NL8100271A - Pyrimidinylethers en werkwijzen voor het bereiden en toepassen van de ethers. - Google Patents

Pyrimidinylethers en werkwijzen voor het bereiden en toepassen van de ethers. Download PDF

Info

Publication number: NL8100271A
Authority: NL; Netherlands
Prior art keywords: hydrogen; group; compound; hydrogen atom; atom
Prior art date: 1980-01-25

Application number

NL8100271A

Other languages

English (en)

Dutch (nl)

Original Assignee

Sandoz Ag

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.)

1980-01-25

Filing date

1981-01-21

Publication date

1981-08-17

1981-01-21 Application filed by Sandoz Ag filed Critical Sandoz Ag

1981-08-17 Publication of NL8100271A publication Critical patent/NL8100271A/nl

Links

238000000034 method Methods 0.000 title claims description 29
-1 PYRIMIDINYL ETHERS Chemical class 0.000 title claims description 11
150000002170 ethers Chemical class 0.000 title description 4
150000001875 compounds Chemical class 0.000 claims description 103
239000000460 chlorine Substances 0.000 claims description 60
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 43
125000004432 carbon atom Chemical group C* 0.000 claims description 38
229910052801 chlorine Inorganic materials 0.000 claims description 32
241000196324 Embryophyta Species 0.000 claims description 31
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 29
229910052739 hydrogen Inorganic materials 0.000 claims description 29
239000001257 hydrogen Substances 0.000 claims description 29
125000000217 alkyl group Chemical group 0.000 claims description 24
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 23
230000002363 herbicidal effect Effects 0.000 claims description 23
239000000203 mixture Substances 0.000 claims description 20
238000002360 preparation method Methods 0.000 claims description 14
150000003839 salts Chemical group 0.000 claims description 14
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 13
239000002253 acid Substances 0.000 claims description 13
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 claims description 13
230000012447 hatching Effects 0.000 claims description 13
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 13
229910052794 bromium Inorganic materials 0.000 claims description 12
KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 claims description 11
229920000742 Cotton Polymers 0.000 claims description 11
244000299507 Gossypium hirsutum Species 0.000 claims description 11
240000007594 Oryza sativa Species 0.000 claims description 11
235000007164 Oryza sativa Nutrition 0.000 claims description 11
235000009566 rice Nutrition 0.000 claims description 11
244000061456 Solanum tuberosum Species 0.000 claims description 10
235000002595 Solanum tuberosum Nutrition 0.000 claims description 10
241000209140 Triticum Species 0.000 claims description 10
235000021307 Triticum Nutrition 0.000 claims description 10
235000003222 Helianthus annuus Nutrition 0.000 claims description 9
235000012015 potatoes Nutrition 0.000 claims description 9
241000208818 Helianthus Species 0.000 claims description 8
238000006243 chemical reaction Methods 0.000 claims description 8
125000001309 chloro group Chemical group Cl* 0.000 claims description 8
125000000753 cycloalkyl group Chemical group 0.000 claims description 8
241000219310 Beta vulgaris subsp. vulgaris Species 0.000 claims description 7
235000021536 Sugar beet Nutrition 0.000 claims description 7
239000004480 active ingredient Substances 0.000 claims description 5
235000013339 cereals Nutrition 0.000 claims description 5
125000005843 halogen group Chemical group 0.000 claims description 5
125000001424 substituent group Chemical group 0.000 claims description 5
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 4
125000003342 alkenyl group Chemical group 0.000 claims description 4
125000002947 alkylene group Chemical group 0.000 claims description 4
125000003545 alkoxy group Chemical group 0.000 claims description 3
125000004429 atom Chemical group 0.000 claims description 3
