CN1281602C - Novel carboxylate herbicides - Google Patents
Novel carboxylate herbicides Download PDFInfo
- Publication number
- CN1281602C CN1281602C CN 03143375 CN03143375A CN1281602C CN 1281602 C CN1281602 C CN 1281602C CN 03143375 CN03143375 CN 03143375 CN 03143375 A CN03143375 A CN 03143375A CN 1281602 C CN1281602 C CN 1281602C
- Authority
- CN
- China
- Prior art keywords
- alkyl
- compound
- conhch
- halo
- thiazolinyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 239000004009 herbicide Substances 0.000 title abstract description 4
- 150000007942 carboxylates Chemical class 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 56
- -1 carboxylate compounds Chemical class 0.000 claims abstract description 39
- 239000000203 mixture Substances 0.000 claims abstract description 30
- 241000196324 Embryophyta Species 0.000 claims abstract description 16
- 238000000034 method Methods 0.000 claims abstract description 15
- 230000002363 herbicidal effect Effects 0.000 claims abstract description 7
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 18
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 15
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 10
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 10
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 10
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 10
- 229910052794 bromium Inorganic materials 0.000 claims description 10
- 229910052801 chlorine Inorganic materials 0.000 claims description 10
- 239000000460 chlorine Substances 0.000 claims description 10
- 229910052731 fluorine Inorganic materials 0.000 claims description 10
- 239000011737 fluorine Substances 0.000 claims description 10
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 9
- 125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims description 5
- 239000004480 active ingredient Substances 0.000 claims description 5
- 230000012010 growth Effects 0.000 claims description 2
- 239000001963 growth medium Substances 0.000 claims description 2
- 229920000742 Cotton Polymers 0.000 abstract description 6
- 244000068988 Glycine max Species 0.000 abstract description 6
- 235000010469 Glycine max Nutrition 0.000 abstract description 6
- 240000007594 Oryza sativa Species 0.000 abstract description 5
- 235000021307 Triticum Nutrition 0.000 abstract description 5
- 240000008042 Zea mays Species 0.000 abstract description 5
- 235000005824 Zea mays ssp. parviglumis Nutrition 0.000 abstract description 5
- 235000002017 Zea mays subsp mays Nutrition 0.000 abstract description 5
- 235000005822 corn Nutrition 0.000 abstract description 5
- 235000007164 Oryza sativa Nutrition 0.000 abstract description 4
- 235000009566 rice Nutrition 0.000 abstract description 4
- 244000105624 Arachis hypogaea Species 0.000 abstract description 3
- 235000020232 peanut Nutrition 0.000 abstract description 3
- 235000013311 vegetables Nutrition 0.000 abstract description 3
- 241000219146 Gossypium Species 0.000 abstract 1
- 244000098338 Triticum aestivum Species 0.000 abstract 1
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 57
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 36
- 125000005843 halogen group Chemical group 0.000 description 36
- 125000003118 aryl group Chemical group 0.000 description 24
- 125000001072 heteroaryl group Chemical group 0.000 description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 20
- 125000004642 (C1-C12) alkoxy group Chemical group 0.000 description 18
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 18
- 238000002360 preparation method Methods 0.000 description 16
- 238000009472 formulation Methods 0.000 description 13
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 12
- 125000004093 cyano group Chemical group *C#N 0.000 description 12
- 125000006711 (C2-C12) alkynyl group Chemical group 0.000 description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 10
- 238000006243 chemical reaction Methods 0.000 description 10
- 239000000470 constituent Substances 0.000 description 10
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 8
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical group O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 7
- 125000000217 alkyl group Chemical group 0.000 description 7
- 239000003795 chemical substances by application Substances 0.000 description 7
- 230000000694 effects Effects 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical compound C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 6
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
- 230000014509 gene expression Effects 0.000 description 6
- 150000003254 radicals Chemical class 0.000 description 6
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 6
- WOJVTGIJKSQDHV-UHFFFAOYSA-N C(CC)(=O)Cl.[O].C1=CC=CC=C1 Chemical compound C(CC)(=O)Cl.[O].C1=CC=CC=C1 WOJVTGIJKSQDHV-UHFFFAOYSA-N 0.000 description 5
- 244000299507 Gossypium hirsutum Species 0.000 description 5
- 239000012141 concentrate Substances 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 239000012044 organic layer Substances 0.000 description 5
- 238000000746 purification Methods 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 238000010898 silica gel chromatography Methods 0.000 description 5
- 238000005406 washing Methods 0.000 description 5
- 125000003601 C2-C6 alkynyl group Chemical group 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 4
- 241000209140 Triticum Species 0.000 description 4
- 239000002585 base Substances 0.000 description 4
- 238000001816 cooling Methods 0.000 description 4
- 150000002240 furans Chemical class 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
- 240000006995 Abutilon theophrasti Species 0.000 description 3
- 244000201986 Cassia tora Species 0.000 description 3
- 235000014552 Cassia tora Nutrition 0.000 description 3
- 244000058871 Echinochloa crus-galli Species 0.000 description 3
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 3
- KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 3
- CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 3
- RWRDLPDLKQPQOW-UHFFFAOYSA-N Pyrrolidine Chemical compound C1CCNC1 RWRDLPDLKQPQOW-UHFFFAOYSA-N 0.000 description 3
- 240000003307 Zinnia violacea Species 0.000 description 3
- 239000013543 active substance Substances 0.000 description 3
- 125000003545 alkoxy group Chemical group 0.000 description 3
- 125000003710 aryl alkyl group Chemical group 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 239000007788 liquid Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000002245 particle Substances 0.000 description 3
- 150000003217 pyrazoles Chemical class 0.000 description 3
- 239000011734 sodium Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- 239000000375 suspending agent Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- 229930192474 thiophene Natural products 0.000 description 3
- 239000004563 wettable powder Substances 0.000 description 3
- 238000005160 1H NMR spectroscopy Methods 0.000 description 2
- 235000017060 Arachis glabrata Nutrition 0.000 description 2
- 235000010777 Arachis hypogaea Nutrition 0.000 description 2
- 235000018262 Arachis monticola Nutrition 0.000 description 2
- 244000025254 Cannabis sativa Species 0.000 description 2
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- ZCQWOFVYLHDMMC-UHFFFAOYSA-N Oxazole Chemical compound C1=COC=N1 ZCQWOFVYLHDMMC-UHFFFAOYSA-N 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 125000004414 alkyl thio group Chemical group 0.000 description 2
- 125000000304 alkynyl group Chemical group 0.000 description 2
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 description 2
- 239000012752 auxiliary agent Substances 0.000 description 2
- CUFNKYGDVFVPHO-UHFFFAOYSA-N azulene Chemical compound C1=CC=CC2=CC=CC2=C1 CUFNKYGDVFVPHO-UHFFFAOYSA-N 0.000 description 2
- IOJUPLGTWVMSFF-UHFFFAOYSA-N benzothiazole Chemical compound C1=CC=C2SC=NC2=C1 IOJUPLGTWVMSFF-UHFFFAOYSA-N 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- 230000018044 dehydration Effects 0.000 description 2
- 238000006297 dehydration reaction Methods 0.000 description 2
- JGUQDUKBUKFFRO-CIIODKQPSA-N dimethylglyoxime Chemical compound O/N=C(/C)\C(\C)=N\O JGUQDUKBUKFFRO-CIIODKQPSA-N 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 150000002430 hydrocarbons Chemical group 0.000 description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 230000008018 melting Effects 0.000 description 2
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- 125000000547 substituted alkyl group Chemical group 0.000 description 2
- 125000004646 sulfenyl group Chemical group S(*)* 0.000 description 2
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 description 2
- 150000003852 triazoles Chemical class 0.000 description 2
- UGUHFDPGDQDVGX-UHFFFAOYSA-N 1,2,3-thiadiazole Chemical class C1=CSN=N1 UGUHFDPGDQDVGX-UHFFFAOYSA-N 0.000 description 1
- 150000000177 1,2,3-triazoles Chemical class 0.000 description 1
- FYADHXFMURLYQI-UHFFFAOYSA-N 1,2,4-triazine Chemical compound C1=CN=NC=N1 FYADHXFMURLYQI-UHFFFAOYSA-N 0.000 description 1
- CSNIZNHTOVFARY-UHFFFAOYSA-N 1,2-benzothiazole Chemical compound C1=CC=C2C=NSC2=C1 CSNIZNHTOVFARY-UHFFFAOYSA-N 0.000 description 1
- 150000004869 1,3,4-thiadiazoles Chemical class 0.000 description 1
- JIHQDMXYYFUGFV-UHFFFAOYSA-N 1,3,5-triazine Chemical compound C1=NC=NC=N1 JIHQDMXYYFUGFV-UHFFFAOYSA-N 0.000 description 1
- 150000000183 1,3-benzoxazoles Chemical class 0.000 description 1
- IANQTJSKSUMEQM-UHFFFAOYSA-N 1-benzofuran Chemical compound C1=CC=C2OC=CC2=C1 IANQTJSKSUMEQM-UHFFFAOYSA-N 0.000 description 1
- FCEHBMOGCRZNNI-UHFFFAOYSA-N 1-benzothiophene Chemical compound C1=CC=C2SC=CC2=C1 FCEHBMOGCRZNNI-UHFFFAOYSA-N 0.000 description 1
