CA2106497A1 - N-hydroxy-n-phenylcarboxamides, their preparation and compositions containing them for controlling harmful fungi - Google Patents

N-hydroxy-n-phenylcarboxamides, their preparation and compositions containing them for controlling harmful fungi

Info

Publication number
CA2106497A1
CA2106497A1 CA002106497A CA2106497A CA2106497A1 CA 2106497 A1 CA2106497 A1 CA 2106497A1 CA 002106497 A CA002106497 A CA 002106497A CA 2106497 A CA2106497 A CA 2106497A CA 2106497 A1 CA2106497 A1 CA 2106497A1
Authority
CA
Canada
Prior art keywords
methyl
ethyl
halogen
chloro
alkyl
Prior art date
Legal status (The legal status 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 status listed.)
Abandoned
Application number
CA002106497A
Other languages
French (fr)
Inventor
Karl Eicken
Eberhard Ammermann
Gisela Lorenz
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
BASF SE
Original Assignee
Individual
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.)
Filing date
Publication date
Application filed by Individual filed Critical Individual
Publication of CA2106497A1 publication Critical patent/CA2106497A1/en
Abandoned legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C233/00—Carboxylic acid amides
    • C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
    • C07C233/02—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals
    • C07C233/04—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • C07C233/07—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having nitrogen atoms of carboxamide groups bound to hydrogen atoms or to carbon atoms of unsubstituted hydrocarbon radicals with carbon atoms of carboxamide groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a six-membered aromatic ring
    • 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
    • A01N43/34—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom
    • A01N43/40—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with one nitrogen atom as the only ring hetero atom six-membered rings
    • 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
    • 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
    • C07D213/78—Carbon atoms having three bonds to hetero atoms, with at the most one bond to halogen, e.g. ester or nitrile radicals
    • C07D213/81—Amides; Imides
    • C07D213/82—Amides; Imides in position 3
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D231/00—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings
    • C07D231/02—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings
    • C07D231/10—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D231/14—Heterocyclic compounds containing 1,2-diazole or hydrogenated 1,2-diazole rings not condensed with other rings having two or three 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
    • C07D277/02—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings
    • C07D277/20—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D277/32—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings not condensed with other rings having two or three 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
    • C07D277/56—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/02—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings
    • C07D307/34—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three double bonds between ring members or between ring members and non-ring members
    • C07D307/56—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom not condensed with other rings having two or three 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
    • C07D307/68—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D309/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings
    • C07D309/16—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D309/28—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only ring hetero atom, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D327/00—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms
    • C07D327/02—Heterocyclic compounds containing rings having oxygen and sulfur atoms as the only ring hetero atoms one oxygen atom and one sulfur atom
    • C07D327/06—Six-membered rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/02—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings
    • C07D333/04—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur atom
    • C07D333/26—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom not condensed with other rings not substituted on the ring sulphur 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
    • C07D333/38—Carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals

Abstract

N-Hydroxy-N-phenylcarboxamides, their manufacture, and agents containing them for for combatting injurious fungi ABSTRACT OF THE DISCLOSURE:
1. N-Hydroxy-N-phenylcarboxamides of the formula I

I

where:
R is substituted or unsubstituted alkyl, alkoxy, alkenyl, alkenyloxy, alkynyl, alkynyloxy, cycloalkyl, cycloalke-nyl, cycloalkyloxy, cycloalkenyloxy or phenyl;
A is one of the radicals A1 to A7 where X is -CH2-, -S-, -SO- or -SO2-;
Y is -O- or -S-;
R1, R2, R4, R5 and R7 are halogen, alkyl or haloalkyl;
R3 and R6 are hydrogen, halogen or alkyl;
n is 1 or 2;
methods of manufacturing them, agents containing them, and their use for combatting injurious fungi.

Description

2 ~ O ~ ~ 9 7 o . z . ooso/43543 N-HyDRoxy-N-pMENyLcARBoxAMIDEs~ THEIR PREPARATION
AND COMPOSITIONS CONTAINING THEM FOR CONTROLLING ~-E~ARMFUL FUNGI
The present invention relates to N-hydroxy-N-phenylcarboxamides of the formula I

R ~ . I
HO - N - CO - A
where the substituents have the following meanings: ..
R is C2-C12-alkyl, C2-C12-alkoxy, C3-C12-alkenyl, C3-Cl2-alkenyloxy~ C3-C6-alkynyl, C3-C6-alkynyloxy, where these groups can be partially or completely halogenated; C3-C7-cycloalkyl, C4-C7-cycloalkenyl, :'.:.
C3-C7-cycloalkoxy or C4-C~-cycloalkenyloxy, where .
these rings can carry one to 3 Cl-C4-alkyls; phenyl which can carry one to five halogen atoms and/or one ~ .
to three of the following radicals: Cl-C4-alkyl, :
C1-C4-haloalkyll C1-C4-alkoxy, C1-C4-haloalkoxy, C1-C4-alkylthio or C1-C4-haloalkylthio; -:
A is a cyclic radical from the group consisting of the formulae Al to A7:

tR3)n Al A2 A3 A4 7~C~ ~ 6 ~5 A6 A7 where the substituen~s have the following meanings:
20 X is -CH2-, -S-, -SO- or -S2-;
Y is -O- or -S-' ::-R1, R2, R4, R' and R7 are halogen, Cl-C4-alkyl or ,::: , '~,~"''' '~.,.', i,, "-"" ", , ,,,; .:- .", , " ~" ;~

'. , ' ' '; ' ' . ' , ! . ' : , ,~ ~ ,', " '.' ."; ' ' ' ', . ,', ' ' ' ~ , ' ,, ",, ' '' ' ' ', ' ,'i' 2106~7 - 2 - O~Z. 0050~43543 C,-C4-haloalkyl;
R3 and R6 are hydrogen, halogen or C,-C4-alkyl;
n is 1 or 2, where the radicals R3 can be different if the value of n is 2.
The invention additionally relates to the preparation of these compounds, compositions containing them and their use for controlling harmful fungi, in particular Botrytis.
N-(2-Chlorophenyl)-2-chloronicotinamide is known from the literature as a fungicidal active compound (DE-A 2 417 216).
It is an object of the present invention to provide novel fungicidally active compounds having an improved spectrum of action.
We have found that this object is achieved by the compounds I defined at the beginning.
We have additionally found processes for pre-paring these compounds, compositions containing them and their use for controlling harmful fungi.
The compounds I are in general obtained by ~-reacting a carboxylic acid halide of the formula II in a manner known per se (eg. J. March, Advanced Organic Chemistry, 2nd Ed., 1977, 382 ~f., McGraw-Hill) with an N-hydroxyaniline of the formula III in the prPsence of a 2~ base.

Hal-CO-A + R ~ - - ~ R~
HO - NH HO - N - CO - A

II III I

~ he radical Hal in the formula II is a halogen ~uch as chlorine, bromine or iodine, in particular chlorine or bromine.
This reaction i8 customarily carried out at temperatures from -20C to 100C, preferably -10~C to : ". ' .. . .. . . . . . .
.. .. . . : .. , . :
, .... ,, ,. . - : ,, . . : . : . :
., , ,, , " ., . , . . . . : :.
, . ., .. :, . , ... , : . . .
., . , . ,:, . .. .. . ., .. , ~ : . :
:;, ., ' .: ' ': ' '. .' , , ' ' . . , ' ~ ' ' , ,, , . ~. . ., ~, . " . , ..... . ", , , i , ~, ...... . . .

210~497 _ 3 _ o.z. 00~0/435~3 50C.
Suitable solvents are:
aliphatic hydrocarbons such as pentane, hexane, cyclo-hexane and petroleum ether, aromatic hydrocarbons such as toluene, o-, m- and p-xylene, halogenated hydrocarbons such as dichloromethane, chloroform and chlorobenzene, ethers such as diethyl ether, diisopropyl ether, tert-butyl methyl ether, dioxane, anisole and tetrahydrofuran, nitriles such as acetonitrile and propionitrile, ketones such as acetone, methyl ethyl ketone, diethyl ketone and tert-butyl methyl ketone, alcohols such as methanol, ethanol, n-propanol, isopropanol, n-butanol and tert-butanol, and also dimethyl sulfoxide and dimethyl-formamide, particularly preferably toluene, xylene and tetrahydrofuran.
Mixtures of the solvents mentioned can also be used.
Suitable bases are generally inorganic compounds such as alkali metal and alkaline earth metal hydroxides such as lithium hydroxide, sodium hydroxide, potassium hydroxide and calcium hydroxide, alkali metal and alkaline earth metal oxides such as l.ithium oxide, sodium oxide, calcium oxide and magnesium oxide, alkali metal : and alkaline earth metal hydrides such as lithium hydride, sodium hydride, potassium hydride and calcium hydride, alkali metal amides such as lithium amide, sodium amide and potassium amide, alkali metal and alkaline earth metal carbonate~ ~uch as lithium carbonate and calcium carbonate and also alkali metal hydrogen-carbonates such as sodium hydrogencarbonate, and organo-metallic compounds, in particular alkali metal alkyls such as methyllithium, butylli~hium and phenyllithium, alkylmagnesium halides such as methylmagnesium chloride and also alkali metal and alkaline earth metal alkoxides such as sodium methoxide, sodium ethoxide, potassium ethoxide, potassium tert-butoxide and dimethoxymagnesium, additionally organic bases, eg. tertiary amines such as , -, . . ... . . . . . . .
, :, .. .
,~. , , ,. :

':' : , ' : .. ', . ' ' ' '' : , .. . .

21~6~97 - 4 - O.Z. 0050/43543 trimethylamine, triethylamine, tri-isopropylethylamine and N-methylpiperidine, pyridine, substituted pyridines such as collidine, lutidine and 4-dimethylaminopyridine and also bicyclic amines.
Sodium hydro~encarbonate, sodium carbonate, triethylamine ~nd pyridine are particularly preferred.
The bases are in general employed in equimolar amounts based on the compound II. However, they can also be used in an excess of from 5 mol% to 30 mol%, preferably 5 mol% to 10 mol%, or - in the case of the use of tertiary amines - if appropriate as a solvent.
The star~ing materials are in general reacted with one another in equimolar amounts. It may be advan-tageous for the yield to employ II in an excess of from 1 mol% to 20 mol~, preferably 1 mol% to 10 mol%, based on III.
The starting substances of the formulae II and III needed for preparing the compounds I are known in the literature (Houben-Weyl, Methoden der org. Chemie (Method~ of Organic Chemistry), Vol. 10/1, pp. 1138-1148) or can be prepared according to the literature cited.
With respect to their use :in fungicidal composi-tions, suitable compounds of the formula I are those in which the substituents have the following meanings:
25 R is C2-Cl2-alkyl such as ethyl and straight-chain or branched propyl, butyl, pentyl, hexyl, heptyl, octyl, nonyl, decyl, undecyl and dodecyl, particu-larly strai~ht-chain or branched C3-C10-alkyl such as propyl, 1-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl, l,1-dimethylethyl, n-pentyl, l-methylbutyl, 2-methylbutyl, 3-methylbutyl, 1,2-dimethylpropyl, 1,1-dimethylpropyl, 2,2-dimethylpropyl, 1-ethylpropyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 3-methylpentyl, 4-methylpentyl, 1,2-dimethylbutyl, 1,3-dimethyl-butyl, l,3-dimethylbutyl, 2,3-dimethylbutyl, 1,1-dimethylbutyl, 2,2-dimethylbutyl, 3,3-dimethyl-,, ,- .. , . ............. , ; . .: .

