CH662564A5 - Derives du n-pyridylpyrazole et composition herbicides les contenant. - Google Patents

Derives du n-pyridylpyrazole et composition herbicides les contenant. Download PDF

Info

Publication number: CH662564A5
Authority: CH; Switzerland
Prior art keywords: formula; carbon atoms; compound; linear; branched
Prior art date: 1983-03-09

Application number

CH1162/84A

Other languages

English (en)

French (fr)

Inventor

Leslie Roy Hatton

Edgar William Parnell

David Alan Roberts

Original Assignee

May & Baker Ltd

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.)

1983-03-09

Filing date

1984-03-08

Publication date

1987-10-15

1983-03-09 Priority claimed from GB838306465A external-priority patent/GB8306465D0/en

1984-01-11 Priority claimed from GB848400690A external-priority patent/GB8400690D0/en

1984-03-08 Application filed by May & Baker Ltd filed Critical May & Baker Ltd

1987-10-15 Publication of CH662564A5 publication Critical patent/CH662564A5/fr

Links

239000000203 mixture Substances 0.000 title claims description 54
230000002363 herbicidal effect Effects 0.000 title claims description 26
XXTPHXNBKRVYJI-UHFFFAOYSA-N 2-pyrazol-1-ylpyridine Chemical class C1=CC=NN1C1=CC=CC=N1 XXTPHXNBKRVYJI-UHFFFAOYSA-N 0.000 title claims description 15
239000004009 herbicide Substances 0.000 title claims description 11
150000001875 compounds Chemical class 0.000 claims description 315
125000004432 carbon atom Chemical group C* 0.000 claims description 205
125000000217 alkyl group Chemical group 0.000 claims description 93
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 93
125000003545 alkoxy group Chemical group 0.000 claims description 56
238000006243 chemical reaction Methods 0.000 claims description 52
241000196324 Embryophyta Species 0.000 claims description 45
-1 cyano, hydroxy Chemical group 0.000 claims description 42
238000000034 method Methods 0.000 claims description 38
238000002360 preparation method Methods 0.000 claims description 36
125000003342 alkenyl group Chemical group 0.000 claims description 33
125000000304 alkynyl group Chemical group 0.000 claims description 32
229910052740 iodine Chemical group 0.000 claims description 28
230000008569 process Effects 0.000 claims description 26
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 23
125000004453 alkoxycarbonyl group Chemical group 0.000 claims description 23
229910052799 carbon Inorganic materials 0.000 claims description 22
229910052801 chlorine Chemical group 0.000 claims description 22
239000003085 diluting agent Substances 0.000 claims description 17
125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 16
239000000460 chlorine Substances 0.000 claims description 16
150000003839 salts Chemical class 0.000 claims description 15
QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 14
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 claims description 14
239000002585 base Substances 0.000 claims description 14
125000005843 halogen group Chemical group 0.000 claims description 14
229910052757 nitrogen Inorganic materials 0.000 claims description 14
239000004094 surface-active agent Substances 0.000 claims description 13
125000001309 chloro group Chemical group Cl* 0.000 claims description 12
BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 claims description 12
125000004433 nitrogen atom Chemical group N* 0.000 claims description 12
125000004429 atom Chemical group 0.000 claims description 11
125000003917 carbamoyl group Chemical group [H]N([H])C(*)=O 0.000 claims description 11
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 claims description 10
150000001335 aliphatic alkanes Chemical group 0.000 claims description 10
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 10
239000002253 acid Substances 0.000 claims description 7
229910021529 ammonia Inorganic materials 0.000 claims description 7
229910052739 hydrogen Inorganic materials 0.000 claims description 7
239000001257 hydrogen Substances 0.000 claims description 7
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 6
235000004977 Brassica sinapistrum Nutrition 0.000 claims description 6
125000002947 alkylene group Chemical group 0.000 claims description 6
125000003277 amino group Chemical group 0.000 claims description 6
230000008030 elimination Effects 0.000 claims description 6
238000003379 elimination reaction Methods 0.000 claims description 6
235000019253 formic acid Nutrition 0.000 claims description 6
125000000951 phenoxy group Chemical group [H]C1=C([H])C([H])=C(O*)C([H])=C1[H] 0.000 claims description 6
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 claims description 6
IXVJKFCFNGQJTG-UHFFFAOYSA-N 3-oxopropanoyl 3-oxopropanoate Chemical compound O=CCC(=O)OC(=O)CC=O IXVJKFCFNGQJTG-UHFFFAOYSA-N 0.000 claims description 5
239000011149 active material Substances 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
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
159000000011 group IA salts Chemical class 0.000 claims description 5
230000007062 hydrolysis Effects 0.000 claims description 5
238000006460 hydrolysis reaction Methods 0.000 claims description 5
102200016458 rs104894274 Human genes 0.000 claims description 5
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical group [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 claims description 4
229910001854 alkali hydroxide Inorganic materials 0.000 claims description 4
150000008044 alkali metal hydroxides Chemical class 0.000 claims description 4
125000005091 alkenylcarbonylamino group Chemical group 0.000 claims description 4
125000000033 alkoxyamino group Chemical group 0.000 claims description 4
239000007864 aqueous solution Substances 0.000 claims description 4
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 4
235000013339 cereals Nutrition 0.000 claims description 4
