SI9300063B - 4-benzoylisoxazole derovatives and their use as herbicides - Google Patents
4-benzoylisoxazole derovatives and their use as herbicides Download PDFInfo
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- SI9300063B SI9300063B SI9300063A SI9300063A SI9300063B SI 9300063 B SI9300063 B SI 9300063B SI 9300063 A SI9300063 A SI 9300063A SI 9300063 A SI9300063 A SI 9300063A SI 9300063 B SI9300063 B SI 9300063B
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- benzoyl
- cyclopropylisoxazole
- chloro
- group
- methyl
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- 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
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/80—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,2
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
- C07D261/08—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to ring carbon atoms
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D261/00—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings
- C07D261/02—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings
- C07D261/06—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two or more double bonds between ring members or between ring members and non-ring members
- C07D261/10—Heterocyclic compounds containing 1,2-oxazole or hydrogenated 1,2-oxazole rings not condensed with other rings having two 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, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D261/18—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen
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- 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)
- Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Plural Heterocyclic Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Hydrogenated Pyridines (AREA)
Claims (16)
1 PATENTNI ZAHTEVKI 1. Derivati 4-benzoil izoksazola s splošno formulo (I): O R2
v kateri: R pomeni atom vodika ali skupino -CCTR3; R1 pomeni ciklopropil; R2 pomeni -S(0)nR51; RJ pomeni: klorov, bromov ali fluorov atom; alkilno ali alkoksilno skupino z nerazvejeno ali razvejeno verigo, ki vsebuje do štiri ogljikove atome, poljubno substituirane z enim ali več atomi halogena; alkenilno skupino z nerazvejeno ali razvejeno verigo, ki vsebuje do šest ogljikovih atomov; ali skupino -C02R52; R4 pomeni: klorov, bromov ali fluorov atom; alkilno skupino z nerazvejeno ali razvejeno verigo, ki vsebuje do štiri ogljikove atome, poljubno substituirane z enim ali več atomi halogena; alkoksilno skupino, ki vsebuje do štiri ogljikove atome, substituirane z enim ali več atomi halogena; -S(0)pR5j ali ciano; R5 pomeni alkilno skupino z nerazvejeno ali razvejeno verigo, ki vsebuje do šest ogljikovih atomov, poljubno substituiranih z enim ali več atomi halogena; R51 pomeni etil ali metil; R32 pomeni metil ali etil; 2 R53 pomeni alkilno skupino z nerazvejeno ali pa razvejeno verigo, ki vsebuje do štiri ogljikove atome; n pomeni nulo, ena ali dva; in p pomeni nulo, ena ali dva.
2. Spojina po zahtevku 1, označena s tem, da: R3 pomeni fluorov, klorov ali bromov atom; metilno ali etilno skupino; alkoksi skupino, ki vsebuje enega ali dva ogljikova atoma, poljubno substituirana z enim ali več halogenimi atomi; alkenilno skupino, ki vsebuje od dva do štiri ogljikove atome; ali -C02R52; in R4 pomeni fluorov, klorov ali bromov atom; alkilno skupino, ki vsebuje enega ali dva ogljikova atoma, substituirana z enim ali več atomi halogena; alkoksi skupino, ki vsebuje enega ali dva ogljikova atoma, substituirana z enim ali več atomi halogena; ali f Λ f Λ -S(0)pR , v kateri p pomeni nulo in je R metilna ali etilna skupina.
3. Spojina po zahtevku 1 ali 2, označena s tem, da: RJ pomeni fluorov, klorov ali bromov atom; metilno, metoksi ali etoksi skupino; alkenilno skupino, ki vsebuje dva ali tri ogljikove atome; ali -CC^R32 kjer je R52 metil; R4 pomeni fluorov, klorov ali bromov atom ali skupino, izbrano med trifluorometilom, trifluorometoksi in -S(0)pMe kjer je p nula; R1 pomeni metilno ali etilno skupino.