239000003085 diluting agent Substances 0.000 claims description 3
238000004519 manufacturing process Methods 0.000 claims description 3
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
MYMOFIZGZYHOMD-UHFFFAOYSA-N Dioxygen Chemical compound O=O MYMOFIZGZYHOMD-UHFFFAOYSA-N 0.000 claims description 2
239000012458 free base Substances 0.000 claims description 2
229910052760 oxygen Inorganic materials 0.000 claims description 2
239000001301 oxygen Substances 0.000 claims description 2
125000004430 oxygen atom Chemical group O* 0.000 claims description 2
229910052717 sulfur Inorganic materials 0.000 claims description 2
125000004434 sulfur atom Chemical group 0.000 claims description 2
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 3
125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims 3
125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims 2
101100167667 Arabidopsis thaliana CML24 gene Proteins 0.000 claims 1
YZCKVEUIGOORGS-UHFFFAOYSA-N Hydrogen atom Chemical compound [H] YZCKVEUIGOORGS-UHFFFAOYSA-N 0.000 claims 1
239000002552 dosage form Substances 0.000 claims 1
150000002391 heterocyclic compounds Chemical class 0.000 claims 1
150000002431 hydrogen Chemical class 0.000 claims 1
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 20
240000005611 Agrostis gigantea Species 0.000 description 8
241000209764 Avena fatua Species 0.000 description 8
235000007320 Avena fatua Nutrition 0.000 description 8
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
239000007858 starting material Substances 0.000 description 6
241001666377 Apera Species 0.000 description 5
241000220244 Capsella <angiosperm> Species 0.000 description 5
244000058871 Echinochloa crus-galli Species 0.000 description 5
235000011999 Panicum crusgalli Nutrition 0.000 description 5
240000006694 Stellaria media Species 0.000 description 5
239000000839 emulsion Substances 0.000 description 5
239000002904 solvent Substances 0.000 description 5
240000002791 Brassica napus Species 0.000 description 4
235000011293 Brassica napus Nutrition 0.000 description 4
235000000540 Brassica rapa subsp rapa Nutrition 0.000 description 4
244000000626 Daucus carota Species 0.000 description 4
235000002767 Daucus carota Nutrition 0.000 description 4
241000192043 Echinochloa Species 0.000 description 4
240000005702 Galium aparine Species 0.000 description 4
235000014820 Galium aparine Nutrition 0.000 description 4
240000004658 Medicago sativa Species 0.000 description 4
235000017587 Medicago sativa ssp. sativa Nutrition 0.000 description 4
244000046052 Phaseolus vulgaris Species 0.000 description 4
235000010627 Phaseolus vulgaris Nutrition 0.000 description 4
240000008042 Zea mays Species 0.000 description 4
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 description 4
235000002017 Zea mays subsp mays Nutrition 0.000 description 4
235000005822 corn Nutrition 0.000 description 4
239000004009 herbicide Substances 0.000 description 4
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
241000508725 Elymus repens Species 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
240000006240 Linum usitatissimum Species 0.000 description 3
235000004431 Linum usitatissimum Nutrition 0.000 description 3
241000780602 Senecio Species 0.000 description 3
239000000654 additive Substances 0.000 description 3
238000011156 evaluation Methods 0.000 description 3
229910052736 halogen Inorganic materials 0.000 description 3
150000002367 halogens Chemical group 0.000 description 3
238000002844 melting Methods 0.000 description 3
230000008018 melting Effects 0.000 description 3
239000003415 peat Substances 0.000 description 3
239000004576 sand Substances 0.000 description 3
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
CFXQEHVMCRXUSD-UHFFFAOYSA-N 1,2,3-Trichloropropane Chemical compound ClCC(Cl)CCl CFXQEHVMCRXUSD-UHFFFAOYSA-N 0.000 description 2
FQWBGZVXVRORRM-UHFFFAOYSA-N 2-pyrimidin-2-yloxypyrimidine Chemical class N=1C=CC=NC=1OC1=NC=CC=N1 FQWBGZVXVRORRM-UHFFFAOYSA-N 0.000 description 2
239000004375 Dextrin Substances 0.000 description 2