, ~ . ., , . . . , , , , . ,. . : .
., ,. , , , . . . , ', . , ', ', . : ~.. '. .'' :' : : ' . ;
...... . , ... . . '. ' .'. ' :. '. :

2 1 ~ 7 - 5 - O.Z. 0050/43543 butyl,l,1,2-trimethylpropyl,1,2,2-trimethylpropyl, l-ethylbutyl, 2-ethylbutyl, 1-ethyl-3-methylpropyl, n-heptyl, 1-methylhexyl, l-ethylpentyl, 2-ethyl-pentyl, 1-propylbutyl, octyl, l-methylheptyl, 2-methylheptyl, l-ethylhexyl, 2-ethylhexyl, l-propylpentyl, 2-propylpentyl, nonyl, l-methyl-octyl, 2-methyloctyl, 1-ethylheptyl, 2-ethylheptyl, l-propylhexyl, 2-propylhexyl, decyl, l-methylnonyl, 2-methylnonyl, l-ethyloctyl, 2-ethyloctyl, 1-propyl-heptyl and 2-propylheptyl, in particular propyl, l-methylethyl, butyl, l-methylbutyl, 2-methylbutyl, l,l-dimethylethyl, pentyl, 1-methylbutyl, hexyl, heptyl and l-methylheptyl, where these groups can be partially or complete1y halogenated, ie. the hydrogens of these groups can be partially or com-pletely replaced by halogens such~ as fluorine, chlorine and bromine, in particular fluorine and chlorine, for example haloalkyl such as chloro-methyl, dichloromethyl, trichloromethyl, fluoro-methyl, difluoromethyl, trifluoromethyl, chloro-fluoromethyl, dichlorofluoromethyl, chlorodifluoro-methyl, l-fluoroethyl, 2-fluoroethyl, 2,2-difluoro-ethyl,2,2,2-trifluoroethyl,2-chloro-2-~luoroethyl, 2-chloro-2,2-difluoroethyl, 2,2-dichloro-2-fluoro-ethyl, 2,2,2-trichloroethyl and pentafluoroethyl;

C2-Cl2-alkoxy such as ethoxy and ~traight-chain or branched propoxy, butoxy, pentoxy, hexyloxy, heptyl-oxy, octyloxy, nonyloxy, decyloxy, undecyloxy and dodecyloxy, particularly straight-chain or branched C2-C10-alkoxy such as ethoxy, propoxy, l-methyl-ethoxy, butoxy, l-methylpropoxy, 2-methylpropoxy, 1,1-dimethylethoxy, n-pentoxy, 1-methylbutoxy, 2-methylbutoxy,3-methylbutoxy~1,2-dimethylpropoxy, 1-ethylpropoxy, n-hexyloxy, 1-methylpentoxy, 2-methylpentoxy, 3-methylpentoxy, 4-methylpentoxy, 1,2-dimethylbutoxy, 1,3-dimethylbutoxy, '.~ . :, . , ,' ; ' ' ' ,. . . . . . . .
~-- ~ , : . , .

210~7 - 6 - O.Z. 0050/43543 2,3-dimethylbutoxy, 1,2-dimethylbutoxy, 2,2-dimethylbutoxy, 3,3-dimethylbutoxy, 1,1,2-tri-methylpropoxy, 1,2,2-trimethylpropoxy, l-ethyl-butoxy, 2-ethylbutoxy, 1-ethyl-2-methylpropoxy, n-heptyloxy, 1-methylhexyloxy, 2-methylhexyloxy, 3-methylhexyloxy, 4-methylhexyloxy, 5-methylhexyl-oxy, 1-ethylpentoxy, 2-ethylpentoxy, l-propylbutoxy, octyloxy, l-methylheptyloxy, 2-methylheptyloxy, 1-ethylhexyloxy, 2-ethylhexyloxy, 1-propylpentoxy, 2-propylpentoxy, nonyloxy, l-methyloctyloxy, 2-methyloctyloxy, l-ethylheptyloxy, 2-ethylheptyl-oxy, l-propylhexyloxy, 2-propylhexyloxy, decyloxy, 1-methylnonyloxy,2-methylnonylox.y,1-ethyloctyloxy, 2-ethyloctyloxy, l-propylheptyloxy and 2-propyl-lS heptyloxy, in particular ethoxy, propoxy, 1-methyl-ethoxy, butoxy, 1-methylpropoxy, 2-me~hylpropoxy, l/1-dimethylethoxy, pentoxy, hexyloxy and 2-ethyl-hexyloxy, where these groups can ~e partlally or completely halogenated, ie. the hydrogens o~ these groups can be partially or completely replaced by halogens such as fluorine, chlorine and bromine, in particular fluorine and chlor.ine, for example halo-alkoxy such as chloromethoxy, dichloromethoxy, trichloromethoxy, fluoromethoxy, difluoromethoxy, trifluoromethoxy, chlorofluoromiethoxy, dichloro-fluoromethoxy, chlorodifluoromethoxy, 1-fluoro-ethoxy, 2-~luoroethoxy, 2,2-difluoroethoxy, 2,2,2-tri~luoroethoxy, 2-chloro-2-fluoroethoxy, 2-chloro-2,2-difluoroethoxyl 2,2-dichloro-2-fluoro-ethoxy, 2,2,2-t~ichloroethoxy and penta~luoroethoxy;

C3-C12-alkenyl such as straight-chain or b~anched propenyl, butenyl, pentenyl, hexenyl, heptenyl, octenyl, nonenyl, decenyl, undecenyl and dodecenyl, particularly straight-chain or branched C3-C10-alkenyl such a5 2-propenyl, 2-butenyl, 3-butenyl,1-methyl-2-propenyl,2-methyl-2-propenyl, .:
' . : ,,., :,, , ,.,,, , ; -, :. , , ,, ., . . ~. . , . ,, , ., ,, ,. , :, . . ..

21~6~7 - 7 - O.Z. 0050/43543 2-pentenyl, 3-pentenyl, 4-pentenyl, 1-methyl-2-butenyl, 2-methyl-2-butenyl, 3-methyl-2-butenyl, 1-methyl-3-blltenyl, 2-methyl-3-butenyl, 3-methyl-3-butenyl, 1,1-dimethyl-2-propenyl, 1,2-dimethyl-2-propenyl,1-ethyl-2-propenyl,2-hexenyl, 3-hexenyl,4-hexenyl, 5-hexenyl,1-methyl-2-pentenyl,2-methyl-2-pentenyl,3-methyl-2-pentenyl,4-methyl-2-pentenyl,1-methyl-3-pentenyl,2-methyl-3-pentenyl,3-methyl-3 pentenyl, 4-methyl-3-pentenyl, 1-methyl-4-pentenyl,2-methyl-4-pentenyl,3-methyl-4-pentenyl, 4-methyl-4-pentenyl, 1,1-dimethyl-2-butenyl, 1,1-dimethyl-3-butenyl, 1,2-dimethyl-2-butenyl, 1,2-dimethyl-3-butenyl, 1,3-dimethyl-2-butenyl, 1,3-dimethyl-3-butenyl, 2,2-dimethyl-3-butenyl, 2,3-dimethyl-2~butenyl, ~2,3-dimethyl-3-butenyl, 1-ethyl-2-butenyl, 1-ethyl~3-butenyl, 2-ethyl-2-butenyl, 2-ethyl-3-butenyl, 1,1,2-tri-methyl-2-propenyl, 1-ethyl-1-methyl-2-propenyl, 1-ethyl-2-methyl-2-propenyl, 1-methyl-2-pentenyl, 2-methyl-2-pentenyl, 1-methyl-3-pentenyl, 2-methyl-3-pentenyl, 1-methyl-2-hexenyl, 2-methyl-2-hexenyl, l-methyl-3-hexenyl,: 2-me~hyl-3-hexenyl, 1-ethyl-2-pentenyl, 2-ethyl-2-pentenyl, 1-ethyl-3-pentenyl, 2-ethyl~3-pentenyl, 1-methyl-2-heptenyl, 2-methyl-2-heptenyl, 1-methyl-3-heptenyl, 2-methyl-3-heptenyl, 1-ethyl-2-hexenyl, 2-ethyl-2-hexenyl, 1-ethyl-3-hexenyl, 2-ethyl-3-hexenyl, l-methyl-2-octsnyl, 2-methyl-2-octenyl, 1-methyl-3-octenyl, 2-methyl-3-octenyl, 1-ethyl-2-heptenyl, 2-ethyl-2-heptenyl, 1-ethyl-3-heptenyl, 2-ethyl-3-heptenyl, l-ethyl-2-octenyl, 2-ethyl-2-octenyl, l-ethyl-3-octenyl and 2-ethyl-3-octenyl, in particular 1-propenyl, 2-propenyl, 1-methylethenyl, l-methyl-2-propenyl,2-methyl-2-propenyl,l-ethyl-2-propenyl, 1-methyl-2-butenyl, 1-ethyl-2-butenyl, 1-(1-methyl-ethyl)-2-butenyl, 1-butyl-2-butenyl, 1-methyl-, 2 1 0 ~ 7 - 8 - O.Z. 0050/43543 2-pentenyl and 1,4-dimethyl-2-pentenyl, where these groups can be partially or completely halogenated, ie. the hydrogens of these groups can be partially or completely replaced by halo~ens such as fluorine, chlorine and bromine, in particular fluorine and chlorine, in particular 3-chloro-2-propenyl and 2,3-dichloro-2-propenyl;

C3-Cl2-alkenyloxy such as straight-chain or branched propenyloxy, butenyloxy, pentenyloxy, hexenyloxy, heptenyloxy, octenyloxy, nonenyloxy, decenyloxy, undecenyloxy and dodecenyloxy, partlcularly straight-chain or branched C3-C10-alkenyloxy such as 2-propenyloxy, 2-butenyloxy, 3-butenyloxy, 1-methyl-2-propenyloxy, 2-methyl-2-propenyloxy, 2-pentenyl-oxy, 3-pentenyloxy, 4-pentenyloxy, l-methyl-2-butenyloxy, 2-methyl-2-butenyloxy, 3-methyl-2-butenyloxy, 1-methyl-3-butenyloxy, 2-methyl-3-butenyloxy, 3~methyl-3-butenyloxy, 1,1-dimethyl-2-propenyloxy, 1,2-dimethyl-2-propenyloxy, 1-ethyl-2-propenyloxy, 2-hexenyloxy, 3-hexenyloxy, 4-hexenyloxy, 5-hexenyloxy, 1-methyl-2-pentenyloxy, 2-methyl-2-pentenyloxy, 3~methyl-2-pentenyloxy, 4-methyl-2-pentenyloxy, 1-methyl-3-pentenyloxy, 2-methyl-3-pentenyloxy, 3-methyl-3-pentenyloxy, 4-methyl-3-pentenyloxy, 1-methyl-4-pentenyloxy, 2-methyl-4-pentenyloxy, 3-methyl-4-pentenyloxy, 4-methyl~4-pentenyloxy, 1,1-dimethyl-2-butenyloxy, 1,1-dimethyl-3-butenyloxy, 1,2-dimethyl-2-butenyloxy, 1,2-dimethyl-3-butenyloxy, 1,3-dimethyl-2-butenyloxy, 1,3-dimethyl-3-butenyl-oxy, 2,2-dimethyl-3-butenyloxy, 2,3-dimethyl-2-butenyloxy, 2,3-dimethyl-3-butenyloxy, 1-ethyl-2-butenyloxy, 1-ethyl-3-butenyloxy, 2-ethyl-2-butenyloxy,2-ethyl-3-butenyloxy,1,1,2~trimethyl-2-propenyloxy, 1-ethyl-1-methyl -2-propenyloxy, 1-ethy1-2-methyl-2 propenyloxy, 1-methyl-2-pentenyl-''. .:
,::' ' '".

