BG105071A - Заместени 2, 4-диамино- 1, 3, 5- триазини, метод за тяхното получаване и тяхната употреба като хербициди и регулатори на растежа на растения - Google Patents

Заместени 2, 4-диамино- 1, 3, 5- триазини, метод за тяхното получаване и тяхната употреба като хербициди и регулатори на растежа на растения Download PDF

Info

Publication number: BG105071A
Authority: BG; Bulgaria
Prior art keywords: group; alkyl; halogen; alkoxy; different
Prior art date: 1998-06-26

Application number

BG105071A

Other languages

Bulgarian (bg)

English (en)

Inventor

Jens Hollander

Lothar Willms

Juergen Zindel

Klemens Minn

Wolfgang Giencke

Christopher Rosinger

Thomas Auler

Hermann Bieringer

Original Assignee

Aventis Cropscience Gmbh

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.)

1998-06-26

Filing date

2000-12-20

Publication date

2001-10-31

2000-12-20 Application filed by Aventis Cropscience Gmbh filed Critical Aventis Cropscience Gmbh

2001-10-31 Publication of BG105071A publication Critical patent/BG105071A/bg

Links

239000004009 herbicide Substances 0.000 title claims abstract description 18
238000000034 method Methods 0.000 title claims abstract description 17
VZXTWGWHSMCWGA-UHFFFAOYSA-N 1,3,5-triazine-2,4-diamine Chemical class NC1=NC=NC(N)=N1 VZXTWGWHSMCWGA-UHFFFAOYSA-N 0.000 title abstract description 9
238000004519 manufacturing process Methods 0.000 title abstract description 4
239000005648 plant growth regulator Substances 0.000 title abstract description 4
125000003118 aryl group Chemical group 0.000 claims abstract description 42
150000003839 salts Chemical class 0.000 claims abstract description 35
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 163
150000001875 compounds Chemical class 0.000 claims description 118
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 110
-1 acyclic hydrocarbon Chemical class 0.000 claims description 108
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 107
229910052760 oxygen Inorganic materials 0.000 claims description 106
239000001301 oxygen Substances 0.000 claims description 105
125000005843 halogen group Chemical group 0.000 claims description 103
229910052739 hydrogen Inorganic materials 0.000 claims description 85
229910052757 nitrogen Inorganic materials 0.000 claims description 85
239000001257 hydrogen Substances 0.000 claims description 84
125000005842 heteroatom Chemical group 0.000 claims description 80
125000004093 cyano group Chemical group *C#N 0.000 claims description 78
229910052736 halogen Inorganic materials 0.000 claims description 72
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 72
125000004432 carbon atom Chemical group C* 0.000 claims description 64
125000004122 cyclic group Chemical group 0.000 claims description 60
150000002367 halogens Chemical class 0.000 claims description 60
125000000623 heterocyclic group Chemical group 0.000 claims description 54
125000004354 sulfur functional group Chemical group 0.000 claims description 53
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 52
229910052717 sulfur Inorganic materials 0.000 claims description 52
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 50
239000011593 sulfur Substances 0.000 claims description 50
125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 44
125000004169 (C1-C6) alkyl group Chemical group 0.000 claims description 40
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 40
125000006413 ring segment Chemical group 0.000 claims description 40
229910052799 carbon Inorganic materials 0.000 claims description 32
ZMZDMBWJUHKJPS-UHFFFAOYSA-M thiocyanate group Chemical group [S-]C#N ZMZDMBWJUHKJPS-UHFFFAOYSA-M 0.000 claims description 31
150000002431 hydrogen Chemical class 0.000 claims description 30
125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 29
239000000203 mixture Substances 0.000 claims description 28
UUEVFMOUBSLVJW-UHFFFAOYSA-N oxo-[[1-[2-[2-[2-[4-(oxoazaniumylmethylidene)pyridin-1-yl]ethoxy]ethoxy]ethyl]pyridin-4-ylidene]methyl]azanium;dibromide Chemical compound [Br-].[Br-].C1=CC(=C[NH+]=O)C=CN1CCOCCOCCN1C=CC(=C[NH+]=O)C=C1 UUEVFMOUBSLVJW-UHFFFAOYSA-N 0.000 claims description 27
239000002253 acid Substances 0.000 claims description 25
125000004429 atom Chemical group 0.000 claims description 24
