | 豬草 | 5 |
義大利黑麥草 | 0 | 義大利黑麥草 | 0 |
大豆 | 20 | 大豆 | 15 |
苘麻 | 15 | 苘麻 | 15 |
小麥 | 0 | 小麥 | 0 |
表C | 化合物 | ||||||||||||||||||||||
125 g ai/ha | 15 | 16 | 20 | 21 | 26 | 30 | 33 | 61 | 72 | 73 | 75 | 77 | 79 | 80 | |||||||||
萌前 | |||||||||||||||||||||||
稗草 | 100 | 75 | 85 | 98 | 100 | 25 | 100 | 65 | 100 | 100 | 100 | 100 | 95 | 100 | |||||||||
黑草 | 80 | 10 | 100 | 90 | 90 | 0 | 90 | 5 | 100 | 100 | 75 | 100 | 90 | 90 | |||||||||
玉米 | 25 | 10 | 30 | 20 | 40 | 5 | 10 | 0 | 60 | 50 | 5 | 35 | 30 | 20 | |||||||||
大馬唐草 | 100 | 100 | 100 | 100 | 100 | 98 | 100 | 90 | 100 | 100 | 98 | 100 | 98 | 98 | |||||||||
大狐尾草 | 100 | 100 | 100 | 90 | 98 | 75 | 100 | 65 | 100 | 100 | 98 | 100 | 98 | 100 | |||||||||
豬殃殃 | - | - | 95 | 100 | 100 | 85 | 95 | 15 | 100 | 100 | 0 | 98 | 5 | 98 | |||||||||
強生草 | - | - | - | - | 98 | 15 | 35 | 20 | 100 | 95 | 70 | - | 70 | 60 | |||||||||
地膚 | - | - | - | - | - | - | - | 30 | - | - | 100 | - | 100 | 100 | |||||||||
藜 | 95 | 50 | 90 | 70 | 95 | 55 | 85 | 60 | 100 | 100 | 70 | 98 | 85 | 98 | |||||||||
牽牛花 | 60 | 25 | 10 | 10 | 95 | 35 | 40 | 0 | 95 | 75 | 10 | 65 | 60 | 75 | |||||||||
顛茄 | - | - | - | - | - | - | - | 75 | - | - | 80 | - | 95 | 90 | |||||||||
油莎草 | 50 | 0 | 10 | 0 | 45 | 5 | 5 | 0 | 0 | 10 | 20 | 30 | 0 | 35 | |||||||||
野生燕麥 | - | - | - | - | - | - | - | 5 | - | - | 5 | - | 40 | 30 | |||||||||
油菜籽 | 100 | 100 | 50 | 100 | 100 | 100 | 100 | 10 | 100 | 65 | 40 | 100 | 95 | 100 | |||||||||
反枝莧 | 100 | 95 | 100 | 100 | 100 | 100 | 100 | - | 100 | 100 | - | 100 | - | - | |||||||||
長芒莧 | - | - | - | - | - | - | - | 75 | - | - | 100 | - | 90 | 98 | |||||||||
猩猩草 | - | - | - | - | - | - | - | 0 | - | - | 35 | - | 40 | 85 | |||||||||
豬草 | 20 | 0 | 0 | 0 | 50 | 0 | 50 | 30 | 45 | 25 | 5 | 45 | 30 | 20 | |||||||||
義大利黑麥草 | 50 | 5 | 70 | 90 | 95 | 5 | 85 | 5 | 100 | 100 | 15 | 90 | 35 | 25 | |||||||||
大豆 | 55 | 5 | 10 | 0 | - | 60 | 30 | 10 | 90 | 40 | 50 | 25 | 5 | 85 | |||||||||
蘇利南草 | - | - | - | - | - | - | - | 25 | - | - | 80 | - | 85 | 98 | |||||||||
苘麻 | 100 | 75 | 50 | 100 | 100 | 40 | 100 | 5 | 100 | 95 | 25 | 100 | 75 | 100 | |||||||||
莧菜藤子 | 100 | 100 | 98 | 98 | 100 | 100 | 100 | 100 | 100 | 100 | 98 | 100 | 100 | 100 | |||||||||
小麥 | 5 | 0 | 5 | 0 | 15 | 10 | 5 | 10 | 80 | 70 | 10 | 0 | 15 | 15 | |||||||||
風剪草 | - | - | - | - | - | - | - | 70 | - | - | 100 | - | 100 | 100 | |||||||||
表C | 化合物 | ||||||||||||||||||||||
125 g ai/ha | 82 | 89 | 92 | 107 | 125 | 130 | 136 | 138 | 143 | 144 | |||||||||||||
萌前 | |||||||||||||||||||||||
稗草 | 90 | 100 | 100 | 100 | - | - | - | 95 | - | 95 | |||||||||||||
黑草 | 5 | 90 | 100 | 90 | 90 | 85 | 95 | 90 | 75 | 30 | |||||||||||||
