US3903303A - Controlling fungi and bacteria with certain oxime esters - Google Patents
Controlling fungi and bacteria with certain oxime esters Download PDFInfo
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- US3903303A US3903303A US172318A US17231871A US3903303A US 3903303 A US3903303 A US 3903303A US 172318 A US172318 A US 172318A US 17231871 A US17231871 A US 17231871A US 3903303 A US3903303 A US 3903303A
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- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N37/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids
- A01N37/16—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom having three bonds to hetero atoms with at the most two bonds to halogen, e.g. carboxylic acids containing the group; Thio analogues thereof
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- ABSTRACT A process for controlling fungi and bacteria with compounds having the formula in which X is chlorine or bromine, R is hydrogen or alkyl having fromone to six carbon atoms; R is alkyl having one to four carbon atoms, or haloalkyl having one to four carbon atoms; phenyl, or nuclear substituted derivatives thereof in which the substituents are halogen, nitro or lower alkyl; R is alkyl having from one to six carbon atoms; haloalkyl having from one to six carbon atoms; alkenyl having from two to four carbon atoms; and NHR in which R is alkyl having from one to eight. carbon atoms; halomethyl; phenyl and nuclear substituted derivatives thereof in which said substituents are halogen or nitro; and alkenyl having from two to four carbon atoms.
- This invention relates to the use of certain keto oxime esters in controlling fungi and bacteria.
- the compounds useful in the process of the present invention are those having the formula in which X is chlorine or bromine, preferably chlorine; R is hydrogen or alkyl having from one to six carbon atoms, preferably hydrogen; R is alkyl having one to four carbon atoms, haloalkyl having from one to four carbon atoms, phenyl, or nuclear substituted derivatives thereof in which the substituents are halogen, nitro, and lower alkyl, preferably chloromethyl; R is alkyl having from one to six carbon atoms; haloalkyl having from one to six carbon atoms, preferably halomethy'l; alkenyl having from two to four carbon atoms; NHR in which R is alkyl having from one to eight carbon atoms, preferably methyl; halomethyl; phenyl, and nuclear substituted derivatives thereof in which said substituents are nitro or halogen, preferably 4 chlorophenyl and alkenyl having from two to four carbon atoms; most preferably
- the compounds useful in the process of the present invention can be prepared by reacting a compound of the formula in which X, R and R are as defined with a compound of the formula halo-C-R in which halo is chlorine or bromine and R is as clefined.
- the reaction is carried out in the presence of a base such as pyridine and in a solvent for the reactants.
- a base such as pyridine
- the reaction is exothermic so no heating is required. Cooling is sometimes required to control the reaction rate.
- the compounds of this invention can be recovered from the mixture and purified by standard procedures.
- Compounds of the formula can be prepared by reacting with excess hydroxylamine hydrochloride or hydroxylamine hydrobromide in ethanol and water, wherein X, R, and R are as defined.
- the reaction can be run with heating under reflux for several hours.
- the desired product is recovered and purified by conventional techniques.
- benzene were added to a 500 ml. flask, stirred and cooled to 10C. with an ice bath. 4.7 gms. (0.06 moles) pyridine was added at a rate sufficient to maintain the reaction temperature below 20C. After the addition of the pyridine, the ice bath was removed, and the mixture was stirred at room temperature for 1 hour. An additional 100 ml. benzene was added, and the mixture was washed with 50 m1. dilute HCl followed by two 100 ml. water washes. The benzene phase was dried with MgSO, and evaporated to give 10.4 gms. 1,3- dichloroacetoneoxime trichloroacetate CIH. .C o
- CICH/ EXAMPLE 6 1 ,3-dichloroacetoneoxime-N-(4-chlorophenyl) carbamate 7.1 gms. (0.05 moles) 1.3-d
- This test measures the bactericidal and fungicidal properties of a compound when in contact with a growing bacterium or fungus.
- the test is conducted by partially filling two l-ounce vials with malt broth and one l-ounce vial with nutrient broth. Next the test compound is added to the vials at a certain concentration. expressed in parts per million, and mixed with the broth. A water suspension of spores of the desired fungi or cells of the desired bacteria (one organism per vial) is added. The vials are then sealed and incubated for one week; at this time the vials are examined and the results recorded. Table IV shows the results of various compounds tested by the in yitro vial test.
