NL8400732A - N-pyridylpyrazoolderivaten, werkwijze voor het bereiden daarvan, deze derivaten bevattende herbicidepreparaten en werkwijze voor het bestrijden van onkruid daarmee. - Google Patents
N-pyridylpyrazoolderivaten, werkwijze voor het bereiden daarvan, deze derivaten bevattende herbicidepreparaten en werkwijze voor het bestrijden van onkruid daarmee. Download PDFInfo
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- NL8400732A NL8400732A NL8400732A NL8400732A NL8400732A NL 8400732 A NL8400732 A NL 8400732A NL 8400732 A NL8400732 A NL 8400732A NL 8400732 A NL8400732 A NL 8400732A NL 8400732 A NL8400732 A NL 8400732A
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- 238000002360 preparation method Methods 0.000 title claims description 50
- 238000000034 method Methods 0.000 title claims description 23
- XXTPHXNBKRVYJI-UHFFFAOYSA-N 2-pyrazol-1-ylpyridine Chemical class C1=CC=NN1C1=CC=CC=N1 XXTPHXNBKRVYJI-UHFFFAOYSA-N 0.000 title claims description 19
- 150000001875 compounds Chemical class 0.000 claims description 307
- 125000004432 carbon atom Chemical group C* 0.000 claims description 208
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 112
- 125000000217 alkyl group Chemical group 0.000 claims description 98
- -1 trifluoromethylpyrid-2-yl Chemical group 0.000 claims description 83
- 238000006243 chemical reaction Methods 0.000 claims description 56
- 241000196324 Embryophyta Species 0.000 claims description 53
- 125000003545 alkoxy group Chemical group 0.000 claims description 51
- 239000000203 mixture Substances 0.000 claims description 41
- 125000003342 alkenyl group Chemical group 0.000 claims description 40
- 125000000304 alkynyl group Chemical group 0.000 claims description 39
- 229910052783 alkali metal Inorganic materials 0.000 claims description 38
- 150000001340 alkali metals Chemical class 0.000 claims description 35
- 230000002363 herbicidal effect Effects 0.000 claims description 34
- 229910052757 nitrogen Inorganic materials 0.000 claims description 30
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 25
- 239000004009 herbicide Substances 0.000 claims description 22
- 150000003839 salts Chemical class 0.000 claims description 22
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 21
- 239000002585 base Substances 0.000 claims description 19
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 18
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 18
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 17
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 17
- 239000003085 diluting agent Substances 0.000 claims description 17
- 125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 14
- 125000003277 amino group Chemical group 0.000 claims description 14
- 229910052801 chlorine Inorganic materials 0.000 claims description 13
- 239000004094 surface-active agent Substances 0.000 claims description 13
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 12
- 125000005843 halogen group Chemical group 0.000 claims description 12
- 125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 11
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 10
- 229910052799 carbon Inorganic materials 0.000 claims description 9
- 239000000460 chlorine Substances 0.000 claims description 9
- 125000001424 substituent group Chemical group 0.000 claims description 9
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 8
- WFDIJRYMOXRFFG-UHFFFAOYSA-N acetic acid anhydride Natural products CC(=O)OC(C)=O WFDIJRYMOXRFFG-UHFFFAOYSA-N 0.000 claims description 7
- 125000004429 atom Chemical group 0.000 claims description 7
- 239000000969 carrier Substances 0.000 claims description 7
- 238000003898 horticulture Methods 0.000 claims description 7
- 125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- 125000002947 alkylene group Chemical group 0.000 claims description 6