玉米 | 5 | 10 | 40 | 45 | 5 | 25 | 5 | 5 | 20 | 30 | |||||||||||||
大馬唐草 | 98 | 98 | 100 | 100 | 100 | 100 | 100 | 98 | 100 | 100 | |||||||||||||
大狐尾草 | 98 | 85 | 100 | 98 | 100 | 100 | 100 | 100 | 100 | 100 | |||||||||||||
豬殃殃 | 80 | 0 | - | 95 | 80 | 90 | 90 | 5 | 80 | 55 | |||||||||||||
強生草 | 85 | 60 | - | 80 | 75 | 85 | 70 | 60 | 80 | 70 | |||||||||||||
地膚 | 95 | 90 | - | 100 | 98 | 98 | 98 | 80 | 90 | 100 | |||||||||||||
藜 | 70 | 65 | 100 | 95 | 95 | 95 | 80 | 70 | 95 | 75 | |||||||||||||
牽牛花 | 10 | 20 | 70 | 85 | 50 | 10 | 30 | 10 | 25 | 20 | |||||||||||||
顛茄 | 85 | 85 | - | 90 | - | - | - | 80 | - | 100 | |||||||||||||
油莎草 | 0 | 0 | 50 | 0 | 5 | 0 | 5 | 0 | 5 | 70 | |||||||||||||
野生燕麥 | 5 | 10 | - | 65 | 55 | 60 | 45 | 30 | 5 | 10 | |||||||||||||
油菜籽 | 50 | 15 | 100 | 98 | 80 | 95 | 98 | 20 | 98 | 90 | |||||||||||||
反枝莧 | - | - | 100 | - | - | - | - | - | - | - | |||||||||||||
長芒莧 | 100 | 98 | - | 100 | 100 | 85 | 100 | 100 | 100 | 100 | |||||||||||||
猩猩草 | 20 | 40 | - | 70 | 30 | 45 | 50 | 50 | 25 | 80 | |||||||||||||
豬草 | 30 | 50 | 60 | 50 | 35 | 10 | 40 | 10 | 5 | 10 | |||||||||||||
義大利黑麥草 | 5 | 40 | 95 | 90 | 85 | 70 | 65 | 80 | 45 | 60 | |||||||||||||
大豆 | 0 | 10 | 60 | 45 | 20 | 30 | 40 | 5 | 20 | 60 | |||||||||||||
蘇利南草 | 35 | 75 | - | 98 | 65 | 80 | 100 | 75 | 50 | 60 | |||||||||||||
苘麻 | 10 | 60 | 100 | 98 | 65 | 85 | 65 | 50 | 70 | 45 | |||||||||||||
莧菜藤子 | 100 | 100 | 100 | 100 | 100 | 100 | 100 | 98 | 100 | 100 | |||||||||||||
小麥 | 0 | 5 | 20 | 35 | 5 | 0 | 10 | 10 | 0 | 5 | |||||||||||||
風剪草 | 90 | 100 | - | 100 | 100 | 100 | 100 | 100 | 100 | 90 | |||||||||||||
表C | 化合物 | ||||||||||||||||||||||
62 g ai/ha | 15 | 16 | 20 | 21 | 26 | 30 | 33 | 61 | 72 | 73 | 75 | 77 | 79 | 80 | |||||||||
萌前 | |||||||||||||||||||||||
稗草 | 100 | 30 | 30 | 90 | 100 | 10 | 95 | 50 | 80 | 100 | 80 | 98 | 75 | 70 | |||||||||
黑草 | 50 | 5 | 85 | 55 | 90 | 0 | 70 | 0 | 98 | 100 | 80 | 90 | 75 | 70 | |||||||||
玉米 | 10 | 0 | 0 | 5 | 25 | 0 | 10 | 10 | 20 | 40 | 0 | 20 | 5 | 5 | |||||||||
大馬唐草 | 100 | 90 | 98 | 98 | 100 | 80 | 100 | 75 | 100 | 100 | 98 | 100 | 100 | 100 | |||||||||
大狐尾草 | 100 | 90 | 90 | 95 | 98 | 65 | 98 | 60 | 75 | 100 | 65 | 100 | 80 | 85 | |||||||||
豬殃殃 | - | - | 80 | 5 | 95 | 60 | 60 | 10 | 90 | 100 | 5 | 98 | 70 | 75 | |||||||||
強生草 | - | - | - | - | 80 | 0 | 25 | 0 | 70 | 80 | 30 | - | 50 | 55 | |||||||||
地膚 | - | - | - | - | - | - | - | 5 | - | - | 90 | - | 90 | 100 | |||||||||
藜 | 85 | 20 | 10 | 25 | 95 | 30 | 80 | 50 | 90 | 90 | 35 | 100 | 70 | 95 | |||||||||
牽牛花 | 35 | 25 | 5 | 5 | 85 | 10 | 25 | 0 | 55 | 60 | 20 | 35 | 10 | 40 | |||||||||