125000004399 C1-C4 alkenyl group Chemical group 0.000 claims description 23
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 23
125000006650 (C2-C4) alkynyl group Chemical group 0.000 claims description 22
125000005913 (C3-C6) cycloalkyl group Chemical group 0.000 claims description 22
125000000217 alkyl group Chemical group 0.000 claims description 21
150000001721 carbon Chemical group 0.000 claims description 21
125000003282 alkyl amino group Chemical group 0.000 claims description 18
230000012010 growth Effects 0.000 claims description 18
125000000008 (C1-C10) alkyl group Chemical group 0.000 claims description 17
125000000753 cycloalkyl group Chemical group 0.000 claims description 17
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 16
238000009472 formulation Methods 0.000 claims description 16
230000009261 transgenic effect Effects 0.000 claims description 16
239000000460 chlorine Substances 0.000 claims description 15
230000002363 herbicidal effect Effects 0.000 claims description 15
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 15
125000003342 alkenyl group Chemical group 0.000 claims description 14
125000003545 alkoxy group Chemical group 0.000 claims description 14
125000004433 nitrogen atom Chemical group N* 0.000 claims description 14
125000004390 alkyl sulfonyl group Chemical group 0.000 claims description 12
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 12
238000002360 preparation method Methods 0.000 claims description 12
125000004448 alkyl carbonyl group Chemical group 0.000 claims description 11
150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 11
239000003795 chemical substances by application Substances 0.000 claims description 11
125000004663 dialkyl amino group Chemical group 0.000 claims description 11
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
125000006552 (C3-C8) cycloalkyl group Chemical group 0.000 claims description 10
125000004414 alkyl thio group Chemical group 0.000 claims description 10
229910052801 chlorine Inorganic materials 0.000 claims description 10
125000000000 cycloalkoxy group Chemical group 0.000 claims description 10
125000002485 formyl group Chemical group [H]C(*)=O 0.000 claims description 10
125000004191 (C1-C6) alkoxy group Chemical group 0.000 claims description 9
125000000304 alkynyl group Chemical group 0.000 claims description 9
125000003277 amino group Chemical group 0.000 claims description 9
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 8
PIGFYZPCRLYGLF-UHFFFAOYSA-N Aluminum nitride Chemical compound [Al]#N PIGFYZPCRLYGLF-UHFFFAOYSA-N 0.000 claims description 7
125000003601 C2-C6 alkynyl group Chemical group 0.000 claims description 7
125000003302 alkenyloxy group Chemical group 0.000 claims description 7
125000004397 aminosulfonyl group Chemical group NS(=O)(=O)* 0.000 claims description 7
230000006378 damage Effects 0.000 claims description 7
230000008635 plant growth Effects 0.000 claims description 7
125000004769 (C1-C4) alkylsulfonyl group Chemical group 0.000 claims description 6
125000006625 (C3-C8) cycloalkyloxy group Chemical group 0.000 claims description 6
125000000882 C2-C6 alkenyl group Chemical group 0.000 claims description 6
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 6
125000002950 monocyclic group Chemical group 0.000 claims description 6
229920000180 alkyd Polymers 0.000 claims description 5
229910052740 iodine Inorganic materials 0.000 claims description 5
125000001624 naphthyl group Chemical group 0.000 claims description 5
230000001105 regulatory effect Effects 0.000 claims description 5
125000002015 acyclic group Chemical group 0.000 claims description 4
125000004644 alkyl sulfinyl group Chemical group 0.000 claims description 4
125000005133 alkynyloxy group Chemical group 0.000 claims description 4
229930195733 hydrocarbon Natural products 0.000 claims description 4
125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims description 4
125000003866 trichloromethyl group Chemical group ClC(Cl)(Cl)* 0.000 claims description 4
125000000027 (C1-C10) alkoxy group Chemical group 0.000 claims description 3
125000004768 (C1-C4) alkylsulfinyl group Chemical group 0.000 claims description 3
125000004890 (C1-C6) alkylamino group Chemical group 0.000 claims description 3
125000006768 (C3-C9) cycloalkoxy group Chemical group 0.000 claims description 3