, ~ :

, ~ ' , . ' .'~
" ' ' : "; ~ ' ," , . ' , '. " ' ", " ' ' ' '., " ., ' ' . " . ~

2 1 0 ~ 7 _ g _ o z. 0050~43543 oxy,2-methyl-2-pentenyloxy,1-methyl-3-pentenyloxy, 2-methyl-3-pentenyloxy,1-methyl-2-hexenyloxy, 2-methyl-2-hexenyloxy,1-methyl-3-hexsnyloxy, 2-methyl-3-hexenyloxy,1-ethyl-2-pentenyloxy, 2-ethyl-2-pentenyloxy,1-ethyl-3-pentenyloxy, 2-ethyl-3-pentenyloxy,1-methyl-2-heptenyloxy, 2-methyl-2-heptenyloxy,1-methyl-3-heptenyloxy, 2-methyl-3-heptenyloxy,1-ethyl-2-hexenyloxy, 2-ethyl-2-hexenyloxy,l-ethyl-3-hexenyloxy,2-ethyl-3-hexenyloxy, 1-methyl-2-octenyloxy, 2-methyl-2-octenyloxy, 1-methyl-3-octenyloxy, 2-methyl-3-octenyloxy, 1-ethyl-2-heptenyloxy, 2-ethyl-2-heptenyloxy, 1-ethyl-3-heptenyloxy, 2-ethyl-3-heptenyloxy, 1-ethyl-2-octenyloxy, 2-ethyl-2-octenyloxy, 1-ethyl-3-octenyloxy and 2-ethyl-3-octenyloxy, in particular 2-propenyloxy, 1-methyl-2-propenyloxy, 2-methyl-2-propenyloxy, 2-pentenyl-oxy, 3-pentenyloxy, 1-methyl-2-butenyloxy and 1-methyl-2 pentenyloxy, where these groups can be partially or completely halogenatedt ie. the hydrogens of these groups can be partially or com-pletely replaced ~y halogens such as fluorine, ; chlorine and bromine, in particular fluorine and chlorine, in particular 3-chloro-2-propenyloxy, : 25 2,3-dichloro-2-propenyloxy and 2,3,3-trichloro-: 2-propenyloxy;

C3-C6-alkynyl such as 2-propynyl, 2-butynyl, 3-butynyl, 1-methyl-2-propynyl, 2-pentynyl, 3-pent-ynyl, 4-pentynyl, 1-methyl-3-butynyl, 2-methyl-3-butynyl, 1-methyl-2-butynyl, 1,1-dimethyl-2-propyn-yl, l-ethyl-2-propynyl, 2-hexynyl, 3-hexynyl, 4- :
alkynyl, 5-hexynyl, 1-methyl-2-pentynyl, 1-methyl-3-pentynyl, 1-methyl~4-pentynyl, 2-methyl-3-pentynyl, 2-methyl-4-pentynyl, 3-methyl-4-pentynyl r 4-methyl-2-pentynyl, 1,2-dimethyl-2-butynyl, 1,1-dimethyl-3-butynyl, 1,2-dimethyl-3-butynyl, 2,2-dimethyl-3~
" ,~ .

;' ~ ~ .
' ' , ' :

21~6~97 - 10 - O.Z. OO50/43543 butynyl, 1-ethyl-2-butynyl, 1-ethyl-3-butynyl, 2-ethyl-3-butynyl and 1-ethyl-1-methyl-2-propynyl, in particular 2-propynyl, 2-butynyl and 3-butynyl, where these groups can be partially or completely halogenated, ie. the hydrogens of these groups can be partially or completely replaced by halogens such as fluorine, chlorine and bromine, in particular fluorine and chlorine, for example 3-chloro-2-pro-pynyl, 3-chloro-2-butynyl and 4-chloro-3-butynyl;

C3-C6-alkynyloxy such as 2-propynyloxy, 2-butynyloxy, 3-butynyloxy,l-methyl-2-propynyloxy,2-pentynyloxy, 3-pentynyloxy, 3-pentynyloxy, 4-pentynyloxy, 1-methyl-3-butynyloxy, 2-methyl-3-butynyloxy, 1-methyl-2-butynyloxy,1,1-dimethyl-2-propionyloxy,1-ethyl-2-propynyloxy, 2 hexynyloxy, 3-hexynyloxy, 4-alkynyloxy, 5-hexynyloxy, 1-methyl-2-pentynyloxy, 1-methyl-3-pentynyloxy, 1-methyl-4-pentynyloxy, 2-methyl-3-pentynyloxy, 2-methyl-4-pentynyloxy, 3-methyl-4-pentynyloxy~ 4-methyl-3-pentynyloxy, 1,1-dimethyl-2-butynyloxy, 1,1-dimethyl-3-butynyl-oxy, 1,2-dimethyl-3-butynyloxy, 2,2-dimethyl-3-butynyloxy,1-ethyl-2-butynyloxy,l-ethyl-3-butynyl-oxy, 2-ethyl-3-butynyloxy and 1-ethyl-1-methyl-2-propynyloxy, preferably 2-propynyloxy, 2-butynyloxy, 1-methyl-2-propynyloxy and 1-methyl-2-butynyloxy, 2-propynyloxy, 2-butynyloxy, 3-butynyloxy and 1-methyl-2-propynyloxy, where these groups can be partially or completely halogenated, ie. the hydro-gens of the~e groups can be partially or completely replaced by halo~en~ such as fluorine, chlorine and bromine, in particular fluorine and chlorine, for example 3-chloro-2-propynyloxy, 3-chloro~2-butynyl-oxy and 4-chloro-3-butynyloxy;

C3-C7-cycloalkyl such as cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl and cycloheptyl, where these ........ ..
~'''`'.

. , . "

2~0~497 O.Z. 0050/43543 rings can carry one to 3 Cl-C4-alkyl~ such as methyl, ethyl, propyl, l-methylethyl, butyl, l-methylpropyl, 2-methylpropyl and l, l-dimethylethyl;

C4-C7-cycloalkenyl such as cyclobutenyl, cyclo-pentenyl, cyclohexenyl and cycloheptenyl, where these rings can carry one to three Cl-C4-alkyls such as methyl, ethyl, propyl, l-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl and 1, l-dimethylethyl;

C3-C7-cycloalkoxy such as cyclopropoxy, cyclobutoxy, cyclopentoxy, cyclohexyloxy and cycloheptyloxy, where these rings can carry one to 3 C,-C4-alkyls such as methyl, ethyl, propyl, l-methylethyl, butyl, l-methylpropyl, 2-methylpropyl and 1, l-dimethylethyl;

or C4-C7-cycloalkenyloxy such as l-cyclobutenyloxy, 2-cyclobutenyloxy, l-cyclopentenyloxy, 2-cyclopentenyloxy, 3-cyclopentenyloxy, l-cyclohexenyloxy, 2-cyclohexenyloxy, 3-cyclo-hexenyloxy, l-cycloheptenyloxy, 2-cycloheptenyloxy, 3-cycloheptenyloxy and 4-cyc:loheptenyloxy, where these rings can carry one to 3 C,-C4-al3~yls such as methyl r ethyl, propyl, l-methylethyl, butyl, 1-methylpropyl, 2-methylpropyl and 1, l-dimethylethyl;

phenyl, which can carry one to five halogen ~uch a~
2 5 ~luorine, chlorine, bromine and iodine, in particular fluorine, chlorine and bromine, and/or one to three of the following radicals:

- Cl-C4-alkyl as mentioned above;
- Cl-C4-haloalkyl as mentioned above;
Cl-C4-alkoxy as mentioned above;
- Cl-C4-haloalkoxy as mentioned above;
- Cl-C4-alkylthio such a~ methylthio, ethylthio, : . . . . . .

: .
'' ' ~ : ., : , 2~6497 - 12 - O.Z. 0050/43543 propylthio, 1-methylethylthio, butylthio, 1-methylpropylthio, 2-methylpropylthio and 1,1-dimethylethylthio;
- or Cl-C4-haloalkylthio, particularly C,-C2-halo alkylthio such as chloromethylthio, dichloro-methylthio, trichloromethylthio, fluoromethyl-thio, difluoromethylthio, trifluoromethylthio, chlorofluoromethylthio, dichlorofluoromethylthio, chlorodifluoromethylthio, 1-fluoroethylthio, 2-fluoroethylthio, 2,2-difluoroethylthio, 2,2,2-trifluoroethylthio, 2-chloro-2-fluoroethylthio, 2-chloro-2,2-difluoroethylthio, 2,2-dichloro-2-fluoroethylthio, 2,2,2-trichloroethylthio and pentafluoroethylthio.

15 A is a cyclic radical ~rom the group consisting of the formulae A1 to A7:

~1 ~ R ~ O Ca3 ~3~ C113 Al A2 A3 A4 R3)~ ~Nr;~

2~5 A6 A7 .:
where the sub~tituentæ have the following meanings:
X is -CH2-, -S-, -SO- or -SO
Y . is -O- or -S~
R1, R2, R4, Rs and R' independently of one another are halogen such as fluorine, chlorine and bromine, Cl C4-alkyl as mentioned above, or C1-C4-haloalkyl as mentioned above; .
R3 and R6 independently o one another are hydrogen, halogen such as fluorine, chlorine and bromine or - :,,: : . ~ :: . . , ., .,, . , ., ,.. , . ., .. , ,. . .. .. i i,.. ... ;, , .. , .. . . . :

2~0~97 - 13 - O.Z. 0050~43543 C;-C4-alkyl as mentioned above;
n is 1 or 2, where the radicals R3 can be different if the value of n is 2.
With respect to the biological action, particularly preferred compounds of the formula I are those in which R has the abovementioned meanings and A is a cyclic radical from the group consisting of the formu-lae Al to A7, where X and Y have the abovementioned meaning and the substituents are the following radicals:
R1 is halogen such as fluorine, chlorine and bromine, methyl or C1-haloalkyl such as chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl,trifluoromethyl,chlorofluoromethyl, dichlorofluoromethyl and chlorodifluoromethyl;
R2 is halogen ~uch as fluorine, chlorine and bromine or C,-haloalkyl such as chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl/ difluoromethyl, trifluoromiethyl,chloro~luoromethyl,dichlorofluoro-methyl and chlorodifluoromethyl;
R3 is hydrogen or methyl;
n is 1 or 2, where the radicals R3 can be different if : the value of n is 2;
R4 is halogen such as fluorine, chlorine and ~romine or ~methyl;
- 25 Rs is methyl or C1-haloalkyl such as chloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, : difluoromethyl,trifluoromethyl,chlorofluoromethyl, dichlorofluoromethyl and chlorodifluoromethyl;
: ~ R6 i~ hydrogen, halogen such as ~luorine, chlorine and bromine or methyl;
R7 is halogen ~uch a5 fll~orine, chlorine and bromine, : methyl or CL-haloalkyl ~uch aS ~hloromethyl, dichloromethyl, trichloromethyl, fluoromethyl, difluoromethyl,trifluoromethyl,chlorofluoromethyl, dichlorofluoromethyl and chlorodifluoromethyl.
In particular, those compounds of the formula I
are preferred in which R has the abovementioned meaning .

.. , .,, .. .... ,. .,.,., ,,, . ., . , . . .... . , .. ,... .. , ~ ..... . . . . .

