BE898258A - Dérivés de pyrimidine-4-one dotés d'une activité herbicide. - Google Patents

Dérivés de pyrimidine-4-one dotés d'une activité herbicide. Download PDF

Info

Publication number: BE898258A
Authority: BE; Belgium
Prior art keywords: sep; compound; alkyl; formula; pyrimidine
Prior art date: 1982-11-18

Application number

BE0/211895A

Other languages

English (en)

French (fr)

Inventor

R Colle

F Gozzo

C Preziuso

E Signorini

A Zagni

Original Assignee

Montedison Spa

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.)

1982-11-18

Filing date

1983-11-18

Publication date

1984-05-18

1983-11-18 Application filed by Montedison Spa filed Critical Montedison Spa

1984-05-18 Publication of BE898258A publication Critical patent/BE898258A/fr

Links

230000002363 herbicidal effect Effects 0.000 title claims abstract description 21
DNCYBUMDUBHIJZ-UHFFFAOYSA-N 1h-pyrimidin-6-one Chemical class O=C1C=CN=CN1 DNCYBUMDUBHIJZ-UHFFFAOYSA-N 0.000 title abstract description 9
150000001875 compounds Chemical class 0.000 claims abstract description 59
239000004009 herbicide Substances 0.000 claims abstract description 12
125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 14
239000000203 mixture Substances 0.000 claims description 12
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 claims description 10
238000000034 method Methods 0.000 claims description 10
239000002904 solvent Substances 0.000 claims description 10
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
125000001424 substituent group Chemical group 0.000 claims description 8
125000003277 amino group Chemical group 0.000 claims description 6
125000004414 alkyl thio group Chemical group 0.000 claims description 5
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
125000000217 alkyl group Chemical group 0.000 claims description 4
-1 carbon disulfide, alkyl iodide Chemical class 0.000 claims description 4
238000010992 reflux Methods 0.000 claims description 4
AIHTVBAVVSDYMU-UHFFFAOYSA-N 3-methyl-2-methylsulfanyl-5-phenylpyrimidin-4-one Chemical compound O=C1N(C)C(SC)=NC=C1C1=CC=CC=C1 AIHTVBAVVSDYMU-UHFFFAOYSA-N 0.000 claims description 3
125000003545 alkoxy group Chemical group 0.000 claims description 3
229910052736 halogen Inorganic materials 0.000 claims description 3
125000005843 halogen group Chemical group 0.000 claims description 3
125000004765 (C1-C4) haloalkyl group Chemical group 0.000 claims description 2
125000000175 2-thienyl group Chemical group S1C([*])=C([H])C([H])=C1[H] 0.000 claims description 2
239000004480 active ingredient Substances 0.000 claims description 2
239000000654 additive Substances 0.000 claims description 2
230000001476 alcoholic effect Effects 0.000 claims description 2
125000003342 alkenyl group Chemical group 0.000 claims description 2
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 2
239000012298 atmosphere Substances 0.000 claims description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 2
150000002367 halogens Chemical class 0.000 claims description 2
239000011261 inert gas Substances 0.000 claims description 2
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 2
239000002689 soil Substances 0.000 claims description 2
FVAUCKIRQBBSSJ-UHFFFAOYSA-M sodium iodide Chemical compound [Na+].[I-] FVAUCKIRQBBSSJ-UHFFFAOYSA-M 0.000 claims 3
QSLPNSWXUQHVLP-UHFFFAOYSA-N $l^{1}-sulfanylmethane Chemical compound [S]C QSLPNSWXUQHVLP-UHFFFAOYSA-N 0.000 claims 1
MDFFNEOEWAXZRQ-UHFFFAOYSA-N aminyl Chemical group [NH2] MDFFNEOEWAXZRQ-UHFFFAOYSA-N 0.000 claims 1
238000004519 manufacturing process Methods 0.000 claims 1
235000009518 sodium iodide Nutrition 0.000 claims 1
238000010189 synthetic method Methods 0.000 abstract description 3
235000013350 formula milk Nutrition 0.000 description 29