239000004215 Carbon black (E152) Substances 0.000 claims description 3
125000004457 alkyl amino carbonyl group Chemical group 0.000 claims description 3
150000001412 amines Chemical class 0.000 claims description 3
125000000852 azido group Chemical group *N=[N+]=[N-] 0.000 claims description 3
125000000524 functional group Chemical group 0.000 claims description 3
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 3
125000000168 pyrrolyl group Chemical group 0.000 claims description 3
SNOOUWRIMMFWNE-UHFFFAOYSA-M sodium;6-[(3,4,5-trimethoxybenzoyl)amino]hexanoate Chemical compound [Na+].COC1=CC(C(=O)NCCCCCC([O-])=O)=CC(OC)=C1OC SNOOUWRIMMFWNE-UHFFFAOYSA-M 0.000 claims description 3
125000004750 (C1-C6) alkylaminosulfonyl group Chemical group 0.000 claims description 2
125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 2
125000006376 (C3-C10) cycloalkyl group Chemical group 0.000 claims description 2
125000006374 C2-C10 alkenyl group Chemical group 0.000 claims description 2
PFRUBEOIWWEFOL-UHFFFAOYSA-N [N].[S] Chemical group [N].[S] PFRUBEOIWWEFOL-UHFFFAOYSA-N 0.000 claims description 2
125000004442 acylamino group Chemical group 0.000 claims description 2
125000000499 benzofuranyl group Chemical group O1C(=CC2=C1C=CC=C2)* 0.000 claims description 2
230000033228 biological regulation Effects 0.000 claims description 2
150000001244 carboxylic acid anhydrides Chemical class 0.000 claims description 2
125000003262 carboxylic acid ester group Chemical group [H]C([H])([*:2])OC(=O)C([H])([H])[*:1] 0.000 claims description 2
125000002541 furyl group Chemical group 0.000 claims description 2
125000005844 heterocyclyloxy group Chemical group 0.000 claims description 2
125000002883 imidazolyl group Chemical group 0.000 claims description 2
125000002092 orthoester group Chemical group 0.000 claims description 2
125000001715 oxadiazolyl group Chemical group 0.000 claims description 2
125000002971 oxazolyl group Chemical group 0.000 claims description 2
125000004076 pyridyl group Chemical group 0.000 claims description 2
125000000335 thiazolyl group Chemical group 0.000 claims description 2
125000001544 thienyl group Chemical group 0.000 claims description 2
125000006621 (C3-C8) cycloalkyl-(C1-C6) alkyl group Chemical group 0.000 claims 3
244000045561 useful plants Species 0.000 claims 3
125000004916 (C1-C6) alkylcarbonyl group Chemical group 0.000 claims 2
125000006700 (C1-C6) alkylthio group Chemical group 0.000 claims 1
125000004648 C2-C8 alkenyl group Chemical group 0.000 claims 1
125000004649 C2-C8 alkynyl group Chemical group 0.000 claims 1
230000000735 allogeneic effect Effects 0.000 claims 1
125000001183 hydrocarbyl group Chemical group 0.000 claims 1
150000003918 triazines Chemical class 0.000 abstract 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 339
125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 168
229920005989 resin Polymers 0.000 description 159
239000011347 resin Substances 0.000 description 159
125000001995 cyclobutyl group Chemical group [H]C1([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 153
125000001559 cyclopropyl group Chemical group [H]C1([H])C([H])([H])C1([H])* 0.000 description 151
235000014121 butter Nutrition 0.000 description 95
206010007559 Cardiac failure congestive Diseases 0.000 description 83
238000009563 continuous hemofiltration Methods 0.000 description 83
241000196324 Embryophyta Species 0.000 description 73
125000006414 CCl Chemical group ClC* 0.000 description 59
125000001309 chloro group Chemical group Cl* 0.000 description 48
125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 description 40
239000002904 solvent Substances 0.000 description 24
239000013543 active substance Substances 0.000 description 23
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 21
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 21
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 18
239000000843 powder Substances 0.000 description 18
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 17
239000008187 granular material Substances 0.000 description 16
239000002585 base Substances 0.000 description 15
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 15
238000006243 chemical reaction Methods 0.000 description 14