, . . - . , , ::. :,. . , . . , . . . .. . : . ~ .
, ~. : , " . . .. . . . . . . , . ~ .:
., , . . . , , , . " . . . . . .
,- j :. . . : . , :: , ", "' : .," " , ' ' ' ' , ,; . . .,, i~ . ~ . . .... . .

; 2iO~9~
- 14 - O.Z. 0050/43543 and A is a cyclic radical from the group consisting of the formulae A1 to A7, where X and Y have the above-mentioned meaning and the substituents are the following groups:
Rl is chlorine, bromine, iodine, methyl or trifluoro-methyl;
R2 is chlorine or trifluoromethyl;
R3 is hydrogen or methyl;
n is 1 or 2, where the radicals R3 can be different if the value of n is 2;
R4 is chlorine or methyl;
Rs is methyl, difluoromethyl or trifluoromethyl;
R6 is hydrogen, chlorine or methyl;
R7 is chlorine, methyl or trifluoromethyl.
Particularly preferred compounds of the formula I
are summarized in the following Tables A to ~.

. .. - . .......... .. ... . . .

. .. .: ~ . . . .. : .
. , ; . . , .

sAsF Aktienge~ellCcha~t 920557 0050/43543 ~1~6~97 Table A

!i ~1 Rl R ~ ~ I.l _ .

CF3 i-C3H7 CF3 n-C3H7 . _ .
CF3 n-C4Hg , ~_ CF
CF3 . i-C4Hg CF3 tert.-C4Hg CF3 n--CsH~
CF3 sec-CsH11 .
CF3 _ n-C6H13 .
CF3 n-C7H1s CF3 sec.-C7Hls _ _ _ _ CF3 l-methylvinyl -_ , _ CF3 2-methylvinyl .. ., , _ CF3 allyl :
.
CF3 2-methylallyl . . , CF3 2-ethylallyl .. .
CF3 l-methylallyl . . . . . .. .
: CF3l-ethylallyl CF3 1-methyl-2-butenyl _ .
CF3 1-ethyl-2-butenyl CF3 1-isopropyl-2-butenyl . , , _ C~; l-n-butyl-2-butenyl CF3 1-methyl-2-pentenyl CF3 1, 4-dimethyl-2-pentenyl CF3 propargyl CF3 2-butynyl :~
CF3 3-butynyl CF3 ethox~
CF3 propoxy . CF3 l-methylethoxy :

.
, . .
.: . : . . ; . :, . .
, ~ .";,.. , .. ~ ,,., : .
, . . .

BASF A3ctiengegell~c~ t 920557 O. Z . 0050/43543 2101~97 . _._ R R
.
CF3 n-butoxy . _ _ CF3 l-methylpropoxy . ~_ :-CF3 2-methylpropoxy CF3 l,l-dimethylethoxy CF3 n-pentyloxy CF3 n-hexyloxy CF3 2-ethylhexyloxy . _ . . _ .
CF3 2-propenyloxy CF3 2-butenyloxy -CF3 2-methyl-2-propenyloxy .
CF3 2-pentenyloxy CF3 3-pentenyloxy _ . . ._ _ CF3 3-chloro-2-propenyloxy CF3 2,3-dichloro-2-propenyloxy CF3 2,3,3-trichloropropenyloxy CF3 2-propynyloxy . . . . ~. .
CF3 2-butynyloxy . .
CF3 3-butynyloxy ~ , .
CF3 1-methyl-2-propynyloxy CF3 cyclopropyl ~
.- . .
CF3 cyclobutyl ..
CF3 cyclopentyl CF3 cyclohexyl . .
. __ CF3 2-cyclopentenyl .~ l-cyclopentenyl . . . _ , _ _ CF3 2-cyclohexenyl . _ CF3 l-cyclohexenyl CF3 ~
CF3 cyclohexyloxy :-.--. _ _ .

CF3 2-cyclopentenyloxy . _ . . _ : CF3 2-cyclohexenyloxy . .......
CF3 phenyl . ._. _ - ~ .
Cl i-C3H7 _ _ -- -Cl n-C3H
Cl n-C4Hg Cl sec.-C4Hg ~5 Cl i-C4Hg _ Cl tert.-C4Hg , ::. . : , :. .
.. . . ..
: , ' : ~ ' . ' ':. ''.`, . . ` .
: . `; ' . ' . . , ' . . ' ,; . . , , ' , , ,, . ... . ~ . .. : . : : . .
.
,' ' ; '.`.` : '~, , . . . .

sASF Aktieng~sell~icha~t 920557 o.z. 0050/43543 2~06~7 Rl R
._ _ Cl n-C5Hll Cl sec~-c5Hl 1 _ Cl n-C6H13 .... __ _ _ Cl n-C7Hls :
.,, Cl sec.-C7Hls _ _ Cl l-methylvinyl Cl 2-methylvinyl : -Cl allyl . .
Cl 2-methylvinyl Cl 2-ethylallyl Cl l-methylallyl Cl l-ethylallyl Cl l-methyl-2-butenyl Cl l-ethyl-2-butenyl Cl l-lsopropyl-2-butenyl Cl l-n-butyl-2-butenyl . ~ .
Cl methyl-2-pentenyl _ Cl 1,4-dimethyl-2-pentenyl .
Cl propargyl 25 . _ __ _ . .
Cl 2-butynyl . -. . - . ~
Cl 3-butynyl -. _ _ Cl ethoxy Cl propoxy Cl l-methylethoxy .
Cl n-butoxy :
_ _ _ , Cl l-methylpropoxy Cl 2-methylpropoxy Cl l,l-dimethylethoxy Cl n-pentyloxy , . . . .
Cl ~ n-hexyloxy . .
Cl 2-ethylhexyloxy _ _ Cl 2-propenyloxy . ..
Cl 2-butenyloxy j . . _ _ Cl 2-methyl-2-propenyloxy : Cl 2-pentenyloxy Cl 3-pentenyloxy 45 _ Cl 3-chloro-2-propenyloxy 2,3-dichloro-2-propenyloxy .:

,: ' .:. :' .: ' ' ' . :, . . .. . . . . . .
~, , ~ ' ,''. ; , ', ' '', .' '' , . ' ,''::, ', . `' .

BASF Aktien~esellschaft 920557 O.~. 0050/43543 21~g~97 .. ._ _ . __ _ _ _ Cl 2,3,3-trichloropropenyloxy Cl 2-propynyloxy -_ Cl 2-butynyloxy __ .
Cl 3-butynyloxy _ .
Cl l-methyl-2-propynyloxy Cl cyclopropyl ~ . . _ _ .. ._ ._ lU Cl cyclobutyl Cl cyclopentyl Cl cyclohexyl Cl 2-cyclopentenyl Cl l-cyclopentenyl Cl 2-cyclohexenyl Cl l-cyclohexenyl Cl cyclopentyloxy Cl cyclohexyloxy ___ _ Cl 2-cyclopentenyloxy .-. . _ . _ _ .
Cl 2-cyclohexenyloxy Cl phenyl ~ASF Aktienge~iell~chaft 9205~ ~ a ~ ~ 9~.Z. 0050/43543 Table B

R ~ R2 N I.2 HO - N - CO ~

R R
_ . . .
Cl ~
Cl n-C3H7 . _ _ Cl n-C~jHg Cl sec.-C4Hg . , _ Cl i-C~Hg Cl tert.-C~Hg . _ .. , .. _ _ . _ _ Cl n-C5Hll - -:
~ ,, Cl sec.-CsHll _ _ -Cl n-C6Hl3 . . .
Cl n-C7Hl5 : ::
- Cl : :
Cl l-methylvinyl Cl 2-methylvinyl : Cl allyl Cl 2-methylallyl ;-~__ .
Cl 2-ethylallyl .~ .
.. _ _ _ _~_ _ Cl ~ ~ :
Cl l-ethylallyl .
Cl l-methyl-2-butenyl : Cl l-ethyl-2-butenyl Cl l-isopropyl-2-butenyl Cl l-n-butyl~-2-butenyl :

Cl l-methyl-2-pentenyl . , Cl 1,4-dimethyl-2-pentenyl -: ::
Cl propargyl .~ _ Cl 2-butynyl . ~:. .
Cl 3-butynyl .. ._ __ _ _ _ . _ ~ .. .. _ _ ___ . _ .:
Cl ethoxy :.
. . ~ .~ _ _ _ _.
. Cl propox~
~ S ,, .. ,.. _ . . _ Cl l-methylethoxy . . ~.. _._ _ Cl n-butoxy . . .

, , , . . , . , . :; , : ,,: ; .

., BASF Aktien~e~ell~chaft 920557 O.z. 0050/43543 20 2106~7 R2 ' ,,.___ _ Cl l-methylpropoxy _ Cl 2-methylpropoxy Cl l,l-dimethylethoxy . ~
Cl n-pentyloxy . _ .
Cl n-hexyloxy Cl 2-ethylhexyloxy Cl 2-propenyloxy Cl 2-butenyloxy Cl 2-methyl-2-propenyloxy Cl 2-pentenyloxy Cl 3 -pentenyloxy Cl 3-chloro-2-propenyloxy . - ~
Cl 2,3~dichloro-2-propenyloxy . _ Cl 2,3,3-trichloropropenyloxy __ _ Cl 2-propynyloxy Cl 2-butynyloxy ~ _ . _ Cl 3-butynyloxy Cl l-methyl-2-propynyloxy : .
. _ . _ Cl cyclopropyl Cl cyclobutyl Cl cyclopentyl Cl cyclohexyl Cl 2-cyclopentenyl : 30 Cl l-cyclopentenyl Cl 2-cyclohexenyl Cl l-cyclohexenyl Cl cyclopentyloxy Cl cyclohexyloxy : ~ Cl 2-cyclopentenyloxy Cl 2-cyclohexenyioxy :
Cl . i-C3H7 ~:
Cl n-C3H7 ,, ,~
Cl n-C4Hg .. ._ Cl sec.-C~Hg . , . __ .___ . ....... _ .. _ . _ _ Cl i-C4Hg , . . , . . _ _ . . .
Cl tert.-C~Hg ._ ------ . ..... . __ Cl n-CsHll . __ . .
Cl sec.-C5Hll _ , . .. .
~ ,: , . . .
.
.: . .

. .

BASF Al~tien~esellE~cha*t 920557 O.Z. 0050/43543 21 21~97 ~ ..., , _ - - - . , Cl n-C6H13 .
Cl n-C7H1s 5 ~
Cl sec . -C7H1 5 . .
Cl ethoxy Cl propoxy Cl l-methylethoxy Cl n-buto ~ =
Cl l-methylpropoxy Cl 2-methylpropoxy . _ .
Cl l,l-dimethylethoxy . ._ _.
Cl n-pentyloxy _ , _ _ _ Cl n-hexyloxy . .._ Cl cyclopentyl . . ~ ._ .. _ _ Cl phenyl :

: . .

