US3883343A - Method of tobacco sucker inhibition - Google Patents
Method of tobacco sucker inhibition Download PDFInfo
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- US3883343A US3883343A US340534A US34053473A US3883343A US 3883343 A US3883343 A US 3883343A US 340534 A US340534 A US 340534A US 34053473 A US34053473 A US 34053473A US 3883343 A US3883343 A US 3883343A
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- United States
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- compound
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- tobacco
- propylthiolcarbamate
- inhibition
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- 235000002637 Nicotiana tabacum Nutrition 0.000 title claims abstract description 50
- 241000208125 Nicotiana Species 0.000 title claims description 28
- 238000000034 method Methods 0.000 title claims description 18
- 230000005764 inhibitory process Effects 0.000 title abstract description 22
- 244000061176 Nicotiana tabacum Species 0.000 claims abstract description 23
- 241000252254 Catostomidae Species 0.000 claims abstract description 18
- GZZHLJMVBXKNPP-UHFFFAOYSA-N benzyl n-thiophen-2-ylcarbamate Chemical compound C=1C=CC=CC=1COC(=O)NC1=CC=CS1 GZZHLJMVBXKNPP-UHFFFAOYSA-N 0.000 claims abstract description 15
- 230000002401 inhibitory effect Effects 0.000 claims description 5
- 125000006179 2-methyl benzyl group Chemical group [H]C1=C([H])C(=C(C([H])=C1[H])C([H])([H])*)C([H])([H])[H] 0.000 claims description 2
- 125000006283 4-chlorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1Cl)C([H])([H])* 0.000 claims description 2
- 125000004176 4-fluorobenzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1F)C([H])([H])* 0.000 claims description 2
- 125000006282 2-chlorobenzyl group Chemical group [H]C1=C([H])C(Cl)=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 125000004847 2-fluorobenzyl group Chemical group [H]C1=C([H])C(F)=C(C([H])=C1[H])C([H])([H])* 0.000 claims 1
- 125000006180 3-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C(=C1[H])C([H])([H])[H])C([H])([H])* 0.000 claims 1
- 125000006181 4-methyl benzyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1C([H])([H])[H])C([H])([H])* 0.000 claims 1
- -1 nitro, acetyl Chemical group 0.000 abstract description 18
- 125000003545 alkoxy group Chemical group 0.000 abstract description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 abstract description 4
- 229910052736 halogen Inorganic materials 0.000 abstract description 2
- 150000002367 halogens Chemical class 0.000 abstract description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 abstract description 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 abstract 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 abstract 1
- 125000000218 acetic acid group Chemical group C(C)(=O)* 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 description 38
- 239000004480 active ingredient Substances 0.000 description 26
- 239000000203 mixture Substances 0.000 description 19
- 238000012360 testing method Methods 0.000 description 18
- 241000196324 Embryophyta Species 0.000 description 17
- 239000004615 ingredient Substances 0.000 description 10
- 229940125898 compound 5 Drugs 0.000 description 9
- 125000000217 alkyl group Chemical group 0.000 description 8
- 229940125782 compound 2 Drugs 0.000 description 8
- 229940126214 compound 3 Drugs 0.000 description 8
- 229940125904 compound 1 Drugs 0.000 description 7
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 6
- 208000018380 Chemical injury Diseases 0.000 description 5
- 239000005983 Maleic hydrazide Substances 0.000 description 5
- BGRDGMRNKXEXQD-UHFFFAOYSA-N Maleic hydrazide Chemical compound OC1=CC=C(O)N=N1 BGRDGMRNKXEXQD-UHFFFAOYSA-N 0.000 description 5
- 208000027418 Wounds and injury Diseases 0.000 description 4
- 125000002777 acetyl group Chemical group [H]C([H])([H])C(*)=O 0.000 description 4
- 230000006378 damage Effects 0.000 description 4
- 239000006185 dispersion Substances 0.000 description 4
- 208000014674 injury Diseases 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- WOSRKHLRTBXIGQ-UHFFFAOYSA-N (3,4-dipropylthiophen-2-yl)carbamic acid Chemical compound C(CC)C=1C(=C(SC1)NC(=O)O)CCC WOSRKHLRTBXIGQ-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- KXDHJXZQYSOELW-UHFFFAOYSA-M Carbamate Chemical compound NC([O-])=O KXDHJXZQYSOELW-UHFFFAOYSA-M 0.000 description 3
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 3
- 239000003112 inhibitor Substances 0.000 description 3
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 239000000839 emulsion Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical compound CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 2
- 125000000040 m-tolyl group Chemical group [H]C1=C([H])C(*)=C([H])C(=C1[H])C([H])([H])[H] 0.000 description 2
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000002914 sec-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- MHCJEFFTQFYTLV-UHFFFAOYSA-N (3,4-dimethylthiophen-2-yl)carbamic acid Chemical compound CC=1C(=C(SC=1)NC(=O)O)C MHCJEFFTQFYTLV-UHFFFAOYSA-N 0.000 description 1
- 125000004179 3-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C(Cl)=C1[H] 0.000 description 1
- 239000005995 Aluminium silicate Substances 0.000 description 1
- SPNQRCTZKIBOAX-UHFFFAOYSA-N Butralin Chemical compound CCC(C)NC1=C([N+]([O-])=O)C=C(C(C)(C)C)C=C1[N+]([O-])=O SPNQRCTZKIBOAX-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- 241000982822 Ficus obtusifolia Species 0.000 description 1
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 1