229920001353 Dextrin Polymers 0.000 description 2
244000152970 Digitaria sanguinalis Species 0.000 description 2
235000010823 Digitaria sanguinalis Nutrition 0.000 description 2
241001101998 Galium Species 0.000 description 2
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
239000005909 Kieselgur Substances 0.000 description 2
244000211187 Lepidium sativum Species 0.000 description 2
235000007849 Lepidium sativum Nutrition 0.000 description 2
240000004296 Lolium perenne Species 0.000 description 2
OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
239000000969 carrier Substances 0.000 description 2
229940071162 caseinate Drugs 0.000 description 2
239000007795 chemical reaction product Substances 0.000 description 2
239000007859 condensation product Substances 0.000 description 2
235000019425 dextrin Nutrition 0.000 description 2
229930195733 hydrocarbon Natural products 0.000 description 2
150000002430 hydrocarbons Chemical class 0.000 description 2
239000007788 liquid Substances 0.000 description 2
238000002156 mixing Methods 0.000 description 2
PSZYNBSKGUBXEH-UHFFFAOYSA-M naphthalene-1-sulfonate Chemical compound C1=CC=C2C(S(=O)(=O)[O-])=CC=CC2=C1 PSZYNBSKGUBXEH-UHFFFAOYSA-M 0.000 description 2
230000008635 plant growth Effects 0.000 description 2
239000000741 silica gel Substances 0.000 description 2
229910002027 silica gel Inorganic materials 0.000 description 2
239000007787 solid Substances 0.000 description 2
241000894007 species Species 0.000 description 2
238000010998 test method Methods 0.000 description 2
UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 description 2
230000000007 visual effect Effects 0.000 description 2
239000004563 wettable powder Substances 0.000 description 2
BMVXCPBXGZKUPN-UHFFFAOYSA-N 1-hexanamine Chemical compound CCCCCCN BMVXCPBXGZKUPN-UHFFFAOYSA-N 0.000 description 1
FALCMQXTWHPRIH-UHFFFAOYSA-N 2,3-dichloroprop-1-ene Chemical compound ClCC(Cl)=C FALCMQXTWHPRIH-UHFFFAOYSA-N 0.000 description 1
241000209136 Agropyron Species 0.000 description 1
OSDWBNJEKMUWAV-UHFFFAOYSA-N Allyl chloride Chemical compound ClCC=C OSDWBNJEKMUWAV-UHFFFAOYSA-N 0.000 description 1
241000743985 Alopecurus Species 0.000 description 1
241001621841 Alopecurus myosuroides Species 0.000 description 1
239000005995 Aluminium silicate Substances 0.000 description 1
244000237956 Amaranthus retroflexus Species 0.000 description 1
235000013479 Amaranthus retroflexus Nutrition 0.000 description 1
QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
241001260012 Bursa Species 0.000 description 1
244000025254 Cannabis sativa Species 0.000 description 1
239000004215 Carbon black (E152) Substances 0.000 description 1
241000219312 Chenopodium Species 0.000 description 1
235000008733 Citrus aurantifolia Nutrition 0.000 description 1
244000075634 Cyperus rotundus Species 0.000 description 1
235000016854 Cyperus rotundus Nutrition 0.000 description 1
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
244000020551 Helianthus annuus Species 0.000 description 1
240000005979 Hordeum vulgare Species 0.000 description 1
235000007340 Hordeum vulgare Nutrition 0.000 description 1
241000209082 Lolium Species 0.000 description 1
CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 1
241000209117 Panicum Species 0.000 description 1
240000008114 Panicum miliaceum Species 0.000 description 1
235000007199 Panicum miliaceum Nutrition 0.000 description 1
235000006443 Panicum miliaceum subsp. miliaceum Nutrition 0.000 description 1
235000009037 Panicum miliaceum subsp. ruderale Nutrition 0.000 description 1
241001268782 Paspalum dilatatum Species 0.000 description 1
241000209504 Poaceae Species 0.000 description 1
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
101100293693 Saccharomyces cerevisiae (strain ATCC 204508 / S288c) STO1 gene Proteins 0.000 description 1
101000650578 Salmonella phage P22 Regulatory protein C3 Proteins 0.000 description 1
240000003705 Senecio vulgaris Species 0.000 description 1
235000005775 Setaria Nutrition 0.000 description 1
