DD151938A5 - Verfahren zur herstellung von derivaten von 2-thioxo-3-benzothiazolin-acetonitril - Google Patents

Verfahren zur herstellung von derivaten von 2-thioxo-3-benzothiazolin-acetonitril Download PDF

Info

Publication number: DD151938A5
Authority: DD; German Democratic Republic
Prior art keywords: benzothiazoline; plant; acetonitrile; thioxo; solvent
Prior art date: 1979-07-05

Application number

DD80222377A

Other languages

German (de)

English (en)

Inventor

Amico John J D

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.)

1979-07-05

Filing date

1980-07-03

Publication date

1981-11-11

1980-07-03 Application filed by Monsanto Co filed Critical Monsanto Co

1981-11-11 Publication of DD151938A5 publication Critical patent/DD151938A5/de

Links

238000000034 method Methods 0.000 title claims abstract description 18
BCIJDSPGUOFPAI-UHFFFAOYSA-N 2-(2-sulfanylidene-1,3-benzothiazol-3-yl)acetonitrile Chemical class C1=CC=C2N(CC#N)C(=S)SC2=C1 BCIJDSPGUOFPAI-UHFFFAOYSA-N 0.000 title description 9
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims abstract description 33
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 claims abstract description 18
239000002904 solvent Substances 0.000 claims abstract description 18
150000001875 compounds Chemical class 0.000 claims abstract description 13
238000002360 preparation method Methods 0.000 claims abstract description 10
230000008569 process Effects 0.000 claims abstract description 7
125000000217 alkyl group Chemical group 0.000 claims abstract description 5
125000004432 carbon atom Chemical group C* 0.000 claims abstract description 5
229910052739 hydrogen Inorganic materials 0.000 claims abstract description 5
239000001257 hydrogen Substances 0.000 claims abstract description 5
125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 4
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims abstract description 4
150000003839 salts Chemical class 0.000 claims description 5
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 3
XAEFZNCEHLXOMS-UHFFFAOYSA-M potassium benzoate Chemical compound [K+].[O-]C(=O)C1=CC=CC=C1 XAEFZNCEHLXOMS-UHFFFAOYSA-M 0.000 claims description 2
125000001246 bromo group Chemical group Br* 0.000 claims 2
125000001309 chloro group Chemical group Cl* 0.000 claims 2
125000001153 fluoro group Chemical group F* 0.000 claims 2
NNFCIKHAZHQZJG-UHFFFAOYSA-N potassium cyanide Chemical compound [K+].N#[C-] NNFCIKHAZHQZJG-UHFFFAOYSA-N 0.000 abstract description 7
239000005648 plant growth regulator Substances 0.000 abstract description 3
WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract description 2
PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 abstract description 2
GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract description 2
229910052794 bromium Inorganic materials 0.000 abstract description 2
239000011737 fluorine Substances 0.000 abstract description 2
229910052731 fluorine Inorganic materials 0.000 abstract description 2
XFXPMWWXUTWYJX-UHFFFAOYSA-N Cyanide Chemical compound N#[C-] XFXPMWWXUTWYJX-UHFFFAOYSA-N 0.000 abstract 1
QWPPOHNGKGFGJK-UHFFFAOYSA-N hypochlorous acid Chemical compound ClO QWPPOHNGKGFGJK-UHFFFAOYSA-N 0.000 abstract 1
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 39
241000196324 Embryophyta Species 0.000 description 34
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 21
YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 18
238000006243 chemical reaction Methods 0.000 description 16
239000000203 mixture Substances 0.000 description 13
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
WEVYAHXRMPXWCK-UHFFFAOYSA-N acetonitrile Substances CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 11
239000004480 active ingredient Substances 0.000 description 10
230000008635 plant growth Effects 0.000 description 10
238000002844 melting Methods 0.000 description 8
230000008018 melting Effects 0.000 description 8
230000008859 change Effects 0.000 description 7
239000007787 solid Substances 0.000 description 7
229910052717 sulfur Inorganic materials 0.000 description 7
YXIWHUQXZSMYRE-UHFFFAOYSA-N 1,3-benzothiazole-2-thiol Chemical compound C1=CC=C2SC(S)=NC2=C1 YXIWHUQXZSMYRE-UHFFFAOYSA-N 0.000 description 6
NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 6
230000033228 biological regulation Effects 0.000 description 6
238000011161 development Methods 0.000 description 6
230000018109 developmental process Effects 0.000 description 6
230000012010 growth Effects 0.000 description 6
235000021374 legumes Nutrition 0.000 description 6
238000003756 stirring Methods 0.000 description 6