238000006243 chemical reaction Methods 0.000 description 25
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 15
238000002360 preparation method Methods 0.000 description 12
239000007787 solid Substances 0.000 description 12
241000196324 Embryophyta Species 0.000 description 10
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 9
ROSDSFDQCJNGOL-UHFFFAOYSA-N Dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 8
101100054666 Streptomyces halstedii sch3 gene Proteins 0.000 description 7
238000002844 melting Methods 0.000 description 7
230000008018 melting Effects 0.000 description 7
238000003756 stirring Methods 0.000 description 7
239000000725 suspension Substances 0.000 description 7
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 7
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
150000001412 amines Chemical class 0.000 description 6
239000000543 intermediate Substances 0.000 description 6
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 5
CSCPPACGZOOCGX-UHFFFAOYSA-N acetone Substances CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 5
238000001914 filtration Methods 0.000 description 5
229910000104 sodium hydride Inorganic materials 0.000 description 5
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 5
KEAYESYHFKHZAL-UHFFFAOYSA-N Sodium Chemical compound [Na] KEAYESYHFKHZAL-UHFFFAOYSA-N 0.000 description 4
239000002585 base Substances 0.000 description 4
238000001816 cooling Methods 0.000 description 4
235000019441 ethanol Nutrition 0.000 description 4
OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 4
239000012312 sodium hydride Substances 0.000 description 4
KVDYEXRRTUGKBK-UHFFFAOYSA-N 3-amino-2-methylsulfanyl-5-phenylpyrimidin-4-one Chemical compound O=C1N(N)C(SC)=NC=C1C1=CC=CC=C1 KVDYEXRRTUGKBK-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical group CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
QGJOPFRUJISHPQ-UHFFFAOYSA-N Carbon disulfide Chemical compound S=C=S QGJOPFRUJISHPQ-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
125000003118 aryl group Chemical group 0.000 description 3
230000000694 effects Effects 0.000 description 3
241001233957 eudicotyledons Species 0.000 description 3
238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 3
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
ZRALSGWEFCBTJO-UHFFFAOYSA-N Guanidine Chemical compound NC(N)=N ZRALSGWEFCBTJO-UHFFFAOYSA-N 0.000 description 2
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
239000003513 alkali Substances 0.000 description 2
150000001351 alkyl iodides Chemical class 0.000 description 2
229910021529 ammonia Inorganic materials 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
229940126214 compound 3 Drugs 0.000 description 2
229940125898 compound 5 Drugs 0.000 description 2
238000007796 conventional method Methods 0.000 description 2
230000007123 defense Effects 0.000 description 2
239000006185 dispersion Substances 0.000 description 2
XWIUIRQSQROZGJ-UHFFFAOYSA-N ethyl 2-(2-formylphenyl)acetate Chemical compound CCOC(=O)CC1=CC=CC=C1C=O XWIUIRQSQROZGJ-UHFFFAOYSA-N 0.000 description 2
235000019439 ethyl acetate Nutrition 0.000 description 2
238000009472 formulation Methods 0.000 description 2
150000004678 hydrides Chemical class 0.000 description 2
INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 2
125000000250 methylamino group Chemical group [H]N(*)C([H])([H])[H] 0.000 description 2
239000012299 nitrogen atmosphere Substances 0.000 description 2
239000003880 polar aprotic solvent Substances 0.000 description 2
239000002244 precipitate Substances 0.000 description 2
125000002924 primary amino group Chemical class [H]N([H])* 0.000 description 2
239000000047 product Substances 0.000 description 2
150000003839 salts Chemical class 0.000 description 2
