JPS6225143B2 - - Google Patents

Info

Publication number: JPS6225143B2
Authority: JP; Japan
Prior art keywords: group; formula; dicyano; general formula; derivative
Prior art date: 1979-06-20
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

Application number

JP54077867A

Other languages

English (en)

Japanese (ja)

Other versions

JPS562971A (en

Inventor

Tetsuo Takematsu

Hirozo Segawa

Takamaro Miura

Toshihide Ataka

Michio Chatani

Akira Nakamura

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Kyowa Gas Chemical Industry Co Ltd

Original Assignee

Kyowa Gas Chemical Industry Co Ltd

Priority date (The priority date 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 date listed.)

1979-06-20

Filing date

1979-06-20

Publication date

1987-06-01

1979-06-20 Application filed by Kyowa Gas Chemical Industry Co Ltd filed Critical Kyowa Gas Chemical Industry Co Ltd

1979-06-20 Priority to JP7786779A priority Critical patent/JPS562971A/ja

1981-01-13 Publication of JPS562971A publication Critical patent/JPS562971A/ja

1987-06-01 Publication of JPS6225143B2 publication Critical patent/JPS6225143B2/ja

Status Granted legal-status Critical Current

Links

230000002363 herbicidal effect Effects 0.000 claims description 21
239000004009 herbicide Substances 0.000 claims description 20
125000003545 alkoxy group Chemical group 0.000 claims description 12
125000005843 halogen group Chemical group 0.000 claims description 11
OTVZGAXESBAAQQ-UHFFFAOYSA-N pyrazine-2,3-dicarbonitrile Chemical class N#CC1=NC=CN=C1C#N OTVZGAXESBAAQQ-UHFFFAOYSA-N 0.000 claims description 10
239000002253 acid Substances 0.000 claims description 7
125000004093 cyano group Chemical group *C#N 0.000 claims description 6
125000002541 furyl group Chemical group 0.000 claims description 6
238000004519 manufacturing process Methods 0.000 claims description 6
125000001544 thienyl group Chemical group 0.000 claims description 6
239000004480 active ingredient Substances 0.000 claims description 5
125000003282 alkyl amino group Chemical group 0.000 claims description 5
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 5
229910052801 chlorine Inorganic materials 0.000 claims description 5
230000002140 halogenating effect Effects 0.000 claims description 5
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 5
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 5
DPZSNGJNFHWQDC-ARJAWSKDSA-N (z)-2,3-diaminobut-2-enedinitrile Chemical compound N#CC(/N)=C(/N)C#N DPZSNGJNFHWQDC-ARJAWSKDSA-N 0.000 claims description 4
125000001309 chloro group Chemical group Cl* 0.000 claims description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
MQZGOHPDJLBDAP-UHFFFAOYSA-N 6-oxo-1h-pyrazine-2,3-dicarbonitrile Chemical class OC1=CN=C(C#N)C(C#N)=N1 MQZGOHPDJLBDAP-UHFFFAOYSA-N 0.000 claims description 3
125000000217 alkyl group Chemical group 0.000 claims description 3
150000003973 alkyl amines Chemical class 0.000 claims 1
125000004216 fluoromethyl group Chemical group [H]C([H])(F)* 0.000 claims 1
150000001875 compounds Chemical class 0.000 description 33
241000196324 Embryophyta Species 0.000 description 20
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 15
-1 phosphorus halides Chemical class 0.000 description 13
239000000203 mixture Substances 0.000 description 11
238000006243 chemical reaction Methods 0.000 description 10
XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 10
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 9
238000009472 formulation Methods 0.000 description 9
239000002689 soil Substances 0.000 description 9
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
239000012876 carrier material Substances 0.000 description 8
239000000843 powder Substances 0.000 description 8
239000004094 surface-active agent Substances 0.000 description 8
239000003085 diluting agent Substances 0.000 description 7
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
241000208838 Asteraceae Species 0.000 description 5