'' ' '. ~ ' ' ' ' .. . . :
, B~SF AXtien~esell3cha~t 920557 O.Z. 0050~43543 22 ~ 1 a fi ~ 9 7 Table C
~ ,.
~ I X ~
HO - N - CO ~ \ ~ I.3 rO ' X R
, _ CH2 i-C3H7 CH2 ~
CH2 --n-C4Hg CH2 sec. C4Hg CH2 i-C4Hs _ _ . .
CH2 tert.-C4Hg . .
CH2 n-CsHll ... _ . .
CH2 sec.-CsHl1 . .
CH2 n-C6Hl3 . _ _ . . ~
CH2 n-- C7Hls : 25 CH2 sec.-C7H1s . _ , CH2 1-methylvinyl : , . .
CH2 2-methylvinyl . . __ , CH2 allyl -:i . . . . . _ _ . .. __ , . : -CH2 2-methylallyl ,. ._ _ CH2 2-ethylallyl - _ _ _ CH2 1-methylallyl ~ . -- - . .
: : ~CH2 1-ethylallyl ___ , 5CH2 1-methyl-2-butenyl 3 ~. _ _ CH2 1-ethyl-2-butenyl ... _ . .. _ CH2 1-isopropyl-2-butenyl ~ :
. . .
CH2 1-n-butyl-2-butenyl . .__ : CH2 1-methyl-2-pentenyl 4~ _ ._ v CH2 1,4-dimethyl-2-pentenyl CH2 propargyl . . _ CH2 2-butynyl . .
CH2 3-butynyl . __ .. ~
CH2 ethoxy CH2 propoxy ~, : , ~ . s~sF Aktienge~ell~chaft 920557 O.Z. 0050/43543 23 21~ 7 X R
__ CH2 l-methylethoxy CH2 n-butoxy :
. . _ __ _ _ CH2 l-methylpropoxy 2 2-methylpropoxy CH2 l,l-dimethylethoxy CH2 n-pentyloxy CH2 n-hexyloxy ...... ... .... _ CH2 2-ethylhexyloxy CH2 2-propenyloxy CH2 2-butenyloxy CH2 ~~~~ 2-methyl-2-propenyloxy CH2 2-pentenyloxy CH2 3-pentenyloxy :
~ _ CH2 3-chloro-2-propenyloxy CH2 2,3-dichloro-2-propenyloxy CH2 2,3,3-trichloropropenyloxy CH2 2-propynyloxy CH2 2-butynyloxy -_____ CH2 3-butynyloxy CH2 1-methyl-2-propynyloxy _ _ CH2 cyclopropyl ..... _ . _ , CH2 cyclobutyl .. _ ~._ ._ CH2 cyclopentyl _ CH2 cyclohexyl CH2 2-cyclopentenyl CH2 l-cyclopentenyl . ~ ____ CH2 2-cyclohexenyl :
_ . ._ CH2 l-cyclohexenyl CH2 cyclopentyloxy . : . .
CH2 cyclohexyloxy -, . .
CH2 2-cyclopentenyloxy _. __ _ ~ __ CH2 2-cyclohexenyloxy ... - .
. _ . . .~.
_ _ _ i-C3H7 S n-C3H7 ,_ -- : .
_ _ n-cgH9 s sec . -C4Hg _ , 45 . _ i-C4Hg tert.-C~Hg :.. -. .

BASF AXtiengesellncha~t 920557 O.Z. 0050/43543 2106~97 , . _ .

S n-CsHl 1 __ 5 . sec.-CsH11 n-C6Hl3 -S n-C7H1s .
S sec.-c7Hl S
_ _ S ethoxy propoxy _ _ 1-me~hylethoxy S n-butoxy S 1-methylpropoxy S 2-methylpropoxy _ _ 1,1-dimethylethoxy S n-pentyloxy - .
S n-hexyloxy . cyclopentyl S phenyl . _ '' ' :

.

~0 , ,, , , , , " ,, ,, ": , , , , ,,, ~ ~ ", ' .; '" '",',;". , ', . ., ;-'';' ' ' ', ,':. ' ' i, , ,:,, " ; , ., : ,, , ' , . . . . . . . .

~ B~SF ~ktiengesell~chaft 920557 O.Z. 0050~43543 21~6~7 Table D

HO - N ~ CO - ~ R3 I.4 ~ _ _ R R Y
. . _ _ _ __ Hi-C3H7 , ,, O
Hn-C3H7 Hn-C4Hg O
.... __ . _ _ H s ec.-CgHg O
i-C4Hg .
~ tert.-C4Hg 20 . . . _ . _ H n-CsHll O
. __ _ .
H sec.-C5Hll , . .-H n-C6Hlg O
_ . .~ ., ._ .. _ . .__ :.
H n-C7H15 O
_ _ . :-... sec.-C7Hls H ethoxy O .
. ... . _ . ...
: : H : propoxy O :-:
, . . . _ _ .
~_ H l-methylethoxy: . . _ : 30 H : n-butoxy O
.... _ ... - .. .. _ _ ..
H l-methylpropoxy O ..
. A ~ r~ .
: H l,l-dimethylethoxy O
_ .. . _ _ , , .
H n-pentyloxy O .:~
35 . ___ _ .. ._ __ _ ..
~: n-hexyloxy O .
H cyclopentyl O
. _ ",~ ,., , _. ___ _ H cyclohexyl O ~ .
.... ..... _ _ H 2-cyclopentenyl O
: 40 _ l-cyclopentenyl . : ~ 2-cyclohexenyl O
. _ _ . , ~ .
H l-cyclohexenyl ~ :
H cyclopentyloxy O
H cyclohêxyloxy O
_.
_H _ 2-cyclopentenyloxy O :
'. ': .

,,' ,'' '," ''' .,,', ''.'' ' ' , ' ' ''' . ' ' ' " ' ' '; "' ', ' " ' ' '. " ' ' " ' ' ' ' ' ' ' , ' " ',; ' :; ' ' " " ' " :

,~ . . . . ... .. ... . .

BASF ~ktien~e~ellschaft 920557 O.Z. 0050/43543 26 2~6~97 R3 ~
H 2-cyclohexenyloxy O
_ . .
CH3 i-C3H7 O
__ _ _ _ CH3 n-C3H7 O
_ CH3 n-C4Hg O
, _ .
CH3 sec.-CgHg CH3 i-C4Hs O
CH3 tert.-C4Hg _ CH3 n-C5Hll CH3 sec.-C5Hll O
CH3 n-C6H13 _ O
CH3 n-C7Hls O
.
CH3 sec.-C7H1 5 O
_ . . _._ _ CH3 ethoxy O
.___ _ . _ -- _.
CH3 propoxy O
_ . ~
CH3 l-methylethoxy O
20 _ _ _ _ CH3 n-butoxy O
CH3 l-methylpropoxy .. ~_ ~.-.
CH3 2-methylpropoxy O
CH3 l,l-dimethylethoxy O
CH3 n-pentyloxy CH3 n-hexyloxy __ CH3 cyclopentyl .
3_ phenyl O

:

:, . : , . . ,, . :.
'" ~ : '' ', ,',',"' '' ',' ~, ', '" '' , '' ' . ,' ' -': :' , ' :
.: ,: ' ' , ' .' . , '. :' , . .
;: . ..... . .

BASF Aktien~e~ell~chaft 920557 O.Z. 0050/43543 27 210~497 Table E

~ R4 R ~ I.5 HO - N - CO y _ R R Y
.
CH3 i-C3H7 3 n-C3H7 O
CH3 n-C4Hg _ CH3 sec.-CqHg O
CH3 i-C~Hg O : -CH3 tert.-C4Hg : . .
~Y; ~ _ O ':",, _ _ _ sec.-C5Hll _ , - .
CH3 n-C6Hl3 O
. ._ . ~ r _ _ CH3 n-C7Hls O .. -_ _ . .~. .
CH3 seC~-c7Hls O ~:
._ - ._ . . .~
CH3 ethoxy O
._. . ~ . -CH3 propoxy O .:
. ~ .
CH3 l-me~hylethoxy O
. . . ~ . . -CH3 n-butoxy O
_ CH3 l-methylpropoxy _ _ ..
30 - - C~I3 _ . O
~CH3 1 l-dimethylethoxy O
.~, . _ CH3 n-pentyloxy O
.~__ . .. ..
: CH3 n-hexyloxy O
. .
: 35 CH3 cyclopentyl O
.. .. _ CH3 cyclopentenyl O
_ . _, ,,, ... .. -- . . . ~ - , CH3 i-c3H7 S
~ ... .
CH3 n-C3H7 S
. . _ CH3 --- n-C4Hg S
CH3 sec.-C4Hg S . .:. ~
CH3 i-C4Hg S
.. . _ _ _ CH3 tert.-C4Hg S ~ .
, ~ .
CH3 n-CsHll S
_ CH3 sec.-CsHll S
CH3 n-C6H13 , - _ _ -: ' -: .

~ , . : , . . . . . .
. . , . ~ , . . .
"~ . , - ~ : , .. . . . .
.~ . . . . . ... ..

BASF Aktienge~ell~cha~t 920557 o.z. 0050/~3543 2~064~7 R4 _ ~

CH3 n-C7Hls S
CH3 ~- ~ S
CH3 ethoxy S
CH3 propoxy CH3 l-methylethoxy S
CH3 n-butoxy S
~0 . l-methylpropoxy . _ . .
CH3 2-methylpropoxy S
.
CH3 l,l-dimethylethoxy S
.
CH3 n-pentyloxy S
. ._ CH3 n-hexyloxy S
_ _ .
CH3 cyclopentyl S
_ _ CH3 cyclopentenyl S

.

-~:
,~
.:
''"

. . ,:- . . `.' . . :. ' . ' .'. , : ' ': :,: :': : , ' .' . .':, ' , ' ,, . '~ . ', ,'' '. ', . : . , . , . : : .
., . . , . ::
' ' ;. ~ , ,'. , , -, . . '.' :': .

. BASF Aktienge~llscha~t 9205~7o.z. 0050J43543 29 210~
Table F

R ~ N CH3 I.6 H0 - N - C0 ~ N
Rs ~ _ Rs R6 R
.~', CH3 H i-C3H7 _ CH3 n-C3H7 CH3 H n-C4Hg CH3 H sec.-C4Hg ._.
CH3 H i-C4Hg CH3 H tert.-C4Hg . _ CH3 H n-CsH
~ . ___ ~ __ _ __ _ CH3 H sec.-C5Hll _ _ _ _ . _ CH3 H n-C6H13 . ... _ . _ . .
CH3 H n-C7Hl5 - -CH3 . _ sec.-C7Hl5 . ~ :
. _ . _ _ , .
C~ l-methylvinyl CH3 H 2-methylvinyl CH3 _ aIlyl -:
- _ _ . _~
: 30 CH3 . 2-methylallyl : CH3 ~ 2-ethylallyl CH3 H l-methylallyl ,, " .__ . . ,.
CH3 H l-ethylallyl _ _ _ l-methyl-2-butënyl 35 ~ _ . . . . . -.
CH3 H l-ethyl-2-butenyl . . . .
CH3 H l-isopropyl-2-butenyl . . .. . _ __ - . ,. . _ _ CH3 H l-n-butyl-2-bute~yl , .. _ __ _ CH3 H l-methyl-2-pentenyl .' .
~ O .. _ . __ , . .
CH3 H 1,4-dimethyl-2-pentenyl . __ . _ __ _ _ ., CH3 H propargyl ~ ~
. . . _ _ . _ , _ CH3 H 2-butynyl :~
. _ _ CH3 H 3-butynyl :
CH3 H ethoxy .:.
,- _ ---- ~ . ~ . , , ., CH3 H propoxy : -;
. .

sASF ~kti~nge~ellscha~t 920557 O.Z. 0050/43543 30 21~97 . __ R6 ,_ _ ~.
CH3 H l-methylethoxy . _ ...
CH3 Hn-butoxy _ . _ . -CH3 Hl-methylpropoxy , CH3 H2-methylpropoxy . ...
CH3 Hl,l-dimethylethoxy _ ... _ ..
CH3 - _ n-pentyloxy CH3 H n-hexyloxy CH3 ~ _ 2-ethylhexyloxY
CH3 _ 2-propenyloxy CH3 ~ 2-butenyloxy CH3 E~ 2-methyl-2-propenyloxy CH3 _ 2-pentenyl ~
CH3 H 3-pentenyloxy CH3 3-chloro-2-propenyloxy CH3 H 2,3-dichloro-2-propenyloxy CH3 H 2,3,3-trichloropropenyloxy . ._ . . ._ CH3 H 2-propynyloxy ._ , , CH3 H 2-butynyloxy _ CH3 H 3-butynyloxy 25 . _ ~ . .
CH3 H l-methyl-2-propynyloxy . , CH3 H cyclopropyl -.. _ CH3 H cyclobutyl . . _ _ CH3 H cyclopentyl :
CH3 cyclohexyl . ._ . _ , ,_ . .
CH3 H 2-cyclopentenyl CH3 H l-cyclopentenyl . _ _ ~ _ CH3 H 2-cyclohexenyl . . ..... __ ~ __ _ _ CH3 H l-cyclohexenyl ,, ~ .__ ._ .
CH3 H cyclopentyloxy ~ ._ _ CH3 H cyclohexyloxy . .. , _ CH3 , _ _ 2-cyclopentenyloxy CH3 H 2-cyclohexenyloxY .
CF3 H i-C3H7 _ . _ -- _ CF3 H n-C3H7 ~. __A~__ . _.___ _ __ .
CF3 H n-C4Hs . _ CF3 H sec~-cgH9 CF3 _ _ i-CgHg ~ _ CF3 . ~ tert.-C~Hg , ,:

. , : .
':1 , ~ASF Aktienge~ellschaft 920557 O.Z. 0050/43543 31 2106~97 R5 -- .

