USRE28356E - Antibacterial and anttfungal treatment with sulfones - Google Patents
Antibacterial and anttfungal treatment with sulfones Download PDFInfo
- Publication number
- USRE28356E USRE28356E US12859671A USRE28356E US RE28356 E USRE28356 E US RE28356E US 12859671 A US12859671 A US 12859671A US RE28356 E USRE28356 E US RE28356E
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- fungi
- plants
- active agent
- bacteria
- methylsulfonyl
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- 230000000844 anti-bacterial effect Effects 0.000 title description 4
- 150000003457 sulfones Chemical class 0.000 title description 4
- 238000000034 method Methods 0.000 claims abstract description 31
- 241000894006 Bacteria Species 0.000 claims abstract description 27
- 150000001875 compounds Chemical class 0.000 claims abstract description 19
- 230000002401 inhibitory effect Effects 0.000 claims abstract description 18
- GRNXYJLLHZIBDR-UHFFFAOYSA-N 5-chloro-2-methylsulfonyl-1,3-benzothiazole Chemical compound ClC1=CC=C2SC(S(=O)(=O)C)=NC2=C1 GRNXYJLLHZIBDR-UHFFFAOYSA-N 0.000 claims abstract description 4
- 101100020619 Arabidopsis thaliana LATE gene Proteins 0.000 claims abstract description 3
- 239000013543 active substance Substances 0.000 description 28
- 241000233866 Fungi Species 0.000 description 25
- 241000196324 Embryophyta Species 0.000 description 23
- 239000003795 chemical substances by application Substances 0.000 description 14
- 235000011430 Malus pumila Nutrition 0.000 description 11
- 235000015103 Malus silvestris Nutrition 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 244000141359 Malus pumila Species 0.000 description 10
- 229920001817 Agar Polymers 0.000 description 6
- 206010039509 Scab Diseases 0.000 description 6
- 235000010419 agar Nutrition 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 239000004094 surface-active agent Substances 0.000 description 6
- 239000004563 wettable powder Substances 0.000 description 6
- 239000008272 agar Substances 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 239000000839 emulsion Substances 0.000 description 5
- 239000000725 suspension Substances 0.000 description 5
- 239000006185 dispersion Substances 0.000 description 4
- 230000000855 fungicidal effect Effects 0.000 description 4
- 238000011534 incubation Methods 0.000 description 4
- -1 perfluoro Chemical group 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- 241000222122 Candida albicans Species 0.000 description 3
- 241000221785 Erysiphales Species 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 241000233629 Phytophthora parasitica Species 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 229940095731 candida albicans Drugs 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 235000008504 concentrate Nutrition 0.000 description 3
- 238000010790 dilution Methods 0.000 description 3
- 239000012895 dilution Substances 0.000 description 3
- 239000012153 distilled water Substances 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 235000013399 edible fruits Nutrition 0.000 description 3
- 238000009472 formulation Methods 0.000 description 3
- 229910052736 halogen Inorganic materials 0.000 description 3
- 150000002367 halogens Chemical class 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 244000046052 Phaseolus vulgaris Species 0.000 description 2
- 238000002814 agar dilution Methods 0.000 description 2
- 229940121375 antifungal agent Drugs 0.000 description 2
- 239000007900 aqueous suspension Substances 0.000 description 2
- 229960000892 attapulgite Drugs 0.000 description 2
- 230000001580 bacterial effect Effects 0.000 description 2
- 239000004927 clay Substances 0.000 description 2
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 2
- 125000004663 dialkyl amino group Chemical group 0.000 description 2
- 201000010099 disease Diseases 0.000 description 2
- 208000037265 diseases, disorders, signs and symptoms Diseases 0.000 description 2
- 230000001408 fungistatic effect Effects 0.000 description 2
- 230000035784 germination Effects 0.000 description 2
- 208000015181 infectious disease Diseases 0.000 description 2
- 230000005764 inhibitory process Effects 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000006916 nutrient agar Substances 0.000 description 2
- 239000003960 organic solvent Substances 0.000 description 2