- UMKANAFDOQQUKE-UHFFFAOYSA-N Nitralin Chemical compound CCCN(CCC)C1=C([N+]([O-])=O)C=C(S(C)(=O)=O)C=C1[N+]([O-])=O UMKANAFDOQQUKE-UHFFFAOYSA-N 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 229920002472 Starch Polymers 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001340 alkali metals Chemical class 0.000 description 1
- 125000005210 alkyl ammonium group Chemical group 0.000 description 1
- 150000005215 alkyl ethers Chemical class 0.000 description 1
- 235000012211 aluminium silicate Nutrition 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-O ammonium group Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 1
- 239000000440 bentonite Substances 0.000 description 1
- 229910000278 bentonite Inorganic materials 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
- UENWRTRMUIOCKN-UHFFFAOYSA-N benzyl thiol Chemical compound SCC1=CC=CC=C1 UENWRTRMUIOCKN-UHFFFAOYSA-N 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 125000004803 chlorobenzyl group Chemical group 0.000 description 1
- CWJSHJJYOPWUGX-UHFFFAOYSA-N chlorpropham Chemical compound CC(C)OC(=O)NC1=CC=CC(Cl)=C1 CWJSHJJYOPWUGX-UHFFFAOYSA-N 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 238000012258 culturing Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical class OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- RRMXNBZSHDZAJJ-UHFFFAOYSA-N ethyl n-thiophen-2-ylcarbamate Chemical compound CCOC(=O)NC1=CC=CS1 RRMXNBZSHDZAJJ-UHFFFAOYSA-N 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 238000009472 formulation Methods 0.000 description 1
- 125000005843 halogen group Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 150000002431 hydrogen Chemical class 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 125000003253 isopropoxy group Chemical group [H]C([H])([H])C([H])(O*)C([H])([H])[H] 0.000 description 1
- NLYAJNPCOHFWQQ-UHFFFAOYSA-N kaolin Chemical compound O.O.O=[Al]O[Si](=O)O[Si](=O)O[Al]=O NLYAJNPCOHFWQQ-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 125000006178 methyl benzyl group Chemical group 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- BSCCSDNZEIHXOK-UHFFFAOYSA-N phenyl carbamate Chemical compound NC(=O)OC1=CC=CC=C1 BSCCSDNZEIHXOK-UHFFFAOYSA-N 0.000 description 1
- 229920000259 polyoxyethylene lauryl ether Polymers 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 235000019422 polyvinyl alcohol Nutrition 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 235000019698 starch Nutrition 0.000 description 1
- 239000008107 starch Substances 0.000 description 1
- BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
Classifications
-
- 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
- A01N47/00—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid
- A01N47/08—Biocides, pest repellants or attractants, or plant growth regulators containing organic compounds containing a carbon atom not being member of a ring and having no bond to a carbon or hydrogen atom, e.g. derivatives of carbonic acid the carbon atom having one or more single bonds to nitrogen atoms
- A01N47/10—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof
- A01N47/12—Carbamic acid derivatives, i.e. containing the group —O—CO—N<; Thio analogues thereof containing a —O—CO—N< group, or a thio analogue thereof, neither directly attached to a ring nor the nitrogen atom being a member of a heterocyclic ring
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C333/00—Derivatives of thiocarbamic acids, i.e. compounds containing any of the groups, the nitrogen atom not being part of nitro or nitroso groups
- C07C333/02—Monothiocarbamic acids; Derivatives thereof
Definitions
- R and R are selected from the group consisting of acetyl, cyclohexyl, and C alkyl group;
- X and Y are selected from the group consisting of nitro, acetyl, amino, C, alkyl, C alkoxyl, and halogen;
- This invention relates to a method for inhibiting the growth of tobacco suckers. More particularly, it relates to a method for chemically treating tobacco plants to inhibit the growth of tobacco sucker.
- phenylcarbamate isopropyl N-(3-chlorophenyl) carbamate, isopropyl N-(3-methylphenyl) carbamate, and sec-butyl N-(3-methylphenyl) carbamate; or (b) a 2,6-dinitro-4-substituted aniline derivative such as N- sec-butyl-4-tert-butyl-2,6-dinitroaniline, N,N-di-npropyl-4-trifluoromethyl-2,6-dinitroaniline and N,N- di-n-propyl-4-methylsulfonyl-2,6-dinitroaniline to the tobacco plants.
- a 2,6-dinitro-4-substituted aniline derivative such as N- sec-butyl-4-tert-butyl-2,6-dinitroaniline, N,N-di-npropyl-4-trifluoromethyl-2,6-dinitroaniline and N
- suitable R R R and R groups include C alkyl groups such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, secbutyl, tert-butyl, pentyl and hexyl
- suitable X and Y groups include C alkyl groups such as methyl, ethyl, n-propyl and isopropyl groups and C alkoxyl groups such as methoxy, ethoxy, n-propoxy and iso-propoxy groups.
- the benzylthiolcarbamate or a composition thereof is applied in the form of a solution, an emulsion or a dispersion to tobacco plants in the top-- ping stage of growth. It is especially preferable to apply the composition to the stems and leaves near the suckers of the topped tobacco plants or the plants on which the flower buds have newly formed.
- the benzylthiolcarbamates can be prepared by reactl. a benzylmercaptan having the formula ECH SH (Yl with a carbamoylhalide having the formula 0 ll A 1 CNR R wherein RI Z 1 CHSCN 2 8 2 (X) H128 (Y) with an amine having the formula HNR R CH2SCA1 wherein X, Y, m, n, R R and A are defined as above in the presence of an alkali; or 3.
- ECH SH Yl with a carbamoylhalide having the formula 0 ll A 1 CNR R wherein RI Z 1 CHSCN 2 8 2 (X) H128 (Y) with an amine having the formula HNR R CH2SCA1 wherein X, Y, m, n, R R and A are defined as above in the presence of an alkali; or 3.