顛茄 | - | - | - | - | - | - | - | 50 | - | - | 75 | - | 80 | 85 | |||||||||
油莎草 | 5 | 0 | 0 | 0 | 15 | 0 | 5 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | |||||||||
野生燕麥 | - | - | - | - | - | - | - | 5 | - | - | 0 | - | 5 | 10 | |||||||||
油菜籽 | 100 | 60 | 50 | 75 | 100 | 100 | 85 | 0 | 80 | 50 | 10 | 100 | 70 | 70 | |||||||||
反枝莧 | 100 | 50 | 100 | 98 | 100 | 100 | 100 | - | 100 | 100 | - | 100 | - | - | |||||||||
長芒莧 | - | - | - | - | - | - | - | 70 | - | - | 95 | - | 90 | 100 | |||||||||
猩猩草 | - | - | - | - | - | - | - | 0 | - | - | 35 | - | 10 | 40 | |||||||||
豬草 | 30 | 5 | 0 | 0 | 60 | 0 | 40 | 5 | 40 | 10 | 0 | 40 | 20 | 5 | |||||||||
義大利黑麥草 | 15 | 5 | 30 | 15 | 85 | 0 | 30 | 0 | 45 | 85 | 5 | 35 | 30 | 5 | |||||||||
大豆 | 40 | 0 | 0 | 0 | 35 | 10 | - | 20 | 15 | 25 | 10 | 15 | 5 | 40 | |||||||||
蘇利南草 | - | - | - | - | - | - | - | 60 | - | - | 35 | - | 50 | 60 | |||||||||
苘麻 | 100 | 50 | 5 | 70 | 85 | 10 | 55 | 5 | 55 | 75 | 35 | 70 | 20 | 70 | |||||||||
莧菜藤子 | 100 | 85 | 100 | 95 | 100 | 100 | 100 | 90 | 100 | 100 | 98 | 100 | 95 | 100 | |||||||||
小麥 | 0 | 0 | 0 | 0 | 5 | 0 | 0 | 5 | 30 | 30 | 10 | 0 | 5 | 0 | |||||||||
風剪草 | - | - | - | - | - | - | - | 40 | - | - | 100 | - | 100 | 100 | |||||||||
表C | 化合物 | ||||||||||||||||||||||
62 g ai/ha | 82 | 89 | 92 | 107 | 125 | 130 | 136 | 138 | 143 | 144 | |||||||||||||
萌前 | |||||||||||||||||||||||
稗草 | 20 | 90 | 98 | 100 | - | - | - | 80 | - | 70 | |||||||||||||
黑草 | 5 | 85 | 100 | 90 | 60 | 60 | 60 | 80 | 80 | 40 | |||||||||||||
玉米 | 0 | 0 | 35 | 15 | 5 | 5 | 5 | 5 | 0 | 5 | |||||||||||||
大馬唐草 | 90 | 100 | 100 | 100 | 100 | 100 | 100 | 98 | 100 | 100 | |||||||||||||
大狐尾草 | 90 | 60 | 100 | 98 | 98 | 98 | 70 | 85 | 100 | 100 | |||||||||||||
豬殃殃 | 0 | 0 | - | 90 | 30 | 90 | 50 | 5 | 80 | 50 | |||||||||||||
強生草 | 40 | 30 | - | 70 | 60 | 70 | 35 | 50 | 50 | 40 | |||||||||||||
地膚 | 90 | 85 | - | 100 | 90 | 65 | 85 | 80 | 90 | 100 | |||||||||||||
藜 | 20 | 0 | 100 | 85 | 60 | 35 | 25 | 25 | 95 | 65 | |||||||||||||
牽牛花 | 0 | 5 | 60 | 40 | 10 | 20 | 5 | 0 | 5 | 10 | |||||||||||||
顛茄 | 40 | 65 | - | 80 | - | - | - | 80 | - | 90 | |||||||||||||
油莎草 | 0 | 0 | 5 | 0 | 0 | 0 | 0 | 0 | 0 | 60 | |||||||||||||
野生燕麥 | 5 | 30 | - | 30 | 10 | 35 | 5 | 5 | 5 | 10 | |||||||||||||
油菜籽 | 5 | 0 | 100 | 85 | 50 | 40 | 70 | 5 | 80 | 5 | |||||||||||||
反枝莧 | - | - | 100 | - | - | - | - | - | - | - | |||||||||||||
長芒莧 | 100 | 90 | - | 100 | 100 | 100 | 100 | 100 | 100 | 100 | |||||||||||||
猩猩草 | 0 | 20 | - | 40 | 25 | 10 | 25 | 5 | 20 | 40 | |||||||||||||
豬草 | 20 | 5 | 60 | 50 | 5 | 5 | 0 | 0 | 0 | 0 | |||||||||||||