150000002148 esters Chemical class 0.000 description 14
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 14
239000000126 substance Substances 0.000 description 14
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 13
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 12
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 12
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 12
239000003960 organic solvent Substances 0.000 description 11
239000002689 soil Substances 0.000 description 11
239000007921 spray Substances 0.000 description 11
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 10
108090000623 proteins and genes Proteins 0.000 description 10
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 9
150000004679 hydroxides Chemical class 0.000 description 9
125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 9
240000007594 Oryza sativa Species 0.000 description 8
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 8
238000009835 boiling Methods 0.000 description 8
150000004649 carbonic acid derivatives Chemical class 0.000 description 8
239000000543 intermediate Substances 0.000 description 8
239000003921 oil Substances 0.000 description 8
125000001424 substituent group Chemical group 0.000 description 8
238000012360 testing method Methods 0.000 description 8
YLQBMQCUIZJEEH-UHFFFAOYSA-N Furan Chemical compound C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 7
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 7
235000007164 Oryza sativa Nutrition 0.000 description 7
239000003513 alkali Substances 0.000 description 7
230000000694 effects Effects 0.000 description 7
239000000839 emulsion Substances 0.000 description 7
235000009566 rice Nutrition 0.000 description 7
239000011734 sodium Substances 0.000 description 7
229910052708 sodium Inorganic materials 0.000 description 7
125000000876 trifluoromethoxy group Chemical group FC(F)(F)O* 0.000 description 7
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 6
230000002378 acidificating effect Effects 0.000 description 6
MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 6
239000012141 concentrate Substances 0.000 description 6
239000004495 emulsifiable concentrate Substances 0.000 description 6
229910052731 fluorine Inorganic materials 0.000 description 6
150000002430 hydrocarbons Chemical group 0.000 description 6
241000894007 species Species 0.000 description 6
108020004414 DNA Proteins 0.000 description 5
150000007513 acids Chemical class 0.000 description 5
125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 5
239000000969 carrier Substances 0.000 description 5
239000004927 clay Substances 0.000 description 5
239000003995 emulsifying agent Substances 0.000 description 5
150000004678 hydrides Chemical class 0.000 description 5
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 5
239000000047 product Substances 0.000 description 5
238000010992 reflux Methods 0.000 description 5
229920006395 saturated elastomer Polymers 0.000 description 5
239000000243 solution Substances 0.000 description 5
239000004094 surface-active agent Substances 0.000 description 5
239000004562 water dispersible granule Substances 0.000 description 5
RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 4
244000075850 Avena orientalis Species 0.000 description 4
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 4
IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 4
SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 4
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
239000003054 catalyst Substances 0.000 description 4
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 4
239000006185 dispersion Substances 0.000 description 4
239000011737 fluorine Substances 0.000 description 4
125000001188 haloalkyl group Chemical group 0.000 description 4
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 4
238000002156 mixing Methods 0.000 description 4
150000007530 organic bases Chemical class 0.000 description 4
239000000575 pesticide Substances 0.000 description 4
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 4
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 4
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239000007787 solid Substances 0.000 description 4
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
