DD257380A5 - Herbizide mittel - Google Patents

Herbizide mittel Download PDF

Info

Publication number: DD257380A5
Authority: DD; German Democratic Republic
Prior art keywords: alkyl; formula; atoms; diamino; substituted
Prior art date: 1986-01-22

Application number

DD87299359A

Other languages

German (de)

English (en)

Inventor

Michael Schwamborn

Erich Klauke

Robert R Schmidt

Hans-Joachim Santel

Robert H Strang

Original Assignee

��@��k��

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.)

1986-01-22

Filing date

1987-01-20

Publication date

1988-06-15

1987-01-20 Application filed by ��@��k�� filed Critical ��@��k��

1988-06-15 Publication of DD257380A5 publication Critical patent/DD257380A5/de

Links

230000002363 herbicidal effect Effects 0.000 title claims abstract description 11
239000004009 herbicide Substances 0.000 title claims abstract description 9
241000196324 Embryophyta Species 0.000 claims abstract description 31
239000000203 mixture Substances 0.000 claims abstract description 21
239000004480 active ingredient Substances 0.000 claims abstract description 16
239000004606 Fillers/Extenders Substances 0.000 claims abstract description 6
239000013543 active substance Substances 0.000 claims abstract description 4
125000004432 carbon atom Chemical group C* 0.000 claims description 30
229910052739 hydrogen Inorganic materials 0.000 claims description 25
239000001257 hydrogen Substances 0.000 claims description 25
125000000217 alkyl group Chemical group 0.000 claims description 19
238000000034 method Methods 0.000 claims description 16
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 13
125000004414 alkyl thio group Chemical group 0.000 claims description 12
150000002431 hydrogen Chemical class 0.000 claims description 12
238000002360 preparation method Methods 0.000 claims description 12
125000003545 alkoxy group Chemical group 0.000 claims description 11
125000006350 alkyl thio alkyl group Chemical group 0.000 claims description 8
239000000460 chlorine Chemical group 0.000 claims description 8
125000004183 alkoxy alkyl group Chemical group 0.000 claims description 7
229910052801 chlorine Inorganic materials 0.000 claims description 7
229910052731 fluorine Inorganic materials 0.000 claims description 6
239000011737 fluorine Substances 0.000 claims description 6
125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims description 6
125000000304 alkynyl group Chemical group 0.000 claims description 5
229910052736 halogen Inorganic materials 0.000 claims description 5
150000002367 halogens Chemical group 0.000 claims description 5
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical group [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 4
125000001309 chloro group Chemical group Cl* 0.000 claims description 4
125000004093 cyano group Chemical group *C#N 0.000 claims description 4
125000000753 cycloalkyl group Chemical group 0.000 claims description 4
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 claims description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 2
229910052794 bromium Inorganic materials 0.000 claims description 2
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 2
125000004970 halomethyl group Chemical group 0.000 claims description 2
238000002156 mixing Methods 0.000 claims description 2
125000001153 fluoro group Chemical group F* 0.000 claims 3
239000011814 protection agent Substances 0.000 claims 1
150000003230 pyrimidines Chemical class 0.000 abstract description 15
-1 for example Chemical class 0.000 abstract description 14
229940083082 pyrimidine derivative acting on arteriolar smooth muscle Drugs 0.000 abstract description 11
239000000126 substance Substances 0.000 abstract description 6
QQRJUWIHLNBDQF-UHFFFAOYSA-N 6-chloro-5-methylsulfanylpyrimidine-2,4-diamine Chemical compound CSC1=C(N)N=C(N)N=C1Cl QQRJUWIHLNBDQF-UHFFFAOYSA-N 0.000 abstract description 3
244000038559 crop plants Species 0.000 abstract description 2
239000002837 defoliant Substances 0.000 abstract description 2
239000002274 desiccant Substances 0.000 abstract description 2