- 229910052625 palygorskite Inorganic materials 0.000 description 2
- 244000052769 pathogen Species 0.000 description 2
- 239000000344 soap Substances 0.000 description 2
- 239000002689 soil Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 230000000007 visual effect Effects 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- AVMBLBCBNFYRMX-UHFFFAOYSA-N 2-(1,3-benzothiazol-2-ylsulfonyl)-1,3-benzothiazole Chemical class C1=CC=C2SC(S(=O)(C=3SC4=CC=CC=C4N=3)=O)=NC2=C1 AVMBLBCBNFYRMX-UHFFFAOYSA-N 0.000 description 1
- CGAVIHVJYPJDGP-UHFFFAOYSA-N 2-methylsulfonyl-1,3-benzothiazol-6-amine Chemical group C1=C(N)C=C2SC(S(=O)(=O)C)=NC2=C1 CGAVIHVJYPJDGP-UHFFFAOYSA-N 0.000 description 1
- LPDAQVZLGAHTCQ-UHFFFAOYSA-N 2-methylsulfonyl-5-(trifluoromethyl)-1,3-benzothiazole Chemical compound FC(F)(F)C1=CC=C2SC(S(=O)(=O)C)=NC2=C1 LPDAQVZLGAHTCQ-UHFFFAOYSA-N 0.000 description 1
- XZXMLEUCJADXIG-UHFFFAOYSA-N 2-methylsulfonyl-6-nitro-1,3-benzothiazole Chemical compound C1=C([N+]([O-])=O)C=C2SC(S(=O)(=O)C)=NC2=C1 XZXMLEUCJADXIG-UHFFFAOYSA-N 0.000 description 1
- 241001480175 Angophora hispida Species 0.000 description 1
- 241000228245 Aspergillus niger Species 0.000 description 1
- 241000223678 Aureobasidium pullulans Species 0.000 description 1
- 241000219310 Beta vulgaris subsp. vulgaris Species 0.000 description 1
- 244000045232 Canavalia ensiformis Species 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 241000221955 Chaetomium Species 0.000 description 1
- 241001133184 Colletotrichum agaves Species 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 240000008067 Cucumis sativus Species 0.000 description 1
- 235000010799 Cucumis sativus var sativus Nutrition 0.000 description 1
- 241000588694 Erwinia amylovora Species 0.000 description 1
- 241000221787 Erysiphe Species 0.000 description 1
- 241000896222 Erysiphe polygoni Species 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- 241000221779 Fusarium sambucinum Species 0.000 description 1
- WQZGKKKJIJFFOK-GASJEMHNSA-N Glucose Natural products OC[C@H]1OC(O)[C@H](O)[C@@H](O)[C@@H]1O WQZGKKKJIJFFOK-GASJEMHNSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 229920001732 Lignosulfonate Polymers 0.000 description 1
- 235000007688 Lycopersicon esculentum Nutrition 0.000 description 1
- FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 1
- 241000588701 Pectobacterium carotovorum Species 0.000 description 1
- 235000010617 Phaseolus lunatus Nutrition 0.000 description 1
- 241000233614 Phytophthora Species 0.000 description 1
- 241001337928 Podosphaera leucotricha Species 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 241000221300 Puccinia Species 0.000 description 1
- 241000221535 Pucciniales Species 0.000 description 1
- 241000233639 Pythium Species 0.000 description 1
- 240000003768 Solanum lycopersicum Species 0.000 description 1
- 241000191967 Staphylococcus aureus Species 0.000 description 1
- 235000021536 Sugar beet Nutrition 0.000 description 1
- 244000299461 Theobroma cacao Species 0.000 description 1
- 235000009470 Theobroma cacao Nutrition 0.000 description 1
- 241001045770 Trichophyton mentagrophytes Species 0.000 description 1
- 241000209140 Triticum Species 0.000 description 1
- 241000221576 Uromyces Species 0.000 description 1
- 241000221577 Uromyces appendiculatus Species 0.000 description 1
- 241000228452 Venturia inaequalis Species 0.000 description 1
- 241000589634 Xanthomonas Species 0.000 description 1
- 241000985670 Xanthomonas arboricola pv. pruni Species 0.000 description 1
- 239000011149 active material Substances 0.000 description 1
- 238000007792 addition Methods 0.000 description 1
- 150000008431 aliphatic amides Chemical class 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 239000012871 anti-fungal composition Substances 0.000 description 1
- 230000000843 anti-fungal effect Effects 0.000 description 1
- 239000003429 antifungal agent Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- SVPXDRXYRYOSEX-UHFFFAOYSA-N bentoquatam Chemical compound O.O=[Si]=O.O=[Al]O[Al]=O SVPXDRXYRYOSEX-UHFFFAOYSA-N 0.000 description 1
- 230000002599 biostatic effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000003093 cationic surfactant Substances 0.000 description 1
- 244000038559 crop plants Species 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 239000008121 dextrose Substances 0.000 description 1
