CS209533B2 - Herbicide means - Google Patents
Herbicide means Download PDFInfo
- Publication number
- CS209533B2 CS209533B2 CS784948A CS494878A CS209533B2 CS 209533 B2 CS209533 B2 CS 209533B2 CS 784948 A CS784948 A CS 784948A CS 494878 A CS494878 A CS 494878A CS 209533 B2 CS209533 B2 CS 209533B2
- Authority
- CS
- Czechoslovakia
- Prior art keywords
- chloro
- methylthiopyrimidine
- formula
- group
- mixture
- Prior art date
Links
- 230000002363 herbicidal effect Effects 0.000 title claims description 20
- 239000004009 herbicide Substances 0.000 title description 7
- 239000000203 mixture Substances 0.000 claims description 80
- 150000001875 compounds Chemical class 0.000 claims description 58
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 33
- 238000000034 method Methods 0.000 claims description 17
- 229910021529 ammonia Inorganic materials 0.000 claims description 16
- NQRYJNQNLNOLGT-UHFFFAOYSA-N Piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 claims description 11
- -1 methylamino, ethylamino, isopropylamino, amino Chemical group 0.000 claims description 11
- 125000001424 substituent group Chemical group 0.000 claims description 11
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 claims description 10
- 125000004432 carbon atom Chemical group C* 0.000 claims description 10
- 229910052801 chlorine Inorganic materials 0.000 claims description 10
- 239000004480 active ingredient Substances 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 8
- 150000003839 salts Chemical class 0.000 claims description 8
- QQRJUWIHLNBDQF-UHFFFAOYSA-N 6-chloro-5-methylsulfanylpyrimidine-2,4-diamine Chemical group CSC1=C(N)N=C(N)N=C1Cl QQRJUWIHLNBDQF-UHFFFAOYSA-N 0.000 claims description 7
- 239000000460 chlorine Substances 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- 229910052739 hydrogen Inorganic materials 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- 150000007522 mineralic acids Chemical class 0.000 claims description 6
- 150000007524 organic acids Chemical class 0.000 claims description 6
- 235000005985 organic acids Nutrition 0.000 claims description 6
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 5
- 125000003277 amino group Chemical group 0.000 claims description 5
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 4
- 229910052794 bromium Inorganic materials 0.000 claims description 4
- 239000003795 chemical substances by application Substances 0.000 claims description 4
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 4
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 4
- HNVIQLPOGUDBSU-UHFFFAOYSA-N 2,6-dimethylmorpholine Chemical compound CC1CNCC(C)O1 HNVIQLPOGUDBSU-UHFFFAOYSA-N 0.000 claims description 3
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 3
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 125000004663 dialkyl amino group Chemical group 0.000 claims description 2
- 125000004573 morpholin-4-yl group Chemical group N1(CCOCC1)* 0.000 claims description 2
- XZUBILGXURZFHG-UHFFFAOYSA-N n-[6-chloro-2-(diethylamino)-5-methylsulfanylpyrimidin-4-yl]acetamide Chemical group CCN(CC)C1=NC(Cl)=C(SC)C(NC(C)=O)=N1 XZUBILGXURZFHG-UHFFFAOYSA-N 0.000 claims description 2
- 241000196324 Embryophyta Species 0.000 description 37
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 33
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 28
- 238000006243 chemical reaction Methods 0.000 description 23
- QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 18
- 239000002244 precipitate Substances 0.000 description 16