4. Spojina po kateremkoli od predhodnih zahtevkov, označena s tem, da: R3 pomeni fluor, klor, brom, metil ali metoksi; R4 pomeni fluor, klor, brom ali trifluorometil; R1 pomeni metil ali etil; in R51 pomeni metil. 1 Spojina po kateremkoli od predhodnih zahtevkov, označena s tem, da: R3 pomeni fluor, klor, brom ali metoksi; 3 R4 pomeni fluor, klor, brom ali trifluorometil; R5 pomeni metil ali etil; in R51 pomeni metil.
6. Spojina po kateremkoli od predhodnih zahtevkov, označena s tem, da: R3 pomeni klorov, bromov ali fluorov atom; R4 pomeni fluor, klor, brom ali trifluorometil; R3 pomeni metil ali etil; in R51 pomeni metil.
7. Spojina po zahtevku 1, označena s tem, daje: 5-ciklopropil-4-[3,4-difluoro-2-(metilsulfonil)benzoil]-izoksazol; 5-ciklopropil-4-[3,4-dikloro-2-(metilsulfenil)benzoil]-izoksazol; 5-ciklopropil-4-[3,4-dikloro-2-(metilsulfinil)benzoil]-izoksazol; 5-ciklopropil-4-[3,4-dikloro-2-(metilsulfonil)benzoil]-izoksazol; 5-ciklopropil-4-[4-bromo-3-metoksi-2-(metilsulfenil)benzoil]-izoksazol; 5-ciklopropil-4-[4-bromo-3-metoksi-2-(metilsulfonil)benzoil]-izoksazol; 5-ciklopropil-4-[4-bromo-3-metoksi-2-(metilsulfinil)benzoil]-izoksazol; etil 5-ciklopropil-4-[3,4-dikloro-2-(metilsulfinil)benzoil]-izoksazol-3-karboksilat; 4-[4-kloro-3-metoksi-2-(metilsulfenil)benzoil]-5-ciklpropil izoksazol; ali etil 5-ciklopropil-4-[3,4-dikloro-2-(metilsulfonil)benzoil]-izoksazol-3-karboksilat.
8. Spojina po zahtevku 1, označena s tem, da je etil 5-ciklopropil-4-[3,4-dikloro-2-(metilsulfenil)benzoil]izoksazol-3-karboksilat.
9. Spojina po zahtevku 1, označena s tem, daje 4-[4-kloro-3-metoksi-2-(metilsulfinil)benzoil]-5-ciklopropilizoksazol; 4-[4-kloro-3-metoksi-2-(metilsulfonil)benzoil]-5-ciklopropilizoksazol; 4-[4-kloro-3-metil-2-(metilsulfenil)benzoil]-5-ciklopropilizoksazol; 4 4-[4-kloro-3-fluoro-2-(metilsulfenil)benzoil]-5-ciklopropilizoksazol; 4-[4-kloro-3-fluoro-2-(metilsulfinil)benzoil]-5-ciklopropilizoksazol; 4-[4-kloro-3-fluoro-2-(metilsulfonil)benzoil]-5-ciklopropilizoksazol; 4-[4-kloro-3-metil-2-(metilsulfinil)benzoil]-5-ciklopropilizoksazol; 4- [4-kloro-3-metil-2-(metilsulfonil)benzoil]-5-ciklopropilizoksazol; 5- ciklopropil-4-[3-metoksikarbonil-2-(metilsulfenil)-4-trifluorometil-benzoil]izoksazol; 4-[4-kloro-3-metoksikarbonil-2-(metilsulfenil)benzoil]-5-ciklopropil-izoksazol; 4-[4-bromo-3-kloro-2-(metilsulfenil)benzoil]-5-ciklopropilizoksazol; 4-[4-bromo-3-kloro-2-(metilsulfinil)benzoil]-5-ciklopropilizoksazol; 4-[4-bromo-3-kloro-2-(metilsulfonil)benzoil]-5-ciklopropilizoksazol; 4-[4-kloro-3-metoksikarbonil-2-(metilsulfmil)benzoil]-5-ciklopropilizoksazol; 4-[4-kloro-3-metoksikarbonil-2-(metilsulfonil)benzoil]-5-ciklopropilizoksazol; 4-[3-kloro-2-(metilsulfenil)-4-trifluorometilbenzoil]-5-ciklopropilizoksazol; 4-[3-kloro-2-(metilsulfonil)-4-trifluorometilbenzoil]-5-ciklopropilizoksazol; 4-[4-bromo-3-fluoro-2-(metilsulfenil)benzoil]-5-ciklopropilizoksazol; 4-[4-bromo-3-fluoro-2-(metilsulfinil)benzoil]-5-ciklopropilizoksazol; 4-[4-bromo-3-fluoro-2-(metilsulfonil)benzoil]-5-ciklopropilizoksazol; 4- [4-kloro-3-izopropenil-2-(metilsulfenil)-benzoil]-5-ciklopropilizoksazol; 5- ciklopropil-4-[3-metil-2,4-bis(metilsulfenil)-benzoil]izoksazol; 4- [4-kloro-3 -izopropeni l-2-(meti lsulfmil)-benzoil]-5 -ciklopropilizoksazol; ali 4-[4-kloro-3-izopropenil-2-(metilsulfonil)benzoil]-5-ciklopropilizoksazol.