- concentrations of the active ingredients and the amount of active ingredient used for each tobacco plant are dependent upon the varieties of tobacco, growth conditions and methods of application of the composition.
- concentrations of the active ingredient in the composition range from 100-10,000 ppm, preferably 1,000- ,000 ppm.
- the concentration of each compound in the composition is in the range of 50 4,000 ppm, preferably 500 3,000
- the amounts of the aqueous composition applied to each tobacco plant is in the range of l 100 ml, preferably 100 ml, especially, 50 ml.
- the ratio of the active ingredient to the auxiliary active ingredient is not limited, and it is preferably in the range of 0.05 16, especially 0.1 6 parts by weight of alkyl-N- phenylcarbamate or a 2,6-dinitro-4-substituted aniline derivative per 1 part by weight of N,N-dialkylbenzylthiolcarbamate.
- compositions of this invention can be prepared by dispersing said active ingredient in water, or by admixing the active ingredient with an inert solid carrier such as talc, kaolin, bentonite, Zeeklite, starch or the like, or with an inert liquid carrier such as an alcohol, acetone, xylene, benzene, solvent naphtha, isophorone or the like.
- an inert solid carrier such as talc, kaolin, bentonite, Zeeklite, starch or the like
- an inert liquid carrier such as an alcohol, acetone, xylene, benzene, solvent naphtha, isophorone or the like.
- the compositions can contain a surfactant such as sodium alkylbenzenesulfonate, sodium higher alcohol sulfonate, polyoxyethylene alkylacryl ether, polyoxyethyleneglycol alkyl ether, calcium ligninesulfonate, polyvinylalcohol or the like in order
- the suckers of the plants begin to sprout.
- the growth of the suckers is promoted by a topping treatment.
- the sucker inhibitors are applied to the plants with the topping treatment.
- the sucker inhibitors can also be effectively applied to the plants during the growth of the suckers. If the active ingredient in the compositions of this invention is applied to the stems and leaves of the tobacco plants near the suckers, sprouting and growth of the suckers can be inhibited without chemical injury to the useful tobacco leaves. Thus, the application of the compositions is remarkably effective for the culture of tobacco.
- EXAMPLE 1 In a pot having a diameter of 15 cm, tobacco (var: Bright yellow) was cultured. When the tobacco had grown to a height of about 40 cm and had grown 7 8 nodes, the tobacco was topped. An aqueous dispersion containing 1000 ppm of an active ingredient was sprayed on the stems and leaves of the tobacco plants in quantities of 20 ml per plant. After 20 days from the date of application of the spray, the suckers were removed from the plants and collected. The weight of the fresh suckers was measured, and the extent of chemical injury to the leaves was observed. The percent sucker inhibition was calculated by the following equation.
- Active ingredient N,N-dialky1benzylthiolcarbamate a. 20 parts by weight N,N-dialkylbenzylthiolcarbamate b. 70 parts by weight xylene, and
- Auxiliary active ingredient an alkyl-N- phenylcarbamate or a 4-substituted aniline derivative.
- auxiliary active ingredient An emulsion of the auxiliary active ingredient was prepared in accordance with the method shown above except that N,N-dialkylbenzylthiolcarbamate was replaced with an alkyl-N-phenylcarbamate or a 2,6-dinitro-4-substituted aniline derivative.
- benzylthiol- 0 carbamate is N,N-dialkylbenzylthiolcarbamate having the formula CHZSCN wherein R and R represent C alkyl groups and Z is selected from the group consisting of hydrogen, methyl, chlorine, and fluorine. 5.
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- Life Sciences & Earth Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical & Material Sciences (AREA)
- Dentistry (AREA)
- Health & Medical Sciences (AREA)
- Engineering & Computer Science (AREA)
- Plant Pathology (AREA)
- General Health & Medical Sciences (AREA)
- Wood Science & Technology (AREA)
- Zoology (AREA)
- Environmental Sciences (AREA)
- Pest Control & Pesticides (AREA)
- Agronomy & Crop Science (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
The inhibition of the growth of tobacco plant suckers by the application to the tobacco plant of benzylthiolcarbamate having the formula,
WHEREIN R1 and R2 are selected from the group consisting of acetyl, cyclohexyl, and C1-6 alkyl group; X and Y are selected from the group consisting of nitro, acetyl, amino, C1-3 alkyl, C1-3 alkoxyl, and halogen; and M AND N ARE 0 OR 1.
WHEREIN R1 and R2 are selected from the group consisting of acetyl, cyclohexyl, and C1-6 alkyl group; X and Y are selected from the group consisting of nitro, acetyl, amino, C1-3 alkyl, C1-3 alkoxyl, and halogen; and M AND N ARE 0 OR 1.
Description
United States Patent [191 Fujikawa et al.
[ 51 May 13,1975
[ METHOD OF TOBACCO SUCKER INHIBITION [75] Inventors: Kanichi Fujikawa; Ryohei Takahashi; Isao Yokomichi; Fumio Kimura; Takeo Kaji; Nobuyuki Sakashita, all of Kusatsu, Japan [73] Assignee: Ishihara Sangyo Kaisha Ltd., Japan [22] Filed: Mar. 12, 1973 [21] Appl. No.: 340,534
[30] Foreign Application Priority Data OTHER PUBLICATIONS lchiro et al., Chem. Abst., Vol. 76, (1972), 136878w. Klingman, Chem. Abst., Vol. 58, (1963), 28021 Primary Exanziner-Lewis Gotts Assistant ExaminerCatherine L. Mills Attorney, Agent, or Firm-Oblon, Fisher, Spivak, McClelland & Maier [57] ABSTRACT The inhibition of the growth of tobacco plant suckers by the application to the tobacco plant of benzylthiolcarbamate having the formula,
0 m 3- CH SCN (Y)n/ e? wherein R and R are selected from the group consisting of acetyl, cyclohexyl, and C alkyl group;
X and Y are selected from the group consisting of nitro, acetyl, amino, C, alkyl, C alkoxyl, and halogen; and
m and n are Oor 1.