CLKVACSLYCATTN-UHFFFAOYSA-N 6-chloro-4-n-cyclopropyl-2-n-(3-methoxypropyl)pyrimidine-2,4-diamine Chemical compound COCCCNC1=NC(Cl)=CC(NC2CC2)=N1 CLKVACSLYCATTN-UHFFFAOYSA-N 0.000 abstract 1
241000269420 Bufonidae Species 0.000 abstract 1
150000001875 compounds Chemical class 0.000 description 28
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
239000002253 acid Substances 0.000 description 8
150000001412 amines Chemical class 0.000 description 8
241000219146 Gossypium Species 0.000 description 7
238000009472 formulation Methods 0.000 description 7
239000002904 solvent Substances 0.000 description 7
239000007858 starting material Substances 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
229920000742 Cotton Polymers 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 6
230000006378 damage Effects 0.000 description 6
239000003995 emulsifying agent Substances 0.000 description 6
FKSSZHRRUUZKCM-UHFFFAOYSA-N 2,4-difluoro-6-(trifluoromethyl)pyrimidine Chemical compound FC1=CC(C(F)(F)F)=NC(F)=N1 FKSSZHRRUUZKCM-UHFFFAOYSA-N 0.000 description 5
239000011230 binding agent Substances 0.000 description 5
239000008187 granular material Substances 0.000 description 5
239000003960 organic solvent Substances 0.000 description 5
239000013558 reference substance Substances 0.000 description 5
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical group FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 4
241000209094 Oryza Species 0.000 description 4
241000209149 Zea Species 0.000 description 4
239000003085 diluting agent Substances 0.000 description 4
230000000694 effects Effects 0.000 description 4
229910052500 inorganic mineral Inorganic materials 0.000 description 4
239000000843 powder Substances 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
239000002689 soil Substances 0.000 description 4
FAXDZWQIWUSWJH-UHFFFAOYSA-N 3-methoxypropan-1-amine Chemical compound COCCCN FAXDZWQIWUSWJH-UHFFFAOYSA-N 0.000 description 3
241000219312 Chenopodium Species 0.000 description 3
HTJDQJBWANPRPF-UHFFFAOYSA-N Cyclopropylamine Chemical compound NC1CC1 HTJDQJBWANPRPF-UHFFFAOYSA-N 0.000 description 3
241000208296 Datura Species 0.000 description 3
241001101998 Galium Species 0.000 description 3
235000021506 Ipomoea Nutrition 0.000 description 3
241000207783 Ipomoea Species 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
235000007164 Oryza sativa Nutrition 0.000 description 3
241000209117 Panicum Species 0.000 description 3
235000006443 Panicum miliaceum subsp. miliaceum Nutrition 0.000 description 3
235000009037 Panicum miliaceum subsp. ruderale Nutrition 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 description 3
235000005775 Setaria Nutrition 0.000 description 3
241000232088 Setaria <nematode> Species 0.000 description 3
241000207763 Solanum Species 0.000 description 3
235000002634 Solanum Nutrition 0.000 description 3
240000006394 Sorghum bicolor Species 0.000 description 3
241000209140 Triticum Species 0.000 description 3
235000021307 Triticum Nutrition 0.000 description 3
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 3
235000002017 Zea mays subsp mays Nutrition 0.000 description 3
150000007513 acids Chemical class 0.000 description 3
125000002877 alkyl aryl group Chemical group 0.000 description 3
239000000969 carrier Substances 0.000 description 3
239000012141 concentrate Substances 0.000 description 3
235000005822 corn Nutrition 0.000 description 3
239000000839 emulsion Substances 0.000 description 3
229920000151 polyglycol Polymers 0.000 description 3
239000010695 polyglycol Substances 0.000 description 3
235000009566 rice Nutrition 0.000 description 3
239000007787 solid Substances 0.000 description 3
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
ODNBVEIAQAZNNM-UHFFFAOYSA-N 1-(6-chloroimidazo[1,2-b]pyridazin-3-yl)ethanone Chemical compound C1=CC(Cl)=NN2C(C(=O)C)=CN=C21 ODNBVEIAQAZNNM-UHFFFAOYSA-N 0.000 description 2
ZTNFYAJHLPMNSN-UHFFFAOYSA-N 2,4-dichloro-6-(trifluoromethyl)pyrimidine Chemical compound FC(F)(F)C1=CC(Cl)=NC(Cl)=N1 ZTNFYAJHLPMNSN-UHFFFAOYSA-N 0.000 description 2