- 239000000047 product Substances 0.000 description 16
- 238000001914 filtration Methods 0.000 description 15
- 239000000243 solution Substances 0.000 description 15
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 11
- 238000002329 infrared spectrum Methods 0.000 description 11
- 235000007238 Secale cereale Nutrition 0.000 description 10
- 238000000655 nuclear magnetic resonance spectrum Methods 0.000 description 10
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
- WFDIJRYMOXRFFG-UHFFFAOYSA-N Acetic anhydride Chemical compound CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000003960 organic solvent Substances 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 6
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- GKIRPKYJQBWNGO-OCEACIFDSA-N clomifene Chemical compound C1=CC(OCCN(CC)CC)=CC=C1C(\C=1C=CC=CC=1)=C(\Cl)C1=CC=CC=C1 GKIRPKYJQBWNGO-OCEACIFDSA-N 0.000 description 6
- 230000006378 damage Effects 0.000 description 6
- 239000000706 filtrate Substances 0.000 description 6
- 238000002844 melting Methods 0.000 description 6
- 230000008018 melting Effects 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 5
- 238000002474 experimental method Methods 0.000 description 5
- 238000004949 mass spectrometry Methods 0.000 description 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 230000010933 acylation Effects 0.000 description 4
- 238000005917 acylation reaction Methods 0.000 description 4
- 239000007864 aqueous solution Substances 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 238000011156 evaluation Methods 0.000 description 4
- 238000004817 gas chromatography Methods 0.000 description 4
- 239000000155 melt Substances 0.000 description 4
- 239000011541 reaction mixture Substances 0.000 description 4
- 239000002689 soil Substances 0.000 description 4
- 239000002904 solvent Substances 0.000 description 4
- 239000000725 suspension Substances 0.000 description 4
- XGEKILUCSILUEW-UHFFFAOYSA-N 2,6-dichloro-n-ethyl-5-methylsulfanylpyrimidin-4-amine Chemical compound CCNC1=NC(Cl)=NC(Cl)=C1SC XGEKILUCSILUEW-UHFFFAOYSA-N 0.000 description 3
- GNTCSLONGFJXEG-UHFFFAOYSA-N 2-chloro-4-n-methyl-5-methylsulfanylpyrimidine-4,6-diamine Chemical compound CNC1=NC(Cl)=NC(N)=C1SC GNTCSLONGFJXEG-UHFFFAOYSA-N 0.000 description 3
- QBXCNNSODJPQAW-UHFFFAOYSA-N 4,6-dichloro-n-ethyl-5-methylsulfanylpyrimidin-2-amine Chemical compound CCNC1=NC(Cl)=C(SC)C(Cl)=N1 QBXCNNSODJPQAW-UHFFFAOYSA-N 0.000 description 3
- 241000743985 Alopecurus Species 0.000 description 3
- 240000005979 Hordeum vulgare Species 0.000 description 3
- 235000007340 Hordeum vulgare Nutrition 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 235000005775 Setaria Nutrition 0.000 description 3
- 241000232088 Setaria <nematode> Species 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 240000005592 Veronica officinalis Species 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 3
- KOCAZZKMEQPVSB-UHFFFAOYSA-N 2,4,6-trichloro-5-ethylsulfanylpyrimidine Chemical compound CCSC1=C(Cl)N=C(Cl)N=C1Cl KOCAZZKMEQPVSB-UHFFFAOYSA-N 0.000 description 2
- DDWBEROMBZXLNB-UHFFFAOYSA-N 2,4,6-trichloro-5-methylsulfanylpyrimidine Chemical compound CSC1=C(Cl)N=C(Cl)N=C1Cl DDWBEROMBZXLNB-UHFFFAOYSA-N 0.000 description 2
- DQGFHDMKKLPPCA-UHFFFAOYSA-N 2,6-dichloro-5-methylsulfanylpyrimidin-4-amine Chemical compound CSC1=C(N)N=C(Cl)N=C1Cl DQGFHDMKKLPPCA-UHFFFAOYSA-N 0.000 description 2