5 Claims, No Drawings 1 METHOD OF TOBACCO SUCKER INHIBITION BACKGROUND OF THE INVENTION 1. Field of the Invention This invention relates to a method for inhibiting the growth of tobacco suckers. More particularly, it relates to a method for chemically treating tobacco plants to inhibit the growth of tobacco sucker.
2. Description of the Prior Art In the culturing of tobacco, sucker development causes a decrease in the effective yield of tobacco leaves and in the quality of the leaves. Thus, removal of the suckers from the plants is an indispensable operation. In the past, removal of the suckers by hand has been a laborious and time-consuming process. A need, therefore, exists for an effective means of chemically treating tobacco plants to inhibit the growth of tobacco suckers.
SUMMARY OF THE INVENTION wherein R and R and C alkyl groups, the acetyl group or the cyclohexyl group; X and Y are C alkyl groups, C alkoxy groups, the nitro group, the acetyl group, the amino group or a halogen atom; and m and n are or 1, to tobacco plants.
DETAILED DESCRIPTION OF THE PREFERRED EMBODIMENTS I It is preferable in the method of this invention to apply a tobacco sucker inhibitory amount of N,N- dialkylbenzylthiolcarbamate having the formula,
phenylcarbamate, isopropyl N-(3-chlorophenyl) carbamate, isopropyl N-(3-methylphenyl) carbamate, and sec-butyl N-(3-methylphenyl) carbamate; or (b) a 2,6-dinitro-4-substituted aniline derivative such as N- sec-butyl-4-tert-butyl-2,6-dinitroaniline, N,N-di-npropyl-4-trifluoromethyl-2,6-dinitroaniline and N,N- di-n-propyl-4-methylsulfonyl-2,6-dinitroaniline to the tobacco plants.
In the benzylthiolcarbamates (l) and N,N- dialkylbenzylthiolcarbamates (2), suitable R R R and R groups include C alkyl groups such as methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, secbutyl, tert-butyl, pentyl and hexyl, and suitable X and Y groups include C alkyl groups such as methyl, ethyl, n-propyl and isopropyl groups and C alkoxyl groups such as methoxy, ethoxy, n-propoxy and iso-propoxy groups.
Generally, the benzylthiolcarbamate or a composition thereof is applied in the form of a solution, an emulsion or a dispersion to tobacco plants in the top-- ping stage of growth. It is especially preferable to apply the composition to the stems and leaves near the suckers of the topped tobacco plants or the plants on which the flower buds have newly formed.
The benzylthiolcarbamates can be prepared by reactl. a benzylmercaptan having the formula ECH SH (Yl with a carbamoylhalide having the formula 0 ll A 1 CNR R wherein RI Z 1 CHSCN 2 8 2 (X) H128 (Y) with an amine having the formula HNR R CH2SCA1 wherein X, Y, m, n, R R and A are defined as above in the presence of an alkali; or 3. a benzylhalide having the formula CII A mm 2 1 with a thiolcarbamate having the formula wherein X, Y, m, n, R R and A are defined as above and A represents an alkali metal, the ammonium group or a lower alkyl ammonium group.
The concentrations of the active ingredients and the amount of active ingredient used for each tobacco plant are dependent upon the varieties of tobacco, growth conditions and methods of application of the composition. When a benzylthiolcarbamate is applied to the plants without an auxiliary active ingredient, the concentrations of the active ingredient in the composition range from 100-10,000 ppm, preferably 1,000- ,000 ppm.
When N,N-dialkylbenzylthiolcarbamate is applied to the tobacco plants with an alkyl N-phenylcarbamate or a 2,6-dinitro-4-substituted aniline derivative, the concentration of each compound in the composition is in the range of 50 4,000 ppm, preferably 500 3,000
The amounts of the aqueous composition applied to each tobacco plant is in the range of l 100 ml, preferably 100 ml, especially, 50 ml. The ratio of the active ingredient to the auxiliary active ingredient is not limited, and it is preferably in the range of 0.05 16, especially 0.1 6 parts by weight of alkyl-N- phenylcarbamate or a 2,6-dinitro-4-substituted aniline derivative per 1 part by weight of N,N-dialkylbenzylthiolcarbamate.
The compositions of this invention can be prepared by dispersing said active ingredient in water, or by admixing the active ingredient with an inert solid carrier such as talc, kaolin, bentonite, Zeeklite, starch or the like, or with an inert liquid carrier such as an alcohol, acetone, xylene, benzene, solvent naphtha, isophorone or the like. In addition, the compositions can contain a surfactant such as sodium alkylbenzenesulfonate, sodium higher alcohol sulfonate, polyoxyethylene alkylacryl ether, polyoxyethyleneglycol alkyl ether, calcium ligninesulfonate, polyvinylalcohol or the like in order to disperse the mixture in water.
When the tobacco plants are fully grown, the suckers of the plants begin to sprout. The growth of the suckers is promoted by a topping treatment. Usually, the sucker inhibitors are applied to the plants with the topping treatment. However, the sucker inhibitors can also be effectively applied to the plants during the growth of the suckers. If the active ingredient in the compositions of this invention is applied to the stems and leaves of the tobacco plants near the suckers, sprouting and growth of the suckers can be inhibited without chemical injury to the useful tobacco leaves. Thus, the application of the compositions is remarkably effective for the culture of tobacco.