239000011734 sodium Substances 0.000 description 2
238000009331 sowing Methods 0.000 description 2
239000007858 starting material Substances 0.000 description 2
239000000126 substance Substances 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
238000005160 1H NMR spectroscopy Methods 0.000 description 1
XMLATHPZYRZZDI-UHFFFAOYSA-N 2-(dimethylamino)-3-methyl-5-phenylpyrimidin-4-one Chemical compound O=C1N(C)C(N(C)C)=NC=C1C1=CC=CC=C1 XMLATHPZYRZZDI-UHFFFAOYSA-N 0.000 description 1
VONWPEXRCLHKRJ-UHFFFAOYSA-N 2-chloro-n-phenylacetamide Chemical compound ClCC(=O)NC1=CC=CC=C1 VONWPEXRCLHKRJ-UHFFFAOYSA-N 0.000 description 1
DZXDCBAYZIHWGI-UHFFFAOYSA-N 2-methylsulfanyl-5-phenyl-1h-pyrimidin-6-one Chemical compound OC1=NC(SC)=NC=C1C1=CC=CC=C1 DZXDCBAYZIHWGI-UHFFFAOYSA-N 0.000 description 1
125000004105 2-pyridyl group Chemical group N1=C([*])C([H])=C([H])C([H])=C1[H] 0.000 description 1
GQRPSMWRJRFHNC-UHFFFAOYSA-N 3-amino-2-(dimethylamino)-5-phenylpyrimidin-4-one Chemical compound O=C1N(N)C(N(C)C)=NC=C1C1=CC=CC=C1 GQRPSMWRJRFHNC-UHFFFAOYSA-N 0.000 description 1
125000003349 3-pyridyl group Chemical group N1=C([H])C([*])=C([H])C([H])=C1[H] 0.000 description 1
125000000339 4-pyridyl group Chemical group N1=C([H])C([H])=C([*])C([H])=C1[H] 0.000 description 1
NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
102100022749 Aminopeptidase N Human genes 0.000 description 1
101150041968 CDC13 gene Proteins 0.000 description 1
HNUALPPJLMYHDK-UHFFFAOYSA-N C[CH]C Chemical compound C[CH]C HNUALPPJLMYHDK-UHFFFAOYSA-N 0.000 description 1
101000757160 Homo sapiens Aminopeptidase N Proteins 0.000 description 1
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
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 1
206010061217 Infestation Diseases 0.000 description 1
241000209510 Liliopsida Species 0.000 description 1
CHJJGSNFBQVOTG-UHFFFAOYSA-N N-methyl-guanidine Natural products CNC(N)=N CHJJGSNFBQVOTG-UHFFFAOYSA-N 0.000 description 1
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 1
240000006694 Stellaria media Species 0.000 description 1
HEDRZPFGACZZDS-MICDWDOJSA-N Trichloro(2H)methane Chemical compound [2H]C(Cl)(Cl)Cl HEDRZPFGACZZDS-MICDWDOJSA-N 0.000 description 1
235000010726 Vigna sinensis Nutrition 0.000 description 1
241000219994 Vigna unguiculata subsp. unguiculata Species 0.000 description 1
241000607479 Yersinia pestis Species 0.000 description 1
229960000583 acetic acid Drugs 0.000 description 1
239000002253 acid Substances 0.000 description 1
239000013543 active substance Substances 0.000 description 1
229910001854 alkali hydroxide Inorganic materials 0.000 description 1
150000008044 alkali metal hydroxides Chemical class 0.000 description 1
239000002168 alkylating agent Substances 0.000 description 1
229940100198 alkylating agent Drugs 0.000 description 1
125000006319 alkynyl amino group Chemical group 0.000 description 1
125000000304 alkynyl group Chemical group 0.000 description 1
150000001409 amidines Chemical class 0.000 description 1
238000004458 analytical method Methods 0.000 description 1
DXHPZXWIPWDXHJ-UHFFFAOYSA-N carbon monosulfide Chemical compound [S+]#[C-] DXHPZXWIPWDXHJ-UHFFFAOYSA-N 0.000 description 1
229940125782 compound 2 Drugs 0.000 description 1
230000001143 conditioned effect Effects 0.000 description 1
238000002425 crystallisation Methods 0.000 description 1
230000008025 crystallization Effects 0.000 description 1
238000000354 decomposition reaction Methods 0.000 description 1
125000004663 dialkyl amino group Chemical group 0.000 description 1
SWSQBOPZIKWTGO-UHFFFAOYSA-N dimethylaminoamidine Natural products CN(C)C(N)=N SWSQBOPZIKWTGO-UHFFFAOYSA-N 0.000 description 1
QHNXEVRKFKHMRL-UHFFFAOYSA-N dimethylazanium;acetate Chemical compound CNC.CC(O)=O QHNXEVRKFKHMRL-UHFFFAOYSA-N 0.000 description 1