241000232088 Setaria <nematode> Species 0.000 description 1
240000005498 Setaria italica Species 0.000 description 1
235000007226 Setaria italica Nutrition 0.000 description 1
PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 1
235000011941 Tilia x europaea Nutrition 0.000 description 1
101001040920 Triticum aestivum Alpha-amylase inhibitor 0.28 Proteins 0.000 description 1
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 1
WDJHALXBUFZDSR-UHFFFAOYSA-N acetoacetic acid Chemical compound CC(=O)CC(O)=O WDJHALXBUFZDSR-UHFFFAOYSA-N 0.000 description 1
239000002318 adhesion promoter Substances 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
150000004996 alkyl benzenes Chemical class 0.000 description 1
235000012211 aluminium silicate Nutrition 0.000 description 1
150000001408 amides Chemical class 0.000 description 1
150000001412 amines Chemical class 0.000 description 1
239000007900 aqueous suspension Substances 0.000 description 1
238000003556 assay Methods 0.000 description 1
239000011230 binding agent Substances 0.000 description 1
OOCMUZJPDXYRFD-UHFFFAOYSA-L calcium;2-dodecylbenzenesulfonate Chemical compound [Ca+2].CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O.CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O OOCMUZJPDXYRFD-UHFFFAOYSA-L 0.000 description 1
150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
101150050497 cbc1 gene Proteins 0.000 description 1
239000003795 chemical substances by application Substances 0.000 description 1
150000008280 chlorinated hydrocarbons Chemical class 0.000 description 1
238000004587 chromatography analysis Methods 0.000 description 1
229940125904 compound 1 Drugs 0.000 description 1
238000009833 condensation Methods 0.000 description 1
230000005494 condensation Effects 0.000 description 1
VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
239000002270 dispersing agent Substances 0.000 description 1
230000000694 effects Effects 0.000 description 1
239000003480 eluent Substances 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
239000012259 ether extract Substances 0.000 description 1
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
238000002474 experimental method Methods 0.000 description 1
230000035784 germination Effects 0.000 description 1
230000012010 growth Effects 0.000 description 1
238000010438 heat treatment Methods 0.000 description 1
125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
239000012456 homogeneous solution Substances 0.000 description 1
239000000543 intermediate Substances 0.000 description 1
NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000004571 lime Substances 0.000 description 1
VYQNWZOUAUKGHI-UHFFFAOYSA-N monobenzone Chemical compound C1=CC(O)=CC=C1OCC1=CC=CC=C1 VYQNWZOUAUKGHI-UHFFFAOYSA-N 0.000 description 1
MWFIYTHIZQQGES-UHFFFAOYSA-N n-hexylpyrimidin-2-amine Chemical compound CCCCCCNC1=NC=CC=N1 MWFIYTHIZQQGES-UHFFFAOYSA-N 0.000 description 1
239000002245 particle Substances 0.000 description 1
231100000208 phytotoxic Toxicity 0.000 description 1
230000000885 phytotoxic effect Effects 0.000 description 1
239000011591 potassium Substances 0.000 description 1
229910052700 potassium Inorganic materials 0.000 description 1
230000003389 potentiating effect Effects 0.000 description 1
239000000047 product Substances 0.000 description 1
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
150000003222 pyridines Chemical class 0.000 description 1
150000003230 pyrimidines Chemical class 0.000 description 1
238000002390 rotary evaporation Methods 0.000 description 1
238000000926 separation method Methods 0.000 description 1
229910000029 sodium carbonate Inorganic materials 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000002689 soil Substances 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
238000006277 sulfonation reaction Methods 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
239000008096 xylene Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/47—One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines

