CH637947A5 - Substituted isoxazolylbenzoates - Google Patents

Substituted isoxazolylbenzoates Download PDF

Info

Publication number: CH637947A5
Authority: CH; Switzerland
Prior art keywords: formula; compound; growth; benzoate; methyl
Prior art date: 1977-05-12

Application number

CH506478A

Other languages

German (de)

English (en)

Inventor

Robert Kenneth Howe

Original Assignee

Monsanto Co

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.)

1977-05-12

Filing date

1978-05-11

Publication date

1983-08-31

1977-05-12 Priority claimed from US05/796,295 external-priority patent/US4140515A/en

1978-05-11 Application filed by Monsanto Co filed Critical Monsanto Co

1983-08-31 Publication of CH637947A5 publication Critical patent/CH637947A5/de

Links

CRDOTKAIWZFYMN-UHFFFAOYSA-N 2-(1,2-oxazol-3-yl)benzoic acid Chemical class OC(=O)C1=CC=CC=C1C1=NOC=C1 CRDOTKAIWZFYMN-UHFFFAOYSA-N 0.000 title abstract 2
150000001875 compounds Chemical class 0.000 claims abstract description 44
230000012010 growth Effects 0.000 claims abstract description 30
230000001105 regulatory effect Effects 0.000 claims abstract description 10
238000002360 preparation method Methods 0.000 claims description 27
238000000034 method Methods 0.000 claims description 15
-1 3- [3- (trifluoromethyl) phenyl] -5-isoxazolyl benzoate Chemical compound 0.000 claims description 13
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 12
125000004076 pyridyl group Chemical group 0.000 claims description 8
150000001768 cations Chemical class 0.000 claims description 7
LFCBRWNOAMIITG-UHFFFAOYSA-N 1,2-oxazol-5-yl benzoate Chemical class C=1C=CC=CC=1C(=O)OC1=CC=NO1 LFCBRWNOAMIITG-UHFFFAOYSA-N 0.000 claims description 6
125000000217 alkyl group Chemical group 0.000 claims description 6
230000033228 biological regulation Effects 0.000 claims description 4
239000001257 hydrogen Substances 0.000 claims description 4
229910052739 hydrogen Inorganic materials 0.000 claims description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
ULYBNHOZMNYUQU-UHFFFAOYSA-N 1,2-oxazol-3-yl benzoate Chemical class C=1C=CC=CC=1C(=O)OC=1C=CON=1 ULYBNHOZMNYUQU-UHFFFAOYSA-N 0.000 claims description 3
230000001276 controlling effect Effects 0.000 claims description 2
230000002265 prevention Effects 0.000 claims description 2
238000011161 development Methods 0.000 abstract description 14
241000196324 Embryophyta Species 0.000 description 49
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 44
239000000243 solution Substances 0.000 description 29
230000005764 inhibitory process Effects 0.000 description 22
239000004480 active ingredient Substances 0.000 description 17
239000007787 solid Substances 0.000 description 17
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 16
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239000000203 mixture Substances 0.000 description 15
230000018109 developmental process Effects 0.000 description 13
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CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 10
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 10
UJOQSHCJYVRZKJ-UHFFFAOYSA-N 3-(1,3-benzoxazol-2-yl)-7-(diethylamino)chromen-2-one Chemical compound C1=CC=C2OC(C3=CC4=CC=C(C=C4OC3=O)N(CC)CC)=NC2=C1 UJOQSHCJYVRZKJ-UHFFFAOYSA-N 0.000 description 9
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238000002844 melting Methods 0.000 description 8
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PCLIMKBDDGJMGD-UHFFFAOYSA-N N-bromosuccinimide Chemical compound BrN1C(=O)CCC1=O PCLIMKBDDGJMGD-UHFFFAOYSA-N 0.000 description 7
HZNVUJQVZSTENZ-UHFFFAOYSA-N 2,3-dichloro-5,6-dicyano-1,4-benzoquinone Chemical compound ClC1=C(Cl)C(=O)C(C#N)=C(C#N)C1=O HZNVUJQVZSTENZ-UHFFFAOYSA-N 0.000 description 6
XUDBVJCTLZTSDC-UHFFFAOYSA-N 2-ethenylbenzoic acid Chemical compound OC(=O)C1=CC=CC=C1C=C XUDBVJCTLZTSDC-UHFFFAOYSA-N 0.000 description 6
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QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 5
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WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 5
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DYNFCHNNOHNJFG-UHFFFAOYSA-N 2-formylbenzoic acid Chemical compound OC(=O)C1=CC=CC=C1C=O DYNFCHNNOHNJFG-UHFFFAOYSA-N 0.000 description 4
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WTDHULULXKLSOZ-UHFFFAOYSA-N Hydroxylamine hydrochloride Chemical compound Cl.ON WTDHULULXKLSOZ-UHFFFAOYSA-N 0.000 description 4
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JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 4
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VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 4
FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 4
239000004342 Benzoyl peroxide Substances 0.000 description 3
OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 3
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XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