239000003480 eluent Substances 0.000 description 1
239000004495 emulsifiable concentrate Substances 0.000 description 1
230000007613 environmental effect Effects 0.000 description 1
150000002148 esters Chemical class 0.000 description 1
NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 1
125000004494 ethyl ester group Chemical group 0.000 description 1
238000001704 evaporation Methods 0.000 description 1
230000008020 evaporation Effects 0.000 description 1
239000003337 fertilizer Substances 0.000 description 1
125000002485 formyl group Chemical group [H]C(*)=O 0.000 description 1
230000006870 function Effects 0.000 description 1
239000000417 fungicide Substances 0.000 description 1
230000035784 germination Effects 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
159000000011 group IA salts Chemical class 0.000 description 1
229910052739 hydrogen Inorganic materials 0.000 description 1
239000001257 hydrogen Substances 0.000 description 1
229910052500 inorganic mineral Inorganic materials 0.000 description 1
239000007788 liquid Substances 0.000 description 1
235000014666 liquid concentrate Nutrition 0.000 description 1
NNBBQNFHCVVQHZ-UHFFFAOYSA-N methyl carbamimidothioate;sulfuric acid Chemical compound CSC(N)=N.OS(O)(=O)=O NNBBQNFHCVVQHZ-UHFFFAOYSA-N 0.000 description 1
239000011707 mineral Substances 0.000 description 1
150000007522 mineralic acids Chemical class 0.000 description 1
150000007524 organic acids Chemical class 0.000 description 1
PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 1
235000020610 powder formula Nutrition 0.000 description 1
238000012545 processing Methods 0.000 description 1
239000003586 protic polar solvent Substances 0.000 description 1
239000012429 reaction media Substances 0.000 description 1
239000011541 reaction mixture Substances 0.000 description 1
150000003335 secondary amines Chemical class 0.000 description 1
239000000741 silica gel Substances 0.000 description 1
229910002027 silica gel Inorganic materials 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
QDRKDTQENPPHOJ-UHFFFAOYSA-N sodium ethoxide Chemical compound [Na+].CC[O-] QDRKDTQENPPHOJ-UHFFFAOYSA-N 0.000 description 1
241000894007 species Species 0.000 description 1
238000004611 spectroscopical analysis Methods 0.000 description 1
238000012360 testing method Methods 0.000 description 1
125000004001 thioalkyl group Chemical group 0.000 description 1
230000008511 vegetative development Effects 0.000 description 1
238000012795 verification Methods 0.000 description 1
239000004563 wettable powder Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/32—One oxygen, sulfur or nitrogen atom
- C07D239/34—One oxygen atom
- C07D239/36—One oxygen atom as doubly bound oxygen atom or as unsubstituted hydroxy radical
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/48—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with two nitrogen atoms as the only ring hetero atoms
- A01N43/54—1,3-Diazines; Hydrogenated 1,3-diazines
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D239/00—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings
- C07D239/02—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings
- C07D239/24—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members
- C07D239/28—Heterocyclic compounds containing 1,3-diazine or hydrogenated 1,3-diazine rings not condensed with other rings having three or more double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, directly attached to ring carbon atoms
- C07D239/46—Two or more oxygen, sulphur or nitrogen atoms
- C07D239/47—One nitrogen atom and one oxygen or sulfur atom, e.g. cytosine
- 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
- C07D239/56—One oxygen atom and one sulfur atom