10. Postopek priprave spojine s splošno formulo (I), kot je določena v zahtevku 1, označen s tem, da obsega: a) reakcijo spojine s splošno formulo (II): R2 ° O
(ID R' L 5 kjer so R1, R2, R3 in R4, kot je določeno v zahtevku 1, in je L izstopajoča skupina, s soljo hidroksilamina; b) kjer R pomeni vodik, R2 skupino -SR51 in R4 skupino R41, ki je, kot je določeno za R4, pod pogojem daje p ničla, reakcijo spojine s splošno formulo (III): O N
C1 (ΠΙ) v kateri je R1, kot je določeno v zahtevku 1, s spojino s splošno formulo (IV): R2
(IV) v kateri R2 pomeni skupino.-SR51, R3 je, kot je določeno v zahtevku 1, in R41, kot je določeno zgoraj; c) kadar je R vodik, reakcijo spojine s splošno formulo (V): ,_ P i N'0Ar> <v> v kateri je R1, kot je določeno v zahtevku 1, in Y pomeni karboksi skupino ali njen reaktivni derivat ali ciano skupino, s primernim organokovinskim reagentom; d) kjer je n ena ali dva in/ali p je ena ali dva, oksidacijo žveplovega atoma ustrezne spojine s splošno formulo (I), v kateri je n nula ali ena in/ali p je nula ali ena; e) kjer R pomeni skupino -C02R3, n je nula ali dva in R4 pomeni skupino R42, ki je, kot je določeno za R4, pod pogojem, da je p 0 ali 2, reakcijo spojine s splošno formulo (VI): 6
Rl v kateri so R1, R2, R3 kot je določeno v zahtevku 1, n je nula ali dva, R42 je, kot je zgoraj določeno, in P je izstopajoča skupina, s spojino s splošno formulo R502CC(X)=N0H, v kateri je R5, kot je določeno v zahtevku 1, in X je atom halogena; f) kjer R pomeni skupino -C02R5, n je nula ali dva in R4 pomeni skupino R42, reakcijo spojine s splošno formulo (VII): R- O -R] R3. . J R42' (Vil) v kateri so R1, R2 in R3, kot je določeno v zahtevku 1, n je 0 ali 2, in R42 je, kot je določeno zgoraj, s spojino s splošno formulo R502CC(X)=N0H, v kateri je R5, kot je določeno v zahtevku 1, in X je atom halogena; ali g) kjer R pomeni -C02R5, nje nula ali dva in R4 pomeni skupino R42, reakcijo soli spojine s splošno formulo (VIII):
Rl (VIII) 7 I η ^ 1Λ 1Λ v kateri so R , R , R in R , kot je določeno v zahtevku 1, n je 0 ali 2, in R je, kot je določeno zgoraj, s spojino s splošno formulo R502CC(X)=N0H, v kateri je R5, kot je določeno v zahtevku 1, in X je atom halogena.