Having generally described this invention, a further understanding can be obtained by reference to certain specific examples which are provided herein for purposes of illustration only and are not intended to be limiting unless otherwise specified.
The following examples show some of the typical formulations of this invention and the test results from the application of the compositions to tobacco plants. These results include the sucker inhibitory effects of the compositions and the extent of chemical injury to the plants.
EXAMPLE 1 In a pot having a diameter of 15 cm, tobacco (var: Bright yellow) was cultured. When the tobacco had grown to a height of about 40 cm and had grown 7 8 nodes, the tobacco was topped. An aqueous dispersion containing 1000 ppm of an active ingredient was sprayed on the stems and leaves of the tobacco plants in quantities of 20 ml per plant. After 20 days from the date of application of the spray, the suckers were removed from the plants and collected. The weight of the fresh suckers was measured, and the extent of chemical injury to the leaves was observed. The percent sucker inhibition was calculated by the following equation.
weight of fresh sucker per plant in the treated pot weight of fresh sucker per plant in the untreated pot sucker inhibition l X Table l Com- Active ingredient poun No. Sucker Chemical Inhibition Injury l benzyl N,N-di-n-propylthiolcarbamate 100 none 2 2-methylbenzyl-N,N-di-npropylthiolcarbamate 100 none (b.p. l58-l62C/2 r'nmHg) 3 3-methylbenzyl-N,N-di-npropylthiolcarbamate 100 none (b.p. l54156C/l.5 mmHg) 4 4-methylbenzyl-N,N-di-npropylthiolcarbamate 100 none (b.p. 147l49C/l mmHg) 5 2-chlorobenzyl-N,N-di-npropylthiolcarbamate 100 none (b.p. l62-165C/2 mmHg) 6 4-chlorobenzyl-N,N-di-npropylthiolcarbamate 100 none (b.p. 163166C/l.5 mmHg) 7 2-fluorobenzyl-N,Ndi-npropylthiolcarbamate 100 none (b.p. l54l58C/2 mmHg) 8 4fluorobenzyl-N,N-di-npropylthiolcarbamate 100 none (b.p. l55l60C/2 mmHg) 9 Z-methyl-S-chlorobenzyl- N,N-di-n-propylthiolcarbamate 100 none 10 2-methoxy-5-chlorobenzyl- N ,N-di-n-propylthiolcarbamate 100 none 1 l 2-methyl-3-bromobenzyl- N,N-di-n-propylthiolcarbamate 100 none 12 4nitrobenzylN,N-di-npropylthiolcarbamate 100 none 13 2-methyl-5-nitrobenzyl N,N
di-n-propylthiolcarbamate 100 none 14 4-aminobenzyl-N,N-di-npropylthiclcarbamate l 00 none 15 2,5-dichlorobenzyl-N,N-din-propylthiolcarbamate 100 none 16 2,4-dimethylbenzyl-N,N-din-propylthiolcarbamate 100 none Table I-Continued Com- Active ingredient pound No. Sucker Chemical Inhibition Injury l7 3-chloro-4-methylbenzyl-N,N-
di-n-propylthiolcarbamate 100 none 1 8 2-methoxy-5-bromobcnzyl- N ,N-di-n-propylthiolcarbamate I00 none 19 2-ethoxy-5-chlorobenzyl-N,N-
di-n-propylthiolcarbamate 100 none 20 3-acetylbenzyl N,N-din-propylthiolcarbamate 100 none 2l 2-ethoxybenzyl'N,N-
dimethylthiolcarbamate 100 none 22 2,5-dimethoxybenzyl-N,N-
dim ethylthiolcarbamate 100 none 23 2-methoxy-5-chlorobenzyl- N,N-dimethylthiolcarbamate l 00 small 24 2-ethylbenzyl-N,N-diethylthiolcarbamate 100 none 25 benzyl N,N-diethylthiolcarbamatc 100 none 26 4-chlorobenzyl-N,N-
d iethylthiolcarbam ate 100 none 27 benzyl N,N-di-nbutylthiolcarbamate 100 none 28 2-chlorobenzyl-N,N-di-nbutylthiolcarbamate 100 none 29 4-methylbenzyl-N,N-di'nbutylthiolcarbam ate 100 none 30 2-methyl-5-chlorobenzyl N,N-di-iso-propylthiolcarbamate l00 none 3] 4-fluorobenzyl-N,N-di-isopropylthiolcarbamate l00 none 32 4-chlorobenzyl N-methyl- Nac etylthiolcarb amate 100 none 33 benzyl-N-ethyl-N-acetylthiolcarbamate l 00 none 34 4-chlorobenzyl-N-ethyl-N- acetylthiolearbamate 100 none 35 benzyl-N-ethyl-N- cyclohexylthiolcarbamate 100 none 36 2,5-dichlorobenzyl-N-ethyl- N-cyclohexylthiolcarbamate 100 none 37 benzyl-N-methyl-N- cyclohexylthiolcarbamate 100 none 38 4-chlorobenzyl-N-methyl-N- cyclohexylthiolcarbamate I00 none 39 2,5-dichlorobenzyl-N- methyl-N-cyclohexylthiolcarbamate 100 none 40 Z-methylbenzyl-N-methyl- N-cyclohexylthiolcarbamate 100 none 41 4-methylbenzyl-N-methyl- N-cyclohexylthiolcarbamate I00 none Cont. l none 0 none EXAMPLE 2 In accordance with the method of Experiment 1 further tobacco sucker inhibition tests were conducted except that the concentration of the active ingredients in the solutions applied to the plants was 250, 500 and 2000 ppm. The results of the example are shown in Table II.