義大利黑麥草 | 5 | 15 | 55 | 70 | 40 | 60 | 35 | 20 | 30 | 0 | |||||||||||||
大豆 | 0 | 5 | 70 | 35 | 0 | 10 | 15 | 0 | 15 | 30 | |||||||||||||
蘇利南草 | 25 | 65 | - | 98 | 40 | 65 | 10 | 65 | 35 | 70 | |||||||||||||
苘麻 | 0 | 25 | 100 | 98 | 60 | 75 | 15 | 20 | 40 | 15 | |||||||||||||
莧菜藤子 | 100 | 100 | 100 | 100 | 100 | 100 | 100 | 100 | 100 | 98 | |||||||||||||
小麥 | 0 | 0 | 0 | 15 | 0 | 5 | 0 | 5 | 0 | 0 | |||||||||||||
風剪草 | 80 | 65 | - | 100 | 90 | 100 | 85 | 100 | 100 | 80 | |||||||||||||
表C | 化合物 | ||||||||||||||||||||||
31 g ai/ha | 13 | 15 | 16 | 20 | 21 | 26 | 30 | 33 | 61 | 72 | 73 | 75 | 77 | 79 | |||||||||
萌前 | |||||||||||||||||||||||
稗草 | 40 | 85 | 15 | 5 | 55 | 75 | 15 | 40 | 0 | 90 | 80 | 60 | 60 | 60 | |||||||||
黑草 | 0 | 0 | 0 | 40 | 35 | 90 | 0 | 10 | 0 | 98 | 98 | 5 | 15 | 10 | |||||||||
玉米 | 10 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 20 | 20 | 0 | 15 | 0 | |||||||||
大馬唐草 | 85 | 100 | 75 | 50 | 75 | 100 | 35 | 98 | 10 | 100 | 100 | 85 | 100 | 98 | |||||||||
大狐尾草 | 95 | 100 | 25 | 50 | 80 | 98 | 30 | 95 | 50 | 80 | 100 | 25 | 100 | 70 | |||||||||
豬殃殃 | - | - | - | 0 | 0 | 90 | 10 | 60 | 0 | 75 | 10 | 0 | 0 | 0 | |||||||||
強生草 | - | - | - | - | - | 50 | 0 | 5 | 0 | 65 | 40 | 0 | - | 5 | |||||||||
地膚 | - | - | - | - | - | - | - | - | 5 | - | - | 50 | - | 90 | |||||||||
藜 | 15 | 70 | 20 | 5 | 30 | 85 | 25 | 60 | 15 | 80 | 90 | 10 | 60 | 10 | |||||||||
牽牛花 | 5 | 20 | 0 | 0 | 0 | 10 | 10 | 0 | 0 | 40 | 10 | 0 | 20 | 10 | |||||||||
顛茄 | - | - | - | - | - | - | - | - | 60 | - | - | 75 | - | 65 | |||||||||
油莎草 | 5 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | |||||||||
野生燕麥 | - | - | - | - | - | - | - | - | 0 | - | - | 0 | - | 0 | |||||||||
油菜籽 | 50 | 100 | 50 | 0 | 0 | 85 | 55 | 80 | 0 | 80 | 20 | 0 | 55 | 0 | |||||||||
反枝莧 | 60 | 100 | 0 | 55 | 55 | 100 | 95 | 100 | - | 100 | 95 | - | 100 | - | |||||||||
長芒莧 | - | - | - | - | - | - | - | - | 50 | - | - | 100 | - | 85 | |||||||||
猩猩草 | - | - | - | - | - | - | - | - | 0 | - | - | 40 | - | 0 | |||||||||
豬草 | 10 | 10 | 0 | 0 | 0 | 30 | 0 | 35 | 0 | 0 | 0 | 0 | 0 | 0 | |||||||||
義大利黑麥草 | 0 | 5 | 0 | 0 | 10 | 75 | 0 | 30 | 0 | 45 | 35 | 5 | 30 | 10 | |||||||||
大豆 | 5 | 10 | 0 | 0 | 0 | 10 | - | - | 20 | 0 | 0 | 0 | 5 | 0 | |||||||||
蘇利南草 | - | - | - | - | - | - | - | - | 10 | - | - | 30 | - | 30 | |||||||||
苘麻 | 70 | 85 | 5 | 0 | 40 | 30 | 0 | 30 | 5 | 60 | 30 | 5 | 30 | 5 | |||||||||
莧菜藤子 | 100 | 100 | 60 | 85 | 75 | 100 | 100 | 100 | 75 | 100 | 100 | 95 | 100 | 98 | |||||||||
小麥 | 5 | 0 | 0 | 0 | 0 | 20 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 5 | |||||||||
風剪草 | - | - | - | - | - | - | - | - | 5 | - | - | 45 | - | 80 | |||||||||