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 6
- IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 6
- 229910000041 hydrogen chloride Inorganic materials 0.000 claims description 6
- 230000007062 hydrolysis Effects 0.000 claims description 6
- 238000006460 hydrolysis reaction Methods 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 6
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 claims description 5
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 5
- 125000005091 alkenylcarbonylamino group Chemical group 0.000 claims description 5
- 125000004450 alkenylene group Chemical group 0.000 claims description 5
- 125000004419 alkynylene group Chemical group 0.000 claims description 5
- 229910021529 ammonia Inorganic materials 0.000 claims description 5
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical group BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 5
- 235000019253 formic acid Nutrition 0.000 claims description 5
- 239000000575 pesticide Substances 0.000 claims description 5
- 125000000033 alkoxyamino group Chemical group 0.000 claims description 4
- 125000004414 alkyl thio group Chemical group 0.000 claims description 4
- 150000001721 carbon Chemical group 0.000 claims description 4
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical group [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 claims description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 3
- 229910000272 alkali metal oxide Inorganic materials 0.000 claims description 3
- 229910052794 bromium Inorganic materials 0.000 claims description 3
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 3
- 125000005265 dialkylamine group Chemical group 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- 229910052740 iodine Chemical group 0.000 claims description 3
- 238000007363 ring formation reaction Methods 0.000 claims description 3
- IXVJKFCFNGQJTG-UHFFFAOYSA-N 3-oxopropanoyl 3-oxopropanoate Chemical compound O=CCC(=O)OC(=O)CC=O IXVJKFCFNGQJTG-UHFFFAOYSA-N 0.000 claims description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 2
- 150000008044 alkali metal hydroxides Chemical class 0.000 claims description 2
- 125000003302 alkenyloxy group Chemical group 0.000 claims description 2
- 125000004694 alkoxyaminocarbonyl group Chemical group 0.000 claims description 2
- 239000007864 aqueous solution Substances 0.000 claims description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 2
- HHLFWLYXYJOTON-UHFFFAOYSA-N glyoxylic acid Chemical group OC(=O)C=O HHLFWLYXYJOTON-UHFFFAOYSA-N 0.000 claims description 2
- 125000005842 heteroatom Chemical group 0.000 claims description 2
- LXUSZJHDRRITIO-UHFFFAOYSA-N n-[2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]-4-cyanopyrazol-3-yl]acetamide Chemical compound CC(=O)NC1=C(C#N)C=NN1C1=NC=C(C(F)(F)F)C=C1Cl LXUSZJHDRRITIO-UHFFFAOYSA-N 0.000 claims description 2
- YWNOYSATMHTXQJ-UHFFFAOYSA-N n-acetyl-n-[2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]-4-cyanopyrazol-3-yl]acetamide Chemical compound CC(=O)N(C(C)=O)C1=C(C#N)C=NN1C1=NC=C(C(F)(F)F)C=C1Cl YWNOYSATMHTXQJ-UHFFFAOYSA-N 0.000 claims description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 2
- 229910052760 oxygen Inorganic materials 0.000 claims description 2
- 239000001301 oxygen Substances 0.000 claims description 2
- CJVFSYAPMDUCDE-UHFFFAOYSA-N prop-2-enyl N-[2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]-4-cyanopyrazol-3-yl]carbamate Chemical compound ClC=1C(=NC=C(C1)C(F)(F)F)N1N=CC(=C1NC(=O)OCC=C)C#N CJVFSYAPMDUCDE-UHFFFAOYSA-N 0.000 claims description 2
- ZXKCLCKTBJRYLP-UHFFFAOYSA-N propan-2-yl N-[2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]-4-cyanopyrazol-3-yl]carbamate Chemical compound ClC=1C(=NC=C(C1)C(F)(F)F)N1N=CC(=C1NC(=O)OC(C)C)C#N ZXKCLCKTBJRYLP-UHFFFAOYSA-N 0.000 claims description 2