- 238000003113 dilution method Methods 0.000 description 1
- 239000004495 emulsifiable concentrate Substances 0.000 description 1
- 229910000286 fullers earth Inorganic materials 0.000 description 1
- 230000002538 fungal effect Effects 0.000 description 1
- 244000053095 fungal pathogen Species 0.000 description 1
- 239000000417 fungicide Substances 0.000 description 1
- 230000002070 germicidal effect Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 244000052637 human pathogen Species 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- 150000002431 hydrogen Chemical group 0.000 description 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000011081 inoculation Methods 0.000 description 1
- 239000002054 inoculum Substances 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 230000002147 killing effect Effects 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 230000017066 negative regulation of growth Effects 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 229960000988 nystatin Drugs 0.000 description 1
- VQOXZBDYSJBXMA-NQTDYLQESA-N nystatin A1 Chemical compound O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1/C=C/C=C/C=C/C=C/CC/C=C/C=C/[C@H](C)[C@@H](O)[C@@H](C)[C@H](C)OC(=O)C[C@H](O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 VQOXZBDYSJBXMA-NQTDYLQESA-N 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 230000001717 pathogenic effect Effects 0.000 description 1
- 238000003359 percent control normalization Methods 0.000 description 1
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920000233 poly(alkylene oxides) Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 235000014483 powder concentrate Nutrition 0.000 description 1
- 229920005552 sodium lignosulfonate Polymers 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 230000004763 spore germination Effects 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 230000003068 static effect Effects 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- JSPLKZUTYZBBKA-UHFFFAOYSA-N trioxidane Chemical class OOO JSPLKZUTYZBBKA-UHFFFAOYSA-N 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/68—Benzothiazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
- C07D277/70—Sulfur atoms
- C07D277/74—Sulfur atoms substituted by carbon atoms
-
- A—HUMAN NECESSITIES
- A01—AGRICULTURE; FORESTRY; ANIMAL HUSBANDRY; HUNTING; TRAPPING; FISHING
- A01N—PRESERVATION OF BODIES OF HUMANS OR ANIMALS OR PLANTS OR PARTS THEREOF; BIOCIDES, e.g. AS DISINFECTANTS, AS PESTICIDES OR AS HERBICIDES; PEST REPELLANTS OR ATTRACTANTS; PLANT GROWTH REGULATORS
- A01N43/00—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds
- A01N43/72—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms
- A01N43/74—Biocides, pest repellants or attractants, or plant growth regulators containing heterocyclic compounds having rings with nitrogen atoms and oxygen or sulfur atoms as ring hetero atoms five-membered rings with one nitrogen atom and either one oxygen atom or one sulfur atom in positions 1,3
- A01N43/78—1,3-Thiazoles; Hydrogenated 1,3-thiazoles
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D277/00—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings
- C07D277/60—Heterocyclic compounds containing 1,3-thiazole or hydrogenated 1,3-thiazole rings condensed with carbocyclic rings or ring systems
- C07D277/62—Benzothiazoles
- C07D277/68—Benzothiazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached in position 2
- C07D277/70—Sulfur atoms
- C07D277/76—Sulfur atoms attached to a second hetero atom
-
- C—CHEMISTRY; METALLURGY
- C22—METALLURGY; FERROUS OR NON-FERROUS ALLOYS; TREATMENT OF ALLOYS OR NON-FERROUS METALS
- C22C—ALLOYS
- C22C27/00—Alloys based on rhenium or a refractory metal not mentioned in groups C22C14/00 or C22C16/00
- C22C27/04—Alloys based on tungsten or molybdenum
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Dentistry (AREA)
- Plant Pathology (AREA)
- Health & Medical Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Materials Engineering (AREA)
- Mechanical Engineering (AREA)
- Metallurgy (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
Abstract
12. THE PROCESS FOR CONTROLLING LATE BLIGHT INFESTED PLANTS WHICH COMPRISES CONTACTING SAID PLANTS WITH AN EFFECTIVE PLANT BACTERIA AND FUNGI INHIBITING AMOUNT O (A COMPOUND DEFINED IN CLAIM 1.) 2-METHYLSULFONYL-5-CHLOROBENZOTHIAZOLE.