表C | 化合物 | ||||||||||||||||||||||
31 g ai/ha | 80 | 82 | 89 | 92 | 107 | 125 | 130 | 136 | 138 | 143 | 144 | ||||||||||||
萌前 | |||||||||||||||||||||||
稗草 | 30 | 5 | 35 | 85 | 85 | - | - | - | 40 | - | 40 | ||||||||||||
黑草 | 10 | 0 | 15 | 80 | 90 | 60 | 30 | 35 | 50 | 75 | 10 | ||||||||||||
玉米 | 5 | 0 | 0 | 15 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | ||||||||||||
大馬唐草 | 80 | 70 | 98 | 100 | 98 | 98 | 100 | 85 | 95 | 100 | 98 | ||||||||||||
大狐尾草 | 40 | 80 | 5 | 100 | 98 | 85 | 70 | 65 | 80 | 98 | 85 | ||||||||||||
豬殃殃 | 5 | 0 | 0 | - | 60 | 5 | 50 | 0 | 0 | 30 | 50 | ||||||||||||
強生草 | 30 | 5 | 40 | - | 30 | 5 | 10 | 25 | 0 | 25 | 10 | ||||||||||||
地膚 | 95 | 50 | 60 | - | 100 | 60 | 65 | 80 | 75 | 80 | 90 | ||||||||||||
藜 | 70 | 20 | 0 | 100 | 75 | 30 | 30 | 30 | 35 | 10 | 40 | ||||||||||||
牽牛花 | 20 | 0 | 0 | 40 | 0 | 10 | 5 | 0 | 0 | 0 | 0 | ||||||||||||
顛茄 | 70 | 20 | 75 | - | 60 | - | - | - | 50 | - | 65 | ||||||||||||
油莎草 | 0 | 0 | 0 | 5 | 0 | 0 | 0 | 0 | 0 | 0 | 20 | ||||||||||||
野生燕麥 | 0 | 0 | 10 | - | 5 | 0 | 15 | 0 | 0 | 0 | 5 | ||||||||||||
油菜籽 | 80 | 0 | 0 | 100 | 40 | 5 | 10 | 5 | 0 | 5 | 0 | ||||||||||||
反枝莧 | - | - | - | 100 | - | - | - | - | - | - | - | ||||||||||||
長芒莧 | 85 | 85 | 70 | - | 100 | 100 | 75 | 75 | 60 | 100 | 100 | ||||||||||||
猩猩草 | 30 | 0 | 0 | - | 10 | 0 | 0 | 5 | 0 | 5 | 5 | ||||||||||||
豬草 | 0 | 0 | 0 | 55 | 30 | 10 | 0 | 20 | 0 | 0 | 0 | ||||||||||||
義大利黑麥草 | 0 | 0 | 5 | 5 | 35 | 30 | 35 | 30 | 10 | 20 | 0 | ||||||||||||
大豆 | 20 | 0 | 5 | 40 | 20 | 0 | 0 | 0 | 0 | 0 | 0 | ||||||||||||
蘇利南草 | 50 | 10 | 35 | - | 60 | 20 | 50 | 25 | 65 | 10 | 5 | ||||||||||||
苘麻 | 55 | 0 | 20 | 75 | 75 | 5 | 10 | 5 | 25 | 10 | 0 | ||||||||||||
莧菜藤子 | 100 | 50 | 85 | 100 | 98 | 100 | 100 | 100 | 85 | 98 | 98 | ||||||||||||
小麥 | 0 | 0 | 0 | 0 | 10 | 0 | 0 | 0 | 5 | 0 | - | ||||||||||||
風剪草 | 60 | 30 | 50 | - | 100 | 85 | 70 | 30 | 100 | 85 | 30 | ||||||||||||
表C | 化合物 | ||||||||||||||||||||||
16 g ai/ha | 13 | 15 | 16 | 20 | 21 | 26 | 30 | 33 | 61 | 72 | 73 | 75 | 77 | 79 | |||||||||
萌前 | |||||||||||||||||||||||
稗草 | 10 | 10 | 0 | 0 | 10 | 40 | 10 | 20 | 0 | 25 | 15 | 5 | 20 | 5 | |||||||||
黑草 | 0 | 0 | 0 | 0 | 5 | 45 | 0 | 0 | 0 | 60 | 5 | 0 | 5 | 5 | |||||||||
玉米 | 5 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 5 | 0 | 0 | 0 | 0 | |||||||||
大馬唐草 | 60 | 95 | 5 | 5 | 20 | 98 | 0 | 75 | 0 | 100 | 98 | 65 | 98 | 65 | |||||||||
大狐尾草 | 0 | 100 | 5 | 35 | 20 | 95 | 5 | 60 | 0 | 55 | 98 | 0 | 95 | 40 | |||||||||
豬殃殃 | - | - | - | 10 | - | 5 | 80 | 0 | 0 | 5 | 5 | 0 | 0 | 0 | |||||||||
強生草 | - | - | - | - | - | 55 | 0 | 0 | 0 | 5 | 0 | 0 | - | 0 | |||||||||