- JVKPTZKUDMSJBB-UHFFFAOYSA-N 2-chloro-4-n-ethyl-5-methylsulfanylpyrimidine-4,6-diamine Chemical compound CCNC1=NC(Cl)=NC(N)=C1SC JVKPTZKUDMSJBB-UHFFFAOYSA-N 0.000 description 2
- XMTQQYYKAHVGBJ-UHFFFAOYSA-N 3-(3,4-DICHLOROPHENYL)-1,1-DIMETHYLUREA Chemical compound CN(C)C(=O)NC1=CC=C(Cl)C(Cl)=C1 XMTQQYYKAHVGBJ-UHFFFAOYSA-N 0.000 description 2
- SRBYFAHJCYQXNV-UHFFFAOYSA-N 4,6-dichloro-n-methyl-5-methylsulfanylpyrimidin-2-amine Chemical compound CNC1=NC(Cl)=C(SC)C(Cl)=N1 SRBYFAHJCYQXNV-UHFFFAOYSA-N 0.000 description 2
- HFWAQKGJOUEQBB-UHFFFAOYSA-N 5-butylsulfanyl-2,4,6-trichloropyrimidine Chemical compound CCCCSC1=C(Cl)N=C(Cl)N=C1Cl HFWAQKGJOUEQBB-UHFFFAOYSA-N 0.000 description 2
- NUVUCPLQXPKFJS-UHFFFAOYSA-N 6-chloro-2-n-ethyl-5-methylsulfanylpyrimidine-2,4-diamine Chemical compound CCNC1=NC(N)=C(SC)C(Cl)=N1 NUVUCPLQXPKFJS-UHFFFAOYSA-N 0.000 description 2
- UKKVKXLZHGULLF-UHFFFAOYSA-N 6-chloro-2-n-methyl-5-methylsulfanylpyrimidine-2,4-diamine Chemical compound CNC1=NC(N)=C(SC)C(Cl)=N1 UKKVKXLZHGULLF-UHFFFAOYSA-N 0.000 description 2
- TZASLIRWZKXVEL-UHFFFAOYSA-N 6-chloro-4-n-ethyl-5-methylsulfanylpyrimidine-2,4-diamine Chemical compound CCNC1=NC(N)=NC(Cl)=C1SC TZASLIRWZKXVEL-UHFFFAOYSA-N 0.000 description 2
- OCACERDEHTWHGI-UHFFFAOYSA-N 6-chloro-5-methylsulfanyl-2-n-propan-2-ylpyrimidine-2,4-diamine Chemical compound CSC1=C(N)N=C(NC(C)C)N=C1Cl OCACERDEHTWHGI-UHFFFAOYSA-N 0.000 description 2
- SKWRMFIVLRFCCM-UHFFFAOYSA-N 6-chloro-5-methylsulfanyl-4-n-propan-2-ylpyrimidine-2,4-diamine Chemical compound CSC1=C(Cl)N=C(N)N=C1NC(C)C SKWRMFIVLRFCCM-UHFFFAOYSA-N 0.000 description 2
- 244000056139 Brassica cretica Species 0.000 description 2
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- 235000003343 Brassica rupestris Nutrition 0.000 description 2
- 241000217446 Calystegia sepium Species 0.000 description 2
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- 244000298479 Cichorium intybus Species 0.000 description 2
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- 238000005481 NMR spectroscopy Methods 0.000 description 2
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- 239000005631 2,4-Dichlorophenoxyacetic acid Substances 0.000 description 1
- HXKWSTRRCHTUEC-UHFFFAOYSA-N 2,4-Dichlorophenoxyaceticacid Chemical compound OC(=O)C(Cl)OC1=CC=C(Cl)C=C1 HXKWSTRRCHTUEC-UHFFFAOYSA-N 0.000 description 1
- KJDQJTUAGOWMNO-UHFFFAOYSA-N 2,6-dichloro-n-methyl-5-methylsulfanylpyrimidin-4-amine Chemical compound CNC1=NC(Cl)=NC(Cl)=C1SC KJDQJTUAGOWMNO-UHFFFAOYSA-N 0.000 description 1
- WNTGYJSOUMFZEP-UHFFFAOYSA-N 2-(4-chloro-2-methylphenoxy)propanoic acid Chemical compound OC(=O)C(C)OC1=CC=C(Cl)C=C1C WNTGYJSOUMFZEP-UHFFFAOYSA-N 0.000 description 1
- OWZPCEFYPSAJFR-UHFFFAOYSA-N 2-(butan-2-yl)-4,6-dinitrophenol Chemical compound CCC(C)C1=CC([N+]([O-])=O)=CC([N+]([O-])=O)=C1O OWZPCEFYPSAJFR-UHFFFAOYSA-N 0.000 description 1
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- 125000004189 3,4-dichlorophenyl group Chemical group [H]C1=C([H])C(Cl)=C(Cl)C([H])=C1* 0.000 description 1
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- WXZVAROIGSFCFJ-UHFFFAOYSA-N N,N-diethyl-2-(naphthalen-1-yloxy)propanamide Chemical compound C1=CC=C2C(OC(C)C(=O)N(CC)CC)=CC=CC2=C1 WXZVAROIGSFCFJ-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
- MKYBYDHXWVHEJW-UHFFFAOYSA-N N-[1-oxo-1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)propan-2-yl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(C(C)NC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 MKYBYDHXWVHEJW-UHFFFAOYSA-N 0.000 description 1
- 239000005585 Napropamide Substances 0.000 description 1