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VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
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ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
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OSGAYBCDTDRGGQ-UHFFFAOYSA-L calcium sulfate Chemical compound [Ca+2].[O-]S([O-])(=O)=O OSGAYBCDTDRGGQ-UHFFFAOYSA-L 0.000 description 3
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WEQPBCSPRXFQQS-UHFFFAOYSA-N 4,5-dihydro-1,2-oxazole Chemical compound C1CC=NO1 WEQPBCSPRXFQQS-UHFFFAOYSA-N 0.000 description 2
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IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
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KZBUYRJDOAKODT-UHFFFAOYSA-N Chlorine Chemical compound ClCl KZBUYRJDOAKODT-UHFFFAOYSA-N 0.000 description 2
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
240000001579 Cirsium arvense Species 0.000 description 2
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IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
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QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
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238000000023 Kugelrohr distillation Methods 0.000 description 2
JGFZNNIVVJXRND-UHFFFAOYSA-N N,N-Diisopropylethylamine (DIPEA) Chemical compound CCN(C(C)C)C(C)C JGFZNNIVVJXRND-UHFFFAOYSA-N 0.000 description 2
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UIIMBOGNXHQVGW-UHFFFAOYSA-M Sodium bicarbonate Chemical compound [Na+].OC([O-])=O UIIMBOGNXHQVGW-UHFFFAOYSA-M 0.000 description 2
WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 2
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MVPPADPHJFYWMZ-UHFFFAOYSA-N chlorobenzene Chemical compound ClC1=CC=CC=C1 MVPPADPHJFYWMZ-UHFFFAOYSA-N 0.000 description 2
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CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 description 2
GBSSKSLSRHWNBX-UHFFFAOYSA-N methyl 2-(5-pyridin-2-yl-4,5-dihydro-1,2-oxazol-3-yl)benzoate Chemical compound COC(=O)C1=CC=CC=C1C1=NOC(C=2N=CC=CC=2)C1 GBSSKSLSRHWNBX-UHFFFAOYSA-N 0.000 description 2
NBIDVCVACJYHEQ-UHFFFAOYSA-N methyl 2-(hydroxyiminomethyl)benzoate Chemical compound COC(=O)C1=CC=CC=C1C=NO NBIDVCVACJYHEQ-UHFFFAOYSA-N 0.000 description 2
MPHUYCIKFIKENX-UHFFFAOYSA-N methyl 2-ethenylbenzoate Chemical compound COC(=O)C1=CC=CC=C1C=C MPHUYCIKFIKENX-UHFFFAOYSA-N 0.000 description 2
YRMODRRGEUGHTF-UHFFFAOYSA-N methyl 2-formylbenzoate Chemical compound COC(=O)C1=CC=CC=C1C=O YRMODRRGEUGHTF-UHFFFAOYSA-N 0.000 description 2
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ARHOUOIHKWELMD-UHFFFAOYSA-N 1-ethenyl-3-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=CC(C=C)=C1 ARHOUOIHKWELMD-UHFFFAOYSA-N 0.000 description 1
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239000000725 suspension Substances 0.000 description 1
239000000454 talc Substances 0.000 description 1
229910052623 talc Inorganic materials 0.000 description 1
150000003512 tertiary amines Chemical class 0.000 description 1
238000012360 testing method Methods 0.000 description 1
DGQOCLATAPFASR-UHFFFAOYSA-N tetrahydroxy-1,4-benzoquinone Chemical compound OC1=C(O)C(=O)C(O)=C(O)C1=O DGQOCLATAPFASR-UHFFFAOYSA-N 0.000 description 1
238000009827 uniform distribution Methods 0.000 description 1
230000000007 visual effect Effects 0.000 description 1
235000020234 walnut Nutrition 0.000 description 1
238000009736 wetting Methods 0.000 description 1
239000002023 wood Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D413/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having nitrogen and oxygen atoms as the only ring hetero atoms
- 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
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/347—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups
- C07C51/353—Preparation of carboxylic acids or their salts, halides or anhydrides by reactions not involving formation of carboxyl groups by isomerisation; by change of size of the carbon skeleton
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C51/00—Preparation of carboxylic acids or their salts, halides or anhydrides
- C07C51/41—Preparation of salts of carboxylic acids
- C07C51/412—Preparation of salts of carboxylic acids by conversion of the acids, their salts, esters or anhydrides with the same carboxylic acid part
- 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
- C07D263/00—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings
- C07D263/02—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings
- C07D263/30—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
- C07D263/32—Heterocyclic compounds containing 1,3-oxazole or hydrogenated 1,3-oxazole rings not condensed with other rings having two or three 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