- HECLRDQVFMWTQS-RGOKHQFPSA-N 1755-01-7 Chemical compound C1[C@H]2[C@@H]3CC=C[C@@H]3[C@@H]1C=C2 HECLRDQVFMWTQS-RGOKHQFPSA-N 0.000 description 1
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 1
- RAXXELZNTBOGNW-UHFFFAOYSA-N 1H-imidazole Chemical class C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 1
- SNTWKPAKVQFCCF-UHFFFAOYSA-N 2,3-dihydro-1h-triazole Chemical compound N1NC=CN1 SNTWKPAKVQFCCF-UHFFFAOYSA-N 0.000 description 1
- 125000002941 2-furyl group Chemical group O1C([*])=C([H])C([H])=C1[H] 0.000 description 1
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- 229920002134 Carboxymethyl cellulose Polymers 0.000 description 1
- LVZWSLJZHVFIQJ-UHFFFAOYSA-N Cyclopropane Chemical compound C1CC1 LVZWSLJZHVFIQJ-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Chemical group CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 241000209510 Liliopsida Species 0.000 description 1
- 235000011999 Panicum crusgalli Nutrition 0.000 description 1
- PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 1
- 239000005614 Quizalofop-P-ethyl Substances 0.000 description 1
- 240000003461 Setaria viridis Species 0.000 description 1
- 235000002248 Setaria viridis Nutrition 0.000 description 1
- 229910004298 SiO 2 Inorganic materials 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 1
- CWRYPZZKDGJXCA-UHFFFAOYSA-N acenaphthene Chemical compound C1=CC(CC2)=C3C2=CC=CC3=C1 CWRYPZZKDGJXCA-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000003905 agrochemical Substances 0.000 description 1
- 150000001335 aliphatic alkanes Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 125000004644 alkyl sulfinyl group Chemical group 0.000 description 1
- 125000004688 alkyl sulfonyl alkyl group Chemical group 0.000 description 1
- 125000004390 alkyl sulfonyl group Chemical group 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
- 239000012964 benzotriazole Substances 0.000 description 1
- 229940073608 benzyl chloride Drugs 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000004071 biological effect Effects 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002775 capsule Substances 0.000 description 1
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- 150000001733 carboxylic acid esters Chemical class 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- 125000000392 cycloalkenyl group Chemical group 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- DMEGYFMYUHOHGS-UHFFFAOYSA-N cycloheptane Chemical compound C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 1
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 description 1
- WJTCGQSWYFHTAC-UHFFFAOYSA-N cyclooctane Chemical compound C1CCCCCCC1 WJTCGQSWYFHTAC-UHFFFAOYSA-N 0.000 description 1
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- 150000001941 cyclopentenes Chemical class 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- FPAFDBFIGPHWGO-UHFFFAOYSA-N dioxosilane;oxomagnesium;hydrate Chemical compound O.[Mg]=O.[Mg]=O.[Mg]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O FPAFDBFIGPHWGO-UHFFFAOYSA-N 0.000 description 1
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- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
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- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
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- 125000003136 n-heptyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000001069 nematicidal effect Effects 0.000 description 1
- 239000005645 nematicide Substances 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000000361 pesticidal effect Effects 0.000 description 1
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- 230000000704 physical effect Effects 0.000 description 1
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- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
- 125000004076 pyridyl group Chemical group 0.000 description 1
- 150000003233 pyrroles Chemical class 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
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 230000007226 seed germination Effects 0.000 description 1
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- 238000005507 spraying Methods 0.000 description 1
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- 125000003831 tetrazolyl group Chemical group 0.000 description 1
- 150000004867 thiadiazoles Chemical class 0.000 description 1
- 125000002769 thiazolinyl group Chemical group 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
- 238000009333 weeding Methods 0.000 description 1
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Pyridine Compounds (AREA)
- Plural Heterocyclic Compounds (AREA)
Abstract
The present invention relates to novel carboxylate compounds, a composition thereof and a use method for preventing weed by the compounds. A herbicide containing the compounds can be used for preventing weed among fields with wheat, corn, soy beans, cotton, peanuts, vegetables, paddy rice, etc. The novel carboxylate compounds can be represented by a general formula I.
Description
Technical field
The invention belongs to the agricultural herbicide field.What relate to is a class novel carboxylic acid ester compound and composition, their purposes and using method.
Background technology
Weeds are to crop, especially for agricultural-food such as grain that can satisfy human primary demand and fibers, as cotton, and paddy rice, corn, wheat, soybean etc. are caused very big infringement.Kill or avoid when suppressing weed growth or the infringement that reduces crop is a kind of effective way of improving agriculture production.Therefore need continually develop more effective new herbicides.Carboxylic acid ester compound such as quizalofopPethyl etc. are known weedicides, but novel carboxylic acid ester compound of the present invention is not seen reported in literature.
Summary of the invention
In order to satisfy the requirement on the agricultural, the invention provides the using method and the application of weedicide on agricultural that contains these compounds of a kind of novel carboxylic acid ester compound and management of weeds thereof.As weedicide, can effectively control Tanakas' such as wheat, corn, soybean, cotton, peanut, vegetables and paddy rice weeds, and to these crop safeties.
The novel carboxylic acid ester compound that the present invention proposes, shown in general formula I:
In the formula:
X-X
1-Z is selected from one of following group:
When-X-is selected from CH
2CH
2OCH
2CH
2, CH
2CH
2SCH
2CH
2, CH
2CH
2N (CH
3) CH
2CH
2,
CH
2CH
2, CH
2CH
2SO
2CH
2CH
2Or CH
2CH
2SOCH
2CH
2The time, X
1Be selected from O, Z is selected from Q;
Wherein:
R
1, R
2Can be identical or different, be selected from H respectively, halogen, CN, CO
2R
3, CONR
2R
3, CHR
2CO
2R
3, CHR
2CONR
2R
3, C
1-C
12Alkyl, ring C
3-C
8Alkyl, C
2-C
12Thiazolinyl, ring C
3-C
8Thiazolinyl, C
2-C
12Alkynyl, halo C
1-C
12Alkyl, halo C
2-C
12Thiazolinyl, halo C
2-C
12Alkynyl, C
1-C
12Alkoxyl group, C
1-C
12Alkylthio, C
1-C
12Alkyl sulphonyl C
1-C
12Alkyl, C
1-C
12Alkyl sulphinyl C
1-C
12Alkyl, C
1-C
12Alkyl sulfonyl basic ring C
3-C
8Alkyl, C
1-C
12Alkyl sulfenyl ring C
3-C
8Alkyl, cyano group C
1-C
12Alkoxyl group, cyano group C
1-C
12Alkyl, cyano group ring C
3-C
8Alkyl, halo C
1-C
12Alkoxyl group, halo C
1-C
12Alkylthio, halo ring C
3-C
8Alkane, aryl, heteroaryl, aryl C
1-C
12Alkyl or heteroaryl C
2-C
12Alkyl, all these groups can be undertaken 1-3 time by following radicals and replace: bromine, chlorine, fluorine, C
1-C
12Alkyl, ring C
3-C
8Alkyl, C
2-C
12Thiazolinyl, ring C
3-C
8Thiazolinyl, C
2-C
12Alkynyl, halo C
1-C
12Alkyl, halo C
2-C
12Thiazolinyl, halo C
2-C
12Alkynyl, C
1-C
12Alkoxyl group, C
1-C
12Alkylthio, C
1-C
12Alkyl sulphonyl, C
1-C
12Alkyl sulphinyl, phenyl, benzene is for C
1-C
12Alkyl, benzene is for C
2-C
12Thiazolinyl, benzene is for C
2-C
12Alkynyl, cyano group or halo C
1-C
12Alkoxyl group, all these groups can also further be replaced;
R
3And R
4Identical or different, be selected from H respectively, CO
2R
3, CONR
2R
3, CHR
2CO
2R
3, CHR
2CONR
2R
3, C
1-C
12Alkyl, ring C
3-C
8Alkyl, C
2-C
12Thiazolinyl, ring C
3-C
8Thiazolinyl, C
2-C
12Alkynyl, halo C
1-C
12Alkyl, halo C
2-C
12Thiazolinyl, halo C
2-C
12Alkynyl, C
1-C
12Alkoxyl group, C
1-C
12Alkylthio, C
1-C
12Alkyl sulphonyl C
1-C
12Alkyl, C
1-C
12Alkyl sulphinyl C
1-C
12Alkyl, C
1-C
12Alkyl sulfonyl basic ring C
3-C
8Alkyl, C
1-C
12Alkyl sulfenyl ring C
3-C
8Alkyl, cyano group C
1-C
12Alkoxyl group, cyano group C
1-C
12Alkyl, cyano group ring C
3-C
8Alkyl, halo C
1-C
12Alkoxyl group, halo C
1-C
12Alkylthio, halo ring C
3-C
8Alkane, aryl, heteroaryl, aryl C
1-C
12Alkyl or heteroaryl C
2-C
12) base, all these groups can be undertaken 1-3 time by following radicals and replace: bromine, chlorine, fluorine, C
1-C
12Alkyl, ring C
3-C
8Alkyl, C
2-C
12Thiazolinyl, ring C
3-C
8Thiazolinyl, C
2-C
12Alkynyl, halo C
1-C
12Alkyl, halo C
2-C
12Thiazolinyl, halo C
2-C
12Alkynyl, C
1-C
12Alkoxyl group, C
1-C
12Alkylthio, C
1-C
12Alkyl sulphonyl, C
1-C
12Alkyl sulphinyl, phenyl, substituted-phenyl, benzene are for C
1-C
12Alkyl, benzene is for C
2-C
12Thiazolinyl, benzene is for C
2-C
12Alkynyl, cyano group or halo C
1-C
12Alkoxyl group, all these groups can also further be replaced;
NR
3R
4, NR
2R
3Can form five circle or six annulus respectively; Perhaps also can be
Wherein: R
5Be R
1, R
6Be R
2R
5And R
6Can also form five circle or six annulus;
Q is selected from Q1, Q2, and Q3, Q4, Q5, Q6, Q7, Q8, Q9, Q10, Q11, R represents optically active isomer R configuration in Q12 or the Q13:(structure)
" aryl " among the present invention refers to monocycle or polynuclear compound, as benzene, and naphthalene, indenes, anthracene, dicyclopentadiene and, fluorenes, acenaphthene, phenanthrene and azulene to dihydrobenzene.