- the compounds chloromethyl find particular utility as bacter cides and fungicides.
- the compounds can be applied in a variety of ways at chloromethyl various concentrations. They can be combined with suitable carriers and applied as dusts. sprays, or drenches. The amount applied will depend on the nature of 50 the utility. The rate of application can also vary with the microbiological use intended.
- the method of inhibiting the growth of fungi which comprises applying thereto a fungicidally effective amount of the compound having the formula chlommethyl O chloromcthyl 2.
- the method ofinhibiting the growth of fungi which comprises applying thereto a fungicidally effective amount of the compound having the formula 5.
- the method of inhibiting the growth of fungi which comprises applying thereto a fungicidally effective amount of the compound having the formula chloromethyl chloromethyl 7.
- the method of inhibiting the growth of fungi which chlmomflhyl H comprises applying thereto a fungicidally effective amount of the compound having the formula ehloromcthyl chlmomelhyl O 10.
- the method of inhibiting the growth of bacteria which comprises applying thereto a bacterically effec- 'T" tive amount of a compound of the formula chloromelhyl l O chlorometh'yl ⁇ 8.
- the method of inhibiting the growth of bacteria which comprises applying thereto a bacterically effecchloromcthvl tlve amount of a compound of the formula chloromcthyl chloromcthyl 2O 9.
- the method of inhibiting the growth of bacteria chloromethyl/ which comprises applying thereto a bacterically effec- I tive amount of a compound of the formula
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- Life Sciences & Earth Sciences (AREA)
- Agronomy & Crop Science (AREA)
- Pest Control & Pesticides (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
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- General Health & Medical Sciences (AREA)
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- Agricultural Chemicals And Associated Chemicals (AREA)
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Abstract
A process for controlling fungi and bacteria with compounds having the formula
in which X is chlorine or bromine, R is hydrogen or alkyl having from one to six carbon atoms; R1 is alkyl having one to four carbon atoms, or haloalkyl having one to four carbon atoms; phenyl, or nuclear substituted derivatives thereof in which the substituents are halogen, nitro or lower alkyl; R2 is alkyl having from one to six carbon atoms; haloalkyl having from one to six carbon atoms; alkenyl having from two to four carbon atoms; and -NHR3 in which R3 is alkyl having from one to eight carbon atoms; halomethyl; phenyl and nuclear substituted derivatives thereof in which said substituents are halogen or nitro; and alkenyl having from two to four carbon atoms.
in which X is chlorine or bromine, R is hydrogen or alkyl having from one to six carbon atoms; R1 is alkyl having one to four carbon atoms, or haloalkyl having one to four carbon atoms; phenyl, or nuclear substituted derivatives thereof in which the substituents are halogen, nitro or lower alkyl; R2 is alkyl having from one to six carbon atoms; haloalkyl having from one to six carbon atoms; alkenyl having from two to four carbon atoms; and -NHR3 in which R3 is alkyl having from one to eight carbon atoms; halomethyl; phenyl and nuclear substituted derivatives thereof in which said substituents are halogen or nitro; and alkenyl having from two to four carbon atoms.
Description
United States Patent [191 Gutman Sept. 2, 1975 CONTROLLING FUNGI AND BACTERIA WITH CERTAIN OXIME ESTERS Arnold D. Gutman, Berkeley, Calif.
Related US. Application Data [60] Division of Ser. No. 52,769, July 6, 1970, abandoned, which is a continuation-in-part of Ser. No. 879,967, Dec. 4, 1969, abandoned, which is a division of Ser. No. 649,024, June 26, 1967, abandoned.