. __ _ _ _ .
CF3 H n-C5Hll _ .. _ CF3 H sec.-CsHl1 ~-.
_ _ -- .. ___ CF3 H n-C6H13 CF3 H n-C7H15 CF3 -. SeC.-C7Hl5 . _-- -CF3 H ethoxy ~ CF3 . _ propoxy CF3 H 1-methylethoxy .
CF3 H n-butoxy _ , . . . _ , _ CF3 H 1-methylpropoxy :
CF3 H 2-methylpropoxy .-.. _ . ._ CF3 H l,1-dimethylethoxy .
__3 H n-pentyloxy :
CF3 H n-hexyloxy CF3 H cyc lopentyl CF3 H Cyc lopentenyl 3 H phenyl ' -':
.
.

:
:.

- .

4() : . .

' '': ,. '" ' ", ` :' '' ';; ,' ," ' ~, ; ~ ,. .
'.'. . '; . ~''. ''' . -, ~.' . ' . . ,: ' ,, , , . . , . ::
,:'` . ' ` `' . :. ' :

"' , BASF A~tienge~ellschaft 920557 o.z. 0050/43543 - 2~6~7 Table G

R J~3 R~ N
HO - N - CO S ~ I. 7 1 0 ` ! _ __ .
R R R
. _ . . .
CF3 Ch3 i-C3H7 CF3 CH3 n-C3H7 , ~ , ,, CF3 ~ CH3 n-C4Hg CF3 CH3 sec.-C4Hg : -CF3 CH3 i-CgHg CF3 CH3 tert.-C4Hg 2 CF3 CH3 n-CsH11 O _ . ~. . _ . , , ,, CF3 CH3 sec.-CsHl1 :~
CF3 - CH3 n-C6H13 CF3 CH3 n-C7H1s -- -:
CF3 CH3 sec.-C7H1s _ :-CF3 CH3 1-methylvinyl . . - ~ . . . _. ._ .
CF3 CH3 2-met hylviny l --:
CF3 CH3 allyl . _. _ .... _ . ~ .
CF3 CH3 2-methylallyl - -. . . _. ~ . ... _ : 30 CF3 CH3 2-ethylallyl : -_ _ CF3 CH3 1-methylallyl Lr~ CH3 1-ethylall~l : ; CF3 ~ CH3 1-methyl-2-butenyl ~-CF3 CH3 1-ethyl-2-butenyl _ CH3 1-isopropyl-2-butenyl . .
~ . CH~ l-n-butyl-2-butenyl ___ : CF3 CH3 1-methyl-2-pentenyI -.:
.__ _ _ , _ _ CF3 CH3 1,4-dimethyl-2-pentenyl 40 .
3~-- --- CH3 propargyl CF3 CH3 2-butynyl :
CF3 CH3 3-butynyl :
CF3 CH3 ethoxy 45CF3 CH3 propoxy ~ -~-~~-- :
CF3 CH~ 1-methylethoxy , - .: - , " ,, , -, . , : .. ; . ,, . , . . , .. : .

', ' ' ` . '. ' " " '' ' " '.' ', ,' `, ' ., ' . " ' . ' ' ~; ' ', ., ~ ' ; ' " " ' ' ' ' ' ' ' ~ ' ' ~AS~ ~Xtienge2ell~ch~ft 920557 ~ ~0~ ~95~/435~3 __ _ ,, _ . . . _ __ _ _ .~ ..
_ _ _ CH3 n-butoxy CF3 CH3 l-methylpropoxy CF3 CH3 2-methylpropoxy CF3 CH3 l,l-dimethylethoxy CF3 CH3 n--pentyloxy :
_ CF3 CH3 n-hexyloxy CF3 CH3 2-ethylhexyloxy CF3 - CH3 2-propenyloxy _ ._ CF3 CH3 2-butenyloxy CF3 CH3 2-methyl--2-propenyloxy .:
_ . .__ .
3 CH3 2-pentenyloxy CF3 CH3 3-pentenyloxy : .
CF3 CH3 3-chioro-2-propenyloxy .
= CH3 2,3-dichloro-2-propenyloxy ;~
20 CF3 CH3 2,3,3-trichloropropenyloxy CF3 CH3 2-propynyloxy CF3 CH3 2-butynyloxy : :
CF3 CH3 3-butynyloxy CF3 CH3 1-methyl-2-propynyloxy ___ . . .
_ 3 CH3 cyclopropyl .
CF3 CH3 cyclobutyl . _ . _ CF3 CH3 cyclopentyl .
CF3 CH3 cyclohexyl CF3 CH3 2-cyclopentenyl .
_ . CH3 l-cyclopentenyl CF3 CH3 2-cyclohexenyl CF3 CH3 l-cyclohexenyl . _ . _ . . -CF3 CH3 cyclopentyloxy CF3 C~ cyclohexyloxy :.:

CF3 CH3 2-cyclopentenyloxy .
. _ _ ._v__ . _ , .
o,/ CH3 2-cyclohexenyloxy CH3 CH3 i-C3H7 4~ _ __ _ _ CH3 CH3n-C3H7 - ~-CH3 CH3n-C4Hg -- . ,. . _ CH3 CH3sec . -CgHg _ - _ _ _ . ___ _. _ CH3 CH3i-C4Hs A ~. . . .. _.. _ __ ~ CH3 CH3 tert.-C~Hg . . . . ._ ---- ----CH3 CH3 n-C5H~

,: . : . ., , . . :
- .
, ,,, : : , ;
~, .. . . , . . :: . ~ :
; : : ' : ', , ' ;
. ~ . , , , . , , ,, ~ , . .

BASF ~ktiengesell~cha~t 920557 O.Z. OQ50/43543 34 21~6497 ~ ~ _ _ . ._ __ CH3 CH3 sec.-C5Hll . _ . .
CH3 CH3 n-C6Hl3 __ _ _ _ CH3 CH3 n-C7Hls _ _ CH3 CH3 sec.-C7Hls .. _ . _ .. __ CH3 CH3 ethoxy . . ..
CH3 CH3 propoxy ~ , lu CH3 CH3 l-methylethoxy CH3 CH3 n-butoxy CH3 CH3 l-methylpropoxy CH3 CH3 2-methylpropoxy CH3 CH3 l,l-dlmethyletho CH3 CH3 n-pentyloxy CH3 CH3 n-hexyloxy CH3 CH3 cyclopentyl _ _ _ . . __ .
CH3 CH3 cyclopentenyl . .

CH3 CH3 phenyl .

3û

4û

., " , , . : : , .. . . . .
.: . .: . ' ' ' , . . . . . . . .
.
,' , ' ~:

sASF Aktiengesell~chaft 920S57 o.z. 0050/43543 21~497 The novel active ingredients are particularlY suitable for pro-tecting various materials against degradation or destruction by bacteria or fungi or from being attacked by and covered with mi-croorganisms. Examples of materials which can be preserved or mi-5 crobicidally finished with the novel active ingredients are gluesand adhesives, starch solutions, wax emulsions, clay emulsions, sizes, finishes, spinning baths, gelatine formulations, putty, joint sealants, cooling lubricants, drilling oils, fuels, plastic dispersions, emulsion paints, textiles, leather, raw hides and 10 cosmetics. The compounds are also suitable as anti-slime agents in the paper industry, in cooling towers and in air moistening units.
.
The compounds I are also suitable for protecting the following 15 plant species against attack by microorganisms:
cereals (e.g., wheat, barley, rye, oats, rice, sorghum and re-lated species); beets (e.g., sugar and fodder beets); pomes, drupes and aggregate fruit (e.g., apples, pears, plums, peaches, 20 almonds, cherries, strawberries, raspberries and blackberries);
legumes (e.g., beans, lentils, peas, soybeans); oil-yielding crops (e.g., rape, mustard, poppies, olives, sunflowers, coco-nuts, castor-oil beans, cocoa beans, groundnuts); cucurbits (e.g., pumpkins, cucumbers, melons); fiber-yielding plants (e.g., 25 cotton, flax, hemp, jute); citrus fruit (e.g., oranges, lemons, grapefruit, tangerines); vegetables (e.g., spinach, lettuce, as-paragus, cabbage varieties, carrots, onions, tomatoes, potatoes, paprika); laurel species (e.g., avocado, cinnamomum, camphor) or plants such as Indian corn, tobacco, nuts, coffee, sugar cane, 30 tea, grapes, hops, and banana and rubber trees. For the purposes of the present invention, the term ~plants~ is also taken to mean all types of other green growth, whether ornamentals, grassy areas, embankments, or generally low-growing cover crops.
35 For example the following microorganisms may be combatted with the novel compounds I:
Straphylococcus aureus, Escherichia coli, Klebsielle pneumoniae, Citrobacter freundii, Proteus vulgaris, Pseudomonas aeruginosa, 40 Desulfovibrio desulfuricans, Streptoverticillium rubrireticuli, Aspergillus niger, Aspergillus versicolor, Penicillium funiculo-sum, Penicillium expansum, Penicillium glaucum, PaecilomyCeS va-riotii, Trichoderma viride, Chaetomium globosum, Aspergillus ams-telodami, Phoma pigmentovora, Phoma violacea, Aureobasidium pul-45 lulans, Saccharomyces cerevisiae, Alternaria tenuis, Stemphyliummacrosporoideum, Cladosporium herbarum, Cladosporium resinae, Candida albicans, Trichophyton mentagrophytes, Geotrichum candi-,, - . .. . ~ , . .. .

,, ~ - - . .. . . . . .. . .