Description
United St:
28,356 ANTIBACTERIAL AND ANTIFUNGAL TREATMENT WITH SULFONES Ivan C. Popoif, Ambler, Bernard Buchholz, Blue Bell, and Harold J. Miller, Newtown Square, Pa., assignors to Pennwalt Corporation, Philadelphia, Pa.
No Drawing. Original No. 3,519,630, dated July 7, 1970,
Ser. No. 797,255, Feb. 6, 1969, which is a continuationln-part of application Ser. No. 636,026, May 4, 1967, which in turn is a continuation-impart of application Ser. No. 553,615, May 31, 1966, both now abandoned. Application for reissue Mar. 26, 1971, Ser. No. 128,596
Int. Cl. Allln 7/00, 9/22 US. Cl. 424-270 10 Claims Matter enclosed in heavy brackets II] appears in the original patent but forms no part of this reissue specification; matter printed in italics Indicates the additions made by reissue.
ABSTRACT OF THE DISCLOSURE Process of controlling bacteria and fungi with compounds of the structure:
where R is an alkyl group containing from 1 to 12 carbon atoms and R is hydrogen, [nitro,] amino, halogen, perfluoroalkyl, or monoand dialkylamino, R being located in the or 6 position.
[This application is a continuation-in-part of Ser. No. 636,026 filed May 4, 1967 which is a continuation-in-part of Ser. No. 553,615, filed May 31, 1966 both abandoned] This application is a reissue application of U .5. 3,519,- 630, July 7, I970, Ser. No. 797,255, filed Feb. 6, 1969, a continuation-in-part of application Ser. No. 636,026, filed May 4, I967, abandoned, which is a continuation-in-part of Ser. No. 553,615, filed May 31, 1966, abandoned.
This invention relates to anti-bacterial and antifungal compositions and to the process of using them, and is particularly concerned with the use as the active agent of an alkyl benzothiazolyl sult'one having the structure 5 N n' J- 1 son a S 1 where R is an alkyl group (including cycloalkyl) containing from 1 to-l2 carbon atoms and R is a member selected from the group consisting of hydrogen, [nitro,] amino, halogen, perfluoro lower alkyl, and monoand dialkylamino, (preferably, in the latter case, a group of the structure where R, and R, are alkyl groups containing from one to six carbon atoms) and with the proviso that the R substituent be located in the 5 or 6 position.
The above described benzothiazolyl sulfones are prepared from the corresponding Z-mercaptobenzothiazoles which are S-alkylated and oxidized to the sulfone (Wagner and look, Synthetic Organic Chemistry," John Wiley 8: Sons, Inc. 1953, pages 787 and 801). Alternatively, substituent groups may be introduced on the benzene ring after formation of the sulfone. The compounds are used in accordance with the usual procedures where bacterio- Re. 28,356 ued Nlar. 4, 1975 static, bactericidal, fungistatic, and fungicidal activity against plant and human pathogens is desired, but the invention will preferably be used for treating seeds, plants and fruits to prevent or control attack by fungi. One of the advantages of the compounds described above is that they may be used under controlling conditions without being toxic to the treated plants. The compounds will be useful in controlling numerous fungi affecting fruits, vegetables and crop plants, including powdery mildews, late blight, damping-off, organisms, apple scab and other fruit diseases, rusts, bacterial plant diseases, etc.
The procedure which will be used for applying the compositions of the invention to plants will be in accord with the usual practices known in the art. Since the active compounds have limited water solubility they will usually be applied to the plant as an aqueous dispersion, which is preferably obtained from a wettable powder. In a preferred embodiment of the invention a concentrate of the active agent together with a carrier and containing a surfactant will be manufactured and sold as an article of commerce. Preferably, this concentrate will be in the form of a wettable powder made simply by blending the active agent with a carrier such as clay or other finelydivided or particulate inert matter, e.g. attapulgite, bentonite, fullers earth, and the like. As a surfactant there may be used one or more of the many surface active agents generally employed such as polyalkylene oxide, a lignin sulfonate, or the various other cationic, anionic and nonionic surfactants available for such purposes. Generally, the wettable powder concentrate will contain from about 5 to about by Weight of the active agent, the balance being the carrier and the surfactant.