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- 229920002048 Pluronic® L 92 Polymers 0.000 description 1
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- 235000008930 Primula sp Nutrition 0.000 description 1
- 241000208476 Primulaceae Species 0.000 description 1
- RJKFOVLPORLFTN-LEKSSAKUSA-N Progesterone Chemical compound C1CC2=CC(=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H](C(=O)C)[C@@]1(C)CC2 RJKFOVLPORLFTN-LEKSSAKUSA-N 0.000 description 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 1
- 241001107098 Rubiaceae Species 0.000 description 1
- 241000220261 Sinapis Species 0.000 description 1
- 240000003768 Solanum lycopersicum Species 0.000 description 1
- 235000012480 Solanum sp Nutrition 0.000 description 1
- 240000006694 Stellaria media Species 0.000 description 1
- 244000032225 Stellaria sp Species 0.000 description 1
- NBQCNZYJJMBDKY-UHFFFAOYSA-N Terbacil Chemical compound CC=1NC(=O)N(C(C)(C)C)C(=O)C=1Cl NBQCNZYJJMBDKY-UHFFFAOYSA-N 0.000 description 1
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
- 244000213376 Veronica sp Species 0.000 description 1
- 235000009038 Veronica sp Nutrition 0.000 description 1
- 241000209149 Zea Species 0.000 description 1
- JAWMENYCRQKKJY-UHFFFAOYSA-N [3-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-ylmethyl)-1-oxa-2,8-diazaspiro[4.5]dec-2-en-8-yl]-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]methanone Chemical compound N1N=NC=2CN(CCC=21)CC1=NOC2(C1)CCN(CC2)C(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F JAWMENYCRQKKJY-UHFFFAOYSA-N 0.000 description 1
- 150000008065 acid anhydrides Chemical class 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 125000004414 alkyl thio group Chemical group 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 235000011114 ammonium hydroxide Nutrition 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000003963 antioxidant agent Substances 0.000 description 1
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- MXWJVTOOROXGIU-UHFFFAOYSA-N atrazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)C)=N1 MXWJVTOOROXGIU-UHFFFAOYSA-N 0.000 description 1
- 239000012752 auxiliary agent Substances 0.000 description 1
- HNYOPLTXPVRDBG-UHFFFAOYSA-N barbituric acid Chemical compound O=C1CC(=O)NC(=O)N1 HNYOPLTXPVRDBG-UHFFFAOYSA-N 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 238000006065 biodegradation reaction Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 235000013339 cereals Nutrition 0.000 description 1
- WYKYKTKDBLFHCY-UHFFFAOYSA-N chloridazon Chemical compound O=C1C(Cl)=C(N)C=NN1C1=CC=CC=C1 WYKYKTKDBLFHCY-UHFFFAOYSA-N 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 229940089960 chloroacetate Drugs 0.000 description 1
- JXCGFZXSOMJFOA-UHFFFAOYSA-N chlorotoluron Chemical compound CN(C)C(=O)NC1=CC=C(C)C(Cl)=C1 JXCGFZXSOMJFOA-UHFFFAOYSA-N 0.000 description 1
- 238000004587 chromatography analysis Methods 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 235000011655 cotton Nutrition 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- IWEDIXLBFLAXBO-UHFFFAOYSA-N dicamba Chemical compound COC1=C(Cl)C=CC(Cl)=C1C(O)=O IWEDIXLBFLAXBO-UHFFFAOYSA-N 0.000 description 1
- 238000010790 dilution Methods 0.000 description 1
- 239000012895 dilution Substances 0.000 description 1