11. Herbicidni sestavek, označen s tem, da kot aktivno sestavino vsebuje herbicidno učinkovito količino derivata izoksazola s splošno formulo (I), kot je določeno v kateremkoli od zahtevkov 1 do 9 skupaj z razredčilom ali nosilcem in/ali površinsko aktivnim sredstvom, ki so sprejemljivi za poljedelstvo.
12. Herbicidni sestavek po zahtevku 11, označen s tem, da vsebuje 0,05 do 90 masnih % aktivne sestavine.
13. Herbicidni sestavek po zahtevku 11, označen s tem, da je v obliki tekočine in da vsebuje od 0,05 do 25 % površinsko aktivnega sredstva.
14. Herbicidni sestavek po zahtevku 11, označen s tem, daje v obliki koncentrata suspenzije v vodi, zmočljivega praška, praška, topnega v vodi, ali praška, ki se lahko dispergira v vodi, tekočega koncentrata, topnega v vodi, tekočega koncentrata suspenzije, ki se lahko emulgira, granul ali koncentrata, ki se lahko emulgira.
15. Postopek kontrole rasti plevela na zemljišču, označen s tem, da vključuje aplikacijo herbicidno učinkovite količine derivata izoksazola s splošno formulo (I), kot je določeno v kateremkoli od zahtevkov 1 do 9, na zemljišče.
16. Postopek po zahtevku 15, označen s tem, da se zemljišče uporablja, ali je namenjeno uporabi za gojitev poljščin in da se spojina aplicira v dozah od 0,01 kg do 4,0 kg na hektar.
17. Postopek po zahtevku 15, označen s tem, daje zemljišče površina na kateri se ne gojijo poljščine, in da se spojina aplicira v dozah od 1,0 kg do 20,0 kg na hektar.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US85012892A | 1992-03-12 | 1992-03-12 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| SI9300063A SI9300063A (sl) | 1993-12-31 |
| SI9300063B true SI9300063B (en) | 2001-08-31 |
Family
ID=25307335
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| SI9300063A SI9300063B (en) | 1992-03-12 | 1993-02-04 | 4-benzoylisoxazole derovatives and their use as herbicides |
Country Status (32)
| Country | Link |
|---|---|
| US (1) | US5334753A (sl) |
| EP (1) | EP0560482B1 (sl) |
| JP (1) | JP3310039B2 (sl) |
| KR (1) | KR100278704B1 (sl) |
| CN (1) | CN1057524C (sl) |
| AT (1) | ATE156483T1 (sl) |
| AU (1) | AU664229B2 (sl) |
| BG (1) | BG62151B1 (sl) |
| BR (1) | BR9300324A (sl) |
| CA (1) | CA2088840C (sl) |
| CZ (1) | CZ282051B6 (sl) |
| DE (1) | DE69312769T2 (sl) |
| DK (1) | DK0560482T3 (sl) |
| ES (1) | ES2105098T3 (sl) |
| FI (1) | FI930496A7 (sl) |
| GR (1) | GR3024373T3 (sl) |
| HR (1) | HRP930106B1 (sl) |
| HU (1) | HU217562B (sl) |
| IL (1) | IL104614A (sl) |
| MA (1) | MA22920A1 (sl) |
| MX (1) | MX9300627A (sl) |
| NZ (1) | NZ245844A (sl) |
| PL (1) | PL172002B1 (sl) |
| RO (1) | RO112029B1 (sl) |
| RU (1) | RU2105761C1 (sl) |
| SI (1) | SI9300063B (sl) |
| SK (1) | SK280521B6 (sl) |
| TR (1) | TR27630A (sl) |
| TW (1) | TW250426B (sl) |
| YU (1) | YU48749B (sl) |
| ZA (1) | ZA93769B (sl) |
| ZW (1) | ZW2293A1 (sl) |
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| GB9115377D0 (en) * | 1991-07-17 | 1991-09-04 | Rhone Poulenc Agriculture | New compositions of matter |
| US5530028A (en) * | 1992-11-23 | 1996-06-25 | Rohm And Haas Company | Insecticidal N'-substituted-N,N'-diacylhydrazines |
| GB9302072D0 (en) * | 1993-02-03 | 1993-03-24 | Rhone Poulenc Agriculture | New compositions of matter |