.
;, .
, sASF Aktiengesell~cha~t 920557 O.Z. 0050/~35~3 2105~97 dans, Monilia sitophila, Scenedesmus quadricauda, Chlorella vul-garis, Nostoc muscorium, Oscillatoria limosa and Anabaena constricta.
5 The novel substances can be converted into conventional formula-tions such as solutions, emulsions, suspensions, dusts, powders, pastes and granules. The application forms depend entirely on the purposes for which they are intended; they should at all events ensure a fine and uniform distribution of the active ingredient.
10 The formulations are produced in known manner, for example by extending the active ingredient with solvents and/or carriers, with or without the use of emulsifiers and dispersants; if water is used as solvent, it is also possible to employ other organic solvents as auxiliary solvents. Suitable auxiliaries for this 15 purpose are solvents such as aromatic~ (e.g., xylene), chlori-nated aromatics (e.g., chlorobenzenes), paraffins (e.g., crude oil fractions), alcohols (e.g., methanol, butanol), ketones (e.g., cyclohexanone), amines (e.g., ethanolamine, dimethylforma-mide), and water; carriers such as ground natural-minerals (e.g., 20 kaolins, aluminas, talc and chalk) and ground synthetic minerals ~e.g., highly disperse silica and silicates); emulsifiers such as nonionic and anionic emulsifiers (e.g., polyoxyethylene fatty alcohol ethers, alkyl sulfonates and aryl sulfonates)i and dis-persants such as lignin-sulfite waste liquors and methylcellu-25 lose.
''` ' '~:The fungicides generally contain from 0.1 to 95, and preferably from 0.5 to 90, wt% of active ingredient. The active ingredients are used in a purity of from 90 to 100, and preferably from 95 to 30 100, % (according to the NMR/HPLC/GC spectrum).
Usual application concentrations are - based on the weight of the material to be protected - from 0.001 to 5, and preferably from 0.01 to 2, wt~ of active ingredient; when the active ingredients 35 are used for treating water, in oil production, in drilling and cutting oils, fuels, in swimming baths, cooling towers, air moistening units or in the paper industr~, amounts of from 5 to 500 ppm are sufficient. Ready-to-use disinfectant solutions con-tain for instance from 0.5 to 10wt% of active ingredient.
Examples of such formulations are given below:
~ : ' I. A solution of 90 parts by weight of compound no. 3 and 10 part~ by weight of N-methyl-a-pyrrolidone, which is suitable for 45 application in the form of very fine drops.

.. . . . . .... . ... .. . . . . .
; - , . . ~ . .... . .

',.. ' : ' ' ' ' , ,', :,'", ' ' ,' : ' , ' ~

,,: , . ,-, ,, ., , , ~ .

BASF Aktienges~ll~chaft 920557 O.z. 0050/43543 2 1 ~ 7 II. A mixture of 20 parts by weight of compound no. 4, 80 parts by weight of xylene, 10 parts by weight of the adduct of 8 to 10 moles of ethylene oxide and 1 mole of oleic acid-N-monoethanola-mide, 5 parts by weight of the calcium salt of dodecylbenzenesul-5 fonic acid, and 5 parts by weight of the adduct of 40 moles ofethylene oxide and 1 mole of castor oil. By finely dispersing the mixture in 100,000 parts by weight of water, an aqueous disper-sion is obtained.
10 III. An aqueous dispersion of 20 parts by weight of compound no.
1, 40 parts by weight of cyclohexanone, 30 parts by weight of isobutanol, 20 parts by weight of the adduct of 40 moles of ethylene oxide and 1 mole of castor oil. A mixture of this dis-persion with 100,000 parts by weight of water contains 0.02wt~ of 15 the active ingredient.
IV. An aqueous dispersion of 20 parts by weight of compound no.
3, 25 parts by weight of cyclohexanol, 65 parts by weight of a mineral oil fraction having a boiling point between 210 and 280C, 20 and 10 parts by weight of the adduct of 40 moles of ethylene oxide and 1 mole of castor oil. The mixture of this dispersion with 100,000 parts by weight of water contains 0.02wt~ of the active ingredient.
25 V. A hammer-milled mixture of 80 parts by weight of compound no.
2, 3 parts by weight of the sodium salt of diisobutylnaPhthalene-~-sulfonic acid, 10 parts by weight of the sodium salt of a lignin-sulfonic acid obtained from a sulfite waste liquor, and 7 parts by weight of powdered silica gel. By finely dispersing the 30 mixture in 20,000 parts by weight of water, a spray liquor con-taining O.lwt% of the active ingredient is obtained.
VI. An intimate mixture of 3 parts by weight of compound no. 1 and 97 parts by weight of particulate kaolin. The dust contains 35 3wt% of the active ingredient.
~ , VII. An intimate mixture of 30 parts by weight of compound no.
4, 92 parts by weight of powdered silica gel and 8 parts by weight of paraffin oil sprayed onto the surface of this silica 40 gel. This formulation of the active ingredient exhibits good adherence.
VIII. A stable aqueous dispersion of 40 parts by weight of com-pound no. 2, 10 parts of the sodium salt of a phenolsulfonic 45 acid-urea-formaldehyde condensate, 2 parts of silica gel and 48 ~ -parts of water, which dispersion can be further diluted.

: , . , , , , . , ." , , . , ; . ,. ~ , `- ' ' ' ', , , ,' ,: . ' , ,:, . .. . . . .
:, :
~'.,- '"' ,, , , ': ' ~, , ' " ' : ' : ,. . .

s~SF Aktien~e~ell~cha~t 920557 O.Z. 0050/43543 38 2106~97 IX. A stable oily dispersion of 20 parts by weight of compound no. 3, 2 parts by weight of the calcium salt of dodecylbenzene-sulfonic acid, 8 parts by weight of a fat~y alcohol polyglycol ether, 2 parts by weight of the sodium salt of a phenolsulfonic 5 acid-urea-formaldehyde condensate and 68 parts by weight of a paraffinic mineral oil.
X. A hammer-milled mixture of 10 parts by weight of compound no.
1, 4 parts by weight of the sodium salt of diisobutylnaphthalene-19 ~-sulfonic acid, 20 parts by weight of the sodium salt of a lignin-sulfonic acid obtained from a sulfite waste liquor, 38 parts by weight of silica gel, and 38 parts by weight of kaolin.
By finely dispersing the mixture in 10,000 parts by weight of water, a spray liquor containing O.lwt% of the active ingredient 15 is obtained.
Used alone, the active ingredients act as low-foaming biocides. A
significant increase in the action of biocidal formulations con-taining these compounds is achieved if tri-C6- to~Cl2-alkylmethy-20 lammonium salts, preferably in amounts of from 20 to 40wt~, basedon the weight of compounds of the general formula I, are added.
The active ingredients may also be mixed with other, prior art, microbicides. In many instances, a synergistic effect is 25 achieved, i.e., the microbicidal action of the mixture is greater than the added actions of its individual components.
Prior art microbicides may be added to the novel substances in a weight ratio of from 1:100 to 100:1.
Examples of such active ingredients are as follows:
.
2-(thiocyanomethylthio)-benzothiazole 1-~2-(2,4-dichlorophenyl)-2-(2-propenyloxy)-ethyl]-lH-imidazole 35 2,4,5,6-tetrachloroisophthalodinitrile methylene bisthiocyanate tributyltin oxide, naphthenate, benzoate, salicylate mercaptobenzothiazole 1,2-benzisothiazolone and its alkali metal salts ~0 alkali metal compounds of N~-hydroxy-N-cyclohexyldiazenium oxide 2-(methoxycarbonylamino)-benzimidazole 2-methyl-3-oxo-5-chlorothiazolin-3-one trihydroxymethylnitromethane glutardialdehyde 45 chloroacetamide ;~ -polyhexamethylene bisguanide 5-chloro-2-methyl-4-isothiazolin-3-one ~ magnesium salts . , , . . , : i : . . , . ., . . , . ". .: .: ,~ . ,.. : . . . . . . : : . :
i:: ., i, ,- . . . . . . . . . . . .
,, , , , , : ' , ' ' . .: : . ' : ' ' ' : ' : . ~ : ' ' ,. . ,. , ' ' ,,: . '' ' " . ' ' ' , ; . ' ' ' BASF Aktienge~ell~chaft 920557 O.Z. 0050/43543 39 2 ~ 0 ~ll 9 7 3/5-dimethyltetrahydro-l~3~5-2H-thiadiazine-2-thione hexahydrotriazine N,N-methylolchloroacetamide 2-n-octyl-4-isothiazolin-3-one 5 oxazolidines bisoxazolidines 2,5-dihydro-2,5-dialkoxy-2,5-dialkylfurans diethyldodecylbenzylammonium chloride dimethyloctadecyldimethylbenzylammonium chloride 10 dimethyldidecylammonium chloride dimethyldidodecylammonium chloride trimethyltetradecylammonium chloride benzyldimethylalkyl-~Cl2-Cl8)-ammonium chloride dichlorobenzyldimethyldodecylammonium chloride 15 cetylpyridinium chloride cetylpyridinium brcmide cetyltrimethylammonium chloride laurylpyridinium chloride laurylpyridinium bisulfate - ~
20 benzyldodecyldi(beta-oxyethyl)-ammonium chloride dodecylbenzyltrimethylammonium chloride n-alkyldimethylbenzylammonium ~hloride (alkyl radical: 40% Cl2, 50% Cl4, 10% Cl6) lauryldimethylethylammonium ethyl sul~ate 25 n-alkyldimethyl-(l-naphthylmethyl)-ammonium chloride (alkyl radical: 98% Cl2, 2% C14) cetyldimethylbenzylammonium chloride lauryldimethylbenzylammonium chloride 30 Examples of further compounds which may be admixed are:
1,3-dimethylol-5,5-dimethylhYdantoin dimethylolurea : tetramethylolacetylenediurea 35 dimethylolglyoxalmonoureine hexamethylenetetramine glyoxal glutardialdehyde N-methylolchloroacetamide 40 1-(hydroxymethyl)-5,5-dimethylhydantoin 1,3-bis-~hydroxymethyl)-5,5-dimethylhydantoin imidazolidinylurea 1-(3-chloroallyl)-3,5~7-triaza-1-azonia-adamantan chloride 1,3-bis-(~-ethylhexyl)-5-methy,:1-5-amino-hexahydropyrimidine 45 1,3,5-tris-(hydroxyethyl)-1,3~5-hexahydrotriazine 1,2-dibromo-2,4-dicyanobutane 5-bromo-5-nitro-1,3-dioxane ... . , - . , .
. ~ . . ~ . . . . . , :. , ~ : .
,. , : . : ., ':, ,' .: : '. .' . ,. ' ,; . , ` :
, . : .: . ' ' . , '' ' . ' '' ' .

BASF Aktien~esellschaft 9~0557 O.Z. 0050/~3543 43 21 0~97 2-bromo-2-nitropropanediol 1,1'-hexamethylene-bis-[5-(4-chlorophenyl)-biguanide]
4,4-diaminodiphenoxypropane 2-bromo-2-nitropropane-1,3-diol 5 sorbic acid and its salts p-hydroxybenzoic acid and its esters and salts zinc-2-pyridinethiol-N-oxide 2-~(hydroxylmethyl)amino]-ethanol dithio-2,2'-bls(benzmethylamide) 10 5-chloro-2-(2,4-dichlorophenoxy)-phenol thio-bis-(4-chlorophenol) o-phenylphenol chloromethyl-diiodomethylsulfone p-chlorophenyl-3-iodopropargylformal.
Synthesis examples The directions given in the synthesis examples below were used, after appropriate modification of the starting materials, to ob-20 tain further compounds I. The compounds thus obtained are listedin the tables below with their physical data.
1. N-hydroxy-N-(2-propylphenyl)-2-chloronicotinamide -~
H3CH2CH2C ~ ~ N
HO - N - CO ~ / \~
~ .
At 0C, 14 ml of water and 19.6 g of sodium bicarbonate are added to a solution of 15.1 g of 2-n-propylphenylhydroxylamine in 75 ml -of a 2:1 mixture of ether and ligroin, and 13.6 g of 2-chloroni-cotinamide is then dripped in while stirring vigorouslY. The mix-35 ture is stirred overnight at room temperature and then suction filtered. The residue is stirred for 15 minutes in 10~ strength ~;-sodium bicarbonate solution, suction filtered, dissolved in ethyl acetate and dried, and the solvent is evaporated off under re-duced pressure. ~rom the crude product (14.6 g) there is iso-40 lated, after recrystallization from ethanol, 12.5 g of 2-chloro-nicotic acid-N-hydroxy-2-n-propylanilide of m.p. 134-135C.
~ ~ .
,:
qs .