241000234646 Cyperaceae Species 0.000 description 5
241000209504 Poaceae Species 0.000 description 5
241000219050 Polygonaceae Species 0.000 description 5
239000003795 chemical substances by application Substances 0.000 description 5
239000000839 emulsion Substances 0.000 description 5
239000008187 granular material Substances 0.000 description 5
238000000034 method Methods 0.000 description 5
239000011541 reaction mixture Substances 0.000 description 5
239000007787 solid Substances 0.000 description 5
239000000243 solution Substances 0.000 description 5
239000002904 solvent Substances 0.000 description 5
241000219321 Caryophyllaceae Species 0.000 description 4
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
241000721692 Lythrum Species 0.000 description 4
240000007594 Oryza sativa Species 0.000 description 4
KYQCOXFCLRTKLS-UHFFFAOYSA-N Pyrazine Chemical compound C1=CN=CC=N1 KYQCOXFCLRTKLS-UHFFFAOYSA-N 0.000 description 4
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
150000001412 amines Chemical class 0.000 description 4
125000004432 carbon atom Chemical group C* 0.000 description 4
239000002552 dosage form Substances 0.000 description 4
230000035784 germination Effects 0.000 description 4
238000005658 halogenation reaction Methods 0.000 description 4
239000012442 inert solvent Substances 0.000 description 4
239000007788 liquid Substances 0.000 description 4
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
241000219317 Amaranthaceae Species 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 3
235000007164 Oryza sativa Nutrition 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
238000004587 chromatography analysis Methods 0.000 description 3
235000014113 dietary fatty acids Nutrition 0.000 description 3
238000004821 distillation Methods 0.000 description 3
230000000694 effects Effects 0.000 description 3
238000000921 elemental analysis Methods 0.000 description 3
238000000605 extraction Methods 0.000 description 3
239000000194 fatty acid Substances 0.000 description 3
229930195729 fatty acid Natural products 0.000 description 3
238000001914 filtration Methods 0.000 description 3
238000002844 melting Methods 0.000 description 3
230000008018 melting Effects 0.000 description 3
238000002156 mixing Methods 0.000 description 3
229910052698 phosphorus Inorganic materials 0.000 description 3
239000011574 phosphorus Substances 0.000 description 3
235000009566 rice Nutrition 0.000 description 3
238000003756 stirring Methods 0.000 description 3
238000003786 synthesis reaction Methods 0.000 description 3
239000008096 xylene Substances 0.000 description 3
QPUYECUOLPXSFR-UHFFFAOYSA-N 1-methylnaphthalene Chemical compound C1=CC=C2C(C)=CC=CC2=C1 QPUYECUOLPXSFR-UHFFFAOYSA-N 0.000 description 2
OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 2
VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
241000207782 Convolvulaceae Species 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 2
241000219991 Lythraceae Species 0.000 description 2
240000007019 Oxalis corniculata Species 0.000 description 2
235000016499 Oxalis corniculata Nutrition 0.000 description 2
PCNDJXKNXGMECE-UHFFFAOYSA-N Phenazine Natural products C1=CC=CC2=NC3=CC=CC=C3N=C21 PCNDJXKNXGMECE-UHFFFAOYSA-N 0.000 description 2
NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
125000001931 aliphatic group Chemical group 0.000 description 2
150000001346 alkyl aryl ethers Chemical class 0.000 description 2
239000000440 bentonite Substances 0.000 description 2
229910000278 bentonite Inorganic materials 0.000 description 2
SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 2
239000011230 binding agent Substances 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
239000003054 catalyst Substances 0.000 description 2
238000005119 centrifugation Methods 0.000 description 2
238000009833 condensation Methods 0.000 description 2
230000005494 condensation Effects 0.000 description 2