" heteroaryl " refers to monocycle or polycyclic furans, thiophene, pyrroles, isoxzzole, oxazole, different thiadiazoles, thiazole, pyrazoles, imidazoles, 1,2,3-triazoles, 1,1, the 4-triazole, tetrazolium, 1,2,3-thiadiazoles, 1,1, the 4-thiadiazoles, 1,3,4-thiadiazoles, 1,2, the 3-thiadiazoles, 1,1,4-thiadiazoles, 1,3, the 4-thiadiazoles, pyridine, pyridazine, pyrimidine, pyrazine, 1,3,5-triazine, 1,1,4-triazine, 1,1,4,5-tetrazine, cumarone, thionaphthene, indoles, the benzisoxa oxazole, benzoxazoles, benzisothiazole, benzothiazole, benzopyrazoles, benzoglyoxaline, benzotriazole, 1,2-methylenedioxyphenyl, ethylene dioxy base benzene, quinoline and isoquinoline 99.9.
" alkyl " comprises the alkyl group of side chain and straight chain.Typical alkyl has methyl, ethyl, n-propyl, sec.-propyl, normal-butyl, sec-butyl, isobutyl-, the tertiary butyl, n-pentyl, isopentyl, n-hexyl, n-heptyl, iso-octyl, nonyl, decyl, undecyl, dodecyl and other.
" cycloalkyl " refers to the compound of fatty family ring structure, as cyclopropane, tetramethylene, pentamethylene, hexanaphthene, suberane, cyclooctane and other.
" haloalkane " refers to one or more halogen group substituted alkyls.
" halogen " refers to fluorine, chlorine, bromine or iodine.
" alkyl sulfonyl alkyl " refers to alkyl sulphonyl (alkyl-SO
2) substituted alkyl, as the sulfonyloxy methyl methyl.
" alkyl sulfenyl alkyl " refers to alkyl sulphinyl, and (substituted alkyl of alkyl-SO) is as methyl sulfinyl methyl.
" thiazolinyl " refers to undersaturated hydrocarbon group, contains one or two pair key on the straight or branched.
" cycloalkenyl group " refers to the aliphatics ring and contains one or two pair key, as cyclopentenes, tetrahydrobenzene, and 1,4-tetrahydrobenzene and other.
" haloalkene " refers to one or more halogen substituted alkenyls." alkynyl " refers to undersaturated hydrocarbon group, contains one or two triple bond in the straight or branched.
" aralkyl " refers in alkyl group side chain or the straight chain and is called aralkyl by the formed part that contains aryl of aryl replacement.
" heteroaralkyl " refers in alkyl group side chain or the straight chain and is called aralkyl by the formed part that contains aryl of heteroaryl replacement.
The alkyl that " alkoxyl group " refers in side chain or the straight chain is connected with Sauerstoffatom, and typical alkoxyl group has methoxyl group, oxyethyl group, positive propoxy, isopropoxy, tert.-butoxy and other.
" halogenated alkoxy " refers to one or more halogen atom substituted alkoxies.
The alkyl that " alkylthio " refers in side chain or the straight chain is connected with sulphur atom.
" halogenated alkylthio " refers to one or more halogen atom substituted alkane sulphur bases.
Further preferred compound is among the general formula compound I among the present invention: X-X
1-Z is selected from one of following group:
When-X-is selected from CH
2CH
2OCH
2CH
2, CH
2CH
2SCH
2CH
2, CH
2CH
2N (CH
3) CH
2CH
2,
CH
2CH
2, CH
2CH
2SO
2CH
2CH
2Or CH
2CH
2SOCH
2CH
2The time, X
1Be selected from O, Z is selected from Q.
Wherein:
R
1, R
2Can be identical or different, be selected from H respectively, bromine, chlorine, fluorine, CN, CO
2R
3, CONR
2R
3, CHR
2CO
2R
3, CHR
2CONR
2R
3, C
1-C
6Alkyl, ring C
5-C
6Alkyl, C
2-C
6Thiazolinyl, ring C
3-C
8Thiazolinyl, C
2-C
6Alkynyl, halo C
1-C
6Alkyl, halo C
2-C
6Thiazolinyl, halo C
2-C
6Alkynyl, C
1-C
6Alkoxyl group, C
1-C
6Alkylthio, aryl, heteroaryl, aryl C
1-C
12Alkyl or heteroaryl C
2-C
12Alkyl, wherein aryl or heteroaryl are furans, naphthalene, phenyl, pyrazoles, pyridine, pyrimidine, thiophene or triazole; Aryl or heteroaryl can be undertaken 1-3 time by following radicals and replace: bromine, chlorine, fluorine, C
1-C
12Alkyl, ring C
3-C
8Alkyl, C
2-C
12Thiazolinyl, ring C
3-C
8Thiazolinyl, C
2-C
12Alkynyl, halo C
1-C
12Alkyl, halo C
2-C
12Thiazolinyl, halo C
2-C
12Alkynyl, C
1-C
12Alkoxyl group, C
1-C
12Alkylthio, C
1-C
12Alkyl sulphonyl, C
1-C
12Alkyl sulphinyl, phenyl, benzene is for C
1-C
12Alkyl, benzene is for C
2-C
12Thiazolinyl, benzene is for C
2-C
12Alkynyl, cyano group or halo C
1-C
12Alkoxyl group, all these groups can also further be replaced;
R
3And R
4Can be identical or different, be selected from H respectively, CO
2R
3, CONR
2R
3, CHR
2CO
2R
3, CHR
2CONR
2R
3, C
1-C
6Alkyl, ring C
5-C
6Alkyl, C
2-C
6Thiazolinyl, ring C
3-C
8Thiazolinyl, C
2-C
6Alkynyl, halo C
1-C
6Alkyl, halo C
2-C
6Thiazolinyl, halo C
2-C
6Alkynyl, C
1-C
6Alkoxyl group, C
1-C
6Alkylthio, aryl, heteroaryl, aryl C
1-C
12Alkyl or heteroaryl C
2-C
12Alkyl, wherein aryl or heteroaryl are furans, naphthalene, phenyl, pyrazoles, pyridine, pyrimidine, thiophene or triazole, aryl or heteroaryl can be undertaken 1-3 time by following radicals and replace: bromine, chlorine, fluorine, C
1-C
12Alkyl, ring C
3-C
8Alkyl, C
2-C
12Thiazolinyl, ring C
3-C
8Thiazolinyl, C
2-C
12Alkynyl, halo C
1-C
12Alkyl, halo C
2-C
12Thiazolinyl, halo C
2-C
12Alkynyl, C
1-C
12Alkoxyl group, C
1-C
12Alkylthio, C
1-C
12Alkyl sulphonyl, C
1-C
12Alkyl sulphinyl, phenyl, benzene is for C
1-C
12Alkyl, benzene is for C
2-C
12Thiazolinyl, benzene is for C
2-C
12Alkynyl, cyano group or halo C
1-C
12Alkoxyl group, all these groups can also further be replaced.
NR
3R
4, NR
2R
3Can form five circle or six annulus respectively; Perhaps also can be
Wherein: R
5Be R
1, R
6Be R
2R
5And R
6Can also form five circle or six annulus;
Q is selected from Q1, Q2, Q3, Q4, Q5, Q6, Q7, Q8, Q9, Q10, Q11, Q12 or Q13.
Further preferred compound is among the general formula compound I among the present invention, X-X
1-Z is selected from one of following group:
When-X-is selected from CH
2CH
2OCH
2CH
2, CH
2CH
2SCH
2CH
2, CH
2CH
2N (CH
3) CH
2CH
2,
CH
2CH
2, CH
2CH
2SO
2CH
2CH
2Or CH
2CH
2SOCH
2CH
2The time, X
1Be selected from O, Z is selected from Q;
Wherein:
R
1, R
2Can be identical or different, be selected from H respectively, bromine, chlorine, fluorine, CN, CO
2R
3, CONR
2R
3, CHR
2CO
2R
3, CHR
2CONR
2R
3, C
1-C
6Alkyl, ring C
5-C
6Alkyl, C
2-C
6Thiazolinyl, ring C
3-C
8Thiazolinyl, C
2-C
6Alkynyl, halo C
1-C
6Alkyl, halo C
2-C
6Thiazolinyl, halo C
2-C
6) alkynyl, C
1-C
6Alkoxyl group, C
1-C
6Alkylthio, aryl, heteroaryl, aryl C
1-C
12Alkyl or heteroaryl C
2-C
12Alkyl, wherein aryl or heteroaryl are selected from furans, phenyl or pyridine; Aryl or heteroaryl can be undertaken 1-3 time by following radicals and replace: bromine, chlorine, fluorine, C
1-C
12Alkyl, ring C
3-C
8Alkyl, halo C
1-C
12Alkyl, C
1-C
12Alkoxyl group, C
1-C
12Alkylthio, C
1-C
12Alkyl sulphonyl, phenyl, benzene is for C
1-C
12Alkyl, cyano group or halo C
1-C
12Alkoxyl group, all these groups can also further be replaced;
R
3And R
4Identical or different is H, CO
2R
3, CONR
2R
3, CHR
2CO
2R
3, CHR
2CONR
2R
3, C
1-C
6Alkyl, ring C
5-C
6Alkyl, C
2-C
6Thiazolinyl, ring C
3-C
8Thiazolinyl, C
2-C
6Alkynyl, halo C
1-C
6Alkyl, halo C
2-C
6Thiazolinyl, halo C
2-C
6Alkynyl, C
1-C
6Alkoxyl group, C
1-C
6Alkylthio, aryl, heteroaryl, aryl C
1-C
12Alkyl or heteroaryl C
2-C
12Alkyl, wherein aryl or heteroaryl are selected from furans, phenyl or pyridine; Aryl and heteroaryl can be undertaken 1-3 time by following radicals and replace: bromine, chlorine, fluorine, C
1-C
12Alkyl, ring C
3-C
8Alkyl, halo C
1-C
12Alkyl, C
1-C
12Alkoxyl group, C
1-C
12Alkylthio, phenyl, benzene is for C
1-C
12Alkyl, cyano group or halo C
1-C
12Alkoxyl group, all these groups can also further be replaced;
NR
3R
4, NR
2R
3Can form Pyrrolidine, morpholine or hexahydropyridine respectively; Perhaps also can be
Wherein: R
5Be R
1, R
6Be R
2R
5And R
6All right makeup ring pentane or hexanaphthene;
Q is selected from Q1, Q2, Q3, Q4, Q5, Q6, Q7, Q8, Q9, Q10, Q11, Q12 or Q13.