Table II-Continued Test Active ingredient Concent- No. ration sucker Chemical (ppm) inhibition Injury 500 I00 250 2 5 Compound 5 2,000 I00 none 500 100 250 100 2 6 Compound 6 2,000 100 none 500 I00 250 I00 2 7 Compound 7 2,000 I00 none 500 I00 250 100 2 8 Compound 8 2,000 100 none 500 I00 250 I00 2 9 Compound 9 2,000 I00 small 500 I00 none 250 I00 Control l 0 none EXAMPLE 3 In a pot having a diameter of 15 cm, a tobacco (var: Bright yellow) was cultured. When the tobacco had grown to a height of about 1 m when 20 25 nodes had grown, and when from 1 2 flower buds had bloomed, the tobacco was topped. When the suckers had grown to a length of to 2 3 cm after 7 days from topping, various concentrations of each active ingredient in aqueous dispersions were sprayed onto the stems and leaves of tobacco plants in quantities of 20 ml per plant.
In a comparative test (Control-2), a 58 percent aqueous dispersion of the diethanolamine salt of maleic hydrazide was sprayed onto the stems and leaves of tobacco plants. Twenty days after the day of application, the percent of sucker inhibition and the extent of chemical injury were measured in accordance with the method of Experiment 1. The results are shown in Table III. The concentration of Test Nos. 3-10 is in terms of maleic hydrazide in Table III.
Table III Test Active ingredient Concen- Chemical No. tration sucker injury inhibition (pp 3 1 Compound 1 4,000 100 none 2,000 100 1,000 100 500 100 3 2 Compound 2 4,000 100 none 2,000 100 1,000 I00 500 100 3 3 Compound 3 4,000 100 small 2,000 100 small 1,000 100 none 500 100 3 4 Compound 4 4,000 100 none 2,000 100 1,000 100 500 I00 3 5 Compound 5 4,000 l00 none 2,000 100 L000 100 500 100 3 6 Compound 6 4,000 100 none 2,000 100 1,000 100 500 100 3 7 Compound 7 4,000 100 none 2,000 100 1,000 l00 500 I00 3 8 Compound 8 4,000 100 none In a pot of 1/2000 are (1/81000 acre) on a wet field, tobacco (var: Bright yellow) was cultured. When the tobacco had grown to a height of about 1 m, and when the flower buds had just begun to bloom, the tobacco was topped. This tobacco was used for the tests. The tobacco was planted in quantities of 1 plant per pot, and the tests were conducted twice. The active ingredients and the auxiliary active ingredients were formulated as follows:
1. Active ingredient N,N-dialky1benzylthiolcarbamate: a. 20 parts by weight N,N-dialkylbenzylthiolcarbamate b. 70 parts by weight xylene, and
c. 10 parts by weight polyoxyethylene laurylether were mixed and the mixture was emulsified for each of the desired concentration;
2. Auxiliary active ingredient: an alkyl-N- phenylcarbamate or a 4-substituted aniline derivative.
An emulsion of the auxiliary active ingredient was prepared in accordance with the method shown above except that N,N-dialkylbenzylthiolcarbamate was replaced with an alkyl-N-phenylcarbamate or a 2,6-dinitro-4-substituted aniline derivative.
In order to test the differences in effectiveness between the active ingredients of this invention, and especially the special effectiveness of the compositions containing the active ingredient and the auxiliary active ingredient, the sucker inhibition percentage was measured days after the date of application of sprays containing the compositions indicated. The results are shown in Tables IV X.
Table IV Test Active Auxiliary active No. ingredient concentingredient concent- Sucker ration ration inhibition (pp (pp Control 1 0 0 0 Control 2 maleic hydrazide 4000 2000 63 I000 25 4 0 0 lsopropyl-N- 4000 69 (3-chlorophenyl) 2000 53 carbamate 1000 41 4 1 Compound 1 4,000 0 75 2,000 1000 1,000 1000 100 500 1000 100 4 2 Compound 2 4,000 0 84 2,000 1000 100 1,000 1000 100 500 I000 100 4 3 Compound 3 4,000 0 81 2,000 1000 100 1,000 1000 100 500 1000 100 4 4 Compound 4 4,000 0 73 I 2,000 1000 100 1,000 1000 100 500 1000 100 4 5 Compound 5 4,000 0 82 2,000- 1000 100 1,000 1000 100 500 1000 100 4 6 Compound 6 4,000 0 84 2,000 1000 100 1,000 1000 100 500 1000 100 4 7 Compound 7 4,000 0 78 2,000 1000 100 1,000 1000 100 v500 1000 100 4 8 Compound 8 4,000 0 i 77 2,000 1000 100 1,000 1000 100 500 1000 100 Table V Test Active Auxiliary active N0. ingredient Coneentingredient Concentsucker ration ration inhibition (pp (PP 5 0 lsopropyl N 4,000 46 phenylearbamate 2,000 31 1,000 18 