Landscapes

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

BE0/211895A 1982-11-18 1983-11-18 Dérivés de pyrimidine-4-one dotés d'une activité herbicide. BE898258A (fr)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
IT24311/82A IT1153066B (it)	1982-11-18	1982-11-18	Derivati del pirimidin-4-one ad attivita' erbicida

Publications (1)

Publication Number	Publication Date
BE898258A true BE898258A (fr)	1984-05-18

Family

ID=11213052

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
BE0/211895A BE898258A (fr)	1982-11-18	1983-11-18	Dérivés de pyrimidine-4-one dotés d'une activité herbicide.

Country Status (7)

Country	Link
JP (1)	JPS59106472A (it)
BE (1)	BE898258A (it)
CH (1)	CH658652A5 (it)
DE (1)	DE3341343A1 (it)
FR (1)	FR2536394B1 (it)
GB (1)	GB2130214B (it)
IT (1)	IT1153066B (it)

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
EP0338686B1 (en) *	1988-04-22	1994-06-22	Zeneca Limited	Pyrimidinone derivatives
US5149810A (en) *	1988-04-22	1992-09-22	Imperial Chemical Industries Plc	Pyrimidine compounds
GB8908638D0 (en) *	1989-04-17	1989-06-01	Ici Plc	Novel compounds
TW229142B (it) *	1992-04-15	1994-09-01	Nissan Detrochem Corp
ATE144500T1 (de) *	1992-07-17	1996-11-15	Rohm & Haas	2-substituierte pyrimidine und ihre verwendung als herbizide
US5298481A (en) *	1992-07-17	1994-03-29	Rohm And Haas Company	6-arylpyrimidines and herbicidal use
WO1997006150A1 (en)	1995-08-10	1997-02-20	Sumitomo Chemical Company, Limited	Pyrimidin-4-one derivatives, their use as herbicides, intermediates for their production and processes for producing these compounds
KR20200011946A (ko) *	2017-06-01	2020-02-04	수미토모 케미칼 컴퍼니 리미티드	복소환 화합물 및 그것을 함유하는 조성물

Family Cites Families (7)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
FR1032239A (fr) *	1950-02-15	1953-06-30	Wellcome Found	Dérivés de pyrimidine et leur préparation
GB1182584A (en) *	1966-03-31	1970-02-25	Ici Ltd	Pyrimidine derivates and the use thereof as fungicides
BE792206A (it) *	1971-12-02	1973-06-01	Byk Gulden Lomberg Chem Fab
GB1523274A (en) *	1974-08-05	1978-08-31	Ici Ltd	Herbicidal compositions containing substituted pyrimidine
US4012388A (en) *	1975-12-11	1977-03-15	Eli Lilly And Company	Herbicidal 4-pyrimidinones and pyrimidinethiones
ZA793443B (en) *	1978-07-26	1980-12-31	Glaxo Group Ltd	Heterocyclic derivatives
JPS5659762A (en) *	1979-10-22	1981-05-23	Teijin Ltd	5-aryl-2-thiouracil derivative and its preparation

1982
- 1982-11-18 IT IT24311/82A patent/IT1153066B/it active
1983
- 1983-11-14 CH CH6116/83A patent/CH658652A5/it not_active IP Right Cessation
- 1983-11-14 JP JP58212640A patent/JPS59106472A/ja active Pending
- 1983-11-15 DE DE19833341343 patent/DE3341343A1/de not_active Ceased
- 1983-11-17 FR FR8318301A patent/FR2536394B1/fr not_active Expired
- 1983-11-17 GB GB08330735A patent/GB2130214B/en not_active Expired
- 1983-11-18 BE BE0/211895A patent/BE898258A/fr not_active IP Right Cessation