HMWXCSCBUXKXSA-UHFFFAOYSA-N 2-propoxyethanamine Chemical compound CCCOCCN HMWXCSCBUXKXSA-UHFFFAOYSA-N 0.000 description 2
UTOXFQVLOTVLSD-UHFFFAOYSA-N 3-propoxypropan-1-amine Chemical compound CCCOCCCN UTOXFQVLOTVLSD-UHFFFAOYSA-N 0.000 description 2
XTSJDLYPECYTDK-UHFFFAOYSA-N 4-chloro-5-(difluoromethyl)-2,6-difluoropyrimidine Chemical compound FC(F)C1=C(F)N=C(F)N=C1Cl XTSJDLYPECYTDK-UHFFFAOYSA-N 0.000 description 2
OSFFLVBIKMCIHS-UHFFFAOYSA-N 4-n-cyclopropyl-2-n-(3-methoxypropyl)-6-(trifluoromethyl)pyrimidine-2,4-diamine Chemical compound FC(F)(F)C1=NC(NCCCOC)=NC(NC2CC2)=C1 OSFFLVBIKMCIHS-UHFFFAOYSA-N 0.000 description 2
241000219144 Abutilon Species 0.000 description 2
VVJKKWFAADXIJK-UHFFFAOYSA-N Allylamine Chemical compound NCC=C VVJKKWFAADXIJK-UHFFFAOYSA-N 0.000 description 2
241000219318 Amaranthus Species 0.000 description 2
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
GUNJVIDCYZYFGV-UHFFFAOYSA-K Antimony trifluoride Inorganic materials F[Sb](F)F GUNJVIDCYZYFGV-UHFFFAOYSA-K 0.000 description 2
235000005781 Avena Nutrition 0.000 description 2
244000075850 Avena orientalis Species 0.000 description 2
241000339490 Brachyachne Species 0.000 description 2
244000192528 Chrysanthemum parthenium Species 0.000 description 2
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
241000192043 Echinochloa Species 0.000 description 2
QUSNBJAOOMFDIB-UHFFFAOYSA-N Ethylamine Chemical compound CCN QUSNBJAOOMFDIB-UHFFFAOYSA-N 0.000 description 2
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
DHMQDGOQFOQNFH-UHFFFAOYSA-N Glycine Chemical compound NCC(O)=O DHMQDGOQFOQNFH-UHFFFAOYSA-N 0.000 description 2
240000005979 Hordeum vulgare Species 0.000 description 2
235000007340 Hordeum vulgare Nutrition 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical class [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
235000017945 Matricaria Nutrition 0.000 description 2
235000007232 Matricaria chamomilla Nutrition 0.000 description 2
RRVIAQKBTUQODI-UHFFFAOYSA-N Methabenzthiazuron Chemical compound C1=CC=C2SC(N(C)C(=O)NC)=NC2=C1 RRVIAQKBTUQODI-UHFFFAOYSA-N 0.000 description 2
BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 2
LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
241000209048 Poa Species 0.000 description 2
229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
241000219295 Portulaca Species 0.000 description 2
235000011684 Sorghum saccharatum Nutrition 0.000 description 2
240000006694 Stellaria media Species 0.000 description 2
150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
VMPVEPPRYRXYNP-UHFFFAOYSA-I antimony(5+);pentachloride Chemical compound Cl[Sb](Cl)(Cl)(Cl)Cl VMPVEPPRYRXYNP-UHFFFAOYSA-I 0.000 description 2
125000004429 atom Chemical group 0.000 description 2
238000009835 boiling Methods 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
239000002270 dispersing agent Substances 0.000 description 2
238000001035 drying Methods 0.000 description 2
239000000975 dye Substances 0.000 description 2
235000013399 edible fruits Nutrition 0.000 description 2
150000002170 ethers Chemical class 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
238000000605 extraction Methods 0.000 description 2
239000005457 ice water Substances 0.000 description 2
239000007788 liquid Substances 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
VHCNQEUWZYOAEV-UHFFFAOYSA-N metamitron Chemical compound O=C1N(N)C(C)=NN=C1C1=CC=CC=C1 VHCNQEUWZYOAEV-UHFFFAOYSA-N 0.000 description 2
FOXFZRUHNHCZPX-UHFFFAOYSA-N metribuzin Chemical compound CSC1=NN=C(C(C)(C)C)C(=O)N1N FOXFZRUHNHCZPX-UHFFFAOYSA-N 0.000 description 2
239000011707 mineral Substances 0.000 description 2
239000002480 mineral oil Substances 0.000 description 2
RSXJYJMFIXTVGF-UHFFFAOYSA-N n-cyclopropyl-2-fluoro-6-(trifluoromethyl)pyrimidin-4-amine Chemical compound FC(F)(F)C1=NC(F)=NC(NC2CC2)=C1 RSXJYJMFIXTVGF-UHFFFAOYSA-N 0.000 description 2
229910052757 nitrogen Inorganic materials 0.000 description 2
235000015097 nutrients Nutrition 0.000 description 2
239000012074 organic phase Substances 0.000 description 2