238000006482 condensation reaction Methods 0.000 description 2
238000001816 cooling Methods 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
150000002170 ethers Chemical class 0.000 description 2
235000019253 formic acid Nutrition 0.000 description 2
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 description 2
229910000041 hydrogen chloride Inorganic materials 0.000 description 2
150000007529 inorganic bases Chemical class 0.000 description 2
HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
150000007530 organic bases Chemical class 0.000 description 2
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 2
WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
150000003216 pyrazines Chemical class 0.000 description 2
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 2
239000000376 reactant Substances 0.000 description 2
238000001953 recrystallisation Methods 0.000 description 2
238000010992 reflux Methods 0.000 description 2
125000001424 substituent group Chemical group 0.000 description 2
239000000454 talc Substances 0.000 description 2
229910052623 talc Inorganic materials 0.000 description 2
150000003512 tertiary amines Chemical class 0.000 description 2
VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 2
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
239000004563 wettable powder Substances 0.000 description 2
LDVVMCZRFWMZSG-OLQVQODUSA-N (3ar,7as)-2-(trichloromethylsulfanyl)-3a,4,7,7a-tetrahydroisoindole-1,3-dione Chemical compound C1C=CC[C@H]2C(=O)N(SC(Cl)(Cl)Cl)C(=O)[C@H]21 LDVVMCZRFWMZSG-OLQVQODUSA-N 0.000 description 1
LVGUZGTVOIAKKC-UHFFFAOYSA-N 1,1,1,2-tetrafluoroethane Chemical compound FCC(F)(F)F LVGUZGTVOIAKKC-UHFFFAOYSA-N 0.000 description 1
OGFAWKRXZLGJSK-UHFFFAOYSA-N 1-(2,4-dihydroxyphenyl)-2-(4-nitrophenyl)ethanone Chemical compound OC1=CC(O)=CC=C1C(=O)CC1=CC=C([N+]([O-])=O)C=C1 OGFAWKRXZLGJSK-UHFFFAOYSA-N 0.000 description 1
FECOOTOWJXGHGV-UHFFFAOYSA-N 2-(3,4-dichlorophenyl)-2-oxoacetic acid Chemical compound OC(=O)C(=O)C1=CC=C(Cl)C(Cl)=C1 FECOOTOWJXGHGV-UHFFFAOYSA-N 0.000 description 1
LMKCKLHDJRAHMG-UHFFFAOYSA-N 2-(3,4-dichlorophenyl)pyrazine Chemical compound C1=C(Cl)C(Cl)=CC=C1C1=CN=CC=N1 LMKCKLHDJRAHMG-UHFFFAOYSA-N 0.000 description 1
HIXDQWDOVZUNNA-UHFFFAOYSA-N 2-(3,4-dimethoxyphenyl)-5-hydroxy-7-methoxychromen-4-one Chemical compound C=1C(OC)=CC(O)=C(C(C=2)=O)C=1OC=2C1=CC=C(OC)C(OC)=C1 HIXDQWDOVZUNNA-UHFFFAOYSA-N 0.000 description 1
FFKZZCMVJFZYQQ-UHFFFAOYSA-N 2-(3-methoxyphenyl)pyrazine Chemical compound COC1=CC=CC(C=2N=CC=NC=2)=C1 FFKZZCMVJFZYQQ-UHFFFAOYSA-N 0.000 description 1
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
239000005995 Aluminium silicate Substances 0.000 description 1
241000982775 Ammodramus Species 0.000 description 1
244000296825 Amygdalus nana Species 0.000 description 1
235000003840 Amygdalus nana Nutrition 0.000 description 1
241000209034 Aquifoliaceae Species 0.000 description 1
241000209524 Araceae Species 0.000 description 1
241000269837 Artemisia dubia Species 0.000 description 1
235000003261 Artemisia vulgaris Nutrition 0.000 description 1
240000008100 Brassica rapa Species 0.000 description 1
235000011292 Brassica rapa Nutrition 0.000 description 1
235000004977 Brassica sinapistrum Nutrition 0.000 description 1
241000219193 Brassicaceae Species 0.000 description 1
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 1
DKPFZGUDAPQIHT-UHFFFAOYSA-N Butyl acetate Natural products CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 1
JGLMVXWAHNTPRF-CMDGGOBGSA-N CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O Chemical compound CCN1N=C(C)C=C1C(=O)NC1=NC2=CC(=CC(OC)=C2N1C\C=C\CN1C(NC(=O)C2=CC(C)=NN2CC)=NC2=CC(=CC(OCCCN3CCOCC3)=C12)C(N)=O)C(N)=O JGLMVXWAHNTPRF-CMDGGOBGSA-N 0.000 description 1
244000025254 Cannabis sativa Species 0.000 description 1
235000011305 Capsella bursa pastoris Nutrition 0.000 description 1
240000008867 Capsella bursa-pastoris Species 0.000 description 1
240000004160 Capsicum annuum Species 0.000 description 1