[75] Inventor:
[52] US. Cl 424/327; 424/300 [51] Int. Cl. A01N 9/20; AOlN 9/24 [58] Field of Search 424/300, 327
[56] References Cited UNITED STATES PATENTS 3,063,823 11/1962 Kuhle et al. 71/2.6
FOREIGN PATENTS OR APPLICATIONS 103,373 3/1966 Denmark 424/327 825,709 10/1969 Canada 424/327 Primary Examiner-Albert T. Meyers Assistant Examiner-Norman A. Drezin Attorney, Agent, or FirmEdwin H. Baker [57] ABSTRACT A process for controlling fungi and bacteria with compounds having the formula in which X is chlorine or bromine, R is hydrogen or alkyl having fromone to six carbon atoms; R is alkyl having one to four carbon atoms, or haloalkyl having one to four carbon atoms; phenyl, or nuclear substituted derivatives thereof in which the substituents are halogen, nitro or lower alkyl; R is alkyl having from one to six carbon atoms; haloalkyl having from one to six carbon atoms; alkenyl having from two to four carbon atoms; and NHR in which R is alkyl having from one to eight. carbon atoms; halomethyl; phenyl and nuclear substituted derivatives thereof in which said substituents are halogen or nitro; and alkenyl having from two to four carbon atoms.
11 Claims, No Drawings CONTROLLING FUNGI AND BACTERIA WITH CERTAIN OXIME ESTERS This application. is a division of application Ser. No. 52,769, filed July 6, 1970, which is a continuation-inpart of application Ser. No. 879,967 filed Dec. 4, 1969, which is a divisional of application Ser. No. 649,024, filed June 26, 1967, all abandoned.
This invention relates to the use of certain keto oxime esters in controlling fungi and bacteria.
The compounds useful in the process of the present invention are those having the formula in which X is chlorine or bromine, preferably chlorine; R is hydrogen or alkyl having from one to six carbon atoms, preferably hydrogen; R is alkyl having one to four carbon atoms, haloalkyl having from one to four carbon atoms, phenyl, or nuclear substituted derivatives thereof in which the substituents are halogen, nitro, and lower alkyl, preferably chloromethyl; R is alkyl having from one to six carbon atoms; haloalkyl having from one to six carbon atoms, preferably halomethy'l; alkenyl having from two to four carbon atoms; NHR in which R is alkyl having from one to eight carbon atoms, preferably methyl; halomethyl; phenyl, and nuclear substituted derivatives thereof in which said substituents are nitro or halogen, preferably 4 chlorophenyl and alkenyl having from two to four carbon atoms; most preferably, R is alkenyl having two to four carbon atoms.
The compounds useful in the process of the present invention can be prepared by reacting a compound of the formula in which X, R and R are as defined with a compound of the formula halo-C-R in which halo is chlorine or bromine and R is as clefined.
Preferably. the reaction is carried out in the presence of a base such as pyridine and in a solvent for the reactants. Generally, the reaction is exothermic so no heating is required. Cooling is sometimes required to control the reaction rate. The compounds of this invention can be recovered from the mixture and purified by standard procedures.
Compounds of the formula can be prepared by reacting with excess hydroxylamine hydrochloride or hydroxylamine hydrobromide in ethanol and water, wherein X, R, and R are as defined. The reaction can be run with heating under reflux for several hours. The desired product is recovered and purified by conventional techniques.
Preparation of the compounds useful in the practice of the process of this invention is illustrated by the following examples.
EXAMPLE 1 l,3-dichloroacetoneoxime 63.5 gms. (0.50 moles) 1,3-dichloropropanone, 69.5 gms. (1.00 moles) hydroxylamine hydrochloride, 250 ml. ethanol and 25 ml. of water were combined and heated under reflux for 4 hours. The cooled mixture was poured into 500 ml. of water. The aqueous solution was extracted with 3 ml. portions of chloroform. The chloroform phases were combined and dried with anhydrous MgSO The chloroform was evaporated to give 66.3 g. (93.6% of theory) of 1,3-
dichloroacetoneoxime,
ClH- ,C
C=NOH cm c EXAMPLE 2 1,3-dichloroacetoneoxime trichloroacetate 7.1 gms. (0.05 moles) 1,3-diehloroacetoneoxime, 9.1 gms. (0.05 moles) trichloroaeetyl chloride and 100 ml.