- SYJFEGQWDCRVNX-UHFFFAOYSA-N diquat Chemical compound C1=CC=[N+]2CC[N+]3=CC=CC=C3C2=C1 SYJFEGQWDCRVNX-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- XXOYNJXVWVNOOJ-UHFFFAOYSA-N fenuron Chemical compound CN(C)C(=O)NC1=CC=CC=C1 XXOYNJXVWVNOOJ-UHFFFAOYSA-N 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 238000001640 fractional crystallisation Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- JJWLVOIRVHMVIS-UHFFFAOYSA-N isopropylamine Chemical compound CC(C)N JJWLVOIRVHMVIS-UHFFFAOYSA-N 0.000 description 1
- PUIYMUZLKQOUOZ-UHFFFAOYSA-N isoproturon Chemical compound CC(C)C1=CC=C(NC(=O)N(C)C)C=C1 PUIYMUZLKQOUOZ-UHFFFAOYSA-N 0.000 description 1
- 150000002561 ketenes Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- VHCNQEUWZYOAEV-UHFFFAOYSA-N metamitron Chemical compound O=C1N(N)C(C)=NN=C1C1=CC=CC=C1 VHCNQEUWZYOAEV-UHFFFAOYSA-N 0.000 description 1
- 239000002480 mineral oil Substances 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- BMLIZLVNXIYGCK-UHFFFAOYSA-N monuron Chemical compound CN(C)C(=O)NC1=CC=C(Cl)C=C1 BMLIZLVNXIYGCK-UHFFFAOYSA-N 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 description 1
- FIKAKWIAUPDISJ-UHFFFAOYSA-L paraquat dichloride Chemical compound [Cl-].[Cl-].C1=C[N+](C)=CC=C1C1=CC=[N+](C)C=C1 FIKAKWIAUPDISJ-UHFFFAOYSA-L 0.000 description 1
- 239000012071 phase Substances 0.000 description 1
- IDOWTHOLJBTAFI-UHFFFAOYSA-N phenmedipham Chemical compound COC(=O)NC1=CC=CC(OC(=O)NC=2C=C(C)C=CC=2)=C1 IDOWTHOLJBTAFI-UHFFFAOYSA-N 0.000 description 1
- NQQVFXUMIDALNH-UHFFFAOYSA-N picloram Chemical compound NC1=C(Cl)C(Cl)=NC(C(O)=O)=C1Cl NQQVFXUMIDALNH-UHFFFAOYSA-N 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 1
- 235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 1
- 238000004262 preparative liquid chromatography Methods 0.000 description 1
- 238000004321 preservation Methods 0.000 description 1
- BDERNNFJNOPAEC-UHFFFAOYSA-N propan-1-ol Chemical compound CCCO BDERNNFJNOPAEC-UHFFFAOYSA-N 0.000 description 1
- VXPLXMJHHKHSOA-UHFFFAOYSA-N propham Chemical compound CC(C)OC(=O)NC1=CC=CC=C1 VXPLXMJHHKHSOA-UHFFFAOYSA-N 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 description 1
- HBCQSNAFLVXVAY-UHFFFAOYSA-N pyrimidine-2-thiol Chemical compound SC1=NC=CC=N1 HBCQSNAFLVXVAY-UHFFFAOYSA-N 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 238000001953 recrystallisation Methods 0.000 description 1
- 235000009566 rice Nutrition 0.000 description 1
- 239000004576 sand Substances 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- ODCWYMIRDDJXKW-UHFFFAOYSA-N simazine Chemical compound CCNC1=NC(Cl)=NC(NCC)=N1 ODCWYMIRDDJXKW-UHFFFAOYSA-N 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- IROINLKCQGIITA-UHFFFAOYSA-N terbutryn Chemical compound CCNC1=NC(NC(C)(C)C)=NC(SC)=N1 IROINLKCQGIITA-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000004809 thin layer chromatography Methods 0.000 description 1
- 239000004563 wettable powder Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/47—One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/38—One sulfur atom
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/48—Two nitrogen atoms
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Dentistry (AREA)
- Wood Science & Technology (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Oxygen Or Sulfur (AREA)
- Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
- Nitrogen Condensed Heterocyclic Rings (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR7723222A FR2398737A1 (fr) | 1977-07-28 | 1977-07-28 | Amino-2 (ou -4) alkylthio-5 pyrimidines herbicides |
| FR7804207A FR2417507A2 (fr) | 1977-07-28 | 1978-02-15 | Diamino-2,4 (ou -4,6) methylthio-5 pyrimidines herbicides |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CS209533B2 true CS209533B2 (en) | 1981-12-31 |