MDBGGTQNNUOQRC-UHFFFAOYSA-N Allidochlor Chemical compound ClCC(=O)N(CC=C)CC=C MDBGGTQNNUOQRC-UHFFFAOYSA-N 0.000 description 3
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BMTAFVWTTFSTOG-UHFFFAOYSA-N Butylate Chemical group CCSC(=O)N(CC(C)C)CC(C)C BMTAFVWTTFSTOG-UHFFFAOYSA-N 0.000 description 3
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235000021536 Sugar beet Nutrition 0.000 description 3
XJCLWVXTCRQIDI-UHFFFAOYSA-N Sulfallate Chemical compound CCN(CC)C(=S)SCC(Cl)=C XJCLWVXTCRQIDI-UHFFFAOYSA-N 0.000 description 3
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229910000095 alkaline earth hydride Inorganic materials 0.000 description 3
235000012211 aluminium silicate Nutrition 0.000 description 3
KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
239000002270 dispersing agent Substances 0.000 description 3
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125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
239000003337 fertilizer Substances 0.000 description 3
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238000005469 granulation Methods 0.000 description 3
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125000004438 haloalkoxy group Chemical group 0.000 description 3
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
229910052943 magnesium sulfate Inorganic materials 0.000 description 3
235000019341 magnesium sulphate Nutrition 0.000 description 3
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VIJMMQUAJQEELS-UHFFFAOYSA-N n,n-bis(ethenyl)ethenamine Chemical compound C=CN(C=C)C=C VIJMMQUAJQEELS-UHFFFAOYSA-N 0.000 description 3
150000002825 nitriles Chemical class 0.000 description 3
230000003287 optical effect Effects 0.000 description 3
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125000006763 (C3-C9) cycloalkyl group Chemical group 0.000 description 2
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125000003226 pyrazolyl group Chemical group 0.000 description 1
VTRWMTJQBQJKQH-UHFFFAOYSA-N pyributicarb Chemical compound COC1=CC=CC(N(C)C(=S)OC=2C=C(C=CC=2)C(C)(C)C)=N1 VTRWMTJQBQJKQH-UHFFFAOYSA-N 0.000 description 1
PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 description 1
125000002098 pyridazinyl group Chemical group 0.000 description 1
125000000714 pyrimidinyl group Chemical group 0.000 description 1
229910052903 pyrophyllite Inorganic materials 0.000 description 1
239000010453 quartz Substances 0.000 description 1
JWVCLYRUEFBMGU-UHFFFAOYSA-N quinazoline Chemical compound N1=CN=CC2=CC=CC=C21 JWVCLYRUEFBMGU-UHFFFAOYSA-N 0.000 description 1
FFSSWMQPCJRCRV-UHFFFAOYSA-N quinclorac Chemical compound ClC1=CN=C2C(C(=O)O)=C(Cl)C=CC2=C1 FFSSWMQPCJRCRV-UHFFFAOYSA-N 0.000 description 1
ALZOLUNSQWINIR-UHFFFAOYSA-N quinmerac Chemical compound OC(=O)C1=C(Cl)C=CC2=CC(C)=CN=C21 ALZOLUNSQWINIR-UHFFFAOYSA-N 0.000 description 1
BACHBFVBHLGWSL-JTQLQIEISA-N rac-diclofop methyl Natural products C1=CC(O[C@@H](C)C(=O)OC)=CC=C1OC1=CC=C(Cl)C=C1Cl BACHBFVBHLGWSL-JTQLQIEISA-N 0.000 description 1
230000006798 recombination Effects 0.000 description 1
238000005215 recombination Methods 0.000 description 1
238000011160 research Methods 0.000 description 1
108091092562 ribozyme Proteins 0.000 description 1
229960004889 salicylic acid Drugs 0.000 description 1
239000004576 sand Substances 0.000 description 1
229930195734 saturated hydrocarbon Natural products 0.000 description 1
DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
238000000926 separation method Methods 0.000 description 1
230000035939 shock Effects 0.000 description 1
ODCWYMIRDDJXKW-UHFFFAOYSA-N simazine Chemical compound CCNC1=NC(Cl)=NC(NCC)=N1 ODCWYMIRDDJXKW-UHFFFAOYSA-N 0.000 description 1
235000019333 sodium laurylsulphate Nutrition 0.000 description 1
NNMHYFLPFNGQFZ-UHFFFAOYSA-M sodium polyacrylate Chemical compound [Na+].[O-]C(=O)C=C NNMHYFLPFNGQFZ-UHFFFAOYSA-M 0.000 description 1
238000007711 solidification Methods 0.000 description 1
230000008023 solidification Effects 0.000 description 1
239000004550 soluble concentrate Substances 0.000 description 1
239000004334 sorbic acid Substances 0.000 description 1
235000010199 sorbic acid Nutrition 0.000 description 1
229940075582 sorbic acid Drugs 0.000 description 1
238000001179 sorption measurement Methods 0.000 description 1
238000001228 spectrum Methods 0.000 description 1