地膚 | - | - | - | - | - | - | - | - | 0 | - | - | 0 | - | 5 | |||||||||
藜 | 50 | 60 | 0 | 0 | 0 | 70 | 10 | 25 | 5 | 65 | 85 | 0 | 50 | 0 | |||||||||
牽牛花 | 5 | 20 | 10 | 0 | 0 | 20 | 0 | 0 | 0 | 10 | 0 | 0 | 10 | 20 | |||||||||
顛茄 | - | - | - | - | - | - | - | - | 60 | - | - | 40 | - | 30 | |||||||||
油莎草 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | |||||||||
野生燕麥 | - | - | - | - | - | - | - | - | 0 | - | - | 0 | - | 0 | |||||||||
油菜籽 | 0 | 30 | 0 | 0 | 0 | 80 | 10 | 50 | 0 | 5 | 0 | 0 | 0 | 0 | |||||||||
反枝莧 | 5 | 98 | 0 | 55 | 5 | 100 | 90 | 80 | - | 100 | 90 | - | 85 | - | |||||||||
長芒莧 | - | - | - | - | - | - | - | - | 40 | - | - | 70 | - | 75 | |||||||||
猩猩草 | - | - | - | - | - | - | - | - | 0 | - | - | 10 | - | 0 | |||||||||
豬草 | 0 | 10 | 0 | 0 | 0 | 20 | 0 | 55 | 0 | 0 | 0 | 0 | 0 | 0 | |||||||||
義大利黑麥草 | 0 | 0 | 0 | 0 | 0 | 35 | 0 | 0 | 0 | 10 | 30 | 0 | 0 | 0 | |||||||||
大豆 | 5 | 0 | 0 | 0 | 0 | - | 0 | 15 | - | 0 | 0 | 0 | 5 | 0 | |||||||||
蘇利南草 | - | - | - | - | - | - | - | - | 0 | - | - | 0 | - | 5 | |||||||||
苘麻 | 20 | 60 | 0 | 0 | 10 | 0 | 0 | 5 | 0 | 10 | 0 | 0 | 10 | 10 | |||||||||
莧菜藤子 | 80 | 90 | 10 | 30 | 70 | 100 | 85 | 100 | 50 | 100 | 65 | 75 | 95 | 100 | |||||||||
小麥 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | |||||||||
風剪草 | - | - | - | - | - | - | - | - | 0 | - | - | 5 | - | 60 | |||||||||
表C | 化合物 | ||||||||||||||||||||||
16 g ai/ha | 80 | 82 | 89 | 92 | 107 | 125 | 130 | 136 | 138 | 143 | 144 | ||||||||||||
萌前 | |||||||||||||||||||||||
稗草 | 10 | 5 | 5 | 35 | 65 | - | - | - | 20 | - | 10 | ||||||||||||
黑草 | 5 | 0 | 5 | 45 | 60 | 5 | 30 | 0 | 10 | 5 | 5 | ||||||||||||
玉米 | 0 | 0 | 0 | 0 | 0 | 0 | 5 | 0 | 0 | 5 | 0 | ||||||||||||
大馬唐草 | 55 | 60 | 75 | 100 | 98 | 35 | 98 | 50 | 75 | 70 | 85 | ||||||||||||
大狐尾草 | 5 | 20 | 0 | 100 | 60 | 30 | 50 | 25 | 35 | 20 | 70 | ||||||||||||
豬殃殃 | 0 | 0 | 0 | - | 5 | 0 | 0 | 0 | 0 | 0 | 0 | ||||||||||||
強生草 | 5 | 0 | 0 | - | 10 | 5 | 10 | 10 | 0 | 5 | 0 | ||||||||||||
地膚 | 70 | 0 | 60 | - | 100 | 5 | 10 | 50 | 5 | 30 | 70 | ||||||||||||
藜 | 30 | 30 | 0 | 90 | 30 | 10 | 35 | 25 | 0 | 5 | 50 | ||||||||||||
牽牛花 | 5 | 0 | 0 | 10 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | ||||||||||||
顛茄 | 55 | 5 | 10 | - | 30 | - | - | - | 40 | - | 35 | ||||||||||||
油莎草 | 0 | 0 | 0 | 0 | 0 | 0 | 5 | 0 | 0 | 0 | 0 | ||||||||||||
野生燕麥 | 0 | 0 | 5 | - | 0 | 5 | 0 | 0 | 0 | 0 | 0 | ||||||||||||
油菜籽 | 35 | 0 | 0 | 85 | 5 | 0 | 0 | 5 | 0 | 0 | 0 | ||||||||||||
反枝莧 | - | - | - | 100 | - | - | - | - | - | - | - | ||||||||||||
長芒莧 | 100 | 55 | 65 | - | 100 | 90 | 85 | 95 | 40 | 65 | 85 | ||||||||||||