239000011593 sulfur Substances 0.000 description 6
239000004094 surface-active agent Substances 0.000 description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 5
239000000460 chlorine Substances 0.000 description 5
-1 derivatives of 2-thioxo-S-benzothiazoline-acetonitrile Chemical class 0.000 description 5
239000007788 liquid Substances 0.000 description 5
230000004048 modification Effects 0.000 description 5
238000012986 modification Methods 0.000 description 5
239000000654 additive Substances 0.000 description 4
238000001816 cooling Methods 0.000 description 4
239000012043 crude product Substances 0.000 description 4
238000001914 filtration Methods 0.000 description 4
238000001953 recrystallisation Methods 0.000 description 4
238000010992 reflux Methods 0.000 description 4
YEDUAINPPJYDJZ-UHFFFAOYSA-N 2-hydroxybenzothiazole Chemical compound C1=CC=C2SC(O)=NC2=C1 YEDUAINPPJYDJZ-UHFFFAOYSA-N 0.000 description 3
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 3
244000068988 Glycine max Species 0.000 description 3
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
239000003085 diluting agent Substances 0.000 description 3
230000005764 inhibitory process Effects 0.000 description 3
230000007935 neutral effect Effects 0.000 description 3
229910052760 oxygen Chemical group 0.000 description 3
239000001301 oxygen Chemical group 0.000 description 3
239000000843 powder Substances 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
230000001105 regulatory effect Effects 0.000 description 3
239000000126 substance Substances 0.000 description 3
NBKRFUZCIPSYBY-UHFFFAOYSA-N (2-oxo-1,3-benzothiazol-3-yl)methyl thiocyanate Chemical class C1=CC=C2N(CSC#N)C(=O)SC2=C1 NBKRFUZCIPSYBY-UHFFFAOYSA-N 0.000 description 2
TXOKQMSSJAIOPM-UHFFFAOYSA-N 2-(2-oxo-1,3-benzothiazol-3-yl)acetonitrile Chemical compound C1=CC=C2N(CC#N)C(=O)SC2=C1 TXOKQMSSJAIOPM-UHFFFAOYSA-N 0.000 description 2
FLFWJIBUZQARMD-UHFFFAOYSA-N 2-mercapto-1,3-benzoxazole Chemical compound C1=CC=C2OC(S)=NC2=C1 FLFWJIBUZQARMD-UHFFFAOYSA-N 0.000 description 2
RENMDAKOXSCIGH-UHFFFAOYSA-N Chloroacetonitrile Chemical compound ClCC#N RENMDAKOXSCIGH-UHFFFAOYSA-N 0.000 description 2
239000004606 Fillers/Extenders Substances 0.000 description 2
235000010469 Glycine max Nutrition 0.000 description 2
229920001213 Polysorbate 20 Polymers 0.000 description 2
VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
230000000996 additive effect Effects 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
239000000969 carrier Substances 0.000 description 2
239000003795 chemical substances by application Substances 0.000 description 2
244000038559 crop plants Species 0.000 description 2
239000002270 dispersing agent Substances 0.000 description 2
239000000428 dust Substances 0.000 description 2
230000000694 effects Effects 0.000 description 2
239000003995 emulsifying agent Substances 0.000 description 2
239000000463 material Substances 0.000 description 2
230000000877 morphologic effect Effects 0.000 description 2
239000000256 polyoxyethylene sorbitan monolaurate Substances 0.000 description 2
235000010486 polyoxyethylene sorbitan monolaurate Nutrition 0.000 description 2
BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Substances [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
239000000047 product Substances 0.000 description 2
235000012239 silicon dioxide Nutrition 0.000 description 2
239000002002 slurry Substances 0.000 description 2
239000002689 soil Substances 0.000 description 2
239000007921 spray Substances 0.000 description 2
239000007858 starting material Substances 0.000 description 2
238000006467 substitution reaction Methods 0.000 description 2
239000000758 substrate Substances 0.000 description 2
238000003786 synthesis reaction Methods 0.000 description 2
ZMZDMBWJUHKJPS-UHFFFAOYSA-N thiocyanic acid Chemical compound SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 2
239000000080 wetting agent Substances 0.000 description 2
JCMLCAKDSHCSFC-UHFFFAOYSA-N (2-oxo-1,3-benzoxazol-3-yl)methyl thiocyanate Chemical class C1=CC=CC2=C1OC(=O)N2CSC#N JCMLCAKDSHCSFC-UHFFFAOYSA-N 0.000 description 1
WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
BCMCBBGGLRIHSE-UHFFFAOYSA-N 1,3-benzoxazole Chemical compound C1=CC=C2OC=NC2=C1 BCMCBBGGLRIHSE-UHFFFAOYSA-N 0.000 description 1
WOHLSTOWRAOMSG-UHFFFAOYSA-N 2,3-dihydro-1,3-benzothiazole Chemical compound C1=CC=C2SCNC2=C1 WOHLSTOWRAOMSG-UHFFFAOYSA-N 0.000 description 1
ASSKVPFEZFQQNQ-UHFFFAOYSA-N 2-benzoxazolinone Chemical class C1=CC=C2OC(O)=NC2=C1 ASSKVPFEZFQQNQ-UHFFFAOYSA-N 0.000 description 1