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)
Agricultural Chemicals And Associated Chemicals (AREA)
Plural Heterocyclic Compounds (AREA)
Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

NL8100271A 1980-01-25 1981-01-21 Pyrimidinylethers en werkwijzen voor het bereiden en toepassen van de ethers. NL8100271A (nl)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB8002573		1980-01-25
GB8002573		1980-01-25

Publications (1)

Publication Number	Publication Date
NL8100271A true NL8100271A (nl)	1981-08-17

Family

ID=10510892

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
NL8100271A NL8100271A (nl)	1980-01-25	1981-01-21	Pyrimidinylethers en werkwijzen voor het bereiden en toepassen van de ethers.

Country Status (17)

Country	Link
US (1)	US4402730A (fr)
JP (1)	JPS56104869A (fr)
KR (1)	KR830005161A (fr)
AU (1)	AU6658981A (fr)
BE (1)	BE887161A (fr)
BR (1)	BR8100367A (fr)
CA (1)	CA1150261A (fr)
DE (1)	DE3101426A1 (fr)
DK (1)	DK33381A (fr)
ES (1)	ES498778A0 (fr)
FR (1)	FR2474496A1 (fr)
IL (2)	IL61969A0 (fr)
IT (1)	IT1142239B (fr)
NL (1)	NL8100271A (fr)
PL (1)	PL125307B1 (fr)
YU (1)	YU16881A (fr)
ZA (1)	ZA81512B (fr)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CN100415725C (zh) *	2000-09-19	2008-09-03	住友化学工业株式会社	嘧啶类化合物及其用途

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR1518112A (fr) *	1966-03-31	1968-03-22	Ici Ltd	Composés organiques et compositions en contenant à base de pyrimidine
CH595061A5 (fr) *	1974-05-10	1978-01-31	Ciba Geigy Ag
GB1523274A (en) *	1974-08-05	1978-08-31	Ici Ltd	Herbicidal compositions containing substituted pyrimidine

1981
- 1981-01-14 US US06/225,046 patent/US4402730A/en not_active Expired - Fee Related
- 1981-01-17 DE DE3101426A patent/DE3101426A1/de not_active Withdrawn
- 1981-01-21 BE BE1/10106A patent/BE887161A/fr not_active IP Right Cessation
- 1981-01-21 NL NL8100271A patent/NL8100271A/nl not_active Application Discontinuation
- 1981-01-22 YU YU00168/81A patent/YU16881A/xx unknown
- 1981-01-22 CA CA000369081A patent/CA1150261A/fr not_active Expired
- 1981-01-23 BR BR8100367A patent/BR8100367A/pt unknown
- 1981-01-23 ES ES498778A patent/ES498778A0/es active Granted
- 1981-01-23 FR FR8101230A patent/FR2474496A1/fr active Granted
- 1981-01-23 AU AU66589/81A patent/AU6658981A/en not_active Abandoned
- 1981-01-23 KR KR1019810000209A patent/KR830005161A/ko not_active Ceased
- 1981-01-23 IL IL61969A patent/IL61969A0/xx unknown
- 1981-01-23 IT IT47622/81A patent/IT1142239B/it active
- 1981-01-23 ZA ZA00810512A patent/ZA81512B/xx unknown
- 1981-01-23 IL IL61970A patent/IL61970A0/xx unknown
- 1981-01-23 PL PL1981229368A patent/PL125307B1/pl unknown
- 1981-01-23 DK DK33381A patent/DK33381A/da not_active Application Discontinuation
- 1981-01-24 JP JP953081A patent/JPS56104869A/ja active Pending

Also Published As

Publication number	Publication date
JPS56104869A (en)	1981-08-20
DK33381A (da)	1981-07-26
KR830005161A (ko)	1983-08-03
BR8100367A (pt)	1981-08-11
BE887161A (fr)	1981-07-22
FR2474496A1 (fr)	1981-07-31
PL229368A1 (fr)	1981-09-18
YU16881A (en)	1983-10-31
IT8147622A0 (it)	1981-01-23
CA1150261A (fr)	1983-07-19
US4402730A (en)	1983-09-06
ES8204426A1 (es)	1982-05-01
DE3101426A1 (de)	1981-11-26
ZA81512B (en)	1982-09-29
IL61970A0 (en)	1981-02-27
FR2474496B1 (fr)	1983-08-19
IL61969A0 (en)	1981-02-27
ES498778A0 (es)	1982-05-01
PL125307B1 (en)	1983-04-30
AU6658981A (en)	1981-07-30
IT1142239B (it)	1986-10-08