The more preferred compound of the present invention is among the general formula compound I,
X-X
1-Z is selected from:
When-X-is selected from:
The time, X
1Be selected from O, Z is selected from Q1, Q3, Q4 or Q6;
Wherein, R
1, R
2, R
3Can be identical or different, be selected from H, C respectively
1-C
4Alkyl, phenyl, halogenophenyl or
The present invention can be prepared by following method by the represented compound of general formula I:
Work as X-X
1When-Z is selected from one of following group:
Method 1:
Among above-mentioned intermediate II and the III, substituting group as previously mentioned, intermediate II and III are prepared by currently known methods.With chloroform, methylene dichloride, tetracol phenixin, normal hexane, benzene, toluene, tetrahydrofuran (THF), dioxane, acetone or butanone are solvent, above-mentioned intermediate II and III under alkaline condition as Et
3N, pyridine, NaOH, KOH, Na
2CO
3, K
2CO
3Or NaHCO
3Existence down or under the neutrallty condition, control reaction temperature can generate the represented compound of general formula I in 30 minutes-8 hours at-40 ℃～reaction solution reflux temperature.Alkali-free exists down also can make object.
Method 2:
Among above-mentioned intermediate II and the IV, substituting group as previously mentioned, intermediate II and IV are prepared by currently known methods.With chloroform, methylene dichloride, tetracol phenixin, normal hexane, benzene, toluene, tetrahydrofuran (THF), dioxane, acetone or butanone are solvent, above-mentioned intermediate II and IV under alkaline condition as Et
3N, pyridine, NaOH, KOH, Na
2CO
3, K
2CO
3Or NaHCO
3Exist down, control reaction temperature can generate the represented compound of general formula I in 30 minutes-8 hours at-40 ℃～reaction solution reflux temperature.
When-X-is selected from CH
2CH
2OCH
2CH
2, CH
2CH
2SCH
2CH
2, CH
2CH
2N (CH
3) CH
2CH
2,
CH
2CH
2, CH
2CH
2SO
2CH
2CH
2Or CH
2CH
2SOCH
2CH
2, X
1Be O, when Z equals Q,
Method 3:
Intermediate II is at solvent such as methylene dichloride, tetracol phenixin, normal hexane, benzene, toluene, tetrahydrofuran (THF), dioxane, in ethyl acetate, acetone or the butanone with intermediate V reaction, at alkali such as triethylamine, pyridine, NaOH, KOH, Na
2CO
3, K
2CO
3Or NaHCO
3Exist down, control reaction temperature is at-40 ℃～reaction solution reflux temperature, react 30 minutes to 8 hours must the represented compound of general formula I.Alkali-free exists down also can make object.
The part of compounds of general formula I sees Table 1-2.In the table, " Pri " represents sec.-propyl, and " Ph " represents phenyl, " Ph-4-Cl " expression 4-chloro-phenyl-, " CH
2Ph " expression benzyl, " CH
2Ph-4-Cl " expression 4-benzyl chloride base, " PY " represents pyridyl, and 2-FUR represents the 2-furyl, and " MORPHOLINE " represents morpholinyl, " 4-C
6H
4-C
6H
4-4 " expression
Table 1
| No | Q | X-X 1-Z |
| 1 | Q1 | CH 2Ph |
| 2 | Q1 | CH 2CH 2Ph |
| 3 | Q1 | CH 2CH 2Ph-4-Cl |
| 4 | Q1 | CH 2CH 2OPh-4-Cl |
| 5 | Q1 | CH 2CH 2SPh-4-Cl |
| 6 | Q1 | CH 2CH 2SCH 2Ph-4-Cl |
| 7 | Q1 | CH 2COPh-4-Cl |
| 8 | Q1 | CH 2COPh-1，4-Cl 2 |
| 9 | Q1 | CH 2C(Ph-4-Cl)＝NOCH3 |
| 10 | Q1 | CH 2C(Ph-1，4-Cl 2)＝NOCH3 |
| 11 | Q1 | CH 2C(Ph-4-Cl)＝NNHCH3 |
| 12 | Q1 | CH 2C(Ph-1，4-Cl 2)＝NNHPh |
| 13 | Q1 | N＝C(CH 3)Ph-4-Cl |
| 14 | Q1 | N＝C(CH 2Br)Ph-4-Cl |
| 15 | Q1 | N＝C(CH 2OCH 3)Ph-4-Cl |
| 16 | Q1 | N＝C(CH 2ON＝C(CH 3) 2)Ph-4-Cl |
| 17 | Q1 | N＝C(CO 2CH 3)Ph-4-Cl |
| 87 | Q3 | CH 2CON(Pr i)Ph-4-Cl |
| 88 | Q3 | CH 2CON(CH 3) 2 |
| 89 | Q3 | CH 2CONHPh |
| 90 | Q3 | CH 2CONH-2-PY |
| 91 | Q3 | CH 2CONHCH 2CN |
| 92 | Q3 | CH 2CONHCH 2CH 2CN |
| 93 | Q3 | CH 2CONHCH 2CO 2C 2H 5 |
| 94 | Q3 | CH 2CONHCH(CH 3)CN |
| 95 | Q3 | CH 2CONHCH(CH 3)(Pr i)CN |
| 96 | Q3 | C(CH 3)＝CHCOCH 3 |
| 97 | Q3 | C(CH 3)＝CHCO 2C 2H 5 |
| 98 | Q4 | CH 2Ph |
| 99 | Q4 | CH 2CH 2Ph |
| 100 | Q4 | CH 2CH 2Ph-4-Cl |
| 101 | Q4 | CH 2CH 2OPh-4-Cl |
| 102 | Q4 | CH 2CH 2SPh-4-Cl |
| 103 | Q4 | CH 2COPh-4-Cl |
| 104 | Q4 | CH 2C(Ph-1，4-Cl 2)＝NOCH3 |
| 105 | Q4 | CH 2C(Ph-4-Cl)＝NNHCH3 |
| 106 | Q4 | CH 2C(Ph-1，4-Cl 2)＝NNHPh |
| 107 | Q4 | N＝C(CH 3)Ph-4-Cl |
| 108 | Q4 | N＝C(CH 2Br)Ph-4-Cl |
| 109 | Q4 | N＝C(CH 2OCH 3)Ph-4-Cl |
| 110 | Q4 | N＝C(CH 2ON＝C(CH 3) 2)Ph-4-Cl |
| 111 | Q4 | N＝C(CO 2CH 3)Ph-4-Cl |
| 112 | Q4 | N＝C(CO 2CH 3)CN |
| 113 | Q4 | N＝C(CO 2C 2H 5) 2 |
| 114 | Q4 | N＝C(CH 3)COCH 3 |
| 115 | Q4 | N＝C(CH 3)C(CH 3)＝NOCH 3 |
| 116 | Q4 | N＝C(CH 3)C(CH 3)＝NOCH 2Ph |
| 117 | Q4 | N＝C(CH 3)C(CH 3)＝NOCH 2-3-PY-5-Cl |
| 118 | Q4 | CH 2CON(Pr i)Ph-4-Cl |
| 119 | Q4 | CH 2CON(Pr i)Ph-4-F |
| 120 | Q4 | CH 2CONHPh |
| 121 | Q4 | CH 2CONH-2-PY |
| 122 | Q4 | CH 2CONHCH 2CN |
| 123 | Q4 | CH 2CONHCH 2CH 2CN |
| 124 | Q4 | CH 2CONHCH 2CO 2C 2H 5 |
| 125 | Q4 | CH 2CONHCH(CH 3)CN |
| 126 | Q4 | CH 2CONHCH(CH 3)(Pr i)CN |
| 127 | Q4 | C(CH 3)＝CHCOCH 3 |
| 128 | Q4 | C(CH 3)＝CHCO 2C 2H 5 |
| 129 | Q5 | CH 2Ph |
| 130 | Q5 | CH 2CH 2Ph |
| 131 | Q5 | CH 2CH 2Ph-4-Cl |
| 132 | Q5 | CH 2CH 2OPh-4-Cl |
| 133 | Q5 | CH 2CH 2SPh-4-Cl |
| 134 | Q5 | CH 2COPh-4-Cl |
| 135 | Q5 | CH 2C(Ph-1，4-Cl 2)＝NOCH3 |
| 136 | Q5 | CH 2C(Ph-4-Cl)＝NNHCH3 |
| 137 | Q5 | CH 2C(Ph-1，4-Cl 2)＝NNHPh |
| 138 | Q5 | N＝C(CH 3)Ph-4-Cl |
| 139 | Q5 | N＝C(CH 2Br)Ph-4-Cl |
| 140 | Q5 | N＝C(CH 2OCH 3)Ph-4-Cl |
| 141 | Q5 | N＝C(CH 2ON＝C(CH 3) 2)Ph-4-Cl |
| 142 | Q5 | N＝C(CO 2CH 3)Ph-4-Cl |
| 143 | Q5 | N＝C(CO 2CH 3)CN |
| 144 | Q5 | N＝C(CO 2C 2H 5) 2 |