XHZRTBILUWRQBR-UHFFFAOYSA-N 3-(chloromethyl)-1,3-benzothiazole-2-thione Chemical compound C1=CC=C2SC(=S)N(CCl)C2=C1 XHZRTBILUWRQBR-UHFFFAOYSA-N 0.000 description 1
ZFCFBWSVQWGOJJ-UHFFFAOYSA-N 4-chlorobutanenitrile Chemical compound ClCCCC#N ZFCFBWSVQWGOJJ-UHFFFAOYSA-N 0.000 description 1
ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
240000007049 Juglans regia Species 0.000 description 1
235000009496 Juglans regia Nutrition 0.000 description 1
239000005909 Kieselgur Substances 0.000 description 1
208000031888 Mycoses Diseases 0.000 description 1
244000061176 Nicotiana tabacum Species 0.000 description 1
235000002637 Nicotiana tabacum Nutrition 0.000 description 1
CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
229930006000 Sucrose Natural products 0.000 description 1
CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
230000001133 acceleration Effects 0.000 description 1
AMSATPOOBZEQHA-UHFFFAOYSA-N acetonitrile;1,3-benzoxazole Chemical compound CC#N.C1=CC=C2OC=NC2=C1 AMSATPOOBZEQHA-UHFFFAOYSA-N 0.000 description 1
230000009471 action Effects 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
YNQLUTRBYVCPMQ-UHFFFAOYSA-N alpha-methyl toluene Natural products CCC1=CC=CC=C1 YNQLUTRBYVCPMQ-UHFFFAOYSA-N 0.000 description 1
230000004075 alteration Effects 0.000 description 1
150000001450 anions Chemical class 0.000 description 1
229910052799 carbon Inorganic materials 0.000 description 1
239000003610 charcoal Substances 0.000 description 1
229910052801 chlorine Inorganic materials 0.000 description 1
238000007796 conventional method Methods 0.000 description 1
239000007799 cork Substances 0.000 description 1
230000006378 damage Effects 0.000 description 1
239000006185 dispersion Substances 0.000 description 1
238000009826 distribution Methods 0.000 description 1
235000013399 edible fruits Nutrition 0.000 description 1
239000000839 emulsion 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
235000013312 flour Nutrition 0.000 description 1
230000005094 fruit set Effects 0.000 description 1
239000000417 fungicide Substances 0.000 description 1
150000002334 glycols Chemical class 0.000 description 1
239000008187 granular material Substances 0.000 description 1
208000037824 growth disorder Diseases 0.000 description 1
239000003630 growth substance Substances 0.000 description 1
230000002363 herbicidal effect Effects 0.000 description 1
239000004009 herbicide Substances 0.000 description 1
150000002431 hydrogen Chemical group 0.000 description 1
239000005457 ice water Substances 0.000 description 1
230000002401 inhibitory effect Effects 0.000 description 1
125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
230000002045 lasting effect Effects 0.000 description 1
238000004519 manufacturing process Methods 0.000 description 1
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
239000003595 mist Substances 0.000 description 1
230000000051 modifying effect Effects 0.000 description 1
125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
229910052757 nitrogen Inorganic materials 0.000 description 1
238000007344 nucleophilic reaction Methods 0.000 description 1
239000008188 pellet Substances 0.000 description 1
230000000737 periodic effect Effects 0.000 description 1
231100000208 phytotoxic Toxicity 0.000 description 1
230000000885 phytotoxic effect Effects 0.000 description 1
239000004033 plastic Substances 0.000 description 1
229910000027 potassium carbonate Inorganic materials 0.000 description 1
230000001737 promoting effect Effects 0.000 description 1
239000008262 pumice Substances 0.000 description 1
239000010453 quartz Substances 0.000 description 1
RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical compound O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
239000008247 solid mixture Substances 0.000 description 1
230000036435 stunted growth Effects 0.000 description 1
239000005720 sucrose Substances 0.000 description 1
239000000375 suspending agent Substances 0.000 description 1
235000012222 talc Nutrition 0.000 description 1
238000012360 testing method Methods 0.000 description 1
229950011008 tetrachloroethylene Drugs 0.000 description 1
230000001052 transient effect Effects 0.000 description 1
235000020234 walnut Nutrition 0.000 description 1
239000002023 wood Substances 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/68—Benzothiazoles 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 in position 2
- C07D277/70—Sulfur 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
- A01N43/74—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 1,3
- A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles