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Engineering & Computer Science (AREA)
Life Sciences & Earth Sciences (AREA)
Oil, Petroleum & Natural Gas (AREA)
Dentistry (AREA)
Health & Medical Sciences (AREA)
Plant Pathology (AREA)
Pest Control & Pesticides (AREA)
General Health & Medical Sciences (AREA)
Wood Science & Technology (AREA)
Zoology (AREA)
Environmental Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Agronomy & Crop Science (AREA)
Heterocyclic Carbon Compounds Containing A Hetero Ring Having Nitrogen And Oxygen As The Only Ring Hetero Atoms (AREA)
Plural Heterocyclic Compounds (AREA)
Agricultural Chemicals And Associated Chemicals (AREA)

CH506478A 1977-05-12 1978-05-11 Substituted isoxazolylbenzoates CH637947A5 (en)

Applications Claiming Priority (2)

Application Number	Priority Date	Filing Date	Title
US79624877A	1977-05-12	1977-05-12
US05/796,295 US4140515A (en)	1977-05-12	1977-05-12	Aryl-3-isoxazole benzoates as plant growth regulants and herbicides

Publications (1)

Publication Number	Publication Date
CH637947A5 true CH637947A5 (en)	1983-08-31

Family

ID=27121715

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CH506478A CH637947A5 (en)	1977-05-12	1978-05-11	Substituted isoxazolylbenzoates

Country Status (18)

Country	Link
AR (1)	AR218912A1 (it)
BR (1)	BR7802953A (it)
CH (1)	CH637947A5 (it)
CS (1)	CS197321B2 (it)
DD (1)	DD140650A5 (it)
DK (1)	DK207478A (it)
EG (1)	EG13353A (it)
HU (1)	HU181477B (it)
IE (1)	IE46956B1 (it)
IL (1)	IL54692A (it)
IT (1)	IT1094829B (it)
MX (1)	MX5300E (it)
MY (1)	MY8200124A (it)
NO (1)	NO151745C (it)
PH (1)	PH14737A (it)
PL (1)	PL110437B1 (it)
RO (2)	RO84914B (it)
SU (1)	SU738490A3 (it)

1978
- 1978-05-10 IL IL54692A patent/IL54692A/xx unknown
- 1978-05-10 EG EG299/78A patent/EG13353A/xx active
- 1978-05-11 PH PH21129A patent/PH14737A/en unknown
- 1978-05-11 CS CS782998A patent/CS197321B2/cs unknown
- 1978-05-11 MX MX787077U patent/MX5300E/es unknown
- 1978-05-11 CH CH506478A patent/CH637947A5/de not_active IP Right Cessation
- 1978-05-11 PL PL1978206702A patent/PL110437B1/pl unknown
- 1978-05-11 DK DK207478A patent/DK207478A/da not_active Application Discontinuation
- 1978-05-11 RO RO108817A patent/RO84914B/ro unknown
- 1978-05-11 HU HU78MO1014A patent/HU181477B/hu unknown
- 1978-05-11 IE IE960/78A patent/IE46956B1/en unknown
- 1978-05-11 NO NO781664A patent/NO151745C/no unknown
- 1978-05-11 RO RO108816A patent/RO84779B/ro unknown
- 1978-05-11 BR BR7802953A patent/BR7802953A/pt unknown
- 1978-05-11 IT IT23288/78A patent/IT1094829B/it active
- 1978-05-11 AR AR272124A patent/AR218912A1/es active
- 1978-05-11 DD DD78205328A patent/DD140650A5/de unknown
- 1978-05-12 SU SU782613105A patent/SU738490A3/ru active
1982
- 1982-12-30 MY MY124/82A patent/MY8200124A/xx unknown