| 145 | Q5 | N＝C(CH 3)COCH 3 |
| 146 | Q5 | N＝C(CH 3)C(CH 3)＝NOCH 3 |
| 147 | Q5 | N＝C(CH 3)C(CH 3)＝NOCH 2Ph |
| 148 | Q5 | N＝C(CH 3)C(CH 3)＝NOCH 2-3-PY-5-Cl |
| 149 | Q5 | CH 2CON(Pr i)Ph-4-Cl |
| 150 | Q5 | CH 2CON(Pr i)CH 2Ph-4-F |
| 151 | Q5 | CH 2CONHPh |
| 152 | Q5 | CH 2CONH-2-PY |
| 153 | Q5 | CH 2CONHCH 2CN |
| 154 | Q5 | CH 2CONHCH 2CH 2CN |
| 155 | Q5 | CH 2CONHCH 2CO 2C 2H 5 |
| 156 | Q5 | CH 2CONHCH(CH 3)CN |
| 157 | Q5 | CH 2CONHCH(CH 3)(Pri)CN |
| 158 | Q5 | C(CH 3)＝CHCOCH 3 |
| 159 | Q5 | C(CH 3)＝CHCO 2C 2H 5 |
| 160 | Q6 | CH 2Ph |
| 161 | Q6 | CH 2CH 2Ph |
| 162 | Q6 | CH 2CH 2Ph-4-Cl |
| 163 | Q6 | CH 2CH 2OPh-4-Cl |
| 164 | Q6 | CH 2CH 2SPh-4-Cl |
| 165 | Q6 | CH 2COPh-4-Cl |
| 166 | Q6 | CH 2C(Ph-1，4-Cl 2)＝NOCH3 |
| 167 | Q6 | CH 2C(Ph-4-Cl)＝NNHCH3 |
| 168 | Q6 | CH 2C(Ph-1，4-Cl 2)＝NNHPh |
| 169 | Q6 | N＝C(CH 3)Ph-4-Cl |
| 170 | Q6 | N＝C(CH 2Br)Ph-4-Cl |
| 171 | Q6 | N＝C(CH 2OCH 3)Ph-4-Cl |
| 172 | Q6 | N＝C(CH 2ON＝C(CH 3) 2)Ph-4-Cl |
| 173 | Q6 | N＝C(CO 2CH 3)Ph-4-Cl |
| 174 | Q6 | N＝C(CO 2CH 3)CN |
| 175 | Q6 | N＝C(CO 2C 2H 5) 2 |
| 176 | Q6 | N＝C(CH 3)COCH 3 |
| 177 | Q6 | N＝C(CH 3)C(CH 3)＝NOCH 3 |
| 178 | Q6 | N＝C(CH 3)C(CH 3)＝NOCH 2Ph |
| 179 | Q6 | N＝C(CH 3)C(CH 3)＝NOCH 2-3-PY-5-Cl |
| 180 | Q6 | CH 2CON(Pri)Ph-4-Cl |
| 181 | Q6 | CH 2CON(Pr i)Ph-4-F |
| 182 | Q6 | CH 2CONHPh |
| 183 | Q6 | CH 2CONH-2-PY |
| 184 | Q6 | CH 2CONHCH 2CN |
| 185 | Q6 | CH 2CONHCH 2CH 2CN |
| 186 | Q6 | CH 2CONHCH 2CO 2C 2H 5 |
| 187 | Q6 | CH 2CONHCH(CH 3)CN |
| 188 | Q6 | CH 2CONHCH(CH 3)(Pri)CN |
| 189 | Q6 | C(CH 3)＝CHCOCH 3 |
| 190 | Q6 | C(CH 3)＝CHCO 2C 2H 5 |
| 191 | Q7 | CH 2Ph |
| 192 | Q7 | CH 2CH 2Ph |
| 193 | Q7 | CH 2CH 2Ph-4-Cl |
| 194 | Q7 | CH 2CH 2OPh-4-Cl |
| 195 | Q7 | CH 2CH 2SPh-4-Cl |
| 196 | Q7 | CH 2COPh-4-Cl |
| 197 | Q7 | CH 2C(Ph-1，4-Cl 2)＝NOCH3 |
| 198 | Q7 | CH 2C(Ph-4-Cl)＝NNHCH3 |
| 199 | Q7 | CH 2C(Ph-1，4-Cl 2)＝NNHPh |
| 200 | Q7 | N＝C(CH 3)Ph-4-Cl |
| 201 | Q7 | N＝C(CH 2Br)Ph-4-Cl |
| 202 | Q7 | N＝C(CH 2OCH 3)Ph-4-Cl |
| 203 | Q7 | N＝C(CH 2ON＝C(CH 3) 2)Ph-4-Cl |
| 204 | Q7 | N＝C(CO 2CH 3)Ph-4-Cl |
| 205 | Q7 | N＝C(CO 2CH 3)CN |
| 206 | Q7 | N＝C(CO 2C 2H 5) 2 |
| 207 | Q7 | N＝C(CH 3)COCH 3 |
| 208 | Q7 | N＝C(CH 3)C(CH 3)＝NOCH 3 |
| 209 | Q7 | N＝C(CH 3)C(CH 3)＝NOCH 2Ph |
| 210 | Q7 | N＝C(CH 3)C(CH 3)＝NOCH 2-3-PY-5-Cl |
| 211 | Q7 | CH 2CON(Pr i)Ph-4-Cl |
| 212 | Q7 | CH 2CON(Pr i)Ph-4-F |
| 213 | Q7 | CH 2CONHPh |
| 214 | Q7 | CH 2CONH-2-PY |
| 215 | Q7 | CH 2CONHCH 2CN |
| 216 | Q7 | CH 2CONHCH 2CH 2CN |
| 217 | Q7 | CH 2CONHCH 2CO 2C 2H 5 |
| 218 | Q7 | CH 2CONHCH(CH 3)CN |
| 219 | Q7 | CH 2CONHCH(CH 3)(Pr i)CN |
| 220 | Q7 | C(CH 3)＝CHCOCH 3 |
| 221 | Q7 | C(CH 3)＝CHCO 2C 2H 5 |
| 222 | Q8 | CH 2Ph |
| 223 | Q8 | CH 2CH 2Ph-4-Cl |
| 224 | Q8 | CH 2CH 2OPh-4-Cl |
| 225 | Q8 | CH 2COPh-4-Cl |
| 226 | Q8 | CH 2C(Ph-1，4-Cl 2)＝NOCH3 |
| 227 | Q8 | CH 2C(Ph-4-Cl)＝NNHCH3 |
| 228 | Q8 | N＝C(CH 3)Ph-4-Cl |
| 229 | Q8 | N＝C(CH 2OCH 3)Ph-4-Cl |
| 230 | Q8 | N＝C(CH 2ON＝C(CH 3) 2)Ph-4-Cl |
| 231 | Q8 | N＝C(CO 2CH 3)Ph-4-Cl |
| 232 | Q8 | N＝C(CO 2CH 3)CN |
| 233 | Q8 | N＝C(CO 2C 2H 5) 2 |
| 234 | Q8 | N＝C(CH 3)COCH 3 |
| 235 | Q8 | N＝C(CH 3)C(CH 3)＝NOCH 2Ph |
| 236 | Q8 | CH 2CON(Pr i)Ph-4-Cl |
| 237 | Q8 | CH 2CONHPh |
| 238 | Q8 | CH 2CONH-2-PY |
| 239 | Q8 | CH 2CONHCH 2CN |
| 240 | Q8 | CH 2CONHCH 2CH 2CN |
| 241 | Q8 | CH 2CONHCH 2CO 2C 2H 5 |
| 242 | Q8 | CH 2CONHCH(CH 3)(Pr i)CN |
| 243 | Q8 | C(CH 3)＝CHCOCH 3 |
| 244 | Q8 | C(CH 3)＝CHCO 2C 2H 5 |
| 245 | Q9 | CH 2Ph |
| 246 | Q9 | CH 2CH 2Ph-4-Cl |
| 247 | Q9 | CH 2CH 2OPh-4-Cl |
| 248 | Q9 | CH 2COPh-4-Cl |
| 249 | Q9 | CH 2C(Ph-1，4-Cl 2)＝NOCH3 |
| 250 | Q9 | CH 2C(Ph-4-Cl)＝NNHCH3 |
| 251 | Q9 | N＝C(CH 3)Ph-4-Cl |
| 252 | Q9 | N＝C(CH 2OCH 3)Ph-4-Cl |
| 253 | Q9 | N＝C(CH 2ON＝C(CH 3) 2)Ph-4-Cl |
| 254 | Q9 | N＝C(CO 2CH 3)Ph-4-Cl |
| 255 | Q9 | N＝C(CO 2CH 3)CN |
| 256 | Q9 | N＝C(CO 2C 2H 5) 2 |
| 257 | Q9 | N＝C(CH 3)COCH 3 |
| 258 | Q9 | N＝C(CH 3)C(CH 3)＝NOCH 2Ph |
| 259 | Q9 | CH 2CON(Pr i)Ph-4-Cl |
| 260 | Q9 | CH 2CONHPh |
| 261 | Q9 | CH 2CONH-2-PY |
| 262 | Q9 | CH 2CONHCH 2CN |
| 263 | Q9 | CH 2CONHCH 2CH 2CN |
| 264 | Q9 | CH 2CONHCH 2CO 2C 2H 5 |
| 265 | Q9 | CH 2CONHCH(CH 3)(Pr i)CN |
| 266 | Q9 | C(CH 3)＝CHCOCH 3 |
| 267 | Q9 | C(CH 3)＝CHCO 2C 2H 5 |
| 268 | Q10 | CH 2Ph |
| 269 | Q10 | CH 2CH 2Ph-4-Cl |
| 270 | Q10 | CH 2CH 2OPh-4-Cl |
| 271 | Q10 | CH 2COPh-4-Cl |
| 272 | Q10 | CH 2C(Ph-1，4-Cl 2)＝NOCH3 |
| 273 | Q10 | CH 2C(Ph-4-Cl)＝NNHCH3 |
| 274 | Q10 | N＝C(CH 3)Ph-4-Cl |
| 275 | Q10 | N＝C(CH 2OCH 3)Ph-4-Cl |
| 276 | Q10 | N＝C(CH 2ON＝C(CH 3) 2)Ph-4-Cl |
| 277 | Q10 | N＝C(CO 2CH 3)Ph-4-Cl |
| 278 | Q10 | N＝C(CO 2CH 3)CN |
| 279 | Q10 | N＝C(CO 2C 2H 5) 2 |
| 280 | Q10 | N＝C(CH 3)COCH 3 |
| 281 | Q10 | N＝C(CH 3)C(CH 3)＝NOCH 2Ph |
| 282 | Q10 | CH 2CON(Pr i)Ph-4-Cl |
| 283 | Q10 | CH 2CONHPh |
| 284 | Q10 | CH 2CONH-2-PY |
| 285 | Q10 | CH 2CONHCH 2CN |
| 286 | Q10 | CH 2CONHCH 2CH 2CN |
| 287 | Q10 | CH 2CONHCH 2CO 2C 2H 5 |
| 288 | Q10 | CH 2CONHCH(CH 3)(Pr i)CN |
| 289 | Q10 | C(CH 3)＝CHCOCH 3 |
| 290 | Q10 | C(CH 3)＝CHCO 2C 2H 5 |
| 291 | Q11 | CH 2Ph |
| 292 | Q11 | CH 2CH 2Ph-4-Cl |
| 293 | Q11 | CH 2CH 2OPh-4-Cl |
| 294 | Q11 | CH 2COPh-4-Cl |
| 295 | Q11 | CH 2C(Ph-1，4-Cl 2)＝NOCH3 |
| 296 | Q11 | CH 2C(Ph-4-Cl)＝NNHCH3 |
| 297 | Q11 | N＝C(CH 3)Ph-4-Cl |
| 298 | Q11 | N＝C(CH 2OCH 3)Ph-4-Cl |
| 299 | Q11 | N＝C(CH 2ON＝C(CH 3) 2)Ph-4-Cl |
| 300 | Q11 | N＝C(CO 2CH 3)Ph-4-Cl |
| 301 | Q11 | N＝C(CO 2CH 3)CN |
| 302 | Q11 | N＝C(CO 2C 2H 5) 2 |
| 303 | Q11 | N＝C(CH 3)COCH 3 |