- 229910052717 sulfur Inorganic materials 0.000 claims description 2
- 239000011593 sulfur Substances 0.000 claims description 2
- KCYFXHFODMCBFN-UHFFFAOYSA-N 1-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]-5-(3-methyl-2-oxoazetidin-1-yl)pyrazole-4-carbonitrile Chemical compound CC1CN(C1=O)C1=C(C=NN1C1=NC=C(C=C1Cl)C(F)(F)F)C#N KCYFXHFODMCBFN-UHFFFAOYSA-N 0.000 claims 1
- DJSIDKYICYAXIF-UHFFFAOYSA-N 2,2-dichloro-N-[2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]-4-cyanopyrazol-3-yl]acetamide Chemical compound ClC=1C(=NC=C(C1)C(F)(F)F)N1N=CC(=C1NC(C(Cl)Cl)=O)C#N DJSIDKYICYAXIF-UHFFFAOYSA-N 0.000 claims 1
- HKROJPSXWYDUBU-UHFFFAOYSA-N 5-isocyanato-1h-pyrazole Chemical compound O=C=NC1=CC=NN1 HKROJPSXWYDUBU-UHFFFAOYSA-N 0.000 claims 1
- 102100027456 Cytochrome c oxidase subunit 2 Human genes 0.000 claims 1
- 101000725401 Homo sapiens Cytochrome c oxidase subunit 2 Proteins 0.000 claims 1
- 101000605127 Homo sapiens Prostaglandin G/H synthase 2 Proteins 0.000 claims 1
- QDFRNIXLGJFJBJ-UHFFFAOYSA-N N-[2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]-4-cyanopyrazol-3-yl]propanamide Chemical compound ClC=1C(=NC=C(C1)C(F)(F)F)N1N=CC(=C1NC(CC)=O)C#N QDFRNIXLGJFJBJ-UHFFFAOYSA-N 0.000 claims 1
- 239000004480 active ingredient Substances 0.000 claims 1
- 150000001408 amides Chemical group 0.000 claims 1
- 125000004122 cyclic group Chemical group 0.000 claims 1
- 125000006413 ring segment Chemical group 0.000 claims 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 72
- 239000011541 reaction mixture Substances 0.000 description 54
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 51
- 238000010992 reflux Methods 0.000 description 47
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 42
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 42
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 36
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 35
- 239000003960 organic solvent Substances 0.000 description 34
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 33
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 32
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 30
- 239000011734 sodium Substances 0.000 description 30
- 229910052708 sodium Inorganic materials 0.000 description 29
- 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 28
- 239000007787 solid Substances 0.000 description 25
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 24
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 22
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 21
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 20
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 20
- 229910052700 potassium Inorganic materials 0.000 description 20
- 239000011591 potassium Substances 0.000 description 20
- 229960003975 potassium Drugs 0.000 description 20
- 239000000243 solution Substances 0.000 description 20
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 16
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 14
- 239000002253 acid Substances 0.000 description 14
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 12
- 229960001701 chloroform Drugs 0.000 description 12
- 239000007788 liquid Substances 0.000 description 12
- BVKZGUZCCUSVTD-UHFFFAOYSA-M Bicarbonate Chemical compound OC([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-M 0.000 description 11
- 238000005507 spraying Methods 0.000 description 11
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 10
- 239000000843 powder Substances 0.000 description 10
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 10
- 239000012141 concentrate Substances 0.000 description 9
- 235000008504 concentrate Nutrition 0.000 description 9
- 239000002904 solvent Substances 0.000 description 9
- CPELXLSAUQHCOX-UHFFFAOYSA-N Hydrogen bromide Chemical compound Br CPELXLSAUQHCOX-UHFFFAOYSA-N 0.000 description 8