猩猩草 | 5 | 0 | 0 | - | 0 | 0 | 0 | 0 | 0 | 5 | 0 | ||||||||||||
豬草 | 0 | 0 | 0 | 30 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | ||||||||||||
義大利黑麥草 | 0 | 0 | 0 | 5 | 10 | 0 | 15 | 5 | 0 | 5 | 0 | ||||||||||||
大豆 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | 0 | ||||||||||||
蘇利南草 | 10 | 40 | 10 | - | 15 | 5 | 10 | 0 | 30 | 5 | 10 | ||||||||||||
苘麻 | 30 | 0 | 10 | 50 | 40 | 10 | 5 | 0 | 5 | 0 | 0 | ||||||||||||
莧菜藤子 | 95 | 60 | 70 | 100 | 100 | 70 | 50 | 65 | 75 | 85 | 98 | ||||||||||||
小麥 | 0 | 0 | 0 | 0 | 5 | 0 | 0 | 0 | 0 | 0 | 0 | ||||||||||||
風剪草 | 5 | 40 | 60 | - | 80 | 20 | 30 | 0 | 70 | 25 | 0 | ||||||||||||
表C | 化合物 | 表C | 化合物 | |
8 g ai/ha | 13 | 4 g ai/ha | 13 | |
萌前 | 萌前 | |||
稗草 | 0 | 稗草 | 0 | |
黑草 | 0 | 黑草 | 0 | |
玉米 | 0 | 玉米 | 0 | |
大馬唐草 | 30 | 大馬唐草 | 25 | |
大狐尾草 | 0 | 大狐尾草 | 0 | |
藜 | 5 | 藜 | 0 | |
牽牛花 | 0 | 牽牛花 | 0 | |
油莎草 | 0 | 油莎草 | 0 | |
油菜籽 | 0 | 油菜籽 | 0 | |
反枝莧 | 10 | 反枝莧 | 5 | |
豬草 | 0 | 豬草 | 0 | |
義大利黑麥草 | 0 | 義大利黑麥草 | 0 | |
大豆 | 0 | 大豆 | 0 | |
苘麻 | 10 | 苘麻 | 5 | |
莧菜藤子 | 10 | 莧菜藤子 | 5 | |
小麥 | 0 | 小麥 | 0 |
表C | 化合物 | 表C | 化合物 | ||||||||
250 g ai/ha | 61 | 66 | 92 | 119 | 125 g ai/ha | 61 | 62 | 66 | 92 | 119 | |
淹沒 | 淹沒 | ||||||||||
稗草 | 40 | 80 | 40 | 25 | 稗草 | 20 | 20 | 25 | 20 | 0 | |
異藥花 | 90 | 95 | 100 | 50 | 異藥花 | 90 | 75 | 85 | 95 | 40 | |
稻米 | 20 | 20 | 15 | 0 | 稻米 | 20 | 10 | 0 | 15 | 0 | |
輪傘草 | 85 | 95 | 100 | 90 | 輪傘草 | 85 | 65 | 85 | 90 | 80 |
表C | 化合物 | 表C | 化合物 | |||||||||
62 g ai/ha | 61 | 62 | 66 | 92 | 119 | 31 g ai/ha | 61 | 62 | 66 | 92 | 119 | |
淹沒 | 淹沒 | |||||||||||
稗草 | 0 | 0 | 0 | 0 | 0 | 稗草 | 0 | 0 | 0 | 0 | 0 | |
異藥花 | 75 | 40 | 80 | 60 | 0 | 異藥花 | 50 | 0 | 40 | 30 | 0 | |
稻米 | 20 | 0 | 0 | 15 | 0 | 稻米 | 20 | 0 | 0 | 10 | 0 | |
輪傘草 | 80 | 60 | 75 | 60 | 55 | 輪傘草 | 80 | 0 | 40 | 20 | 0 |
表C | 化合物 |
16 g ai/ha | 62 |
淹沒 | |
稗草 | 0 |
異藥花 | 0 |
稻米 | 0 |
輪傘草 | 0 |
無
Claims (14)
- 一種選自式 1、其 N‑氧化物、及鹽之化合物, 其中 A係
或 A-1 A-2 - 如請求項1之化合物,其中 R 2係鹵素、C 1–C 4烷基、或C 1–C 4鹵烷基; 各R 3獨立地係鹵素、氰基、CHO、C 1–C 4烷基、C 2–C 4烯基、C 2–C 4炔基、C 1–C 4鹵烷基、C 2–C 4鹵烯基、C 2–C 4鹵炔基、C 3–C 6環烷基、C 3–C 6鹵環烷基、C 4–C 8烷基環烷基、C 2–C 6烷基羰基、C 2–C 6鹵烷基羰基、C 2–C 6烷氧基羰基、C 2–C 4烷氧基、C 3–C 4烯基氧基、C 3–C 4炔基氧基、C 1–C 4鹵烷氧基、C 3–C 4鹵烯基氧基、C 3–C 4鹵炔基氧基、C 3–C 6環烷氧基、C 3–C 6鹵環烷氧基、C 2–C 6烷氧基烷基、C 2–C 6鹵烷氧基烷基、C 2–C 4烷基羰基氧基、C 2–C 6氰基烷基、-C(=O)N(R 11aR 11b)、-C(=NOR 12)H、或-SO nR 14; R 11a係C 1–C 2烷基、或C 1–C 2鹵烷基; R 11b係C 1–C 2烷基、或C 1–C 2鹵烷基; R 12係H或C 1–C 3烷基;且 R 14係C 1–C 3烷基、或C 1–C 3鹵烷基。
- 如請求項2之化合物,其中 R 2係鹵素、或C 1–C 4烷基; 各R 3獨立地係鹵素、氰基、CHO 、C 1–C 4烷基、C2–C4 烯基、C2–C4炔基、C 1–C 4鹵烷基、C2–C4 鹵烯基、C2–C4鹵炔基、C3–C6環烷基、C3–C6鹵環烷基、C2–C6烷基羰基、C2–C6鹵烷基羰基、C2–C6烷氧基羰基、C 2–C 4烷氧基、C1–C4鹵烷氧基、C2–C6 烷氧基烷基、C2–C6鹵烷氧基烷基、C2–C6氰基烷基或-SOnR 14各R 14獨立地係C 1–C 3烷基;且 m係0、1或2。