| 304 | Q11 | N＝C(CH 3)C(CH 3)＝NOCH 2Ph |
| 305 | Q11 | CH 2CON(Pr i)Ph-4-Cl |
| 306 | Q11 | CH 2CONHPh |
| 307 | Q11 | CH 2CONH-2-PY |
| 308 | Q11 | CH 2CONHCH 2CN |
| 309 | Q11 | CH 2CONHCH 2CH 2CN |
| 310 | Q11 | CH 2CONHCH 2CO 2C 2H 5 |
| 311 | Q11 | CH 2CONHCH(CH 3)(Pr i)CN |
| 312 | Q11 | C(CH 3)＝CHCOCH 3 |
| 313 | Q11 | C(CH 3)＝CHCO 2C 2H 5 |
| 314 | Q12 | CH 2Ph |
| 315 | Q12 | CH 2CH 2Ph-4-Cl |
| 316 | Q12 | CH 2CH 2OPh-4-Cl |
| 317 | Q12 | CH 2COPh-4-Cl |
| 318 | Q12 | CH 2C(Ph-1，4-Cl 2)＝NOCH3 |
| 319 | Q12 | CH 2C(Ph-4-Cl)＝NNHCH3 |
| 320 | Q12 | N＝C(CH 3)Ph-4-Cl |
| 321 | Q12 | N＝C(CH 2OCH 3)Ph-4-Cl |
| 322 | Q12 | N＝C(CH 2ON＝C(CH 3) 2)Ph-4-Cl |
| 323 | Q12 | N＝C(CO 2CH 3)Ph-4-Cl |
| 324 | Q12 | N＝C(CO 2CH 3)CN |
| 325 | Q12 | N＝C(CO 2C 2H 5) 2 |
| 326 | Q12 | N＝C(CH 3)COCH 3 |
| 327 | Q12 | N＝C(CH 3)C(CH 3)＝NOCH 2Ph |
| 328 | Q12 | CH 2CON(Pr i)Ph-4-Cl |
| 329 | Q12 | CH 2CONHPh |
| 330 | Q12 | CH 2CONH-2-PY |
| 331 | Q12 | CH 2CONHCH 2CN |
| 332 | Q12 | CH 2CONHCH 2CH 2CN |
| 333 | Q12 | CH 2CONHCH 2CO 2C 2H 5 |
| 334 | Q12 | CH 2CONHCH(CH 3)(Pr i)CN |
| 335 | Q12 | C(CH 3)＝CHCOCH 3 |
| 336 | Q12 | C(CH 3)＝CHCO 2C 2H 5 |
| 337 | Q13 | CH 2Ph |
| 338 | Q13 | CH 2CH 2Ph-4-Cl |
| 339 | Q13 | CH 2CH 2OPh-4-Cl |
| 340 | Q13 | CH 2COPh-4-Cl |
| 341 | Q13 | CH 2C(Ph-1，4-Cl 2)＝NOCH3 |
| 342 | Q13 | CH 2C(Ph-4-Cl)＝NNHCH3 |
| 343 | Q13 | N＝C(CH 3)Ph-4-Cl |
| 344 | Q13 | N＝C(CH 2OCH 3)Ph-4-Cl |
| 345 | Q13 | N＝C(CH 2ON＝C(CH 3) 2)Ph-4-Cl |
| 346 | Q13 | N＝C(CO 2CH 3)Ph-4-Cl |
| 347 | Q13 | N＝C(CO 2CH 3)CN |
| 348 | Q13 | N＝C(CO 2C 2H 5) 2 |
| 349 | Q13 | N＝C(CH 3)COCH 3 |
| 350 | Q13 | N＝C(CH 3)C(CH 3)＝NOCH 2Ph |
| 351 | Q13 | CH 2CON(Pr i)Ph-4-Cl |
| 352 | Q13 | CH 2CONHPh |
| 353 | Q13 | CH 2CONH-2-PY |
| 354 | Q13 | CH 2CONHCH 2CN |
| 355 | Q13 | CH 2CONHCH 2CH 2CN |
| 356 | Q13 | CH 2CONHCH 2CO 2C 2H 5 |
| 357 | Q13 | CH 2CONHCH(CH 3)(Pr i)CN |
| 358 | Q13 | C(CH 3)＝CHCOCH 3 |
| 359 | Q13 | C(CH 3)＝CHCO 2C 2H 5 |
Table 2
| No | Q | X | Z |
| 360 | Q1 | CH 2CH 2OCH 2CH 2 | Q1 |
| 361 | Q1 | CH 2CH 2SCH 2CH 2 | Q1 |
| 362 | Q1 | CH 2CH 2 | Q1 |
| 363 | Q1 | CH 2CH 2SO 2CH 2CH 2 | Q1 |
| 364 | Q1 | CH 2CH 2N(CH 3)CH 2CH 2 | Q1 |
| 365 | Q1 | N＝C(CH 3)C(CH 3)＝N | Q1 |
| 366 | Q1 | 1，2-C 6H 4 | Q1 |
| 367 | Q1 | 1，4-C 6H 4 | Q1 |
| 368 | Q1 | 1，3-C 6H 4 | Q1 |
| 369 | Q1 | 4-C 6H 4-4-C 6H 4-4 | Q1 |
| 370 | Q2 | CH 2CH 2OCH 2CH 2 | Q2 |
| 371 | Q2 | CH 2CH 2SCH 2CH 2 | Q2 |
| 372 | Q2 | CH 2CH 2、 | Q2 |
| 373 | Q2 | CH 2CH 2SO 2CH 2CH 2 | Q2 |
| 374 | Q2 | CH 2CH 2N(CH 3)CH 2CH 2 | Q2 |
| 375 | Q2 | N＝C(CH 3)C(CH 3)＝N | Q2 |
| 376 | Q2 | 1，2-C 6H 4 | Q2 |
| 377 | Q2 | 1，4-C 6H 4 | Q2 |
| 378 | Q2 | 1，3-C 6H 4 | Q2 |
| 379 | Q2 | 4-C 6H 4-4-C 6H 4-4 | Q2 |
| 380 | Q3 | CH 2CH 2OCH 2CH 2 | Q3 |
| 381 | Q3 | CH 2CH 2SCH 2CH 2 | Q3 |
| 382 | Q3 | CH 2CH 2、 | Q3 |
| 383 | Q3 | CH 2CH 2SO 2CH 2CH 2 | Q3 |
| 384 | Q3 | CH 2CH 2N(CH 3)CH 2CH 2 | Q3 |
| 385 | Q3 | N＝C(CH 3)C(CH 3)＝N | Q3 |
| 386 | Q3 | 1，2-C 6H 4 | Q3 |
| 387 | Q3 | 1，4-C 6H 4 | Q3 |
| 388 | Q3 | 1，3-C 6H 4 | Q3 |
| 389 | Q3 | 4-C 6H 4-4-C 6H 4-4 | Q3 |
| 390 | Q4 | CH 2CH 2OCH 2CH 2 | Q4 |
| 391 | Q4 | CH 2CH 2SCH 2CH 2 | Q4 |
| 392 | Q4 | CH 2CH 2、 | Q4 |
| 393 | Q4 | CH 2CH 2SO 2CH 2CH 2 | Q4 |
| 394 | Q4 | CH 2CH 2N(CH 3)CH 2CH 2 | Q4 |
| 395 | Q4 | N＝C(CH 3)C(CH 3)＝N | Q4 |
| 396 | Q4 | 1，2-C 6H 4 | Q4 |
| 397 | Q4 | 1，4-C 6H 4 | Q4 |
| 398 | Q4 | 1，3-C 6H 4 | Q4 |
| 399 | Q4 | 4-C 6H 4-4-C 6H 4-4 | Q4 |
| 400 | Q5 | CH 2CH 2OCH 2CH 2 | Q5 |
| 401 | Q5 | CH 2CH 2、 | Q5 |
| 402 | Q5 | CH 2CH 2SOCH 2CH 2 | Q5 |
| 403 | Q5 | CH 2CH 2SO 2CH 2CH 2 | Q5 |
| 404 | Q5 | CH 2CH 2N(CH 3)CH 2CH 2 | Q5 |
| 405 | Q5 | N＝C(CH 3)C(CH 3)＝N | Q5 |
| 406 | Q5 | 1，2-C 6H 4 | Q5 |
| 407 | Q5 | 1，4-C 6H 4 | Q5 |
| 408 | Q5 | 1，3-C 6H 4 | Q5 |
| 409 | Q5 | 4-C 6H 4-4-C 6H 4-4 | Q5 |
| 410 | Q6 | CH 2CH 2OCH 2CH 2 | Q6 |
| 411 | Q6 | CH 2CH 2、 | Q6 |
| 412 | Q6 | CH 2CH 2SOCH 2CH 2 | Q6 |
| 413 | Q6 | CH 2CH 2SO 2CH 2CH 2 | Q6 |
| 414 | Q6 | CH 2CH 2N(CH 3)CH 2CH 2 | Q6 |
| 415 | Q6 | N＝C(CH 3)C(CH 3)＝N | Q6 |
| 416 | Q6 | 1，2-C 6H 4 | Q6 |
| 417 | Q6 | 1，4-C 6H 4 | Q6 |
| 418 | Q6 | 1，3-C 6H 4 | Q6 |
| 419 | Q6 | 4-C 6H 4-4-C 6H 4-4 | Q6 |
| 420 | Q7 | CH 2CH 2OCH 2CH 2 | Q7 |
| 421 | Q7 | CH 2CH 2SCH 2CH 2 | Q7 |
| 422 | Q7 | CH 2CH 2、 | Q7 |
| 423 | Q7 | CH 2CH 2SO 2CH 2CH 2 | Q7 |
| 424 | Q7 | CH 2CH 2N(CH 3)CH 2CH 2 | Q7 |
| 425 | Q7 | N＝C(CH 3)C(CH 3)＝N | Q7 |
| 426 | Q7 | 1，2-C 6H 4 | Q7 |
| 427 | Q7 | 1，4-C 6H 4 | Q7 |
| 428 | Q7 | 1，3-C 6H 4 | Q7 |
| 429 | Q7 | 4-C 6H 4-4-C 6H 4-4 | Q7 |
| 430 | Q8 | CH 2CH 2OCH 2CH 2 | Q8 |
| 431 | Q8 | CH 2CH 2、 | Q8 |
| 432 | Q8 | CH 2CH 2SOCH 2CH 2 | Q8 |
| 433 | Q8 | CH 2CH 2SO 2CH 2CH 2 | Q8 |
| 434 | Q8 | CH 2CH 2N(CH 3)CH 2CH 2 | Q8 |
| 435 | Q8 | N＝C(CH 3)C(CH 3)＝N | Q8 |
| 436 | Q8 | 1，2-C 6H 4 | Q8 |
| 437 | Q8 | 1，4-C 6H 4 | Q8 |
| 438 | Q8 | 1，3-C 6H 4 | Q8 |
| 439 | Q8 | 4-C 6H 4-4-C 6H 4-4 | Q8 |
| 440 | Q9 | CH 2CH 2OCH 2CH 2 | Q9 |
| 441 | Q9 | CH 2CH 2SCH 2CH 2 | Q9 |
| 442 | Q9 | CH 2CH 2、 | Q9 |
| 443 | Q9 | CH 2CH 2SO 2CH 2CH 2 | Q9 |
| 444 | Q9 | CH 2CH 2N(CH 3)CH 2CH 2 | Q9 |
| 445 | Q9 | N＝C(CH 3)C(CH 3)＝N | Q9 |
| 446 | Q9 | 1，2-C 6H 4 | Q9 |
| 447 | Q9 | 1，4-C 6H 4 | Q9 |
| 448 | Q9 | 1，3-C 6H 4 | Q9 |
| 449 | Q9 | 4-C 6H 4-4-C 6H 4-4 | Q9 |
| 450 | Q10 | CH 2CH 2OCH 2CH 2 | Q10 |
| 451 | Q10 | CH 2CH 2SCH 2CH 2 | Q10 |
| 452 | Q10 | CH 2CH 2、 | Q10 |
| 453 | Q10 | CH 2CH 2SO 2CH 2CH 2 | Q10 |
| 454 | Q10 | CH 2CH 2N(CH 3)CH 2CH 2 | Q10 |