238000001694 spray drying Methods 0.000 description 1
238000003892 spreading Methods 0.000 description 1
230000007480 spreading Effects 0.000 description 1
238000010186 staining Methods 0.000 description 1
238000010561 standard procedure Methods 0.000 description 1
239000007858 starting material Substances 0.000 description 1
230000003068 static effect Effects 0.000 description 1
230000000707 stereoselective effect Effects 0.000 description 1
238000003756 stirring Methods 0.000 description 1
BUUPQKDIAURBJP-UHFFFAOYSA-N sulfinic acid Chemical compound OS=O BUUPQKDIAURBJP-UHFFFAOYSA-N 0.000 description 1
150000003460 sulfonic acids Chemical class 0.000 description 1
YROXIXLRRCOBKF-UHFFFAOYSA-N sulfonylurea Chemical group OC(=N)N=S(=O)=O YROXIXLRRCOBKF-UHFFFAOYSA-N 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
229960001367 tartaric acid Drugs 0.000 description 1
RJKCKKDSSSRYCB-UHFFFAOYSA-N tebutam Chemical compound CC(C)(C)C(=O)N(C(C)C)CC1=CC=CC=C1 RJKCKKDSSSRYCB-UHFFFAOYSA-N 0.000 description 1
FZXISNSWEXTPMF-UHFFFAOYSA-N terbutylazine Chemical compound CCNC1=NC(Cl)=NC(NC(C)(C)C)=N1 FZXISNSWEXTPMF-UHFFFAOYSA-N 0.000 description 1
125000005247 tetrazinyl group Chemical group N1=NN=NC(=C1)* 0.000 description 1
125000004525 thiadiazinyl group Chemical group S1NN=C(C=C1)* 0.000 description 1
SRVJKTDHMYAMHA-WUXMJOGZSA-N thioacetazone Chemical compound CC(=O)NC1=CC=C(\C=N\NC(N)=S)C=C1 SRVJKTDHMYAMHA-WUXMJOGZSA-N 0.000 description 1
229960003231 thioacetazone Drugs 0.000 description 1
150000003566 thiocarboxylic acids Chemical class 0.000 description 1
125000005031 thiocyano group Chemical group S(C#N)* 0.000 description 1
229930192474 thiophene Natural products 0.000 description 1
231100000765 toxin Toxicity 0.000 description 1
108700012359 toxins Proteins 0.000 description 1
XOPFESVZMSQIKC-UHFFFAOYSA-N triasulfuron Chemical compound COC1=NC(C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2)OCCCl)=N1 XOPFESVZMSQIKC-UHFFFAOYSA-N 0.000 description 1
125000004306 triazinyl group Chemical group 0.000 description 1
125000001425 triazolyl group Chemical group 0.000 description 1
YMXOXAPKZDWXLY-QWRGUYRKSA-N tribenuron methyl Chemical group COC(=O)[C@H]1CCCC[C@@H]1S(=O)(=O)NC(=O)N(C)C1=NC(C)=NC(OC)=N1 YMXOXAPKZDWXLY-QWRGUYRKSA-N 0.000 description 1
REEQLXCGVXDJSQ-UHFFFAOYSA-N trichlopyr Chemical compound OC(=O)COC1=NC(Cl)=C(Cl)C=C1Cl REEQLXCGVXDJSQ-UHFFFAOYSA-N 0.000 description 1
ZSDSQXJSNMTJDA-UHFFFAOYSA-N trifluralin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(C(F)(F)F)C=C1[N+]([O-])=O ZSDSQXJSNMTJDA-UHFFFAOYSA-N 0.000 description 1
AKTQJCBOGPBERP-UHFFFAOYSA-N triflusulfuron Chemical compound FC(F)(F)COC1=NC(N(C)C)=NC(NC(=O)NS(=O)(=O)C=2C(=CC=CC=2C)C(O)=O)=N1 AKTQJCBOGPBERP-UHFFFAOYSA-N 0.000 description 1
IMEVJVISCHQJRM-UHFFFAOYSA-N triflusulfuron-methyl Chemical compound COC(=O)C1=CC=CC(C)=C1S(=O)(=O)NC(=O)NC1=NC(OCC(F)(F)F)=NC(N(C)C)=N1 IMEVJVISCHQJRM-UHFFFAOYSA-N 0.000 description 1
125000004953 trihalomethyl group Chemical group 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
238000005406 washing Methods 0.000 description 1
239000001993 wax Substances 0.000 description 1
238000001238 wet grinding Methods 0.000 description 1
239000004563 wettable powder Substances 0.000 description 1
239000002023 wood Substances 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- 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
- A01N43/64—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with three nitrogen atoms as the only ring hetero atoms
- A01N43/66—1,3,5-Triazines, not hydrogenated and not substituted at the ring nitrogen atoms
- A01N43/68—1,3,5-Triazines, not hydrogenated and not substituted at the ring nitrogen atoms with two or three nitrogen atoms directly attached to ring carbon atoms
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
- C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
- C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
- C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
- C07D251/16—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to only one ring carbon atom
- C07D251/18—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to only one ring carbon atom with nitrogen atoms directly attached to the two other ring carbon atoms, e.g. guanamines