Alternatively, the active agents may be formulated in organic solvent systems as a solution or emulsion concentrate containing from 5 to about 90% by weight of active agent and the organic solvent system dispersed in water just prior to use. Generally, the organic material will be an organic hydrocarbon solvent such as xylene, toluene, etc., but other solvent systems such as ketones (methyl ethyl ketone, acetone, etc.) aliphatic amides such as dimethylformamide, dimethylacetamide, ketoalcohols (diacetone alcohol) and the like may also be used.
The rate of application of the fungicides onto the plant, flower, seed or other crops to be treated will vary from about 0.25 lb./ gallons to 10 lbs/100 gallons of active material. Preferably and for economic reasons, the rate of application will be from 0.25 lb. to 3 lbs. per acre or from 0.25 lb. to 2 pounds per gallon for tree applications. Application is made in the usual manner by spraying an aqueous dispersion of the agent onto the plant and treatment in this manner enables control of the pathogen to be obtained.
In order to more fully illustrate the invention the following examples are given:
EXAMPLE l.FORMULATION OF ACTIVE AGENT (a) Aqueous dispersion Ten parts by weight of 2-amylsulfonyl-6dimethylaminobenzothiazole and 90 parts by weight of water are air milled in the presence of an alkyl urea polyether alcohol surfactant until a stable dispersion is obtained.
(b) Wettable powder Ingredients: Percent by wt. 2-methylsulfonyl-G-aminobenzothiazole 50 Surfactants:
Sodium lignosulfonate (Marasperse") 2 Alkylphenoxypoly(ethyleneoxyethanol) (IgepaP' RC-760) Carrier:
Attapulgite 46 The following table indicates the compounds evaluated in the following examples and also indicates code numbers for the compounds:
Active agent:
EXAMPLE 2.ACTIVITY AGAINST POWDERY MILDEW Pinto bean plants in pots are sprayed with a wate' emulsion of the active agent to deposit the agent at various concentrations. Powdery mildew, (Erysiphe polygoni) cultures maintained on other plants are then used to inoculate the treated plants. Percent control is obtained by visual comparisons with a check test using none of the active agent.
The following table indicates the data and the results of the tests:
TABLE A Percent control of powdery Concenmildew tration, (Erysiphe p.p.m polygon i) Agent (Code No EXAMPLE 3.ACTIVITY AGAINST LATE BLIGHT Three to four week old Bonnie Best tomato seedlings are sprayed with a water emulsion of the active agent and inoculated (after drying) with a suspension of zoospores (produced from a sporangia from lima bean agar cultures of Phytophthora infestants). Counts are made of spots of late blight infection when they appear and control is expressed as percentage of check.
The following table indicates the data and results of the tests:
4 EXAMPLE 4.-SPORE GERMINATION ACTIVITY Spores from agar cultures and active agent are mixed together in a drop of water contained in wax rings on 1 x 3 inch glass slides. Rating indicates at what concentration germination occurs after 24 hours: 3+=none at l p.p.m., 3:1 to 10 ppm, 2:10 to 100 p.p.m., 1:100 to 1,000 ppm, 0: 1,000 ppm.
Results are shown in the following table:
TAB LE 0 Agent (Code Monllinla Alternarla Stemphyllum Glomerelln Nor) iructicola brasslcola sarinaeforme clngulata [EXAMPLE 5.SEEDLING DAMPING-OFF CONTROL Tests are conducted on soil infested with damping-off organisms. The amount of compound required as an emulsifiable concentrate to give the indicated rate per acre is mixed with clay and then mixed with seeds to be planted. The remainder of this mixture, which does not cling to the seed, is mixed with soil and used to cover the seeds. The following table indicates the test results:]
TABLE D Percent stand Active agent Code No. Rate Crop Treated Untreated Cotton.... 45 2 10 lbs./acre.. Cucumber. 55 Sugar beets 83 42 EXAMPLE 5 [6].--ACTIVITY AGAINST BEAN RUST Pinto bean plants were sprayed with the active agent similar to Example 2. After drying, the plants are sprayed with a water suspension of urediospores of Uromyces phascoli and immediately placed in a moist chamber and held at 15 to 20 C. for 24 hours. Results in five days are expressed as percent control by visual comparison with an untreated check.