1 Compound 1 2,000 1,000 100 1,000 1,000 100 500 1,000 91 5 2 Compound 2 2,000 1,000 100 1,000 1,000 100 500 1,000 94 5 3 Compound 3 2,000 1,000 100 1,000 1,000 100 500 1,000 88 5 4 Compound 4 2,000 1,000 98 1,000 1,000 94 500 1,000 72 5 5 Compound 5 2,000 1,000 100 l ,000 l .000 100 500 1,000 92 5 6 Compound 6 2,000 1,000 100 1 ,000 1,000 92 500 1,000 5 7 Compound 7 2,000 1,000 100 1,000 1,000 100 500 1.000 5 8 Compound 8 2,000 1,000 93 1,000 1,000 87 500 1,000 75 Table VI Test Active Auxiliary active No. ingredient Concentingredient Concentsucker ration ration inhibition p (pp 6 0 lsopropyl N- 4,000 72 (3-methylphenyl) 2,000 56 0 carbamate 1,000 43 6 1 Compound 1 2,000 1,000 100 1 ,000 1,000 100 500 1,000 96 6 2 Compound 2 2,000 L000 [00 1,000 1,000 100 500 1,000 100 6 3 Compound 3 2,000 1,000 100 1,000 1,000 100 500 1,000 100 6 4 Compound 4 2,000 1,000 100 1,000 1,000 100 500 1,000 6 5 Compound 5 2,000 1,000 1,000 1,000 100 500 1.000 100 6 6 Compound 6 2,000 1,000 100 1,000 1,000 100 500 1,000 100 6 7 Compound 7 2,000 1,000 100 l ,000 1,000 100 500 1,000 l00 6 8 Compound 8 2,000 1,000 100 1,000 1,000 100 500 1,000 89 Table Vll Test Active Auxiliary active No. ingredient Conceningredient Coneentsucker tration trution inhibition (ppm) (ppm) 7 O sec-hutyl N- 4,000 66 (3-methylphenyl) 2,000 44 0 curb-amine 1,000 28 7 1 Compound I 2,000 1,000 100 l ,000 l .000 100 500 1,000 98 7 2 Compound 2 2,000 1,000 100 1,000 1,000 100 500 1,000 98 7 3 Compound 3 2,000 1,000 100 l ,000 1,000 100 500 1,000 92 7 4 Compound 4 2,000 1,000 100 l ,000 1,000 100 500 1,000 88 Table V11 Continued Test Active Auxiliary active No ingredient Cnccningredient Conccnt sucker [ration tration inhibition (pp (pp 0% 7 Compound 5 2,000 1,000 100 1,000 1,000 100 500 1,000 96 7 6 Compound 6 2,000 1,000 100 1,000 1,000 96 500 1,000 97. 7 7 Compound 7 2,000 1,000 100 1,000 1,000 100 500 1,000 89 7 8 Compound 8 2,000 1,000 100 1,000 1,000 91 500 1.000 87 Table VIII Test Active Auxiliary active No. ingredient Conceningredient Concensucker tration tration inhibition (PP (pp 8 0 N-sec-buty1-4- 0 tert-butyl 4,000 68 2,6-dinitro- 2,000 56 aniline 1,000 5 2 8 1 Compound 1 2,000 1,000 100 1,000 1,000 100 500 1,000 100 8 2 Compound 2 2,000 1,000 100 1 ,000 1,000 100 500 1,000 100 8 3 Compound 3 2,000 1,000 100 1,000 1,000 100 500 1,000 100 8 4 Compound 4 2,000 1,000 100 1,000 1,000 100 500 1,000 98 8 5 Compound 5 2,000 1,000 100 1,000 1,000 100 500 1,000 100 8 6 Compound 6 2,000 1,000 100 1,000 1,000 100 500 1,000 100 8 7 Compound 7 2,000 1,000 100 1,000 1,000 100 500 1,000 100 8 8 Compound 8 2,000 1,000 100 1,000 1,000 100 500 1,000 100 Table IX Test Active Auxiliary active No. ingredient Concentingredient Concentsucker ration ration inhibition (ppm) (pp 9 0 N,Ndi-n-propyl 4-trifluoromethyl 4,000 52 2,6-dinitro- 2,000 31 aniline 1,000 1 l 9 1 Compound 1 2,000 1,000 100 1,000 1,000 88 500 1,000 9 2 Compound 2 2,000 1,000 100 1,000 1.000 500 1.000 86 9 3 Compound 3 2,000 1,000 1 ,000 l .000 86 500 1,000 74 9 4 Compound 4 2,000 1,000 100 1,000 1,000 75 500 1,000 60 9 5 Compound 5 2.000 1,000 100 l ,000 1,000 92 500 1,000 84 9 6 Compound 6 2,000 1,000 100 1 ,000 1,000 85 500 1.000 71 9 7 Compound 7 2,001) 1,000 100 1 ,000 1 ,000 85 500 1,000 76 I 9 8 Compound 8 2.000 1,000 92 1,000 1,000 88 500 1,000 72 Table X Test Active Auxiliary activc No. ingredient Concentingredient Concentsucker ration ration inhibition (pp (pp l 0 N,Ndi-n-propyl 4-methylsulfonyl 4,000 49 2,6-dinitro- 2,000 26 aniline 1,000 l2 l0 1 Compound 1 2,000 1,000 96 1,000 1,000 88 500 1,000 66 10 2 Compound 2 2,000 1,000 92 1,000 1,000 78 500 1,000 72 10 3 Compound 3 2,000 1,000 91 1,000 1,000 76 500 1,000 60 10 4 Compound 4 2,000 1,000 96 500 1,000 71 10 5 Compound 5 2,000 1,000 91 l ,000 1,000 77 500 1,000 71 6 Compound 6 2,000 1,000 100 1,000 1,000 82 500 1,000 65 10 7 Compound 7 2,000 1,000 90 1,000 L000 82 500 1,000 79 10 8 Compound 8 2,000 1,000 88 1,000 1,000 72 500 1,000 61 According to the test results, the active benzylthiolcarbamate ingredients of this invention exhibit a remarkable inhibitory effect on the growth of tobacco suckers compared to other sucker inhibitors such as maleic hydrazide. At the same time very little chemical injury is observed on the treated tobacco leaves.