Landscapes

Life Sciences & Earth Sciences (AREA)
Organic Chemistry (AREA)
Chemical & Material 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)
Plural Heterocyclic Compounds (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

BG105071A 1998-06-26 2000-12-20 Заместени 2, 4-диамино- 1, 3, 5- триазини, метод за тяхното получаване и тяхната употреба като хербициди и регулатори на растежа на растения BG105071A (bg)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
DE19828519A DE19828519A1 (de)	1998-06-26	1998-06-26	Substituierte 2,4-Diamino-1,3,5-triazine, Verfahren zu ihrer Herstellung und ihre Verwendung als Herbizide und Pflanzenwachstumsregulatoren
PCT/EP1999/003987 WO2000000480A1 (de)	1998-06-26	1999-06-10	Substituierte 2,4-diamino-1,3,5-triazine, verfahren zu ihrer herstellung und ihre verwendung als herbizide und pflanzenwachstumsregulatoren

Publications (1)

Publication Number	Publication Date
BG105071A true BG105071A (bg)	2001-10-31

Family

ID=7872111

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
BG105071A BG105071A (bg)	1998-06-26	2000-12-20	Заместени 2, 4-диамино- 1, 3, 5- триазини, метод за тяхното получаване и тяхната употреба като хербициди и регулатори на растежа на растения

Country Status (19)

Country	Link
US (1)	US20030186817A1 (id)
EP (1)	EP1089983A1 (id)
JP (1)	JP2002519345A (id)
KR (1)	KR20010053222A (id)
CN (1)	CN1306519A (id)
AR (1)	AR019874A1 (id)
AU (1)	AU4771099A (id)
BG (1)	BG105071A (id)
BR (1)	BR9912219A (id)
CA (1)	CA2336057A1 (id)
DE (1)	DE19828519A1 (id)
HU (1)	HUP0102832A3 (id)
ID (1)	ID29562A (id)
IL (1)	IL140474A0 (id)
PL (1)	PL345277A1 (id)
SK (1)	SK20152000A3 (id)
TR (1)	TR200003607T2 (id)
WO (1)	WO2000000480A1 (id)
ZA (1)	ZA200006520B (id)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE19842894A1 (de) *	1998-09-18	2000-03-23	Hoechst Schering Agrevo Gmbh	Synergistische Wirkstoffkombinationen zur Bekämpfung von Schadpflanzen in Nutzpflanzenkulturen
DE10135043A1 (de) *	2001-07-11	2003-01-30	Bayer Cropscience Gmbh	Substituierte 3-Heteroaryl(amino- oder oxy)-pyrrolidin-2-one, Verfahren zu deren Herstellung und Verwendung als Herbizide oder als Pflanzenwachstumsregulatoren
EP1836894A1 (de)	2006-03-25	2007-09-26	Bayer CropScience GmbH	Neue Sulfonamid-haltige feste Formulungen
EP1790227A1 (de)	2005-11-25	2007-05-30	Bayer CropScience AG	Wässrige Suspensionskonzentrate aus 2,4-Diamino-s-triazinherbiziden
EP1844654A1 (de)	2006-03-29	2007-10-17	Bayer CropScience GmbH	Penetrationsförderer für agrochemische Wirkstoffe
DE102007013362A1 (de)	2007-03-16	2008-09-18	Bayer Cropscience Ag	Penetrationsförderer für herbizide Wirkstoffe
WO2011076731A1 (de)	2009-12-23	2011-06-30	Bayer Cropscience Ag	Flüssige formulierung von 2-iodo-n-[(4-methoxy-6-methyl-1,3,5-triazin-2-yl)carbamoyl] benzolsulfonamid
CN103641781B (zh) *	2013-12-26	2015-02-18	青岛科技大学	一种萘二甲酰胺类化合物及其盐作为植物生长调节剂的应用