Legal Events

Date	Code	Title
1984-09-03	BV	The patent application has lapsed
1985-01-01	A85	Still pending on 85-01-01
1987-01-02	BV	The patent application has lapsed

Publication	Publication Date	Title
FI64361C (fi)	1983-11-10	1,2,3-tiadiazol-5-karboxylsyraderivat anvaendbara som herbicider och till vaextreglerande medel
JPS59205368A (ja)	1984-11-20	殺微生物剤
SU621301A3 (ru)	1978-08-25	Фунгицидна композици
DK163907B (da)	1992-04-21	Fremgangsmaade til bekaempelse af svampe og/eller bekaempelse eller regulering af plantevaekst ved hjaelp af i sidekaeden n-acylerede pyridyl-, pyrazinyl-, pyrimidinyl- eller pyridazinylderivater; i sidekaeden n-acylerede pyridyl-, pyrazinyl-, pyrimidin- og pyridazinylforbindelser til anvendelse ved fremgangsmaaden, fremgangsmaade til fremstilling af saadanne forbindelser samt fungicide og/eller plantevaekst
USRE30574E (en)	1981-04-14	Herbicidal tetrahydrofuran derivatives
HU206953B (en)	1993-03-01	Insecticidal agent comprising tetrahdyropyrimidine derivatives and process for producing such compounds
US4221584A (en)	1980-09-09	Herbicidal and plant-growth-regulating N-(heterocyclyl)-methylacetanilides
KR900008397B1 (ko)	1990-11-20	N-아릴설포닐-n'-트리아졸일우레아류의 제조방법
US4482373A (en)	1984-11-13	Benzoxazolyloxy phenoxy esters and use as monocotyledonous weed grass herbicides
NL193833C (nl)	2000-12-04	5-Amino-3-oxo-4(gesubstitueerd fenyl)-2,3-dihydrofuranverbindingen met herbicide werking en herbicide preparaat dat deze verbindingen bevat.
US4224050A (en)	1980-09-23	Chloroacetanilides having a selective herbicidal activity, ortho-alkenyl-substituted anilines, intermediates in the synthesis of said herbicidal chloroacetanilides, and methods for their preparation
US4657579A (en)	1987-04-14	Novel N-(5-pyrimidinyl)-chloroacetamides
NL8100271A (nl)	1981-08-17	Pyrimidinylethers en werkwijzen voor het bereiden en toepassen van de ethers.
US4747865A (en)	1988-05-31	Substituted phenoxyalkanecarboxylic acid esters
DK166495B1 (da)	1993-06-01	Phenoxyphthalidderivater, en fremgangsmaade til fremstilling af saadanne forbindelser, herbicidpraeparater indeholdende saadanne forbindelser samt deres anvendelse ved bekaempelse af uoensket plantevaekst
US4069036A (en)	1978-01-17	N-haloacyl 4-spirocycloaliphatic oxazolidines
US4511737A (en)	1985-04-16	Bicyclo(2.2.1)heptane oximes
US4021228A (en)	1977-05-03	Sulfide herbicide antidote compositions and method of use
DK164597B (da)	1992-07-20	2-alkoxyaminosulfonylbenzensulfonylurinstofderivater, deres fremstilling og anvendelse som herbicider
IT8320341A1 (it)	1984-09-29	Composti eterociclici ad attivita' erbicida
CS215126B2 (en)	1982-07-30	Herbicide means and method of making the active substance thereof
US3466164A (en)	1969-09-09	Process for the control of plant growth with n-(substituted benzylidene) alkyl amines
JPS59148758A (ja)	1984-08-25	置換されたアルカンチオカルボン酸誘導体類
US4336059A (en)	1982-06-22	Herbicidal and plant-growth-regulating N-(heterocyclyl)-methylacetanilide
US3557112A (en)	1971-01-19	Certain 2-(haloalkenylthio)-4,6-dimethylpyrimidines