Also Published As

Publication number	Publication date
GB2130214A (en)	1984-05-31
IT8224311A1 (it)	1984-05-18
CH658652A5 (it)	1986-11-28
FR2536394A1 (fr)	1984-05-25
GB8330735D0 (en)	1983-12-29
DE3341343A1 (de)	1984-05-24
IT1153066B (it)	1987-01-14
FR2536394B1 (fr)	1986-09-19
IT8224311A0 (it)	1982-11-18
JPS59106472A (ja)	1984-06-20
GB2130214B (en)	1985-11-13

Legal Events

Date

Code

Title

Description

1992-05-31

RE

Patent lapsed

Owner name: MONTEDISON S.P.A.

Effective date: 19911130

Publication	Publication Date	Title
US4314069A (en)	1982-02-02	Herbicidal compound, herbicidal composition containing the same, and method of use thereof
JP2730713B2 (ja)	1998-03-25	Ｎ′−置換−ｎ，ｎ′−ジアシルヒドラジン系化合物の製造方法
AU639777B2 (en)	1993-08-05	Malonic acid derivative compounds
BE1001812A4 (fr)	1990-03-13	Derives du 1,5-diphenyl-1h-1,2,4-triazole-3-carboxamide et compositions herbicides qui les contiennent.
FR2519983A1 (fr)	1983-07-22	Derives de 5-methylthiopyrimidine, procedes pour leur preparation, fongicides les contenant et leur utilisation dans la lutte contre les maladies des vegetaux
FR2590570A1 (fr)	1987-05-29	Triazines, compositions herbicides contenant ces triazines et procede pour combattre les mauvaises herbes
JPH0356466A (ja)	1991-03-12	殺虫及び殺ダニ活性を有するピリダジノン類
BE898258A (fr)	1984-05-18	Dérivés de pyrimidine-4-one dotés d'une activité herbicide.
JPH05178844A (ja)	1993-07-20	除草性化合物
FR2532938A1 (fr)	1984-03-16	Nouveaux derives du thiophene, leur preparation et leur utilisation en tant que fongicides
JPH0242801B2 (it)	1990-09-26
KR950009752B1 (ko)	1995-08-28	1, 5-디페닐-1h-1, 2, 4-트리아졸-3-카르복시아미드 유도체 및 이를 함유하는 제초제 조성물
JPH0466229B2 (it)	1992-10-22
CH659249A5 (fr)	1987-01-15	Derives triazolyles et leur utilisation fongicide dans la domaine agricole.
JP2512303B2 (ja)	1996-07-03	２−オキサゾリン−４，５−ジオンのフエニルヒドラゾン誘導体
BE897705A (fr)	1984-03-08	Nouveaux chloroacetamides, leur preparation et leur utilisation comme herbicides
FR2492823A1 (fr)	1982-04-30	Derives d'aniline, leur procede de preparation et leur application
KR810000466B1 (ko)	1981-05-09	피라졸 유도체의 제조방법
JPS63239276A (ja)	1988-10-05	４、５―ジヒドロ―１ｈ―１、２、４―トリアゾール―３―カルボン酸アミド誘導体、その製造方法及び該誘導体を含有する除草剤
JPH0684341B2 (ja)	1994-10-26	オキサミドのフェニルヒドラゾン誘導体、その製造方法及び該誘導体を含有する除草剤
FR2523581A1 (fr)	1983-09-23	Derives heterocycliques contenant de l'azote dotes d'une activite de regulation de la croissance des plantes
JPS6126991B2 (it)	1986-06-23
JPH05178795A (ja)	1993-07-20	ベンジルエーテル誘導体、及びその製造方法
JPS63230676A (ja)	1988-09-27	４，５−ジヒドロ−１ｈ−１，２，４−トリアゾ−ル−３−カルボン酸アミド誘導体及び該誘導体を含有する除草剤
JPH0678276B2 (ja)	1994-10-05	アルコキシメチル安息香酸誘導体及びその製造方法