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CA2027562C (en) *	1989-02-20	1994-05-10	Masahiro Nishii	Triazine derivative and a herbicide comprising the same as an effective ingredient
JP3029545B2 (ja) *	1995-02-17	2000-04-04	出光興産株式会社	トリアジン誘導体
DE19522137A1 (de) *	1995-06-19	1997-01-02	Hoechst Schering Agrevo Gmbh	2-Amino-1,3,5-triazine, Verfahren zu deren Herstellung und deren Verwendung als Herbizide und Pflanzenwachstumsregulatoren
DE19641691A1 (de) *	1996-10-10	1998-04-16	Bayer Ag	Substituierte 2-Amino-4-alkylamino-1,3,5-triazine
DE19755016A1 (de) *	1997-12-11	1999-06-17	Bayer Ag	Substituierte 2,4-Diamino-1,3,5-triazine

1998
- 1998-06-26 DE DE19828519A patent/DE19828519A1/de not_active Withdrawn
1999
- 1999-06-10 PL PL99345277A patent/PL345277A1/xx unknown
- 1999-06-10 BR BR9912219-7A patent/BR9912219A/pt not_active IP Right Cessation
- 1999-06-10 TR TR2000/03607T patent/TR200003607T2/xx unknown
- 1999-06-10 WO PCT/EP1999/003987 patent/WO2000000480A1/de not_active Ceased
- 1999-06-10 CN CN99807683A patent/CN1306519A/zh active Pending
- 1999-06-10 JP JP2000557241A patent/JP2002519345A/ja active Pending
- 1999-06-10 EP EP99931049A patent/EP1089983A1/de not_active Withdrawn
- 1999-06-10 IL IL14047499A patent/IL140474A0/xx unknown
- 1999-06-10 ID IDW20002589A patent/ID29562A/id unknown
- 1999-06-10 AU AU47710/99A patent/AU4771099A/en not_active Abandoned
- 1999-06-10 HU HU0102832A patent/HUP0102832A3/hu unknown
- 1999-06-10 CA CA002336057A patent/CA2336057A1/en not_active Abandoned
- 1999-06-10 KR KR1020007014835A patent/KR20010053222A/ko not_active Withdrawn
- 1999-06-10 SK SK2015-2000A patent/SK20152000A3/sk unknown
- 1999-06-24 AR ARP990103038A patent/AR019874A1/es not_active Application Discontinuation
- 1999-06-25 US US09/344,603 patent/US20030186817A1/en not_active Abandoned
2000
- 2000-11-10 ZA ZA200006520A patent/ZA200006520B/xx unknown
- 2000-12-20 BG BG105071A patent/BG105071A/bg unknown

Also Published As

Publication number	Publication date
AR019874A1 (es)	2002-03-20
CN1306519A (zh)	2001-08-01
PL345277A1 (en)	2001-12-03
JP2002519345A (ja)	2002-07-02
CA2336057A1 (en)	2000-01-06
SK20152000A3 (sk)	2001-06-11
AU4771099A (en)	2000-01-17
TR200003607T2 (tr)	2001-04-20
WO2000000480A1 (de)	2000-01-06
ZA200006520B (en)	2001-07-05
US20030186817A1 (en)	2003-10-02
HUP0102832A2 (hu)	2001-11-28
HUP0102832A3 (en)	2002-03-28
BR9912219A (pt)	2001-04-24
ID29562A (id)	2001-09-06
IL140474A0 (en)	2002-02-10
KR20010053222A (ko)	2001-06-25
DE19828519A1 (de)	1999-12-30
EP1089983A1 (de)	2001-04-11

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