TABLE E Concentration, Percent p.p.m. control Agent (Code No.):
EXAMPLE 6 [7].ACTIVITY AGAINST PLANT BACTERIA The active agent as a water emulsion is streaked across the surface of nutrient agar seeded with Xanthomonas pruni and inhibition of growth is recorded in 24 hours.
TAB LE F Concentration, Growth ppm inhibition [EXAMPLE 8.ACT[VITY AGAINST PLANT BACTERIA A drop of water emulsion of the agent is placed on a 6 mm. filter disc and allowed to dry. Treated discs are placed on the surface of nutrient agar seeded with Xanthomonas prum' and Erwima amylovora. The diameter of the inhibition zone (minus the disc) is measured in 24 hours.
The following table indicates data and results of these tests:]
TABLE G X. prunt E. amylovora P'D- p.p.m.
2 3 3 3 a i 3 i In addition to the above exemplified compounds the following compounds show similar fungicidal and bacterial activity:
Sol-Ch S N NH SJ-S Oz-CaH NO N LS 01-CzHt S N Cl 5L8 03-0 11 CF N J- S 07-CsH1 S J 'S Og-CJIn 8 EXAMPLE 7 [9] Following the test procedures described above, the compound of structure:
Clin s".
is evaluated and the following data obtained:
Spore germination activity EXAMPLE 8 [10] Tests are made against ten organisms by inoculating agar media containing the test compounds at various concentrations with 7 mm. diameter plugs taken from 10 day old cultures. The data obtained after 48 hours incubation is shown in the following Table H:
TABLE H.-GROWTI-f AFTER 48 HOURS OF TEN ORGANISMS ON MEDIA CONTAINING VARIOUS CONCENTRATIONS OF TEST AGENTS Agent tested:
C ib
r n R on; N02
Organism p.p.m. p.p.m.
Rhlzopus sto1onifer. Aphanornyces euteichee. Botrytls cinerea Penicllllum expansum.--.. Fusarlum oxysporuxn f. cucumelnum.
Fusarlum roseum Pythium ultimo. Monllinia l'ructicola. Alternarla brassleola Glomerella cingulata.. Legend cocoa: coo
cccomc mac:
| col o a'i o Nora:
0= No growth. -Growth on inoculum plug only. Growth.
EXAMPLE 9 [11] (A) Agar dilution method One-half of the area in the Petri dish is covered with agar which contains the germicide at a selected concentration, whereas the other half is covered with an untreated agar. Both the treated and untreated agars are then seeded with bacteria by streaking across the plate. After 48 hours of incubation the plates are examined for any exhibited inhibitory properties of the biostatic agent against the test bacteria. The test data with agent Code No. 2 follows:
Legend Note: 0=No growth; =t==Trace growth; 1 to 4 lndlcatesincreasing amounts of growth.
(B) Minimal inhibitory concentration Using the tube dilution method against Candida albicans, three-fold dilutions are used from 33 to 0.033 mcg./ ml. to determine the minimal inhibitory concentration of active agent code No. 2. Tubes were read after 24 and 72 hours incubation. At 1.0 meg/ml. no growth was observed at 24 hours, but growth began in 72 hours. This activity is comparable to that of Nystatin, a commercial antifungal agent. Upon subculturing the maximal concentration it was found that the minimal inhibitory concentration was 3.3 meg/ml. and was cidal in nature.
Likewise, 2 methylsulfonyl 5 trifluoromethylbenzothiazole was active against Staphylococcus aureus ppm), Candida albicans (I00 p.p.m.). Erwinia carotovora (5 p.p.m.). Fusarium roseum (5 p.p.m.), Trichophyton mentagrophytes p.p.m.). Pullularia pullulans (100 p.p.m.), Aspergillus niger (100 ppm.) and Chaetomium globossum (5 p.p.m.).