235000002567 Capsicum annuum Nutrition 0.000 description 1
239000005745 Captan Substances 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
235000007516 Chrysanthemum Nutrition 0.000 description 1
240000005250 Chrysanthemum indicum Species 0.000 description 1
241000207892 Convolvulus Species 0.000 description 1
XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
241000234653 Cyperus Species 0.000 description 1
241000221017 Euphorbiaceae Species 0.000 description 1
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
239000005909 Kieselgur Substances 0.000 description 1
241000254158 Lampyridae Species 0.000 description 1
241000209499 Lemna Species 0.000 description 1
244000207740 Lemna minor Species 0.000 description 1
235000006439 Lemna minor Nutrition 0.000 description 1
229920001732 Lignosulfonate Polymers 0.000 description 1
244000133810 Montia fontana Species 0.000 description 1
235000008319 Montia fontana Nutrition 0.000 description 1
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 1
JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 description 1
GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 1
241000237503 Pectinidae Species 0.000 description 1
239000004698 Polyethylene Substances 0.000 description 1
244000292697 Polygonum aviculare Species 0.000 description 1
235000006386 Polygonum aviculare Nutrition 0.000 description 1
241000206609 Porphyra Species 0.000 description 1
235000001855 Portulaca oleracea Nutrition 0.000 description 1
235000011432 Prunus Nutrition 0.000 description 1
244000184734 Pyrus japonica Species 0.000 description 1
235000005733 Raphanus sativus var niger Nutrition 0.000 description 1
235000006140 Raphanus sativus var sativus Nutrition 0.000 description 1
240000001970 Raphanus sativus var. sativus Species 0.000 description 1
241000208422 Rhododendron Species 0.000 description 1
241001107098 Rubiaceae Species 0.000 description 1
241000566137 Sagittarius Species 0.000 description 1
241000124033 Salix Species 0.000 description 1
241000208292 Solanaceae Species 0.000 description 1
229920002472 Starch Polymers 0.000 description 1
239000000654 additive Substances 0.000 description 1
239000003905 agrochemical Substances 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
150000008051 alkyl sulfates Chemical class 0.000 description 1
229910000147 aluminium phosphate Inorganic materials 0.000 description 1
235000012211 aluminium silicate Nutrition 0.000 description 1
150000003863 ammonium salts Chemical class 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
244000269888 azena Species 0.000 description 1
150000001555 benzenes Chemical class 0.000 description 1
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 1
229910052794 bromium Inorganic materials 0.000 description 1
229910000019 calcium carbonate Inorganic materials 0.000 description 1
239000001511 capsicum annuum Substances 0.000 description 1
229940117949 captan Drugs 0.000 description 1
239000000460 chlorine Substances 0.000 description 1
239000004927 clay Substances 0.000 description 1
229910052570 clay Inorganic materials 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
239000013078 crystal Substances 0.000 description 1
230000034994 death Effects 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
YWEUIGNSBFLMFL-UHFFFAOYSA-N diphosphonate Chemical compound O=P(=O)OP(=O)=O YWEUIGNSBFLMFL-UHFFFAOYSA-N 0.000 description 1
JMGZBMRVDHKMKB-UHFFFAOYSA-L disodium;2-sulfobutanedioate Chemical compound [Na+].[Na+].OS(=O)(=O)C(C([O-])=O)CC([O-])=O JMGZBMRVDHKMKB-UHFFFAOYSA-L 0.000 description 1
239000003814 drug Substances 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 1
239000003337 fertilizer Substances 0.000 description 1
229910052731 fluorine Inorganic materials 0.000 description 1
239000011737 fluorine Substances 0.000 description 1
239000000417 fungicide Substances 0.000 description 1
239000011521 glass Substances 0.000 description 1