239000006072 paste Substances 0.000 description 2
FDPIMTJIUBPUKL-UHFFFAOYSA-N pentan-3-one Chemical compound CCC(=O)CC FDPIMTJIUBPUKL-UHFFFAOYSA-N 0.000 description 2
WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 2
150000003254 radicals Chemical class 0.000 description 2
238000010992 reflux Methods 0.000 description 2
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 2
239000000243 solution Substances 0.000 description 2
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125000001424 substituent group Chemical class 0.000 description 2
125000005017 substituted alkenyl group Chemical group 0.000 description 2
239000000725 suspension Substances 0.000 description 2
235000015112 vegetable and seed oil Nutrition 0.000 description 2
239000008158 vegetable oil Substances 0.000 description 2
RMDZWDVPOIBMBE-UHFFFAOYSA-N 1,2,2-trimethyl-4,6-dioxo-5-[1-(prop-2-enoxyamino)butylidene]cyclohexane-1-carboxylic acid Chemical compound C=CCONC(CCC)=C1C(=O)CC(C)(C)C(C)(C(O)=O)C1=O RMDZWDVPOIBMBE-UHFFFAOYSA-N 0.000 description 1
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
KOKBUARVIJVMMM-UHFFFAOYSA-N 1-amino-3-(2,2-dimethylpropyl)-6-ethylsulfanyl-1,3,5-triazine-2,4-dione Chemical compound CCSC1=NC(=O)N(CC(C)(C)C)C(=O)N1N KOKBUARVIJVMMM-UHFFFAOYSA-N 0.000 description 1
XDIAMRVROCPPBK-UHFFFAOYSA-N 2,2-dimethylpropan-1-amine Chemical compound CC(C)(C)CN XDIAMRVROCPPBK-UHFFFAOYSA-N 0.000 description 1
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
BQKYJHPMOHHVBV-UHFFFAOYSA-N 2,4-difluoro-6-(trichloromethyl)pyrimidine Chemical compound FC1=CC(C(Cl)(Cl)Cl)=NC(F)=N1 BQKYJHPMOHHVBV-UHFFFAOYSA-N 0.000 description 1
MZHCENGPTKEIGP-UHFFFAOYSA-N 2-(2,4-dichlorophenoxy)propanoic acid Chemical compound OC(=O)C(C)OC1=CC=C(Cl)C=C1Cl MZHCENGPTKEIGP-UHFFFAOYSA-N 0.000 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
GOCUAJYOYBLQRH-UHFFFAOYSA-N 2-(4-{[3-chloro-5-(trifluoromethyl)pyridin-2-yl]oxy}phenoxy)propanoic acid Chemical compound C1=CC(OC(C)C(O)=O)=CC=C1OC1=NC=C(C(F)(F)F)C=C1Cl GOCUAJYOYBLQRH-UHFFFAOYSA-N 0.000 description 1
BLMLZYILSIZQTL-UHFFFAOYSA-N 2-[(2-methylpropan-2-yl)oxy]ethanamine Chemical compound CC(C)(C)OCCN BLMLZYILSIZQTL-UHFFFAOYSA-N 0.000 description 1
QGCCAYANMAYUCD-UHFFFAOYSA-N 2-[4-(2,4-dichlorobenzoyl)-2,5-dimethylpyrazol-3-yl]-4-methylbenzenesulfonic acid Chemical compound CC1=NN(C)C(C=2C(=CC=C(C)C=2)S(O)(=O)=O)=C1C(=O)C1=CC=C(Cl)C=C1Cl QGCCAYANMAYUCD-UHFFFAOYSA-N 0.000 description 1
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BPGIOCZAQDIBPI-UHFFFAOYSA-N 2-ethoxyethanamine Chemical compound CCOCCN BPGIOCZAQDIBPI-UHFFFAOYSA-N 0.000 description 1
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BZCSKDXOXIUCSS-UHFFFAOYSA-N 3-[(2-methylpropan-2-yl)oxy]propan-1-amine Chemical compound CC(C)(C)OCCCN BZCSKDXOXIUCSS-UHFFFAOYSA-N 0.000 description 1
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HJELPNLGHMWKQT-UHFFFAOYSA-N 3-methoxy-n-methylpropan-1-amine Chemical compound CNCCCOC HJELPNLGHMWKQT-UHFFFAOYSA-N 0.000 description 1
KKYSBGWCYXYOHA-UHFFFAOYSA-N 3-methylthiopropylamine Chemical compound CSCCCN KKYSBGWCYXYOHA-UHFFFAOYSA-N 0.000 description 1
YGVDXISEDHSVNH-UHFFFAOYSA-N 4-[(2-methylpropan-2-yl)oxy]butan-2-amine Chemical compound CC(N)CCOC(C)(C)C YGVDXISEDHSVNH-UHFFFAOYSA-N 0.000 description 1
AJJOSOWJKOVQLM-UHFFFAOYSA-N 4-[[4-chloro-6-(ethylamino)-1,3,5-triazin-2-yl]amino]butanenitrile Chemical compound CCNC1=NC(Cl)=NC(NCCCC#N)=N1 AJJOSOWJKOVQLM-UHFFFAOYSA-N 0.000 description 1
LEVGELDCDWLKTD-UHFFFAOYSA-N 4-ethoxybutan-2-amine Chemical compound CCOCCC(C)N LEVGELDCDWLKTD-UHFFFAOYSA-N 0.000 description 1
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241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 1
ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical compound [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 1
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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
- C07D239/30—Halogen atoms or nitro radicals
- 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
- 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