- 229960000583 acetic acid Drugs 0.000 description 8
- 150000002576 ketones Chemical class 0.000 description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 8
- QCCPRTLVGONCQE-UHFFFAOYSA-N 5-amino-1-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]pyrazole-4-carbonitrile Chemical compound NC1=C(C#N)C=NN1C1=NC=C(C(F)(F)F)C=C1Cl QCCPRTLVGONCQE-UHFFFAOYSA-N 0.000 description 7
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical class OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 6
- GNVMUORYQLCPJZ-UHFFFAOYSA-M Thiocarbamate Chemical compound NC([S-])=O GNVMUORYQLCPJZ-UHFFFAOYSA-M 0.000 description 6
- 239000011230 binding agent Substances 0.000 description 6
- 239000013078 crystal Substances 0.000 description 6
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 6
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 6
- 239000000725 suspension Substances 0.000 description 6
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 5
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 5
- 241000209764 Avena fatua Species 0.000 description 5
- 235000007320 Avena fatua Nutrition 0.000 description 5
- WTKZEGDFNFYCGP-UHFFFAOYSA-N Pyrazole Chemical compound C=1C=NNC=1 WTKZEGDFNFYCGP-UHFFFAOYSA-N 0.000 description 5
- 238000007792 addition Methods 0.000 description 5
- 229910052784 alkaline earth metal Inorganic materials 0.000 description 5
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- XHXFXVLFKHQFAL-UHFFFAOYSA-N phosphoryl trichloride Chemical compound ClP(Cl)(Cl)=O XHXFXVLFKHQFAL-UHFFFAOYSA-N 0.000 description 3
- 230000008635 plant growth Effects 0.000 description 3
- 229910000027 potassium carbonate Inorganic materials 0.000 description 3
- 235000011181 potassium carbonates Nutrition 0.000 description 3
- 125000003226 pyrazolyl group Chemical group 0.000 description 3
- 239000012312 sodium hydride Substances 0.000 description 3
- 229910000104 sodium hydride Inorganic materials 0.000 description 3
- 241000894007 species Species 0.000 description 3
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- 229910002027 silica gel Inorganic materials 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- ODCWYMIRDDJXKW-UHFFFAOYSA-N simazine Chemical compound CCNC1=NC(Cl)=NC(NCC)=N1 ODCWYMIRDDJXKW-UHFFFAOYSA-N 0.000 description 1
- 150000003385 sodium Chemical class 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229910000030 sodium bicarbonate Inorganic materials 0.000 description 1
- 235000017557 sodium bicarbonate Nutrition 0.000 description 1
- 239000012279 sodium borohydride Substances 0.000 description 1
- 229910000033 sodium borohydride Inorganic materials 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 238000000638 solvent extraction Methods 0.000 description 1
- 238000009331 sowing Methods 0.000 description 1
- 238000001228 spectrum Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- JDVPQXZIJDEHAN-UHFFFAOYSA-N succinamic acid Chemical compound NC(=O)CCC(O)=O JDVPQXZIJDEHAN-UHFFFAOYSA-N 0.000 description 1
- 150000003458 sulfonic acid derivatives Chemical class 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000004546 suspension concentrate Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 125000004213 tert-butoxy group Chemical group [H]C([H])([H])C(O*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- BSYVTEYKTMYBMK-UHFFFAOYSA-N tetrahydrofurfuryl alcohol Chemical compound OCC1CCCO1 BSYVTEYKTMYBMK-UHFFFAOYSA-N 0.000 description 1
- 239000011573 trace mineral Substances 0.000 description 1
- 235000013619 trace mineral Nutrition 0.000 description 1
- 229940047183 tribulus Drugs 0.000 description 1
- QORWJWZARLRLPR-UHFFFAOYSA-H tricalcium bis(phosphate) Chemical compound [Ca+2].[Ca+2].[Ca+2].[O-]P([O-])([O-])=O.[O-]P([O-])([O-])=O QORWJWZARLRLPR-UHFFFAOYSA-H 0.000 description 1
- 229940078499 tricalcium phosphate Drugs 0.000 description 1