238000000227 grinding Methods 0.000 description 1
230000009036 growth inhibition Effects 0.000 description 1
239000010440 gypsum Substances 0.000 description 1
229910052602 gypsum Inorganic materials 0.000 description 1
150000008282 halocarbons Chemical class 0.000 description 1
230000026030 halogenation Effects 0.000 description 1
FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 description 1
230000000887 hydrating effect Effects 0.000 description 1
229930195733 hydrocarbon Natural products 0.000 description 1
150000002430 hydrocarbons Chemical class 0.000 description 1
208000006278 hypochromic anemia Diseases 0.000 description 1
230000005764 inhibitory process Effects 0.000 description 1
239000002917 insecticide Substances 0.000 description 1
PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
JMMWKPVZQRWMSS-UHFFFAOYSA-N isopropanol acetate Natural products CC(C)OC(C)=O JMMWKPVZQRWMSS-UHFFFAOYSA-N 0.000 description 1
229940011051 isopropyl acetate Drugs 0.000 description 1
GWYFCOCPABKNJV-UHFFFAOYSA-N isovaleric acid Chemical compound CC(C)CC(O)=O GWYFCOCPABKNJV-UHFFFAOYSA-N 0.000 description 1
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
239000003350 kerosene Substances 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000010410 layer Substances 0.000 description 1
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
239000010445 mica Substances 0.000 description 1
229910052618 mica group Inorganic materials 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
229910052901 montmorillonite Inorganic materials 0.000 description 1
PSZYNBSKGUBXEH-UHFFFAOYSA-M naphthalene-1-sulfonate Chemical compound C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-M 0.000 description 1
239000005645 nematicide Substances 0.000 description 1
229910017604 nitric acid Inorganic materials 0.000 description 1
150000002825 nitriles Chemical class 0.000 description 1
230000001473 noxious effect Effects 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
235000005985 organic acids Nutrition 0.000 description 1
230000000144 pharmacologic effect Effects 0.000 description 1
UXCDUFKZSUBXGM-UHFFFAOYSA-N phosphoric tribromide Chemical compound BrP(Br)(Br)=O UXCDUFKZSUBXGM-UHFFFAOYSA-N 0.000 description 1
DLYUQMMRRRQYAE-UHFFFAOYSA-N phosphorus pentoxide Inorganic materials O1P(O2)(=O)OP3(=O)OP1(=O)OP2(=O)O3 DLYUQMMRRRQYAE-UHFFFAOYSA-N 0.000 description 1
FAIAAWCVCHQXDN-UHFFFAOYSA-N phosphorus trichloride Chemical compound ClP(Cl)Cl FAIAAWCVCHQXDN-UHFFFAOYSA-N 0.000 description 1
239000005648 plant growth regulator Substances 0.000 description 1
229920001515 polyalkylene glycol Polymers 0.000 description 1
229920000573 polyethylene Polymers 0.000 description 1
230000001737 promoting effect Effects 0.000 description 1
BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
FVSKHRXBFJPNKK-UHFFFAOYSA-N propionitrile Chemical compound CCC#N FVSKHRXBFJPNKK-UHFFFAOYSA-N 0.000 description 1
235000014774 prunus Nutrition 0.000 description 1
238000010298 pulverizing process Methods 0.000 description 1
125000003373 pyrazinyl group Chemical group 0.000 description 1
238000006798 ring closing metathesis reaction Methods 0.000 description 1
235000020637 scallop Nutrition 0.000 description 1
239000000377 silicon dioxide Substances 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
239000007921 spray Substances 0.000 description 1
239000008107 starch Substances 0.000 description 1
235000019698 starch Nutrition 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000002344 surface layer Substances 0.000 description 1
238000003419 tautomerization reaction Methods 0.000 description 1
239000010455 vermiculite Substances 0.000 description 1
229910052902 vermiculite Inorganic materials 0.000 description 1
235000019354 vermiculite Nutrition 0.000 description 1
238000005406 washing Methods 0.000 description 1
238000009333 weeding Methods 0.000 description 1
230000002087 whitening effect Effects 0.000 description 1