Family
ID=26220145
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CS784948A CS209533B2 (en) | 1977-07-28 | 1978-07-25 | Herbicide means |
Country Status (24)
| Country | Link |
|---|---|
| US (1) | US4528026A (de) |
| EP (1) | EP0000681B1 (de) |
| JP (1) | JPS5427586A (de) |
| AT (2) | AT367044B (de) |
| AU (1) | AU520722B2 (de) |
| BR (1) | BR7804860A (de) |
| CA (1) | CA1116599A (de) |
| CS (1) | CS209533B2 (de) |
| DD (2) | DD147042A5 (de) |
| DE (1) | DE2860979D1 (de) |
| DK (1) | DK300578A (de) |
| ES (2) | ES472182A1 (de) |
| FR (1) | FR2417507A2 (de) |
| GR (1) | GR64849B (de) |
| HU (1) | HU182516B (de) |
| IE (1) | IE47879B1 (de) |
| IL (1) | IL55114A (de) |
| IN (1) | IN149476B (de) |
| IT (1) | IT1160555B (de) |
| NZ (1) | NZ187808A (de) |
| PL (2) | PL114968B1 (de) |
| PT (1) | PT68259A (de) |
| RO (3) | RO79383A (de) |
| YU (1) | YU40529B (de) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS5427580A (en) * | 1977-08-02 | 1979-03-01 | Mitsui Toatsu Chem Inc | Selective herbicides |
| FR2446597A2 (fr) * | 1979-01-16 | 1980-08-14 | Ugine Kuhlmann | Compositions herbicides a base de diamino-2,4 chloro-6 methylthio-5 pyrimidine et de neburon |
| FR2449403A2 (fr) * | 1979-02-23 | 1980-09-19 | Ugine Kuhlmann | Procede de traitement herbicide du sorgho utilisant la diamino-2,4 chloro-6 methylthio-5 pyrimidine |
| FR2459234A1 (fr) * | 1979-06-20 | 1981-01-09 | Ugine Kuhlmann | Hydrazino (ou azido) alkylthio-5 pyrimidines, leurs procedes de preparation et leurs utilisations comme pesticides |
| US4560402A (en) * | 1979-08-15 | 1985-12-24 | Ciba Geigy Corporation | 2,4-Diamo-5-(alkylsulfinyl) or alkylsulphonyl)-6-halopyrimidines |
| FR2467201A1 (fr) * | 1979-10-09 | 1981-04-17 | Ugine Kuhlmann | Alkylsulfinyl-5 pyrimidines, leur procede de preparation et leurs utilisations comme herbicides |
| FR2474279A1 (fr) * | 1980-01-29 | 1981-07-31 | Ugine Kuhlmann | Compositions herbicides a base de diamino-2,4 chloro-6 methylthio pyrimidine et de diclofop methyl et procede de traitement des cultures a l'aide desdites compositions |
| FR2503162A1 (fr) * | 1981-04-07 | 1982-10-08 | Pharmindustrie | Nouveaux derives de piperazino-2 pyrimidine, procedes pour leur preparation et leur utilisation comme medicaments ou comme intermediaires pour la fabrication de medicaments |
| FR2509135A1 (fr) * | 1981-07-10 | 1983-01-14 | Ugine Kuhlmann | Compositions herbicides a base de derives d'amino-4 chloro-6 alkylthio-5 pyrimidine et de derives de la dinitro-2,6 aniline et procede de traitement des cultures a l'aide desdites compositions |
| EP0078623A1 (de) * | 1981-10-29 | 1983-05-11 | Fbc Limited | Benazolin enthaltende herbizide Mischungen |
| FR2516748A1 (fr) * | 1981-11-24 | 1983-05-27 | Ugine Kuhlmann | Compositions herbicides a base de derives d'amino-4 chloro-6 alkylthio-5 pyrimidine et de pyridate, et procede de traitement des cultures a l'aide desdites compositions |
| US4507146A (en) * | 1982-12-28 | 1985-03-26 | Ciba-Geigy Corporation | 2,4-Diamino-6-halo-5-trifluoromethylpyrimidines having herbicidal activity |
| DE3305524A1 (de) * | 1983-02-18 | 1984-08-23 | Celamerck Gmbh & Co Kg, 6507 Ingelheim | Neue pyrimidinderivate |
| DE3417264A1 (de) * | 1984-05-10 | 1985-11-14 | Bayer Ag, 5090 Leverkusen | Neue 2,4-diamino-6-halogen-5-alkylthio-pyrimidine |
| DE3504895A1 (de) * | 1985-02-13 | 1986-08-14 | Basf Ag, 6700 Ludwigshafen | 4-aminopyrimidine und diese enthaltende fungizide |