- 如請求項3之化合物,其中 R 2係鹵素或CH 3;且 各R 3獨立地係鹵素、氰基、C 1–C 4烷基、或C 1–C 4鹵烷基。
- 如請求項4之化合物,其中 A係A-1; Z係O; R 2係鹵素; 各R 3獨立地係鹵素、氰基、C 1–C 3烷基、或C 1–C 3鹵烷基;且 m係1或2。
- 如請求項4之化合物,其中 A係A-2; Z係O; R 2係F、Cl、或Br; 各R 3獨立地係鹵素、氰基、C 1–C 2烷基、或C 1–C 2鹵烷基;且 m係0或1。
- 如請求項1之化合物,其中: A係A-1、R 1係(CH 2) 3CF 3、R 2係Cl且R 3係3-CN;或 A係A-1、R 1係(CH 2) 2CF 3、R 2係Cl且R 3係3-CN;或 A係A-1、R 1係(CH 2) 2CF 3、R 2係Cl且R 3係3-Br;或 A係A-1、R 1係(CH 2) 4CF 3、R 2係Cl且R 3係3-Br;或 A係A-1、R 1係(CH 2) 2CF 3、R 2係Cl且R 3係3-Cl;或 A係A-1、R 1係(CH 2) 4CF 3、R 2係Cl且R 3係3-Cl;或 A係A-1、R 1係(CH 2) 3CF 3、R 2係Cl且R 3係3-Cl;或 A係A-1、R 1係(CH 2) 3CF 3、R 2係Cl且R 3係3-Br。
- 一種除草組合物,其包含如請求項1-7中任一項之化合物、以及至少一種選自由界面活性劑、固體稀釋劑、及液體稀釋劑所組成之群組的組分。
- 一種除草組合物,其包含如請求項1-7中任一項之化合物、至少一種選自由其他除草劑及除草劑安全劑所組成之群組的額外活性成分、以及至少一種選自由界面活性劑、固體稀釋劑、及液體稀釋劑所組成之群組的組分。
- 一種除草混合物,其包含(a)如請求項1-7中任一項之化合物,以及(b)至少一種額外活性成分,其選自(b1)光系統II抑制劑、(b2)乙醯羥酸合成酶(AHAS)抑制劑、(b3)乙醯輔酶A羧化酶(ACCase)抑制劑、(b4)生長素(auxin)模擬物、(b5) 5‑烯醇-丙酮醯莽草酸-3-磷酸(EPSP)合成酶抑制劑、(b6)光系統I電子轉向劑(diverters)、(b7)原紫質原氧化酶(PPO)抑制劑、(b8)麩醯胺酸合成酶(GS)抑制劑、(b9)極長鏈脂肪酸(VLCFA)延長酶抑制劑、(b10)生長素傳輸抑制劑、(b11)八氫番茄紅素去飽和酶(PDS)抑制劑、(b12) 4‑羥基苯基‑丙酮酸二氧合酶(HPPD)抑制劑、(b13)黑尿酸茄尼轉移酶(HST)抑制劑、(b14)纖維素生合成抑制劑、(b15)其他除草劑,包括有絲分裂干擾劑、有機砷劑、亞速爛(asulam)、溴布泰(bromobutide)、環庚草醚(cinmethylin)、苄草隆(cumyluron)、邁隆(dazomet)、燕麥枯(difenzoquat)、汰草龍(dymron)、乙氧苯草胺(etobenzanid)、抑草丁(flurenol)、殺木膦(fosamine)、殺木膦-銨(fosamine‑ammonium)、海丹托西叮(hydantocidin)、威百畝(metam)、甲基汰草龍(methyldymron)、油酸(oleic acid)、噁嗪草酮(oxaziclomefone)、壬酸(pelargonic acid)及稗草畏(pyributicarb)、與(b16)除草劑安全劑;以及(b1)至(b16)之化合物之鹽。
- 一種除草混合物,其包含(a)如請求項1-7中任一項之化合物,以及(b)至少一種選自(b1)光系統II抑制劑、(b2)乙醯羥酸合成酶(AHAS)抑制劑、(b4)生長素模擬物、(b5) 5‑烯醇-丙酮醯莽草酸-3-磷酸(EPSP)合成酶抑制劑、(b7)原紫質原氧化酶(PPO)抑制劑、(b9)極長鏈脂肪酸(VLCFA)延長酶抑制劑、及(b12) 4‑羥苯基‑丙酮酸二氧合酶(HPPD)抑制劑之額外活性成分。
- 一種除草混合物,其包含(a)如請求項1-7中任一項之化合物,以及(b)至少一種選自由2,4-D、乙草胺(acetochlor)、拉草(alachlor)、草脫淨(atrazine)、溴苯腈(bromoxynil)、本達隆(bentazon)、二環吡草酮(bicyclopyrone)、乙唑草酮(carfentrazone-ethyl)、氯酯磺草胺(cloransulam-methyl)、麥草畏(dicamba)、汰草滅-p (dimethenamid-p)、雙氟磺草胺(florasulam)、噻草胺(flufenacet)、丙炔氟草胺(flumioxazin)、氟啶嘧磺隆甲酯(flupyrsulfuron-methyl)、氟氯比(fluroxypyr-meptyl)、草甘膦(glyphosate)、甲基哈洛昔芬(halauxifen-methyl)、異噁唑草酮(isoxaflutole)、MCPA、硝草酮(mesotrione)、莫多草(metolachlor)、甲磺隆(metsulfuron-methyl)、煙嘧磺隆(nicosulfuron)、磺醯草吡唑(pyrasulfotole)、派羅克殺草碸(pyroxasulfone)、啶磺草胺(pyroxsulam)、玉嘧磺隆(rimsulfuron)、嘧啶肟草醚(saflufenacil)、環磺酮(tembotrione)、噻吩磺隆(thifensulfuron-methyl)、苯吡唑草酮(topramazone)、及苯磺隆(tribenuron)所組成的群組之額外活性成分。
- 一種防治非所欲植物生長之方法,其包含使該植物或其環境與除草有效量的如請求項1-7中任一項之化合物接觸。
- 一種防治非所欲植物在基因改造植物中生長之方法,該等基因改造植物展現草甘膦耐受性、草銨膦耐受性、ALS除草劑耐受性、麥草畏耐受性、咪唑啉酮除草劑耐受性、2,4-D耐受性、HPPD耐受性、及硝草酮耐受性的性狀,該方法包含使該植物或其環境與除草有效量的如請求項1-7中任一項之化合物接觸。
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