Landscapes

Plural Heterocyclic Compounds (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)

JP7786779A 1979-06-20 1979-06-20 Novel 2,3,-dicyanopyrazine derivative, its preparation, and herbicide comprising it as active ingredient Granted JPS562971A (en)

Priority Applications (1)

Application Number	Priority Date	Filing Date	Title
JP7786779A JPS562971A (en)	1979-06-20	1979-06-20	Novel 2,3,-dicyanopyrazine derivative, its preparation, and herbicide comprising it as active ingredient

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
JP7786779A JPS562971A (en)	1979-06-20	1979-06-20	Novel 2,3,-dicyanopyrazine derivative, its preparation, and herbicide comprising it as active ingredient

Publications (2)

Publication Number	Publication Date
JPS562971A JPS562971A (en)	1981-01-13
JPS6225143B2 true JPS6225143B2 (ko)	1987-06-01

Family

ID=13645997

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
JP7786779A Granted JPS562971A (en)	1979-06-20	1979-06-20	Novel 2,3,-dicyanopyrazine derivative, its preparation, and herbicide comprising it as active ingredient

Country Status (1)

Country	Link
JP (1)	JPS562971A (ko)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN111995589B (zh)	2015-11-10	2023-12-05	国立大学法人九州大学	2,5－二氰基－3,6－二卤代吡嗪的制造方法

1979
- 1979-06-20 JP JP7786779A patent/JPS562971A/ja active Granted

Also Published As

Publication number	Publication date
JPS562971A (en)	1981-01-13

Publication	Publication Date	Title
JPS6087254A (ja)	1985-05-16	新規尿素化合物及びそれを含有する除草剤
JPH0580470B2 (ko)	1993-11-09
US4003912A (en)	1977-01-18	Dicarboximido-N-phenylsubstituted carbamates and derivatives
JPS59212472A (ja)	1984-12-01	４，５，６，７−テトラヒドロ−２ｈ−イソインド−ル−１，３−ジオン誘導体、その製造法およびそれを有効成分とする除草剤
EP0023725B1 (en)	1982-03-31	Diphenyl ether derivatives, process for preparing the same and herbicidal compositions containing the same
JPH05178844A (ja)	1993-07-20	除草性化合物
CA2116220C (en)	1997-02-04	Sulfamoyltriazole derivatives and fungicidal compositions containing the same as effective component thereof
US5338720A (en)	1994-08-16	Triazole compounds and herbicidal compositions
JPS60109578A (ja)	1985-06-15	３−（置換フエニル）−５−置換−１，３，４−オキサゾリン−２−オン類およびこれを有効成分とする除草剤
JPS61103873A (ja)	1986-05-22	新規な２‐シアノベンズイミダゾール誘導体
JPH02233602A (ja)	1990-09-17	除草剤
JPS6225143B2 (ko)	1987-06-01
JPH10273487A (ja)	1998-10-13	クロモン誘導体並びに該誘導体を有効成分として含有する殺菌及び除草剤
EP0073409B1 (en)	1986-05-07	N-substituted-tetrahydroisophthalimide derivatives
JP2730022B2 (ja)	1998-03-25	３−アルコキシブチリルイミダゾール誘導体、その製造法及び除草剤
JPS61221170A (ja)	1986-10-01	トリフルオロメタンスルホニルアミド誘導体及びそれを有効成分とする除草剤
JPH04112876A (ja)	1992-04-14	ピリミジンまたはトリアジン誘導体及び除草剤
JP3036841B2 (ja)	2000-04-24	トリアゾール系化合物
JP2985990B2 (ja)	1999-12-06	３−アルコキシアルカン酸アミド誘導体、その製造法及び除草剤
JPS6148508B2 (ko)	1986-10-24
JPS59172446A (ja)	1984-09-29	除草剤
JPS6241592B2 (ko)	1987-09-03
JPS626549B2 (ko)	1987-02-12
JPS6115857B2 (ko)	1986-04-26
JPS6257184B2 (ko)	1987-11-30