Landscapes

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

DD80222377A 1979-07-05 1980-07-03 Verfahren zur herstellung von derivaten von 2-thioxo-3-benzothiazolin-acetonitril DD151938A5 (de)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US5510479A	1979-07-05	1979-07-05

Publications (1)

Publication Number	Publication Date
DD151938A5 true DD151938A5 (de)	1981-11-11

Family

ID=21995622

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
DD80222377A DD151938A5 (de)	1979-07-05	1980-07-03	Verfahren zur herstellung von derivaten von 2-thioxo-3-benzothiazolin-acetonitril

Country Status (11)

Country	Link
EP (1)	EP0022353A1 (da)
JP (1)	JPS5610181A (da)
KR (1)	KR830003458A (da)
AU (1)	AU6007480A (da)
BR (1)	BR8004164A (da)
DD (1)	DD151938A5 (da)
DK (1)	DK287280A (da)
FI (1)	FI802136A7 (da)
IL (1)	IL60469A0 (da)
PL (1)	PL225436A1 (da)
ZA (1)	ZA804018B (da)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US4362547A (en) *	1979-07-05	1982-12-07	Monsanto Company	Imides derived from 2-thioxo-3-benzox(thia)azoline acetic, and propionic acids
DE4012512A1 (de) *	1990-04-12	1991-10-17	Schering Ag	Herbizide mittel mit synergistischer wirkung

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
NL244642A (da) *	1958-10-29
US4049419A (en) *	1975-05-12	1977-09-20	Monsanto Company	Use of benzothiazoline compounds as plant growth regulants
US3993468A (en) *	1975-05-12	1976-11-23	Monsanto Company	Use of 3-substituted benzothiazolines as plant growth regulants
US4166265A (en) *	1978-02-03	1979-08-28	Amp Incorporated	Coil bobbins and termination of coil windings

1980
- 1980-07-02 IL IL60469A patent/IL60469A0/xx unknown
- 1980-07-03 BR BR8004164A patent/BR8004164A/pt unknown
- 1980-07-03 AU AU60074/80A patent/AU6007480A/en not_active Abandoned
- 1980-07-03 JP JP9160880A patent/JPS5610181A/ja active Pending
- 1980-07-03 EP EP80302254A patent/EP0022353A1/en not_active Withdrawn
- 1980-07-03 PL PL22543680A patent/PL225436A1/xx unknown
- 1980-07-03 FI FI802136A patent/FI802136A7/fi not_active Application Discontinuation
- 1980-07-03 DK DK287280A patent/DK287280A/da unknown
- 1980-07-03 DD DD80222377A patent/DD151938A5/de unknown
- 1980-07-03 ZA ZA00804018A patent/ZA804018B/xx unknown
- 1980-07-04 KR KR1019800002652A patent/KR830003458A/ko not_active Ceased