230000000694 effects Effects 0.000 claims description 4
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 4
238000009333 weeding Methods 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
240000005979 Hordeum vulgare Species 0.000 claims description 3
235000007340 Hordeum vulgare Nutrition 0.000 claims description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 3
125000004414 alkyl thio group Chemical group 0.000 claims description 3
229910052794 bromium Inorganic materials 0.000 claims description 3
125000000753 cycloalkyl group Chemical group 0.000 claims description 3
LEQPWHOCBNPBLO-UHFFFAOYSA-N 2-[3-chloro-5-(trifluoromethyl)pyridin-2-yl]-3-(hydrazinylmethylidene)-2-hydroxybutanedinitrile Chemical compound ClC=1C(=NC=C(C=1)C(F)(F)F)C(C#N)(O)C(C#N)=CNN LEQPWHOCBNPBLO-UHFFFAOYSA-N 0.000 claims description 2
244000291564 Allium cepa Species 0.000 claims description 2
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244000046052 Phaseolus vulgaris Species 0.000 claims description 2
235000010627 Phaseolus vulgaris Nutrition 0.000 claims description 2
240000004713 Pisum sativum Species 0.000 claims description 2
235000010582 Pisum sativum Nutrition 0.000 claims description 2
235000021307 Triticum Nutrition 0.000 claims description 2
240000008042 Zea mays Species 0.000 claims description 2
235000005824 Zea mays ssp. parviglumis Nutrition 0.000 claims description 2
235000002017 Zea mays subsp mays Nutrition 0.000 claims description 2
125000003302 alkenyloxy group Chemical group 0.000 claims description 2
125000003368 amide group Chemical group 0.000 claims description 2
235000005822 corn Nutrition 0.000 claims description 2
IXCSERBJSXMMFS-UHFFFAOYSA-N hydrogen chloride Substances Cl.Cl IXCSERBJSXMMFS-UHFFFAOYSA-N 0.000 claims description 2
229910000041 hydrogen chloride Inorganic materials 0.000 claims description 2
235000020232 peanut Nutrition 0.000 claims description 2
235000009566 rice Nutrition 0.000 claims description 2
102220024746 rs199473444 Human genes 0.000 claims description 2
239000007858 starting material Substances 0.000 claims description 2
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims 4
125000004093 cyano group Chemical group *C#N 0.000 claims 2
235000016068 Berberis vulgaris Nutrition 0.000 claims 1
241000335053 Beta vulgaris Species 0.000 claims 1
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims 1
244000098338 Triticum aestivum Species 0.000 claims 1
125000005090 alkenylcarbonyl group Chemical group 0.000 claims 1
125000006193 alkinyl group Chemical group 0.000 claims 1
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims 1
150000001733 carboxylic acid esters Chemical class 0.000 claims 1
230000004992 fission Effects 0.000 claims 1
125000005842 heteroatom Chemical group 0.000 claims 1
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims 1
229910052760 oxygen Inorganic materials 0.000 claims 1
239000001301 oxygen Substances 0.000 claims 1
230000000361 pesticidal effect Effects 0.000 claims 1
125000001424 substituent group Chemical group 0.000 claims 1
229940124530 sulfonamide Drugs 0.000 claims 1
239000011593 sulfur Substances 0.000 claims 1
229910052717 sulfur Inorganic materials 0.000 claims 1
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 63
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 53
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 51
238000010992 reflux Methods 0.000 description 41
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ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 36
239000003960 organic solvent Substances 0.000 description 31
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 30
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 30
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 30
239000011734 sodium Substances 0.000 description 30
229910052708 sodium Inorganic materials 0.000 description 30
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 27
ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical compound [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 25
239000011591 potassium Substances 0.000 description 25
229910052700 potassium Inorganic materials 0.000 description 25
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 25
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HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 23
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229910002027 silica gel Inorganic materials 0.000 description 1
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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
YZHUMGUJCQRKBT-UHFFFAOYSA-M sodium chlorate Chemical compound [Na+].[O-]Cl(=O)=O YZHUMGUJCQRKBT-UHFFFAOYSA-M 0.000 description 1
159000000000 sodium salts Chemical class 0.000 description 1
229910052938 sodium sulfate Inorganic materials 0.000 description 1
235000011152 sodium sulphate Nutrition 0.000 description 1
239000008247 solid mixture Substances 0.000 description 1
238000000638 solvent extraction Methods 0.000 description 1
239000011877 solvent mixture Substances 0.000 description 1
238000009331 sowing Methods 0.000 description 1
238000003892 spreading Methods 0.000 description 1
230000007480 spreading Effects 0.000 description 1
239000003381 stabilizer Substances 0.000 description 1
150000003458 sulfonic acid derivatives Chemical class 0.000 description 1
150000003459 sulfonic acid esters Chemical class 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
238000005809 transesterification reaction Methods 0.000 description 1
229940047183 tribulus Drugs 0.000 description 1
235000015112 vegetable and seed oil Nutrition 0.000 description 1
235000013311 vegetables Nutrition 0.000 description 1
230000000007 visual effect Effects 0.000 description 1
239000008096 xylene Substances 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)