benzene were added to a 500 ml. flask, stirred and cooled to 10C. with an ice bath. 4.7 gms. (0.06 moles) pyridine was added at a rate sufficient to maintain the reaction temperature below 20C. After the addition of the pyridine, the ice bath was removed, and the mixture was stirred at room temperature for 1 hour. An additional 100 ml. benzene was added, and the mixture was washed with 50 m1. dilute HCl followed by two 100 ml. water washes. The benzene phase was dried with MgSO, and evaporated to give 10.4 gms. 1,3- dichloroacetoneoxime trichloroacetate CIH. .C o
C=No -CC|,,
C1H2C EXAMPLE 3 l,3-dichloroacetoneoximino N-allylcarbamate 11.7 gms. (0.08 moles) of the 1,3-
dichloroacetoneoxime and 6.7 gms. (0.08 moles) of al lylisocyanate were combined in 100 ml. of benzene. After the exothermic reaction had subsided, the mix 3 ture was washed with 2 50ml. portions of water. The benzene phase was dried with anhydrous MgSO and evaporated to give 12.2 g. (72.8% of theory) of 1.3- dichloroacetoneoximino-N'-allylcarbamate EXAMPLE 4 1,3-dichloroacetoneoximecrotonate 10.0 gms (0.07 moles) 1,3-dich1oroacetoneoxime, 7.2 gms. (0.07 moles) crotonyl chloride were combined in 100 ml. of benzene. The mixture was stirred and cooled to C. 6.3 gms. (0.08 moles) of pyridine was added over a period of minutes. The mixture was stirred at room temperature for 1 hour. An additional 100 ml. benzene was added and the mixture was washed with two 100 ml. portions of water. The benzene phase was dried with anhydrous MgSO and evaporated to give 8.3 g. (55.8% of theory) of 1,3- dichloroacetoneoximinocrotonate clcn CICH
EXAMPLE 5 l.3-dichloroacetoneoxime-N methylcarbamate 14.2 gms. (0.1 moles) of 1,3-dichloroacetoneoxime was dissolved in 50 ml. chloroform and was cooled to 10C. in an icebath. l 1.4 gms. (0.2 moles) of allylisocyanate was added at a temperature between 10 and 35C. After the addition. the mixture was vacuum stripped. The resulting oil was dissolved in 150 ml. benzene and washed with two 100 ml. portions of water. The benzene phase was dried with anhydrous MgSO and evaporated to give 13.7 gms. (68.9% yield) of 1,3- dichloroacetoneoxime N-methy1carbamate,
CICHL, H
\C=NOCNHCH=,
CICH/ EXAMPLE 6 1 ,3-dichloroacetoneoxime-N-(4-chlorophenyl) carbamate 7.1 gms. (0.05 moles) 1.3-d|chloroacetoneoxime. 7.7 gms. (0.05 moles) 4-chlorophenyl isocyanate, and 50 ml. acetone were combined in a 250 ml. flask. The resulting mixture was stirred at room temperature. for 1 hour, poured into 200 m1. benzene. and washed with two 100 ml. portions of water. The benzene phase was then dried with MgSO and evaporated to yield 13.5 gms. of 1,3-dichloroacetoneoximc-N'-(4-chlorophenyl) carbamate.
EXAMPLE 7 l 4-dibromoacetophenone oxime-N-methyl carbamate BrH C m.p. 139-143C.
The following is a table of certain selected compounds that have been prepared according to the procedure described hereto. Compound numbers have been assigned to each compound and are used throughout the remainder of the application.