| 455 | Q10 | N＝C(CH 3)C(CH 3)＝N | Q10 |
| 456 | Q10 | 1，2-C 6H 4 | Q10 |
| 457 | Q10 | 1，4-C 6H 4 | Q10 |
| 458 | Q10 | 1，3-C 6H 4 | Q10 |
| 459 | Q10 | 4-C 6H 4-4-C 6H 4-4 | Q10 |
| 460 | Q11 | CH 2CH 2OCH 2CH 2 | Q11 |
| 461 | Q11 | CH 2CH 2SCH 2CH 2 | Q11 |
| 462 | Q11 | CH 2CH 2SOCH 2CH 2 | Q11 |
| 463 | Q11 | CH 2CH 2SO 2CH 2CH 2 | Q11 |
| 464 | Q11 | CH 2CH 2N(CH 3)CH 2CH 2 | Q11 |
| 465 | Q11 | N＝C(CH 3)C(CH 3)＝N | Q11 |
| 466 | Q11 | 1，2-C 6H 4 | Q11 |
| 467 | Q11 | 1，4-C 6H 4 | Q11 |
| 468 | Q11 | 1，3-C 6H 4 | Q11 |
| 469 | Q11 | 4-C 6H 4-4-C 6H 4-4 | Q11 |
| 470 | Q12 | CH 2CH 2OCH 2CH 2 | Q12 |
| 471 | Q12 | CH 2CH 2SCH 2CH 2 | Q12 |
| 472 | Q12 | CH 2CH 2、 | Q12 |
| 473 | Q12 | CH 2CH 2SO 2CH 2CH 2 | Q12 |
| 474 | Q12 | CH 2CH 2N(CH 3)CH 2CH 2 | Q12 |
| 475 | Q12 | N＝C(CH 3)C(CH 3)＝N | Q12 |
| 476 | Q12 | 1，2-C 6H 4 | Q12 |
| 477 | Q12 | 1，4-C 6H 4 | Q12 |
| 478 | Q12 | 1，3-C 6H 4 | Q12 |
| 479 | Q12 | 4-C 6H 4-4-C 6H 4-4 | Q12 |
| 480 | Q13 | CH 2CH 2OCH 2CH 2 | Q13 |
| 481 | Q13 | CH 2CH 2SCH 2CH 2 | Q13 |
| 482 | Q13 | CH 2CH 2、 | Q13 |
| 483 | Q13 | CH 2CH 2SO 2CH 2CH 2 | Q13 |
| 484 | Q13 | CH 2CH 2N(CH 3)CH 2CH 2 | Q13 |
| 485 | Q13 | N＝C(CH 3)C(CH 3)＝N | Q13 |
| 486 | Q13 | 1，2-C 6H 4 | Q13 |
| 487 | Q13 | 1，4-C 6H 4 | Q13 |
| 488 | Q13 | 1，3-C 6H 4 | Q13 |
| 489 | Q13 | 4-C 6H 4-4-C 6H 4-4 | Q13 |
The expressed compound of general formula I is useful as the effective constituent of weedicide.When the compound of general formula I of the present invention as weedicide, the formulation that effective constituent is fit to depends on specific purposes and suitable application process.Therefore the present invention also comprises by the represented a kind of novel carboxylic acid ester compound and the agriculture formed herbicidal composition of applicable carrier of with weeding activity of general formula I.
In general, effective constituent is dissolved or dilution with inert solvent and solid carrier.Applied formulation has pulvis, wettable powder, and missible oil, aqua and oil suspending agent, granula, capsules etc. need to add tensio-active agent or other auxiliary agent usually.In addition The compounds of this invention can with sterilant, nematocides, sterilant and other weedicide, plant-growth regulator, fertilizer etc. are used with.
The compounds of this invention can be used as single agent or mixture.The preparation method of single agent and mixture sees " Pesticidal FormulationResearch " (1969), Advances in Chemistry Series No.86, Wade Van Valkenburg; " PesticideFormulations " (1973) Wade Van Valkenburg.In these single agent and mixture, acceptable inert thinner or tensio-active agent such as solid carrier or liquid vehicle are mixed on the agricultural of activeconstituents and routine.Carrier not only can dissolve, disperse effective constituent but also not influence the activity of effective constituent, and itself does not have the obvious damage effect to soil, equipment, crop or agricultural environment.Auxiliary agent is generally tensio-active agent, stablizer, defoamer or dispersion agent in single agent and the mixture.Single agent of the present invention and mixture comprise that also its purpose is to enlarge the field of activity of preparation and improves drug effect with being mixed of known agricultural chemical compound.
Its weight percentage of effective constituent is 0.1% to 99% in the preparation, and contains at least 0.1% to 20% show activity agent and 0.1% to 99% solid or liquid diluent.
If the compound of general formula I mixes mutually with another weedicide, according to the difference of active compound, application purpose, envrionment conditions and formulation, the content of effective variation range is very big in the mixture.Active constituent content is generally 1% to 95% in the mixture, and suitable content is 5% to 60%.The effective dosage ranges of The compounds of this invention is generally 1 gram/hectare to 3 kg/ha, and 5 gram/hectares are better to 500 gram/hectares.
Other embodiments of the present invention are method for weed in the prevention target crop field (as Tanakas such as wheat, corn, soybean, cotton, peanut, vegetables and paddy rice), and this method comprises that the novel carboxylic acid ester compound herbicidal composition with compound shown in the general formula I of herbicidally effective amount and acceptable carrier composition imposes on the surface of growth medium of the places of described weeds, described weeds or described weeds.
Embodiment
Below with the preparation and examples of formulations the present invention will be described in more detail.But should point out that the present invention never only limits to these concrete examples.In the example of preparation, " part " expression parts by weight, the content of preparation is weight percentage, compound number with show 1-2 in consistent.
Preparation example 1 (No. 2 compound)
1.0 the benzene oxygen propionyl chloride that gram replaces (R is expressed as optically active isomer R type in the structural formula, down with) and 3.0 gram phenylethyl alcohols reflux 4 hours in 50 milliliters of toluene is after the cooling, heating under vacuum is sloughed toluene, adds water and ethyl acetate, tells organic layer, and water and salt water washing, dry back concentrates.Residuum gets 0.5 gram oily matter with purification by silica gel column chromatography.