In the instances when an auxiliary active ingredient such as an alkyl N-phenylcarbamate or a 2,6-dinitro-4- substituted aniline derivative was blended with an N,N- dialkylbenzylthiolcarbamate for the treatment of tobacco suckers, the blend of ingredients exhibited a remarkable synergistic effect in the treatment of the plants. Inhibition of tobacco sucker for those plants treated with this blend was maintained for a substantially longer period of time than for those plants treated with a single active ingredient or maleic hydrazide.
Having now fully described the invention, it will be apparent to one of ordinary skill in the art that many changes and modifications can be made thereto with out departing from the spirit or scope of the invention as set forth herein.
What is claimed as new and desired to be secured by (X) ECW129101 (Yl wherein R and R are selected from the group consisting of 65 acetyl, cyclohexyl, and C alkyl groups:
5 ing from 1 ml.
3. The method of claim 1, wherein said benzylthiolcarbamate is applied while the tobacco plants are in the topping stage.
4. The method of claim 1, wherein said benzylthiol- 0 carbamate is N,N-dialkylbenzylthiolcarbamate having the formula CHZSCN wherein R and R represent C alkyl groups and Z is selected from the group consisting of hydrogen, methyl, chlorine, and fluorine. 5. The method of claim 1, wherein said benzylthiolcarbamate is selected from the group consisting of 2 methylbenzyl N,N-di-n-propylthiolcarbamate, S-methylbenzyl N,Ndi-n-propylthiolcarbamate, 4=methylbenzyl N,N-di-n-propylthiolcarbamate, Z-ehlorobenzyl N,N-di-n-propylthiolcarbamate, 4=chlorobenzyl N,N-di-n-propylthiolcarbamate, 2-tluorobenzyl N,N-di-n-propylthiolcarbamate, and 4 fluorobenzyl N,N-di-n propylthiolcarbamatei i l =l a
Claims (5)
1. A METHOD OF INHIBITING THE GROWTH OF SUCKERS OF TOBACCO PLANTS WHICH COMPRISES APPLYING TO TOBACCO PLANT, AN EFFECTIVE AMOUNT BENZYLTHIOLCARBAMATE HAVING THE FORMULA,
2. The method of claim 1, wherein said benzylthiolcarbamate is applied to each tobacco plant in the concentration range of 100 -10,000 ppm in amounts ranging from 1 - 100 ml.
3. The method of claim 1, wherein said benzylthiolcarbamate is applied while the tobacco plants are in the topping stage.
4. The method of claim 1, wherein said benzylthiolcarbamate is N,N-dialkylbenzylthiolcarbamate having the formula
5. The method of claim 1, wherein said benzylthiolcarbamate is selected from the group consisting of 2-methylbenzyl N,N-di-n-propylthiolcarbamate, 3-methylbenzyl N,N-di-n-propylthiolcarbamate, 4-methylbenzyl N,N-di-n-propylthiolcarbamate, 2-chlorobenzyl N,N-di-n-propylthiolcarbamate, 4-chlorobenzyl N,N-di-n-propylthiolcarbamate, 2-fluorobenzyl N,N-di-n-propylthiolcarbamate, and 4-fluorobenzyl N,N-di-n-propylthiolcarbamate.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP47026016A JPS5011965B2 (en) | 1972-03-13 | 1972-03-13 |
Related Child Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US50873274A Division | 1972-03-13 | 1974-09-24 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3883343A true US3883343A (en) | 1975-05-13 |
Family
ID=12181883
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US340534A Expired - Lifetime US3883343A (en) | 1972-03-13 | 1973-03-12 | Method of tobacco sucker inhibition |
Country Status (4)
| Country | Link |
|---|---|
| US (1) | US3883343A (en) |
| JP (1) | JPS5011965B2 (en) |
| BR (1) | BR7301785D0 (en) |
| SU (1) | SU584737A3 (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20080202538A1 (en) * | 2003-01-31 | 2008-08-28 | Philip Morris Usa Inc. | SPRAY AND/OR SOIL TREATMENT OF TOBACCO TO REDUCE TSNAs |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3326664A (en) * | 1964-01-10 | 1967-06-20 | Tien C Tso | Method of tobacco sucker control |
| US3746532A (en) * | 1970-07-16 | 1973-07-17 | Kumiai Chemical Industry Co | Herbicidal composition of thiocarbamate and 3(3,4-dichlorophenyl)-1-methoxy-1-methylurea |
-
1972
- 1972-03-13 JP JP47026016A patent/JPS5011965B2/ja not_active Expired
-
1973
- 1973-03-12 SU SU7301892340A patent/SU584737A3/en active
- 1973-03-12 US US340534A patent/US3883343A/en not_active Expired - Lifetime
- 1973-03-13 BR BR731785A patent/BR7301785D0/en unknown
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3326664A (en) * | 1964-01-10 | 1967-06-20 | Tien C Tso | Method of tobacco sucker control |
| US3746532A (en) * | 1970-07-16 | 1973-07-17 | Kumiai Chemical Industry Co | Herbicidal composition of thiocarbamate and 3(3,4-dichlorophenyl)-1-methoxy-1-methylurea |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20080202538A1 (en) * | 2003-01-31 | 2008-08-28 | Philip Morris Usa Inc. | SPRAY AND/OR SOIL TREATMENT OF TOBACCO TO REDUCE TSNAs |
Also Published As
| Publication number | Publication date |
|---|---|
| SU584737A3 (en) | 1977-12-15 |
| BR7301785D0 (en) | 1974-08-15 |
| JPS4892531A (en) | 1973-11-30 |
| JPS5011965B2 (en) | 1975-05-08 |
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