CH1162/84A 1983-03-09 1984-03-08 Derives du n-pyridylpyrazole et composition herbicides les contenant. CH662564A5 (fr)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
GB838306465A GB8306465D0 (en)	1983-03-09	1983-03-09	Compositions of matter
GB848400690A GB8400690D0 (en)	1984-01-11	1984-01-11	Compositions of matter

Publications (1)

Publication Number	Publication Date
CH662564A5 true CH662564A5 (fr)	1987-10-15

Family

ID=26285450

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH1162/84A CH662564A5 (fr)	1983-03-09	1984-03-08	Derives du n-pyridylpyrazole et composition herbicides les contenant.

Country Status (9)

Country	Link
BE (1)	BE899118A (nl)
BR (1)	BR8401052A (nl)
CH (1)	CH662564A5 (nl)
DE (1)	DE3408727A1 (nl)
DK (1)	DK145684A (nl)
FR (1)	FR2543951B1 (nl)
IL (1)	IL71175A0 (nl)
IT (1)	IT1175785B (nl)
NL (1)	NL8400732A (nl)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
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)

* Cited by examiner, † Cited by third party
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 NL NL8400732A patent/NL8400732A/nl not_active Application Discontinuation
- 1984-03-07 IT IT19939/84A patent/IT1175785B/it active
- 1984-03-07 IL IL71175A patent/IL71175A0/xx unknown
- 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 BE BE0/212538A patent/BE899118A/fr not_active IP Right Cessation
- 1984-03-09 DE DE19843408727 patent/DE3408727A1/de not_active Withdrawn