TABLE I H C=NOCR- COM- POUND NO. X R R R 1" Cl hydrogen chloromethyl -NH-methy1 2 Cl hydrogen chloromethyl NH-alalyl 3 Cl hydrogen chloromethyl -NH-isopropyl 4 Cl hydrogen chloromethyl NH-3 4dichlorophenyl 5 Cl hydrogen chloromethyl NH-n-butyl- 6" C1 hydrogen chloromethyl trichloromethyl 7" Cl hydrogen chloromethyl l-propenyl 8 C1 hydrogen chloromethyl NH-4-chlorophenyl 5O 9 Cl hydrogen chloromethyl -NH-4-nitrophenyl 10 Cl hydrogen chloromethyl vinyl 1 1 Cl hydrogen chloromethyl -NH -n-octyl 12 Br hydrogen 4-bromophenyl -NH-methyl 1 3 Cl H phenyl l-propenyl 14 Cl H phcnyl vinyl 5 15 Cl methyl methyl l-propenyl 16 Cl methyl methyl vinyl 17 Cl n-pcntyl methyl l-propenyl 18 Cl ethyl ethyl l-propcnyl l) C l n-propyl methyl 1 -propenyl 20 Cl H chloromethyl allyl 21 C l H chloromethyl hromomethyl 0 22 (1 H methyl l-propenyl 23 Cl H methyl -l lHCH 24 Cl pentyl methyl -NH-4-chlorophenyl 25 Cl ethyl ethyl -NH-4-chlorophenyl 26 (I ethyl ethyl hromomcthyl 27 (l n-propyl methyl hromomethyl a=Pre 1ared in Eunnple I lwlreparud in liwmple 3 c Prepnr-e'd in Example 4 d=Prepuretl in Example 5 e=Prupnrcd in Example (v F=Preparcd in Example 7 In Vitro Vial Test The following test illustrates utility of the compounds in controlling fungi and bacteria. This test measures the bactericidal and fungicidal properties of a compound when in contact with a growing bacterium or fungus. The test is conducted by partially filling two l-ounce vials with malt broth and one l-ounce vial with nutrient broth. Next the test compound is added to the vials at a certain concentration. expressed in parts per million, and mixed with the broth. A water suspension of spores of the desired fungi or cells of the desired bacteria (one organism per vial) is added. The vials are then sealed and incubated for one week; at this time the vials are examined and the results recorded. Table IV shows the results of various compounds tested by the in yitro vial test.
6 chluromethyl (N) C=NOCNH-allyl chloromethyl 3. The method of inhibiting the growth of fungi which comprises applying thereto a fungicidally effective amount of the compound having the formula chloromethyl\ O C=NOCNH-isopropyl chloromethyl 4. The method of inhibiting the growth of fungi which comprises applying thereto a fungicidally effective amount of the compound having the formula TABLE IV Concentration (p.p.m.) which inhibited growth.
' FUNGUS BACTERIA COMPOUND ASPERGILLUS PENlClLLlUM ESCHERICHIA STAPYLOCOCCUS N0. NIGER SP. COLI AUREUS As can be seen by the test results, the compounds chloromethyl find particular utility as bacter cides and fungicides. The compounds can be applied in a variety of ways at chloromethyl various concentrations. They can be combined with suitable carriers and applied as dusts. sprays, or drenches. The amount applied will depend on the nature of 50 the utility. The rate of application can also vary with the microbiological use intended.
It is claimed:
1. The method of inhibiting the growth of fungi which comprises applying thereto a fungicidally effective amount of the compound having the formula chlommethyl O chloromcthyl 2. The method ofinhibiting the growth of fungi which comprises applying thereto a fungicidally effective amount of the compound having the formula 5. The method of inhibiting the growth of fungi which comprises applying thereto a fungicidally effective amount of the compound having the formula chloromethyl chloromethyl 7. The method of inhibiting the growth of fungi which chlmomflhyl H comprises applying thereto a fungicidally effective amount of the compound having the formula ehloromcthyl chlmomelhyl O 10. The method of inhibiting the growth of bacteria which comprises applying thereto a bacterically effec- 'T" tive amount of a compound of the formula chloromelhyl l O chlorometh'yl\ 8. The method of inhibiting the growth of fungi which C=NO -C NH iso rn comprises applying thereto a fungicidally effective chlmommhvl amount of the compound having the formula 11. The method of inhibiting the growth of bacteria which comprises applying thereto a bacterically effecchloromcthvl tlve amount of a compound of the formula chloromcthyl chloromcthyl 2O 9. The method of inhibiting the growth of bacteria chloromethyl/ which comprises applying thereto a bacterically effec- I tive amount of a compound of the formula
Claims (11)
1. THE METHOD OF INHIBITING THE GROWTH OF FUNGI WHICH COMPRISES APPLYING THERETO A FUNGICIDALLY EFFECTIVE AMOUNT OF THE COMPOUND HAVING THE FORMULA