Also Published As

Publication number	Publication date
PL225436A1 (da)	1981-04-24
EP0022353A1 (en)	1981-01-14
DK287280A (da)	1981-01-06
ZA804018B (en)	1981-09-30
JPS5610181A (en)	1981-02-02
IL60469A0 (en)	1980-09-16
FI802136A7 (fi)	1981-01-01
KR830003458A (ko)	1983-06-20
BR8004164A (pt)	1981-01-21
AU6007480A (en)	1981-01-15

Publication	Publication Date	Title
DE2406475C2 (de)	1983-04-28	5-Acetamido-2,4-dimethyltrifluormethansulfonanilid und dessen landwirtschaftlich geeignete Salze, Verfahren zur Herstellung dieser Verbindungen und diese Verbindungen enthaltende Mittel
DE2812622C2 (de)	1986-10-30	(2,3-Dihydro-2,2-dimethyl-benzofuran-7-yl-oxy-N-methyl-carbamoyl)-(N'-alkyl-carbamoyl)-sulfide, Verfahren zu deren Herstellung und diese Verbindungen enthaltende insektizide Mittel
DE2637886C2 (da)	1988-10-13
DE2711230A1 (de)	1977-09-29	N-(4-benzyloxyphenyl)-n'-methyl-n'- methoxyharnstoff, verfahren zu seiner herstellung und seine verwendung als herbizid insbesondere in sojabohnenkulturen
CH632997A5 (en)	1982-11-15	Plant growth regulator
CH619113A5 (en)	1980-09-15	Herbicidal composition
DD151938A5 (de)	1981-11-11	Verfahren zur herstellung von derivaten von 2-thioxo-3-benzothiazolin-acetonitril
DE2034695A1 (de)	1971-01-28	Substituierte 3,4 Dihydro 1H-2,1,3benzothiadiazino 2,2 dioxide mit pestizider Wirkung
DE3300056C2 (de)	1985-06-27	3-Nitrobenzolsulfonanilid-Derivate und diese enthaltende fungizide Mittel
DD156413A5 (de)	1982-08-25	Zusammensetzung mit wachstumsregulierung fuer pflanzen
DD144502A5 (de)	1980-10-22	Pflanzenwachstumsregulator
DE4011781A1 (de)	1990-10-31	Herbizides mittel
DE2644446A1 (de)	1977-04-14	Neue n-(benzolsulfonyl)-thiocarbamate und ihre verwendung als gegenmittel in herbiziden zubereitungen
EP0016731B1 (de)	1983-02-16	Meta-Cyanoalkoxy-Phenylharnstoffe mit herbizider Wirkung, deren Herstellung und sie enthaltende Mittel
DE2624094A1 (de)	1976-12-02	N-carbamoyl-n-phenylaminosaeure-derivate, verfahren zu ihrer herstellung und herbizide mittel
DD236868A5 (de)	1986-06-25	Mittel zum protahieren der wirkungsdauer und zur erhoehung der selektivitaet von herbiziden zusammensetzungen
DD251275A5 (de)	1987-11-11	Als akarizid wirksame zusammensetzungen
EP0106949A2 (de)	1984-05-02	3,7-Dichlor-8-chinolinderivate, Verfahren zu ihrer Herstellung und ihre Verwendung zur Bekämpfung unerwünschten Pflanzenwuchses
DE2548898A1 (de)	1976-05-06	Benzothiazolderivate, verfahren zu ihrer herstellung und ihre verwendung als herbizide
DD145219A5 (de)	1980-12-03	Pflanzenwuchsregulierendes mittel
DD145991A5 (de)	1981-01-21	Landwirtschaftlich verwendbare zusammensetzung
DE1811717A1 (de)	1970-06-11	2,4-Dicyano-6-nitrophenyl-Derivate
DE2431801C3 (de)	1976-09-23	Benzothiazolderivate, Verfahren zu ihrer Herstellung und ihre Verwendung zur selektiven Unkrautbekämpfung in Reis- oder Weizenkulturen
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