,,, ., ,. ,: .. , , ",., . . ,, . .. ; , ;~ . .. . .

. . . . . .
. . .

~ BASF Aktiengesellschaft ~f20557 . o.z. 0050/43543 41 2106~97 `
Table 1 R~J
HO--N--CO--A

10 ~xample _ Phys. data CH(CH~)z ' 01~,~ d:~ 3 ~ 107-111C
CH2CH2CH3 ~ pa- ~ ~ 3 ~ 134-135C
3 CH2CH(CH3)2 2-Cl-pyridin-3-yl oil phenyl 2-Cl-pyridin-3-yl 112-115C
_ CH2CH(CH3)2 2-CH3, 4-CF3-thiazol-4-yl oil 6 phenyl 2-CH3, 4-CF3-thiazol-4-yl173-175C
_ CH2CH(CH3)2 2,4-(CH3)2-thlazol-4-yl oll ~ _ phenyl 2,4-(CH3)2-thiazol-4-yl 58-62C
Examples demonstrating biological action:
Action on Botrytis cinerea Slices of green paprika pods were sprayed to runoff with aqueous suspensions containing (dry basis) 80% of the active ingredient and 20% of emulsifier. After the sprayed-on layer had dried, the slices were sprayed with a spore suspension [1.7-105 spores per 30 ml; 2% biomalt; water] of the fungus Botrytis cinerea and then kept for 4 days at 18~C and in high humidity.
~ After this period, the untreated controls exhibited 90% fungus ; attack, whereas the paprika slices treated with 500 ppm of com-35 pounds nos. 1 and 2 e~hibited 5% attack at most.
At an application rate oE 1000 ppm of compounds nos. 1 and 2 the paprika slices exhibited no attack at all, whereas the slices treated with 1000 ppm of 2-chloronicotinic acid-2-chloroanilide 40 exhibited 90% attack, just as the untreated controls.
:;

.~ ..... .. ..... .. . .. .. .. ...

~: :
.

Claims (7)

1. N-Hydroxy-N-phenylcarboxamides of the formula I

I

where:
R is C2-C12-alkyl, C2-C12-alkoxy, C3-C12-alkenyl, C3-C12-alkenyloxy, C3-C6-alkynyl or C3-C6-alkynyloxy, where these groups are partially or completely halogenated;
C3 C7-cycloalkyl, C4-C7-cycloalkenyl, C3-C7-cycloalkyloxy or C4-C7-cycloalkenyloxy, where these rings may bear from one to three C1-C4-alkyl groups;
phenyl, which may bear from one to five halogen atoms and/or from one to three of the following radicals:
C1-C4-alkyl, C1-C4-haloalkyl, C1-C4-alkoxy, C1-C4-haloal-koxy, C1-C4-alkylthio or C1-C4-haloalkylthio;
A is a cyclic radical selected from the group of formulae A1 to A7 where:

X is -CH2-, -S-, -SO- or -SO2-;
Y is -O- or -S-;
R1, R2, R4, R5 and R7 are halogen, C1-C4-alkyl or C1-C4-halo-alkyl;
R3 and R6 are hydrogen, halogen or C1-C4-alkyl;
n is 1 or 2, and the radicals R3 may be different when n is
2.
2. N-Hydroxy-N-phenylcarboxamides of the formula I as claimed in claim 1, where R has the meanings given in claim 1 and A is a cyclic radical selected from the group having the formulae A1 to A7, where X and Y have the meanings given in claim 1 and the substituents have the following meanings:
R1 is halogen, methyl or C1-haloalkyl;
R2 is halogen or C1-haloalkyl;
R3 is hydrogen or methyl;
n is 1 or 2, and the radicals R3 may be different when n is 2;
R4 is halogen or methyl;
R5 is methyl or C1-haloalkyl;
R6 is hydrogen, halogen or methyl;
R7 is halogen, methyl or C1-haloalkyl.
3. N-Hydroxy-N-phenylcarboxamides of the formula I as claimed in claim 1, where R has the meanings given in claim 1 and A is cyclic radical selected from the group having the formulae A1 to A7, where X and Y have the meanings given in claim 1 and the substituents have the following meanings:
R1 is chloro, bromo, iodo, methyl or trifluoromethyl;
R2 is chloro or trifluoromethyl;
R3 is hydrogen or methyl;
n is 1 or 2, and the radicals R3 may be different when n is 2;
R9 is chloro, or methyl;
R5 is methyl, difluoromethyl or trifluoromethyl;
R6 is hydrogen, chloro or methyl;
R7 is chloro, methyl or trifluoromethyl.
4. An agent for combatting injurious fungi, containing a fungi-cidal amount of a compound of the formula I as claimed in claim 1, 2 or 3, and inert additives.
5. A process for combatting injurious fungi, wherein the fungi, their habitat and/or the plants or materials to be kept free from fungi are treated with a fungicidally effective amount of a compound of the formula I as claimed in claim 1, 2 or 3.
6. The use of compounds I as claimed in claim 1, 2 or 3 for com-batting injurious fungi.
7. The use of compounds I as claimed in claim 1, 2 or 3 for com-batting Botrytis.
CA002106497A 1992-09-21 1993-09-20 N-hydroxy-n-phenylcarboxamides, their preparation and compositions containing them for controlling harmful fungi Abandoned CA2106497A1 (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE4231518A DE4231518A1 (en) 1992-09-21 1992-09-21 N-Hydroxy-N-phenylcarboxamides, process for their preparation and compositions containing them for controlling harmful fungi
DEP4231518.2 1992-09-21

Publications (1)

Publication Number Publication Date
CA2106497A1 true CA2106497A1 (en) 1994-03-22

Family

ID=6468432

Family Applications (1)

Application Number Title Priority Date Filing Date
CA002106497A Abandoned CA2106497A1 (en) 1992-09-21 1993-09-20 N-hydroxy-n-phenylcarboxamides, their preparation and compositions containing them for controlling harmful fungi

Country Status (5)

Country Link
EP (1) EP0591699A1 (en)
JP (1) JPH06211769A (en)
KR (1) KR940006991A (en)
CA (1) CA2106497A1 (en)
DE (1) DE4231518A1 (en)

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7119049B2 (en) 2002-05-23 2006-10-10 Bayer Cropscience Ag Oxathiinecarboxamides
US7179840B2 (en) 2002-05-23 2007-02-20 Bayer Cropscience Ag Furancarboxamides
US7732375B2 (en) 2003-10-23 2010-06-08 Bayer Cropscience Ag Hexyl carboxanilides and their use for controlling fungi
US7847108B2 (en) 2003-02-14 2010-12-07 Bayer Cropscience Ag Oxathiin carboxamides
US7910746B2 (en) 2004-02-06 2011-03-22 Bayer Cropscience Ag Haloalkyl carboxamides

Families Citing this family (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE10250110A1 (en) * 2002-10-28 2004-05-13 Bayer Cropscience Ag Thiazole (bi) cycloalkylcarboxanilides
DE10349502A1 (en) 2003-10-23 2005-05-25 Bayer Cropscience Ag 1.3 Dimethylbutylcarboxanilide
DE102004005785A1 (en) 2004-02-06 2005-08-25 Bayer Cropscience Ag 2-Halogenfuryl / thienyl-3-carboxamide
DE102004005787A1 (en) 2004-02-06 2005-08-25 Bayer Cropscience Ag carboxamides

Family Cites Families (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1642224B2 (en) * 1967-04-28 1976-04-29 Basf Ag, 6700 Ludwigshafen USE OF SUBSTITUTED BENZOIC ANILIDES FOR CONTROL OF FUNGI FROM THE CLASS OF BASIDIOMYCETS
US3541106A (en) * 1967-12-28 1970-11-17 Velsicol Chemical Corp Certain substituted n-phenyl-n-hydroxy-nicotinamides,the corresponding isonicotinamines and picolinamides
US3646042A (en) * 1970-02-09 1972-02-29 Velsicol Chemical Corp Certain n-phenyl n-lower-alkyl-pyridine carboxamides and derivatives thereof
DE2417216A1 (en) * 1974-04-09 1975-11-06 Basf Ag FUNGICIDES

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7119049B2 (en) 2002-05-23 2006-10-10 Bayer Cropscience Ag Oxathiinecarboxamides
US7179840B2 (en) 2002-05-23 2007-02-20 Bayer Cropscience Ag Furancarboxamides
US7847108B2 (en) 2003-02-14 2010-12-07 Bayer Cropscience Ag Oxathiin carboxamides
US7732375B2 (en) 2003-10-23 2010-06-08 Bayer Cropscience Ag Hexyl carboxanilides and their use for controlling fungi
US7910746B2 (en) 2004-02-06 2011-03-22 Bayer Cropscience Ag Haloalkyl carboxamides

Also Published As

Publication number Publication date
KR940006991A (en) 1994-04-26
DE4231518A1 (en) 1994-03-24
EP0591699A1 (en) 1994-04-13
JPH06211769A (en) 1994-08-02

Similar Documents

Publication Publication Date Title
US5438070A (en) Carboxanilides, their preparation and compositions containing them for controlling harmful fungi
US5416103A (en) N-cyclohex(en)yl-pyridine carboxamides and compositions containing them for controlling fungal pests
CA2081935C (en) Anilide derivatives and their use for combating botrytis
JP4104087B2 (en) Compositions and methods for controlling harmful fungi
FI95376C (en) Microbicidal 2-anilino-pyrimidine derivatives
EP0544152B1 (en) Herbicidal quinoline-3-carbonamides
AU2004266447A1 (en) Method of plant growth promotion using amide compounds
JPH11514974A (en) Compositions and methods for controlling harmful fungi
CA2106497A1 (en) N-hydroxy-n-phenylcarboxamides, their preparation and compositions containing them for controlling harmful fungi
NZ332094A (en) Process and agents for controlling harmful fungi contained in a solid or liquid carrier containing at least one p-hydroxyaniline derivative and at least one amine compound and a process for using them
DE3807232A1 (en) SUBSTITUTED ACRYLIC ACID ESTERS
JPS62129205A (en) Use of tetrahydrobenzothienylurea derivative as bactericidalfungicide
CZ254195A3 (en) Immunosubstituted amides of phenylacetic acid, process of their preparation and fungicidal compositions containing thereof
US5602181A (en) Naphthyl ethers, their preparation, compositions containing them and their use
PT87371B (en) Process for the preparation of a fungicidal composition containing substituted and unsubstituted aminomethylheterocyclic derivatives and of novel derivatives substituted aminomethylheterocyclic derivatives
JPH04230353A (en) Oxalylhydroxamic acid derivative and process for controlling growth of plant
JPS63230668A (en) Carbamic acid benzaldoxime derivative

Legal Events

Date Code Title Description
FZDE Dead