Landscapes

Organic Chemistry (AREA)
Chemical & Material Sciences (AREA)
Life Sciences & Earth Sciences (AREA)
Health & Medical Sciences (AREA)
Plant Pathology (AREA)
Engineering & Computer Science (AREA)
Dentistry (AREA)
General Health & Medical Sciences (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Environmental Sciences (AREA)
Pest Control & Pesticides (AREA)
Agronomy & Crop Science (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Plural Heterocyclic Compounds (AREA)
Low-Molecular Organic Synthesis Reactions Using Catalysts (AREA)

DD87299359A 1986-01-22 1987-01-20 Herbizide mittel DD257380A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19863601800 DE3601800A1 (de)	1986-01-22	1986-01-22	Neue 2,4-diamino-6-halogenalkylpyrimidine

Publications (1)

Publication Number	Publication Date
DD257380A5 true DD257380A5 (de)	1988-06-15

Family

ID=6292362

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD87299359A DD257380A5 (de)	1986-01-22	1987-01-20	Herbizide mittel

Country Status (11)

Country	Link
US (1)	US4877443A (da)
EP (1)	EP0230244A3 (da)
JP (1)	JPS62178572A (da)
KR (1)	KR870007136A (da)
BR (1)	BR8700289A (da)
DD (1)	DD257380A5 (da)
DE (1)	DE3601800A1 (da)
DK (1)	DK32487A (da)
HU (1)	HUT42758A (da)
IL (1)	IL81293A0 (da)
ZA (1)	ZA87428B (da)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE4123525A1 (de) *	1991-07-16	1993-01-21	Basf Ag	Substituierte pyrimidinderivate und ihre verwendung zur bekaempfung unerwuenschten pflanzenwuchses
US5665644A (en) *	1995-11-03	1997-09-09	Micron Technology, Inc.	Semiconductor processing method of forming electrically conductive interconnect lines and integrated circuitry
CN113061116B (zh) *	2020-01-02	2023-07-25	上海医药工业研究院	一种氨基嘧啶化合物、其制备方法、组合物及应用

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US3284188A (en) *	1963-04-12	1966-11-08	Toyo Koatsu Ind Inc	Method and composition for suppressing the nitrification of ammonium nitrogen in soil
US4025515A (en) *	1969-02-14	1977-05-24	Sandoz Ltd.	6-Chloro-2,4-diaminopyrimidines
CH512187A (de) *	1969-02-14	1971-09-15	Sandoz Ag	Herbizides Mittel
GB1523274A (en) *	1974-08-05	1978-08-31	Ici Ltd	Herbicidal compositions containing substituted pyrimidine
CH617833A5 (da) *	1975-07-07	1980-06-30	Ciba Geigy Ag
EP0111440A1 (en) *	1982-10-15	1984-06-20	Ciba-Geigy Ag	2-Aminopyrimidines, their production and use
DE3445293A1 (de) *	1984-12-12	1986-06-12	Bayer Ag, 5090 Leverkusen	Neue 2,4-diaminopyrimidine