- 229910000391 tricalcium phosphate Inorganic materials 0.000 description 1
- 235000019731 tricalcium phosphate Nutrition 0.000 description 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-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
- 239000002699 waste material Substances 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/60—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D213/72—Nitrogen atoms
- C07D213/76—Nitrogen atoms to which a second hetero atom is attached
- C07D213/77—Hydrazine radicals
-
- 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
- A01N43/56—1,2-Diazoles; Hydrogenated 1,2-diazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Plural Heterocyclic Compounds (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Applications Claiming Priority (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB838306465A GB8306465D0 (en) | 1983-03-09 | 1983-03-09 | Compositions of matter |
| GB8306465 | 1983-03-09 | ||
| GB8400690 | 1984-01-11 | ||
| GB848400690A GB8400690D0 (en) | 1984-01-11 | 1984-01-11 | Compositions of matter |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| NL8400732A true NL8400732A (nl) | 1984-10-01 |
Family
ID=26285450
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| NL8400732A NL8400732A (nl) | 1983-03-09 | 1984-03-07 | N-pyridylpyrazoolderivaten, werkwijze voor het bereiden daarvan, deze derivaten bevattende herbicidepreparaten en werkwijze voor het bestrijden van onkruid daarmee. |
Country Status (9)
| Country | Link |
|---|---|
| BE (1) | BE899118A (it) |
| BR (1) | BR8401052A (it) |
| CH (1) | CH662564A5 (it) |
| DE (1) | DE3408727A1 (it) |
| DK (1) | DK145684A (it) |
| FR (1) | FR2543951B1 (it) |
| IL (1) | IL71175A0 (it) |
| IT (1) | IT1175785B (it) |
| NL (1) | NL8400732A (it) |
Families Citing this family (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3539844A1 (de) | 1985-11-09 | 1987-05-14 | Bayer Ag | Substituierte 5-amino-1-aryl-pyrazole |
| DE3600287A1 (de) | 1986-01-08 | 1987-07-16 | Bayer Ag | 1-arylpyrazole |
| DE19530606A1 (de) * | 1995-08-21 | 1997-02-27 | Basf Ag | 1-(Pyridyl)-pyrazole |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| MA19540A1 (fr) * | 1981-07-17 | 1983-04-01 | May & Baker Ltd | Derives du n-phenylpyrazole |
-
1984
- 1984-02-29 DK DK145684A patent/DK145684A/da not_active Application Discontinuation
- 1984-03-06 FR FR8403784A patent/FR2543951B1/fr not_active Expired
- 1984-03-07 IL IL71175A patent/IL71175A0/xx unknown
- 1984-03-07 IT IT19939/84A patent/IT1175785B/it active
- 1984-03-07 NL NL8400732A patent/NL8400732A/nl not_active Application Discontinuation
- 1984-03-08 BR BR8401052A patent/BR8401052A/pt unknown
- 1984-03-08 CH CH1162/84A patent/CH662564A5/fr not_active IP Right Cessation
- 1984-03-09 DE DE19843408727 patent/DE3408727A1/de not_active Withdrawn
- 1984-03-09 BE BE0/212538A patent/BE899118A/fr not_active IP Right Cessation
Also Published As
| Publication number | Publication date |
|---|---|
| DK145684A (da) | 1984-09-10 |
| FR2543951B1 (fr) | 1987-01-23 |
| FR2543951A1 (fr) | 1984-10-12 |
| CH662564A5 (fr) | 1987-10-15 |
| BE899118A (fr) | 1984-09-10 |
| BR8401052A (pt) | 1984-10-16 |
| IT1175785B (it) | 1987-07-15 |
| IL71175A0 (en) | 1984-06-29 |
| DE3408727A1 (de) | 1984-09-13 |
| DK145684D0 (da) | 1984-02-29 |
| IT8419939A0 (it) | 1984-03-07 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| A1A | A request for search or an international-type search has been filed | ||
| A85 | Still pending on 85-01-01 | ||
| BT | A notification was added to the application dossier and made available to the public | ||
| BB | A search report has been drawn up | ||
| CNR | Transfer of rights (patent application after its laying open for public inspection) |
Free format text: I.C.I. FRANCE S.A. |
|
| BV | The patent application has lapsed | ||
| BV | The patent application has lapsed |