Family Cites Families (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2257294B1 (de) * | 1973-07-06 | 1977-07-01 | Ugine Kuhlmann | |
| US3892554A (en) * | 1969-02-14 | 1975-07-01 | Sandoz Ltd | 2-Amino-4-isopropylamino-6-chloro-pyrimidine in maize, wheat, potatoes, onions and leeks |
| FR2119234A5 (en) * | 1970-12-24 | 1972-08-04 | Ugine Kuhlmann | 5-alkylthio amino halopyrimidines - fungicides herbicides insecticides and bactericides |
| US3926997A (en) * | 1971-05-17 | 1975-12-16 | Ciba Geigy Corp | 2-Alkylthio-4,6-bis(substituted amino)-5-nitropyrimidines |
| FR2173746B1 (de) * | 1972-03-01 | 1975-04-25 | Ugine Kuhlmann | |
| FR2244520B1 (de) * | 1973-07-06 | 1977-02-04 | Ugine Kuhlmann | |
| US3906953A (en) * | 1974-05-23 | 1975-09-23 | American Optical Corp | Endoscopic surgical laser system |
| GB1523274A (en) * | 1974-08-05 | 1978-08-31 | Ici Ltd | Herbicidal compositions containing substituted pyrimidine |
| FR2281117A2 (fr) * | 1974-08-09 | 1976-03-05 | Ugine Kuhlmann | Nouvelles piperazino-pyrimidines utilisables comme medicaments |
| US4166852A (en) * | 1974-08-09 | 1979-09-04 | Produits Chimiques Ugine Kuhlmann | Piperazino-pyrimidines and their use as spasmolytic agents |
| FR2311776A1 (fr) * | 1975-05-23 | 1976-12-17 | Sogeras | Diamino-2,4 bromo-5 chloro-6 pyrimidines et procede pour leur preparation |
| CH617833A5 (de) * | 1975-07-07 | 1980-06-30 | Ciba Geigy Ag | |
| JPS6053023B2 (ja) * | 1977-01-25 | 1985-11-22 | 三井東圧化学株式会社 | 選択性殺草剤 |
| JPS5427580A (en) * | 1977-08-02 | 1979-03-01 | Mitsui Toatsu Chem Inc | Selective herbicides |
-
1978
- 1978-02-15 FR FR7804207A patent/FR2417507A2/fr active Granted
- 1978-07-03 DK DK300578A patent/DK300578A/da not_active Application Discontinuation
- 1978-07-06 PT PT68259A patent/PT68259A/pt unknown
- 1978-07-07 NZ NZ187808A patent/NZ187808A/xx unknown
- 1978-07-10 IL IL55114A patent/IL55114A/xx unknown
- 1978-07-17 AT AT0516378A patent/AT367044B/de not_active IP Right Cessation
- 1978-07-21 DE DE7878400062T patent/DE2860979D1/de not_active Expired
- 1978-07-21 EP EP78400062A patent/EP0000681B1/de not_active Expired
- 1978-07-25 RO RO78100777A patent/RO79383A/ro unknown
- 1978-07-25 RO RO7894775A patent/RO75259A/ro unknown
- 1978-07-25 RO RO78100776A patent/RO79382A/ro unknown
- 1978-07-25 CS CS784948A patent/CS209533B2/cs unknown
- 1978-07-26 PL PL1978215527A patent/PL114968B1/pl unknown
- 1978-07-26 PL PL1978208647A patent/PL111645B1/pl unknown
- 1978-07-26 GR GR56866A patent/GR64849B/el unknown
- 1978-07-26 JP JP9140278A patent/JPS5427586A/ja active Pending
- 1978-07-26 YU YU1786/78A patent/YU40529B/xx unknown
- 1978-07-27 AU AU38393/78A patent/AU520722B2/en not_active Expired
- 1978-07-27 CA CA000308242A patent/CA1116599A/fr not_active Expired
- 1978-07-27 BR BR7804860A patent/BR7804860A/pt unknown
- 1978-07-28 ES ES472182A patent/ES472182A1/es not_active Expired
- 1978-07-28 DD DD78216615A patent/DD147042A5/de unknown
- 1978-07-28 HU HU78KU535A patent/HU182516B/hu unknown
- 1978-07-28 IE IE1533/78A patent/IE47879B1/en unknown
- 1978-07-28 DD DD78207005A patent/DD140040A5/de unknown
- 1978-07-28 IT IT68803/78A patent/IT1160555B/it active
- 1978-08-28 IN IN632/DEL/78A patent/IN149476B/en unknown
-
1979
- 1979-04-17 ES ES479668A patent/ES479668A1/es not_active Expired
-
1980
- 1980-09-30 US US06/192,564 patent/US4528026A/en not_active Expired - Lifetime
-
1981
- 1981-02-02 AT AT0046181A patent/AT368137B/de not_active IP Right Cessation
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