EXAMPLE I0 [12] Sixto one-year old actively growing apple seedlings are sprayed on both top and bottom leaf surfaces at the appropriate concentrations of active agents in a 25% wettable powder formulation. The plants are allowed to dry for four hours and placed in a moist chamber for 12 hours to simulate weathering. Spores of apple scab (Venturia inaequalis) are atomized from an aqueous suspension onto the tops and bottom of the apple tree leaves and held in the moist chamber at 20 C. for 36 to 48 hours. Counts are made on three leaves per plant with scab and control expressed as percent of check.
[When dwarf apple trees are sprayed with a wettable powder formulation containing 1.5 pounds of active agent per 100 gallons of liquid, very effective control of apple scab is obtained with agents code No. 2 and 8.]
EXAMPLE II [13].CONTROL OF APPLE MILDEW The agent of Code No. 10 formulated in xylene is diluted with distilled water to the desired concentration and apple seedlings are sprayed until run-0E. After drying, the plants are dusted with spores of Podosphaera leucotricha grown on infected plants. After ten days, average percent control is reported. At 1000 ppm, 100% control is obtained, and at 200 p.p.m., the control is 92.5%.
EXAMPLE 12 [14].CONTROL OF WHEAT RUST The formulated agent is diluted with distilled water to obtain the desired concentrations and six-day old potted Seneca wheat plants are sprayed with an atomizer to apply the test agent. Ten ml. of diluted compound is used to treat each pot.
Urcdiospores of Puccinia rocondita are washed from previously infected leaves with distilled water containing 125 ppm. Ivory soap. This spore suspension is placed in a small vial and the capped vial is placed on a ball mill. After one hour the liquid is removed from the Washed spores and now soap water is added to obtain a spore suspension containing 100,000 spores per ml.
After the treated plants have dried, about 50 ml. of the spore suspension is used to spray inoculate every ten pots. Immediately after inoculation the plants are placed in a high humidity chamber and kept at room temperature for another six days when infection readings are made.
Test results follow:
Concentratlon, Percent ppm. control [EXAMPLE l5.-AOAC FUNGICIDAL TEST Five ml. portions of each fungicidal concentration are inoculated with 0.5 ml. spore suspension of the test culture. From this mixture samples are transferred after 5, 10, and minute intervals into dextrose broth subculture tubes. After 10 days incubation the tubes are examined for the presence or absence of fungal growth. The highest dilution that kills spores within 10 minutes is commonly considered as the highest dilution that could be expected to disinfect an inanimate surface contaminated with pathogenic fungi. The data obtained with Z-methylsulfonyl--nitrobenzothiazole follow:
FUNGISTATIC ACTIVITY.AGAR DILUTION METHOD WITH Z-METHYLSULFONYL-fi-NITROBENZOTHIAZOLE Legend: 0=No growth; :l==trace growth; 1 to 4 indicates increasing amounts of growth. 1
We claim:
[1. The process of controlling bacteria and fungi which comprises contacting said pathogens with an effective plant bacteria and fungi inhibiting amount of a compound having the structure:
LSOzR S where R is allcyl containing from one to twelve carbon atoms and R is selected from the group consisting of hydrogen, nitro, halogen, pertluoro lower alkyl, amino and alkylamino containing from 1 to 6 carbon atoms] [2. The process of claim 1 where the active agent is Z-methylsulfonylbenzothiazole.]
[3. The process of claim 1 where the active agent is 2-methylsulfony1-6-nitrobenzothiazole] [4. The process of claim 1 where the active agent is 2-butylsulfonylbenzothiazole] [5. The process of claim 1 where the active agent is 2- amylsulfonylbenzothiazole] [6. The process of claim 1 where the active agent is 2- heptylsulfonylbenzothiazole] [7. The process of claim 1 where the active agent is Z-butylsulfonyl-6-nitrobenzothiazole] [8. The process of claim 1 where the active agent is 2- methylsulfonyl-6-aminobenzothiazole.]
[9. The process of claim 1 where the active agent is Z-methylsulfonyl-6-chlorobenzothiazo1e.]
[10. The process of claim 1 where the active agent is Z-methylsulfonyl-S-chlorobenzothiazole] [11. The process of claim 1 where the active agent is 2-methylsulfonyl-S-trifiuoromethylbenzothiazole.]
12. The process for controlling late blight infested plants which comprises contacting said plants with an effective plant bacteria and fungi inhibiting amount of [a compound defined in claim 1.] 2-methylsulfonyl-5-chlorobenzothiazole.