2. The method of inhibiting the growth of fungi which comprises applying thereto a fungicidally effective amount of the compound having the formula
3. The method of inhibiting the growth of fungi which comprises applying thereto a fungicidally effective amount of the compound having the formula
4. The method of inhibiting the growth of fungi which comprises applying thereto a fungicidally effective amount of the compound having the formula
5. The method of inhibiting the growth of fungi which comprises applying thereto a fungicidally effective amount of the compound having the formula
6. The methoD of inhibiting the growth of fungi which comprises applying thereto a fungicidally effective amount of the compound having the formula
7. The method of inhibiting the growth of fungi which comprises applying thereto a fungicidally effective amount of the compound having the formula
8. The method of inhibiting the growth of fungi which comprises applying thereto a fungicidally effective amount of the compound having the formula
9. The method of inhibiting the growth of bacteria which comprises applying thereto a bacterically effective amount of a compound of the formula
10. The method of inhibiting the growth of bacteria which comprises applying thereto a bacterically effective amount of a compound of the formula
11. The method of inhibiting the growth of bacteria which comprises applying thereto a bacterically effective amount of a compound of the formula
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US172318A US3903303A (en) | 1970-07-06 | 1971-08-16 | Controlling fungi and bacteria with certain oxime esters |
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US5276970A | 1970-07-06 | 1970-07-06 | |
| US172318A US3903303A (en) | 1970-07-06 | 1971-08-16 | Controlling fungi and bacteria with certain oxime esters |
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| Publication Number | Publication Date |
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| US3903303A true US3903303A (en) | 1975-09-02 |
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US172318A Expired - Lifetime US3903303A (en) | 1970-07-06 | 1971-08-16 | Controlling fungi and bacteria with certain oxime esters |
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Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4281011A (en) * | 1972-11-07 | 1981-07-28 | Bayer Aktiengesellschaft | Insecticidal N-methyl-N-(benzene sulfonic acid methylamide-N'-sulfenyl)-carbamic acid oxime esters |
| DE3310148A1 (en) * | 1982-03-31 | 1983-10-06 | Hoffmann La Roche | HETEROCYCLIC COMPOUNDS |
| US4879314A (en) * | 1986-01-08 | 1989-11-07 | Hsu Adam C | Dihaloformaldoxime |
| US4886832A (en) * | 1987-03-14 | 1989-12-12 | Bayer Aktiengesellschaft | Fungicidal benzaldoxime derivatives |
| US5134167A (en) * | 1989-07-19 | 1992-07-28 | Basf Aktiengesellschaft | 1-azabutadienes and fungicides containing these compounds |
| EP2118052A2 (en) * | 2007-03-15 | 2009-11-18 | Sun Pharma Advanced Research Company Ltd | Novel prodrugs |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3063823A (en) * | 1957-01-21 | 1962-11-13 | Bayer Ag | Method of killing weeds and influencing plant growth |
-
1971
- 1971-08-16 US US172318A patent/US3903303A/en not_active Expired - Lifetime
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3063823A (en) * | 1957-01-21 | 1962-11-13 | Bayer Ag | Method of killing weeds and influencing plant growth |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4281011A (en) * | 1972-11-07 | 1981-07-28 | Bayer Aktiengesellschaft | Insecticidal N-methyl-N-(benzene sulfonic acid methylamide-N'-sulfenyl)-carbamic acid oxime esters |
| DE3310148A1 (en) * | 1982-03-31 | 1983-10-06 | Hoffmann La Roche | HETEROCYCLIC COMPOUNDS |
| US4879314A (en) * | 1986-01-08 | 1989-11-07 | Hsu Adam C | Dihaloformaldoxime |
| US4886832A (en) * | 1987-03-14 | 1989-12-12 | Bayer Aktiengesellschaft | Fungicidal benzaldoxime derivatives |
| US5134167A (en) * | 1989-07-19 | 1992-07-28 | Basf Aktiengesellschaft | 1-azabutadienes and fungicides containing these compounds |
| EP2118052A2 (en) * | 2007-03-15 | 2009-11-18 | Sun Pharma Advanced Research Company Ltd | Novel prodrugs |
| EP2118052A4 (en) * | 2007-03-15 | 2010-04-14 | Sun Pharma Advanced Res Co Ltd | Novel prodrugs |
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Owner name: AKZO AMERICA INC., A CORP. OF DE, NEW YORK Free format text: ASSIGNMENT OF ASSIGNORS INTEREST.;ASSIGNOR:STAUFFER CHEMICAL COMPANY;REEL/FRAME:005080/0328 Effective date: 19890213 |