| US5962370A (en) * | 1993-12-10 | 1999-10-05 | Rhone-Poulenc Agriculture Ltd | Herbicidal compositions comprising a 4-benzoylisoxazole and a triazine herbicide |
| GB9325284D0 (en) * | 1993-12-10 | 1994-02-16 | Rhone Poulenc Agriculture | Herbicidal compositions |
| GB9325618D0 (en) * | 1993-12-15 | 1994-02-16 | Rhone Poulenc Agriculture | New herbicides |
| US5795846A (en) * | 1994-08-01 | 1998-08-18 | Rhone-Poulenc Agriculture Limited | Herbicidal compositions |
| US5552367A (en) * | 1994-11-18 | 1996-09-03 | Rhone-Poulenc Agriculture Ltd. | Synergistic herbicidal compositions comprising 4-benzoylisoxazole and dinitroaniline herbicides |
| US5912206A (en) * | 1994-12-09 | 1999-06-15 | Rhone-Poulenc Agrochimie | Herbicidal compositions |
| WO1997000013A1 (en) * | 1995-06-19 | 1997-01-03 | Rhone-Poulenc Agrochimie | New fungicidal compositions and the use thereof |
| US6004904A (en) * | 1995-06-19 | 1999-12-21 | Rhone-Poulenc Inc. | Use of 4-benzoylisoxazoles for the protection of turfgrass |
| ZA9610348B (en) * | 1995-12-20 | 1997-07-11 | Rhone Poulenc Agriculture | Herbicidal compositions |
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| MX2012012775A (es) | 2010-05-04 | 2012-12-17 | Basf Se | Plantas que tienen tolerancia incrementada a herbicidas. |
| CA2820706C (en) | 2010-12-03 | 2018-05-22 | Ms Technologies, Llc | Optimized expression of glyphosate resistance encoding nucleic acid molecules in plant cells |
| US8648230B2 (en) | 2011-03-18 | 2014-02-11 | Ms Technologies, Llc | Regulatory regions preferentially expressing in non-pollen plant tissue |
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| MX360318B (es) | 2013-11-04 | 2018-10-29 | Dow Agrosciences Llc | Óptimos loci de maíz. |
| UY35812A (es) | 2013-11-04 | 2015-05-29 | Dow Agrosciences Llc | ?loci de maíz óptimos?. |
| EP3066202B1 (en) | 2013-11-04 | 2021-03-03 | Dow AgroSciences LLC | Optimal soybean loci |
| TW201527314A (zh) | 2013-12-31 | 2015-07-16 | Dow Agrosciences Llc | 新穎玉米泛素啓動子（三） |
| TW201527313A (zh) | 2013-12-31 | 2015-07-16 | Dow Agrosciences Llc | 新穎玉米泛素啓動子（二） |
| TW201527316A (zh) | 2013-12-31 | 2015-07-16 | Dow Agrosciences Llc | 新穎玉米泛素啓動子（五） |
| TW201527312A (zh) | 2013-12-31 | 2015-07-16 | Dow Agrosciences Llc | 新穎玉米泛素啓動子（一） |
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| US4323692A (en) * | 1978-08-04 | 1982-04-06 | Rohm And Haas Company | Process for preparing phenoxybenzoic acids |
| GB8920519D0 (en) * | 1989-09-11 | 1989-10-25 | Rhone Poulenc Ltd | New compositions of matter |
| GB9025469D0 (en) * | 1990-11-22 | 1991-01-09 | Rhone Poulenc Agriculture | New compositions of matter |
| GB9017539D0 (en) * | 1990-08-10 | 1990-09-26 | Rhone Poulenc Agriculture | New compositions of matter |
| GB9116834D0 (en) * | 1991-08-05 | 1991-09-18 | Rhone Poulenc Agriculture | Compositions of new matter |
| IL102674A (en) * | 1991-08-05 | 1996-11-14 | Rhone Poulenc Agriculture | 4-Benzoyl isoxazole derivatives process for their preparation and herbicidal compositions containing them |
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1992
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1993
- 1993-02-03 HR HR07/850,128A patent/HRP930106B1/xx not_active IP Right Cessation
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