1H NMR(CDCl
3)：8.48(s，1H)，7.87(d，1H)，7.46(m，2H)，7.08～6.91(m，8H)，6.81(s，1H)，4.58(q，1H)，4.32(t，2H)，2.89(t，2H)，1.56(d，3H)。
Preparation example 2 (No. 20 compound)
2.1 benzene oxygen propionyl chloride that gram replaces and 0.5 gram dimethylglyoxime are heated to 80 ℃ of reactions 8 hours in 50 milliliters of toluene, after the cooling, heating under vacuum is sloughed toluene, adds water and ethyl acetate, tells organic layer, and water and salt water washing, and dry back concentrates.Residuum gets 0.5 gram object, 116～119 ℃ of fusing points with purification by silica gel column chromatography.
1H NMR(CDCl
3)：8.69(s，1H)，8.07(1H)，8.00(2H)，7.68(1H)，7.60(1H)，7.18(2H)，4.84(m，1H)，3.74(s，6H)，1.72(d，3H)。
Preparation example 3 (No. 367 compound)
2.2 in 35～40 ℃ of stirrings 8 hours, heating under vacuum was sloughed toluene, adds water and ethyl acetate, tells organic layer, and water and salt water washing in 50 milliliters of toluene for benzene oxygen propionyl chloride that gram replaces and 0.3 gram Resorcinol, dry back concentrates.Residuum gets 0.5 gram object, 121～125 ℃ of fusing points with purification by silica gel column chromatography.
Preparation example 4 (No. 365 compound)
4.0 benzene oxygen propionyl chloride that gram replaces and 0.3 gram dimethylglyoxime are heated to 80 ℃ of reactions 8 hours in 50 milliliters of toluene, after the cooling, heating under vacuum is sloughed toluene, adds water and ethyl acetate, tells organic layer, and water and salt water washing, and dry back concentrates.Residuum gets 0.5 gram object, 149～151 ℃ of fusing points with purification by silica gel column chromatography.
Preparation example 5 (No. 33 compound)
1.7 the benzene oxygen propionyl chloride that gram replaces is dissolved in the methylene dichloride, is added drop-wise to 0.4 gram 2, in the methylene dichloride of 4-diacetylmethane and 0.6 gram triethylamine, and room temperature reaction 4 hours, after the cooling, heating under vacuum is sloughed toluene, adds water and ethyl acetate, tell organic layer, and water and salt water washing, dry back concentrates.Residuum gets 0.3 gram object, 66～68 ℃ of fusing points with purification by silica gel column chromatography.
Can synthesize the compound shown in table 1 and the table 2 with method.
The physical properties of part of compounds is as follows: 81～84 ℃ of No. 360 melting point compounds, and 139～141 ℃ of No. 362 melting point compounds, the 25th, 30, No. 361 compound is oily matter.
Formulation examples 1
50 parts of No. 20 compounds, 5 parts of polyoxyethylene alkane aryl oxides, 5 parts of pelopon A parts, 40 parts of levigate and abundant mixings of artificial hydrated SiO 2 promptly get 50% wettable powder.
Arbitrary solid chemical compound can make 50% wettable powder as stated above in the compound table.
Formulation examples 2a
10 parts of the 2nd compounds, 6 parts of polyoxyethylene alkane aryl oxides, 4 parts of pelopon As, 30 parts of dimethylbenzene and 50 parts of levigate and abundant mixings of cyclohexanone promptly get 10% missible oil.
Formulation examples 2b-j
Preparation method and feeding quantity are the same, only active ingredient are changed the 20th, 25,30,33,360,361,362,365, No. 367 successively into compound.
Formulation examples 3a
20 parts of No. 362 compounds, 2 parts of artificial hydrated SiO 2s, 3 parts of the pure monooleates of polyoxyethylene dehydration sorb (sugar), 5 parts of carboxymethyl celluloses are levigate and and 70 parts of abundant mixings of water, and make the effective constituent particle less than 5 microns, promptly get 20% water suspending agent.
Formulation examples 3b-d
Preparation method and feeding quantity are the same, only active ingredient are changed the 360th, 365, No. 367 successively into compound.
Formulation examples 4a
5 parts of No. 365 compounds, 1 part of isopropyl acid phosphoric acid salt, 64 parts and 30 parts levigate and abundant mixings of talcum powder of kaolin, and make the effective constituent particle less than 5 microns, promptly get 5% pulvis.
Formulation examples 4b-d
Preparation method and feeding quantity are the same, only active ingredient are changed the 360th, 362, No. 367 successively into compound.
Formulation examples 5a
25 parts of No. 367 compounds, 3 parts of the pure monooleates of the rare dehydration sorb of polyoxy second (sugar), 2 parts of polyvinyl alcohols are levigate and and 70 parts of abundant mixings of water, and the effective constituent particle promptly gets 25% water suspending agent less than 5 microns.
Formulation examples 5b-d
Preparation method and feeding quantity are the same, only active ingredient are changed the 360th, 362, No. 365 successively into compound.
Biological activity determination
With broadleaf weeds Cassia tora (Cassia tora), piemarker (Abutilon theophrasti), youth-and-old-age (Zinnia elegans Jacq), monocotyledon weed barnyard grass grass (Echinochloa crus-galli), lady's-grass (Digtaria sanguinalis), Herba Setariae Viridis (Setaria viridis), with crop such as wheat, corn, paddy rice, soybean and cotton be tested object, above-claimed cpd is measured.
According to follow procedure each compound is measured.
Measure behind the seedling, seed germination also grew 10-21 days, made the examination material that has a series of growing stages before the processing.Select size, the consistent examination material of growing stage, handle, processing places the greenhouse and waters.The examination material with compound treatment does not compare.
Testing compound is with suitable solvent (generally using acetone) dissolving, and its preparation is directly used water dissolution, the processing of spraying then, and spouting liquid is 187 or the 468L/ hectare, effective dose is g/ha.2 weeks or the investigation of 4 weeks after processing, with the 0-100 classification, 0 represents non-activity to medicament to each activity of trying material, 100 expressions suppress fully.
At 600g/ha partial test result (the 2nd, 20,25,30,34,36,360,361,362,365, No. 367 arbitrary compound), to safety such as broad leaf crop such as soybean, cottons.
The partial test compound to seedling after weed control efficacy see Table 3:
Table 3
| Compound | Dosage g/ha | The barnyard grass grass | Lady's-grass | Herba Setariae Viridis | Cassia tora | Piemarker | Youth-and-old-age |
| 2 20 25 30 33 34 36 360 361 362 365 367 | 300 300 300 300 300 300 300 100 12.5 100 12.5 100 12.5 300 300 | 100 100 100 100 100 100 100 100 100 100 75 100 100 100 100 | 100 100 100 100 100 100 100 99 90 90 80 99 98 100 100 | 100 100 100 100 100 100 100 90 85 75 65 100 85 100 100 | 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 | 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 | 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 |
Claims (6)
1. carboxylic acid ester compound, shown in general formula I:
In the formula:
X is selected from:
CH
2CH
2，CH
2CH
2OCH
2CH
2，CH
2CH
2SCH
2CH
2
Or
X
1Be selected from O,
Z is selected from Q;
Wherein, R
1, R
2Can be identical or different, be selected from H respectively, bromine, chlorine, fluorine, C
1-C
6Alkyl, C
1-C
6Alkoxyl group, C
1-C
6Alkylthio, phenyl, pyridine or halogenophenyl;
R
3Be selected from H, C
1-C
6Alkyl, C
1-C
6Alkoxyl group, phenyl or halogenophenyl;
Q is selected from Q
1, represent following group:
2. according to the described carboxylic acid ester compound of claim 1, it is characterized in that: in the compound of Formula I,
R
1, R
2, R
3Can be identical or different, be selected from H, C respectively
1-C
4Alkyl, phenyl or halogenophenyl.
3. the purposes of the described compound of claim 1 aspect management of weeds.
4. herbicidal composition, it is characterized in that: the active ingredient in the said composition is the compound described in the claim 1, weight content is 0.1% to 99%.
5. according to the described herbicidal composition of claim 4, it is characterized in that: also contain agricultural in the composition and go up applicable carrier.
6. the method for a management of weeds, it is characterized in that: weeds, weed growth ground or weed growth medium to farm crop Tanaka are used herbicidal composition as claimed in claim 5.
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|---|---|---|---|
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN 03143375 CN1281602C (en) | 2003-09-29 | 2003-09-29 | Novel carboxylate herbicides |
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| CN1281602C true CN1281602C (en) | 2006-10-25 |
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| CN100443475C (en) * | 2005-09-08 | 2008-12-17 | 沈阳化工研究院 | Compound of 2-substituted alkylacrylate and application thereof |
| CN100364955C (en) * | 2005-09-18 | 2008-01-30 | 大连理工大学 | 2-(dibasic) methyl acrylic ester compound and its use |
| CN102718722B (en) * | 2012-07-10 | 2016-02-17 | 南开大学 | The novel fragrant phenoxy ramification of carboxylic esters preparations and applicatio research that a kind of water oil is double molten |
| CN104803987B (en) * | 2014-01-28 | 2017-05-17 | 沈阳中化农药化工研发有限公司 | Oxime-containing carboxylate compound and use thereof |
| CN105439945A (en) * | 2015-12-03 | 2016-03-30 | 长江大学 | Aryloxy anilino propionic ester compound and application thereof as herbicide |
| CN106632097A (en) * | 2016-12-15 | 2017-05-10 | 三峡大学 | Condensed heterogeneous oxyphenoxy carboxylic acid derivative and application thereof |
| CN106632007B (en) * | 2016-12-15 | 2019-12-31 | 三峡大学 | Pyridine-3-radical aryloxy phenoxy alkyl acid ester compound and application thereof |
| CN106632293B (en) * | 2016-12-15 | 2019-02-26 | 三峡大学 | Biologically active virtue phenoxy acid derivative and preparation method thereof |
| CN114957166B (en) * | 2022-05-26 | 2023-07-25 | 湖南省农业生物技术研究所 | Phenylacetamide compound and preparation method and application thereof |
| CN116283802A (en) * | 2023-03-21 | 2023-06-23 | 中国农业大学 | Herbicidal compound containing (R) -2- [4- (6-chloroquinolin-2-yloxy) phenoxy ] propionyl structure, and preparation and application thereof |
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