13. A process for controlling apple scab infested apple trees which comprises contacting apple trees with an effective apple scab inhibiting amount of [a compound defined in claim 1.] Z-merhylsulfonyl-5-chlorobenzothiazole.
[14. A process for controlling fungi which comprises contacting fungi with 2-methylsulfonyl-6-nitrobenzothiazole.]
[15. The process of claim 14 where the fungi is Candida albicans] 16. The process of controlling bacteria and fungi which comprises contacting said bacteria or fungi with an effective inhibiting amount of 2-methylsulfonylbenzozhiazole.
17. The process of controlling bacteria and fungi which comprises contacting said bacteria or fungi with an efiective inhibiting amount of 2-burylsulfonylbenzothiazole.
18. The process of controlling bacteria and fungi which comprises contacting said bacteria or fungi with an e fective inhibiting amount of 2-arnylsulfonylbenzothiazole.
19. The process of controlling bacteria and fungi which comprises contacting said bacteria or fungi with an efiecrive inhibiting amount of Z-heptylsulfonylbenzorhiazole.
20. The process of controlling bacteria and fungi which comprises contacting said bacteria or fungi with an efiecrive inhibiting amount of 2-methylsulfonyl-6-aminobenzorhiazale.
21. The process of controlling bacteria and fungi which comprises contacting said bacteria or fungi with an efiecrive inhibiting amount of 2-merhylsulfonyl-6-chlorobenzothiazole.
22. The process of controlling bacteria and fungi which comprises contacting said bacteria or fungi with an effective inhibiting amount of Z-methylsulfonyl-S-chlorobenzo- :hiazole.
23. The process of controlling bacteria and fungi which comprises contacting said bacteria or fungi with an efleclive inhibiting amount of Z-methylsulfonyl-S-rrifluoromelhylbenzothiazole.
9/1950 Russell 260-306 7/1957 Larive et a1. 260-304 STANLEY J. FRIEDMAN, Primary Examiner
Claims (1)
12. THE PROCESS FOR CONTROLLING LATE BLIGHT INFESTED PLANTS WHICH COMPRISES CONTACTING SAID PLANTS WITH AN EFFECTIVE PLANT BACTERIA AND FUNGI INHIBITING AMOUNT O (A COMPOUND DEFINED IN CLAIM 1.) 2-METHYLSULFONYL-5-CHLOROBENZOTHIAZOLE. PLANTS WHICH COMPRISES CONTACTING SAID PLANTS WITH AN EFFECTIVE PLANT BACTERIA AND FUNGI INHIBITING AMOUNT OF (A COMPOUND DEFINED IN CLAIM 1.) 2-METHYLSULFONYL-5-CHLOROBENZOTHIAZOLE.
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US12859671 USRE28356E (en) | 1966-05-31 | 1971-03-26 | Antibacterial and anttfungal treatment with sulfones |
Applications Claiming Priority (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US55361566A | 1966-05-31 | 1966-05-31 | |
US63602667A | 1967-05-04 | 1967-05-04 | |
US79725569A | 1969-02-06 | 1969-02-06 | |
US12859671 USRE28356E (en) | 1966-05-31 | 1971-03-26 | Antibacterial and anttfungal treatment with sulfones |
Publications (1)
Publication Number | Publication Date |
---|---|
USRE28356E true USRE28356E (en) | 1975-03-04 |
Family
ID=27494742
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US12859671 Expired USRE28356E (en) | 1966-05-31 | 1971-03-26 | Antibacterial and anttfungal treatment with sulfones |
Country Status (1)
Country | Link |
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US (1) | USRE28356E (en) |
Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2509454A (en) * | 1947-09-05 | 1950-05-30 | Vanderbilt Co R T | Salts of benzothiazyl sulfinic acids |
US2798066A (en) * | 1956-01-27 | 1957-07-02 | Eastman Kodak Co | Method for preparing cyanine bases |
-
1971
- 1971-03-26 US US12859671 patent/USRE28356E/en not_active Expired
Patent Citations (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2509454A (en) * | 1947-09-05 | 1950-05-30 | Vanderbilt Co R T | Salts of benzothiazyl sulfinic acids |
US2798066A (en) * | 1956-01-27 | 1957-07-02 | Eastman Kodak Co | Method for preparing cyanine bases |
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