Also Published As

Publication number	Publication date
CS197321B2 (en)	1980-04-30
RO84914B (ro)	1984-09-30
BR7802953A (pt)	1979-01-02
HU181477B (en)	1983-07-28
AR218912A1 (es)	1980-07-15
RO84914A (ro)	1984-08-17
NO151745B (no)	1985-02-18
SU738490A3 (ru)	1980-05-30
DK207478A (da)	1978-11-13
NO151745C (no)	1985-05-29
RO84779A (ro)	1984-07-17
MX5300E (es)	1983-06-13
EG13353A (en)	1981-06-30
PL206702A1 (pl)	1979-02-12
PH14737A (en)	1981-11-20
PL110437B1 (en)	1980-07-31
IL54692A (en)	1982-08-31
IE780960L (en)	1978-11-12
IT1094829B (it)	1985-08-10
IL54692A0 (en)	1978-07-31
DD140650A5 (de)	1980-03-19
MY8200124A (en)	1982-12-31
IT7823288A0 (it)	1978-05-11
NO781664L (no)	1978-11-14
IE46956B1 (en)	1983-11-16
RO84779B (ro)	1984-09-30

Legal Events

Date	Code	Title	Description
1986-01-31	PL	Patent ceased
2024-10-31	PL	Patent ceased

Publication	Publication Date	Title
DE2546251C3 (it)	1980-10-02
EP0243313B1 (de)	1990-05-16	Acyl-cyclohexandione und deren Oximäther mit herbizider und das Pflanzenwachstum regulierender Wirkung
DD283995A5 (de)	1990-10-31	Verfahren zur herstellung eines benzamid-derivats
DE3108873A1 (de)	1982-09-16	Dichlorchinolinderivate, ihre herstellung, ihre verwendung als herbizide und mittel dafuer
EP0388871B1 (de)	1993-01-13	Herbizide und pflanzenwachstumsregulierende Azolylmethyloxirane
DE3415820A1 (de)	1984-10-31	1-carbalkoxyalkyl-3-aryloxy-4-(2'-carboxyphenyl)-azet-2-one, diese enthaltende pflanzenwachstumsregulierende mittel und verfahren zum regulieren des pflanzenwachstums
DE2157048A1 (it)	1972-05-25
DE2820655A1 (de)	1978-11-16	Substituierte isoxazolylbenzoate, verfahren zu ihrer herstellung und ihre verwendung
EP0414058B1 (de)	1994-06-15	Carbonsäurederivate
EP0472091A1 (de)	1992-02-26	Synergistische Mittel zur Regulierung des Pflanzenwachstums
DE2615878C2 (de)	1985-09-19	Polycyclische stickstoffhaltige Verbindungen
EP0007089B1 (de)	1981-09-16	Acylanilide mit herbicider und fungicider Wirkung, Verfahren zu ihrer Herstellung und ihre Verwendung
DE2657380B2 (de)	1980-05-29	Halogenäthyl-sulfone, Verfahren zu ihrer Herstellung sowie ihre Verwendung zur Regulierung des Pflanzenwachstums
DD201750A5 (de)	1983-08-10	Herbizide mittel
DE3226009A1 (de)	1983-01-20	Als unkrautvernichtungs- und pflanzenwachstumsregulierungsmittel geeignete 2,4-hexadiensaeurederivate
DE2842801A1 (de)	1980-04-10	Beta-triazolyloxime
EP0422537A1 (de)	1991-04-17	Cyclohexenonverbindungen, Verfahren zu ihrer Herstellung sowie ihre Verwendung als Herbizide oder das Pflanzenwachstum regulierende Mittel
DE3601066A1 (de)	1987-07-23	Cyclohexenonderivate, ein verfahren zu ihrer herstellung sowie ihre verwendung als herbizide und das pflanzenwachstum regulierende mittel
DE2459129A1 (de)	1975-06-26	Ammoniumverbindungen
DD140650A5 (de)	1980-03-19	Verfahren und zubereitung zur verhinderung oder regulierung von pflanzenwachstum
EP0000474B1 (de)	1980-11-26	Substituierte 3-(2'-Nitro-phenoxy)-alpha-phenoxy-alkancarbonsäure und ihre Derivate, deren Herstellung und Verwendung als Herbizide
DE1542809A1 (de)	1970-03-26	Pflanzenbehandlungsmittel
DE2601376A1 (de)	1977-07-21	Phenoxycarbonsaeure-aryloxy(thio)carbonylaminomethylester, verfahren zu ihrer herstellung sowie ihre verwendung zur regulierung des pflanzenwachstums
EP0230260B1 (de)	1990-12-27	Cyclohexenonderivate, Verfahren zu ihrer Herstellung und ihre Verwendung als herbizide und das Pflanzenwachstum regulierende Mittel
CH624554A5 (en)	1981-08-14	Method of protecting crops of plants