1986
- 1986-01-22 DE DE19863601800 patent/DE3601800A1/de not_active Withdrawn
1987
- 1987-01-12 EP EP87100289A patent/EP0230244A3/de not_active Withdrawn
- 1987-01-13 US US07/002,881 patent/US4877443A/en not_active Expired - Fee Related
- 1987-01-19 IL IL81293A patent/IL81293A0/xx unknown
- 1987-01-20 DD DD87299359A patent/DD257380A5/de not_active IP Right Cessation
- 1987-01-21 JP JP62010114A patent/JPS62178572A/ja active Pending
- 1987-01-21 DK DK032487A patent/DK32487A/da not_active Application Discontinuation
- 1987-01-21 ZA ZA87428A patent/ZA87428B/xx unknown
- 1987-01-21 HU HU87177A patent/HUT42758A/hu unknown
- 1987-01-21 KR KR870000452A patent/KR870007136A/ko not_active Withdrawn
- 1987-01-22 BR BR8700289A patent/BR8700289A/pt unknown

Also Published As

Publication number	Publication date
IL81293A0 (en)	1987-08-31
US4877443A (en)	1989-10-31
EP0230244A2 (de)	1987-07-29
EP0230244A3 (de)	1988-03-23
BR8700289A (pt)	1987-12-08
JPS62178572A (ja)	1987-08-05
ZA87428B (en)	1987-09-30
KR870007136A (ko)	1987-08-17
HUT42758A (en)	1987-08-28
DK32487A (da)	1987-07-23
DK32487D0 (da)	1987-01-21
DE3601800A1 (de)	1987-07-23

Legal Events

Date	Code	Title	Description
1994-01-27	PJ	Ceased due to non-payment of renewal fee (addendum to changes before extension act)

Publication	Publication Date	Title
EP0137358A2 (de)	1985-04-17	1,3-Diaryl-5-methylen-perhydropyrimidin-2-one
EP0184752A2 (de)	1986-06-18	Neue 2,4-Diaminopyrimidine
EP0173958A2 (de)	1986-03-12	1-(2-Oxyaminocarbonylphenylsulfonyl)-3-heteroaryl-harnstoffe
EP0173312A1 (de)	1986-03-05	1-(2-Trifluormethoxy-phenylsulfonyl)-3-heteroaryl-(thio)-harnstoffe
DD257380A5 (de)	1988-06-15	Herbizide mittel
EP0173320A1 (de)	1986-03-05	Substituierte Carbonylphenylsulfonylguanidine
EP0173322B1 (de)	1988-12-28	(1-(2-Oxyaminosulfonylphenylsulfonyl)-3-heteroaryl-harnstoffe
DE3431916A1 (de)	1986-03-13	Fluoralkoxyphenylsulfonylguanidine
EP0173319A1 (de)	1986-03-05	Substituierte Arylsulfonylguanidine
EP0332963A1 (de)	1989-09-20	Pyrimidin-Derivate
EP0217038B1 (de)	1989-06-07	Benzo-[b]-1,4,5,7-dithiadiazepin-1,1,4,4-tetraoxydderivate
EP0173323A1 (de)	1986-03-05	Amidinoazole
EP0254183A2 (de)	1988-01-27	Neue 2,4-Diaminopyrimidine
DE4022478A1 (de)	1992-01-16	Nicotinsaeurederivate
DE3431933A1 (de)	1986-03-06	Heteroarylthioharnstoffe
DE3539994A1 (de)	1987-05-14	Herbizide mittel enthaltend photosynthesehemmer-herbizide in kombination mit harnstoffderivaten
DE3431913A1 (de)	1986-03-13	Oxyguanidin-derivate
DE3528100A1 (de)	1987-02-19	1-(2-oxyaminosulfonylphenylsulfonyl) -3-triazinyl-harnstoffe
DE3626860A1 (de)	1988-02-11	Acylierte 1-(2-oxyaminosulfonylphenylsulfonyl)-3-heteroaryl-harnstoffe
EP0236829A2 (de)	1987-09-16	2-Trifluormethyl-5-pyrimidinyloxy-phenyl-harnstoffe und ein Verfahren zu ihrer Herstellung
DE3601801A1 (de)	1987-07-23	Herbizide mittel
EP0264021A2 (de)	1988-04-20	0-Aryl-N'-(triazin-2-yl)-isoharnstoffe
EP0289927A2 (de)	1988-11-09	Herbizide Mittel
DD237780A5 (de)	1986-07-30	Herbizide mittel
DE3510785A1 (de)	1986-09-25	4-formylamino-6-t-butyl-1,2,4-triazin-5-one