Also Published As

Publication number	Publication date
FR2543951B1 (fr)	1987-01-23
BE899118A (fr)	1984-09-10
FR2543951A1 (fr)	1984-10-12
BR8401052A (pt)	1984-10-16
DK145684A (da)	1984-09-10
DE3408727A1 (de)	1984-09-13
NL8400732A (nl)	1984-10-01
IT8419939A0 (it)	1984-03-07
IT1175785B (it)	1987-07-15
IL71175A0 (en)	1984-06-29
DK145684D0 (da)	1984-02-29

Publication	Publication Date	Title
ES2300107T3 (es)	2008-06-01	Derivados de piridazin-3-ona, su utilizacion e intermediarios para su produccion.
KR100203826B1 (ko)	1999-06-15	우라실 유도체
RU2278113C2 (ru)	2006-06-20	Новые замещенные производные пиразола, способ их получения и гербицидные композиции, содержащие эти производные
CH655310A5 (fr)	1986-04-15	Derives acylamino du n-phenylpyrazole, compositions les contenant et leur utilisation comme herbicides.
KR880000155B1 (ko)	1988-03-12	2-치환페닐-4, 5, 6, 7-데트라하이드로-2h-인다졸류의 제조방법
RU2670439C2 (ru)	2018-10-23	Производное замещенного пиразолилпиразола и его применение в качестве гербицида
KR0155560B1 (ko)	1998-11-16	우라실 유도체, 그의 제법 및 용도
JP2015036371A (ja)	2015-02-23	置換ピラゾリルピラゾール誘導体とその除草剤としての使用
CN114644622A (zh)	2022-06-21	一种含异噁唑啉的吡啶联苯类化合物及其制备方法与用途
EP0197495B1 (en)	1990-07-11	4,5,6,7-tetrahydro-2h-indazole derivatives and herbicides containing them
KR0160307B1 (ko)	1998-12-01	이미노티아졸린, 그의 제조방법 및 제초제로서의 용도, 및 그의 제조용 중간체
CH660006A5 (fr)	1987-03-13	Derives du n-phenylpyrazole.
US4729784A (en)	1988-03-08	1-(1,4-benzoxazin-3-on-6-yl)-dialkylmaleimides and use as herbicides
EP0527016A1 (en)	1993-02-10	Herbicidal quinoxalinyloxy ethers
RU2056413C1 (ru)	1996-03-20	Иминотиазолины, способы их получения, гербицидная композиция, способ уничтожения нежелательных сорняков
US6156891A (en)	2000-12-05	Production of pyridazine herbicides
WO1994004511A1 (fr)	1994-03-03	Derive de pyrimidine et herbicide
CH662564A5 (fr)	1987-10-15	Derives du n-pyridylpyrazole et composition herbicides les contenant.
CH657360A5 (fr)	1986-08-29	Derives du n-phenylpyrazole utilises dans des compositions herbicides et procede pour leur preparation.
JPH11292720A (ja)	1999-10-26	縮合イミダゾリノン誘導体を含有する除草剤
KR19990044698A (ko)	1999-06-25	피라진-2-온 유도체, 그의 용도 및 그를 제조하기 위한 중간물
US5238906A (en)	1993-08-24	Pyridone derivatives and use
JP2762505B2 (ja)	1998-06-04	縮合ヘテロ環誘導体、その製法及び除草剤
FR2503706A1 (fr)	1982-10-15	Derives de pyrazole, procede pour leur preparation et herbicides les contenant
US6232271B1 (en)	2001-05-15	1-Methyl-5-alkylsulfonyl-, 1-methyl-5-alkylsulfinyl- and 1-methyl-5-alkylthio- substituted pyrazolylpyrazoles, processes for their preparation and their use as herbicides

Legal Events

Date	Code	Title	Description
1989-11-30	PL	Patent ceased
2024-10-31	PL	Patent ceased